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Full text of "Dictionary Of Organic Compounds Volume One Abadole Cytosine"

1 



v.l 54-603056 



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Htbrarp 




This Volume is for 
REFERENCE USE ONLY 



KANSAS CITY, MO PUBLIC LIBRARY 



D DOD1 D2Ufl225 2 



DICTIONARY OF ORGANIC COMPOUNDS 
VOLUME 1 



DICTIONARY OF 
ORGANIC COMPOUNDS 

The Constitution and Physical and Chemical Properties of the Principal 
Carbon Compounds and their Derivatives, together with the relevant 

Literature References 

VOLUME ONE 
ABADOLE CYTOSINE 

Editor s-in-Ch ief 
PROFESSOR SIR IAN HEILBRON, D.S.O., D.Sc., LL.D., F.R.I.C., F.R.S. 

H. M. RUNBURY, M.Sc., F.R.I.C. 

Editors 

A. H. COOK, D.Sc., F.R.I.C,, F.R.S. 
PROFESSOR E. R. H. JONES, D.Sc., F.R.I.C, F.R.S. 

Assistant Editors 

T. G. HALSALL, PH.D., A.RJ.C. 
J. R. A. POLLOCK, PH.D., DJ.C. 

Contributors 

G. W. H. CHEESEMAN, PH.D., D.I.C., S. F. Cox, PH.D., A.R.I. C., D.I.C., 
G. D. HUNTER, PH.D., D.I.C., J. C. LUNT, PH.D., D.I.C., E. SMITH, 
PH.D., D.I.C., F. SONDHEIMER, Pn.D., A.R.I.C., D.I.C., J. M. SWAN, PH.D., 
D.I.C., G. H. THOMAS, PH.D., D.I.C., C. J. TIMMONS, PH.D., A.R.I. C.., 
D.I.C., R. J. WOODS, PH.D., A.R.I.C., D.I.C. 



NEW YORK 

OXFORD UNIVERSITY PRESS 
1 95 3 



First published in three volumes : 

FoL I 1934 

Vol. II 1936 

Vol. Ill 1937 

New, revised edition of FoL I 1943 ; Fols. II and 
III reprinted, with supplements , 1944. 

Fols. I, // and III reprinted 1947 
New, revised edition in four volumes 1953 



PRINTED IN GREAT BRITAIN 



Reference 



PREFACE 

WHEN the Dictionary was first produced during the years 1934-37 it was intended that it should 
be kept up to date by complete revision every five or six years. A new edition of Volume I, cover- 
ing the letters A to D, was published in 1943. As explained in the Preface to that Volume, the 
war made completion impracticable. Volumes II and III were reprinted with short supplements 
containing new entries of special interest and importance for which data and information had been 
gathered meanwhile. For several years nothing further could be done but, with the approach of 
more normal conditions following the cessation of hostilities, the task of preparing a new and com- 
pletely revised edition was taken up again. 

Progress in many lines of research had inevitably been arrested, with the consequent diminution 
in the flow of new compounds and data. On the other hand, war conditions had created fresh 
demands, resulting in rapid developments in all branches of chemistry, none, perhaps, more striking 
than those in the field of biochemistry. Further, in the manufacturing sphere new industries were 
set up to produce materials such as plastics, synthetic fibres and other polymers, directly or in- 
directly required for war purposes. As a result many new organic compounds, both natural and 
synthetic, have come into prominence. 

In view of these developments and the subsequent revival of peace-time research activities, 
revision of the Dictionary was now clearly required. In this new edition the whole of the text has 
been carefully scrutinized and brought up to date to the end of 1950. In addition, every opportunity 
has been taken during passage through the press to include results of more recent research even up 
to the early months of 1953. Over 2,500 compounds appear for the first time as principal entries, 
while some thousands of additions or amendments have been made to existing entries following upon 
the publication of fuller or more accurate data and information. 

In order to facilitate easier handling, it has been decided to issue the Dictionary in four volumes 
instead of three. Considerable economy of space has been achieved by deletion of many super- 
fluous constitutional formulae and by increasing the type area of each page. No other changes 
have been made either ia format or lay-out because the original style appears to have met with 
wide approval. 

Once again our thanks are due to the printers for the exemplary care and precision which they 
have given to the work at every stage in its preparation. 

July, 1953. I- M. H. 

H. M. B. 



INTRODUCTION 

ALL the compounds in this dictionary are arranged in strictly alphabetical order. The dictionary 
is therefore its own index, and any required data and information should be readily accessible. 
A difficulty sometimes arises, however, on account of the fact that most organic compounds possess 
more than one name, and questions of orientation introduce a further complication. An alpha- 
betical classification is thus inadequate per se, and some further rules are necessary if that otherwise 
simple system is to possess its maximum utility. In order to facilitate the use of the dictionary 
an explanation of the general rules which have been adopted and followed throughout the work is 
given in the following notes. 

Arrangement of the Text 

PRINCIPAL REFERENCES 

The majority of compounds can be named in a variety of ways, some popular (or trivial) and 
others systematic or strictly chemical. But in practice it is found that for any one compound 
preference is usually given to one particular name, and it is this name which has been selected for 
the principal reference. It sometimes happens, however, that such a compound is one of a number 
of isomers having a systematic or chemical name. In certain cases of this kind the general rule has 
been departed from, the whole series of isomers being grouped together under the systematic name. 
For example, Orthanilic, Metanilic, and Sulphanilic Acids are not separated under letters O, M, 
and S, but are given together under letter A as Aniline-o-, m-, and #>-sulphonic Acids respectively. 
Similarly Gamma Acid, J-Acid, M-Acid, and S-Acid are included with the other Aminonaphthol- 
sulphonic Acids. Trade and proprietary names are not used for the principal references, except 
where they come within the general rule as being in common use or where, usually for reasons of 
complex structure, no other names are feasible. 

The name selected for a parent compound is, with a few exceptions, retained for all its deriv- 
atives. For example, Alizarin having been chosen for 1 : 2-Dihydroxyanthraquinone, all the 
derivatives of the latter will be found as derivatives of Alizarin. 

CROSS-REFERENCES 

A generous number of cross-references, sometimes as many as three or four, are given, by means 
of which the principal references can readily be found. For instance iV-Carboxyurea, Carbamyl- 
carbamic Acid, and Ureidoformic Acid are given as cross-references to Allophanic Acid. Where 
cross-references are given for a parent compound, these are not, in general, repeated for the deriv- 
atives. Thus Diphenyl Ketone will be found as a cross-reference to Benzophenone, but Amino- 
ancl Bromo-diphenyl Ketones are not given as cross-references to Amino- and Bromo-benzophenones. 
Owing to their large number many nitriles are not included under Cyano- : those not so given will 
bo found either under their own name (e.g. Acetonitrile, Benzonitrile) or under the parent acid. 



The full constitutional formula is given for each compound with, of course, the exception of 
those whose constitutions have not yet been ascertained. In the case of many compounds of the 
carbohydrate, steroid, and polyterpene classes, the constitution is represented by simple skeletal 
structures and configuration by heavy oir dotted lines in conformity with modern practice. Where 
there is a group of isomers, however, it is considered to be sufficient in most cases to set out the full 
formula for the first member only. This applies also to the molecular formula and molecular 
weight. For instance, the complete formula is given for o-Chlorotoluene, but none for the m-, and 
p~, which follow. 'For acyclic compounds, however, particularly those with long or branched 
chains or with varying degrees of unsaturation, orientation is less simple, and full formulae are 
given in every case, e.g., the Hexenols. 

The order of the elements in the molecular formula* is C H N 01 Br F S P, other elements 
following in alphabetical order. In calculating molecular (formula) weight the following approxi- 
mate atomic weights have been employed : C 12, H 1, 16, N 14, 01 35-5, Br 80, 1 127, F 19, S 32, 
P 31, F 56, Mg 24, Pb 207, Se 79, Si 28, and for other elements the whole number nearest to the 
atomic weight adopted by the International Committee on Atomic Weights in 1942. 



Introduction 

DERIVATIVES 

Functional derivatives, as distinct from substitution compounds, are given under the parent 
compound except where they are sufficiently important to justify separate inclusion as principal 
references. Thus under an acid will be found its esters, halides, anhydride, amide, nitrile, anilide, 
etc. Esters in which the alcohol or phenol component is of more importance than the acid com- 
ponent are given under the alcohol or phenol, as, e.g., in the case of the acetates and benzoates of 
Borneol, Eesorcinol and sec.-n-Qctyl alcohol. Under a base are given its salts, acyl derivatives, 
addition compounds, etc. ; under an alcohol or phenol, the ethers and certain esters (v. supra) ; 
under an aldehyde or ketone, the acetals, oximes, semicarbazones, phenylhydrazones, etc. 

LITERATURE REFERENCES 

The literature references relate primarily to the best method of preparation, but in some cases 
publications are cited which refer to earlier methods of preparation or which contain useful sum- 
maries or bibliographies. Where considerations of molecular structure or constitution are of im- 
portance, reference is made to the most recent views on the subject. This is particularly the case 
with many of the complex naturally occurring compounds. To some of the very common com- 
pounds, e.g., Acetone, Acetic acid and Ethyl alcohol, no useful references can be given. 

The journal abbreviations used are listed in the Table on p. xiii. They are largely those adopted 
for the Chemical Abstracts of the American Chemical Society (Index to Chemical Abstracts, 45, 1951 ). 



Nomenclature and Orientation 

In the introduction to Richter's Lexicon (1910) the following passage occurs : " Of the many 
difficulties which, in writing this work, presented themselves, the greatest was undoubtedly the 
question e which nomenclature is to be adopted for the sake of uniformity and clearness.' " Tho 
vast number of compounds already known when that was written has since been contiimouHly 
added to, and new types of compound have appeared, thus rendering the problem of nomenclature 
more difficult and complex to-day than it was in 1910. The only system which can be regarded as 
having the merit of completeness is that of Beilstein, but it is very complicated, and possesses other 
features which reduce its value as a practical scheme. The Geneva system, although occasionally 
utilised for aliphatic compounds, has never found universal favour. Many attempts have boon 
made in recent years to introduce new systems both of nomenclature and of orientation, but none 
of these has been exclusively used in this Dictionary. Preference has usually boon given to the 
nomenclature and orientation employed in the original publication, but, in cases where ambiguity 
may arise, adjustment has sometimes been necessary in the interests of clarity. 

In order to avoid re-setting in a large number of compounds scattered over the 3,000 pages of 
this edition, the recently introduced convention of using small roman capitals, B, L, in place of 
italic, d-, 1-, for optically active compounds, has not been adopted except in a few instances. 

NOMENOLATUBE 

The prefixes cyclo-, homo-, iso-, etc., are treated as part of the name. Thus Gyclopentano, 
Homocatechol, Isophthalic Acid, are to be found under letters C, H, I, respectively. Tho prefixes 
allo-, epi-, and nor-, have also in general been prefered as part of the name, but where this has not 
been convenient sufficient cross-references have been given. An exception is made in the ease of 
pseudo-, which is represented by the Greek letter $, |-Aconitine (Pseudo-aconitine), for instance, 
being included under letter A and not letter P. The prefixes benz- and naphtha- are uaod for 
condensed (fused) benzene and naphthalene rings, not benzo- and naphtho-. E.g., Benzthiaaole, 
Benzcarbazole, Naphthafluorene. For compounds containing the fused naphthalene ring and for 
whose names both benz- and naphtha- have been used, the preference has been given to the former 
in principal references, e.g., Benzcoumarin not Naphthacoumarin, Benzacridine not Naphtha widiue. 
For acetylenic compounds -in- has been replaced by -yn-, e.g., Butyn not Butine, Hoxynol not 
HexinoJ, and similarly ethynyl instead of ethinyl. 

All "double" derivatives take the prefix di-. E.g., Diallyl sulphide, not AIM sulphide; 
Diethyl Ether, not Ethyl Ether; Dimethyl sulphate, not Methyl sulphate. The Greek di- is pre- 
ferred to the Latin bi- or bis-, e.g., di-semiearbazone, di-phenylhydrazone. 



Introduction j x 

In substituted or derived compounds the order in which the substituent group names appear 
in the compound name is that given in the Table on p. xv, List of Substituents. Thus, for the 
common substituents the order is, Halogen (F, 01, Br, I), Nitro, Hydroxy, Amino, Alkyl, Aryl, AcyL 
Wherever possible, the aldehyde, carboxyl, and sulphonic groups are preferred as suffixes. E.g., 
Anthraquinonesulphonic Acid, not Sulphoanthraquinone (but cf. e.g., Disulphobenzoic Acid y 
Aldehydosalicylic Acid) ; ChloroanthraquinonecarboxyHc Acid, not Chlorocarboxyanthraquinone. 

ORIENTATION 

Acyclic Compounds. The numbering system is used in preference to Greek letters. The CH0 7 
ON, and COOH groups are generally regarded as substituents and, as such, their carbon atoms are 
not numbered. 

In the saturated branched chains numbering commences in the longest chain at the terminal carbon 
nearest to the side- chain. If there are two or more side-chains or groups of different lengths, num- 
bering commences at the end carbon nearest to the shortest of such side-chains. E.g., 



CH 3 -CH 2 -CH-CH 8 CH 3 -CO-CO-CH 2 -CH 2 -CH-CH 3 

4321 / fi 3 4 3 2 1 

Isopentane Acetylisocaproyl 

There are two exceptions to the above rule. (1) Where the chain contains a CHO, CN, or COOH 
group, numbering begins at the carbon carrying this group. E.g., 



CH 3 -CH'CH 2 -CH 2 -COOH 

Isocaproic Acid 
(2) In the primary alcohols numbering commences at the carbon of the CH 2 OH group. E.g., 



CH 3 -CH*CH,-CH 2 OH 

4 3 2 " 1 

Isoamyl Alcohol 

In the unsaturated compounds the double or triple bonds are given the lowest numbers possible 
whether the chain is branched or not. Where both double and triple bonds are present, the latter 
takes the lowest number. E.g., 

<X 
CH 3 -CH 2 -CH:CH 2 CH 3 -CH-CH:CH 2 CH 2 :CH-C:CH 

4321 4321 4321 

1 -Butylene 3 -Methyl- 1 -butylene Vinylacetylene 

The rule applies to compounds containing the CHO, CN, or COOH groups provided the name of 
the parent hydrocarbon is retained. E.g., 

900H 
HOOC-CH 2 -CH 2 -C:CH 2 

4 3 21 

l-Butylene-2 : 4-dicarboxyhc Acid 
(not 3-Butylene-l : 3-dicarboxylic Acid) 

but in all other cases the rule for saturated compounds is followed, viz. numbering begins at the 
carbon carrying the CHO, CN, or COOH group or, in the case of primary alcohols, at the carbon of 
the CH 2 OH group. Thus 

CH 2 :CH-CH 2 -COOH CH H -[CH 2 ] 7 -CH:CH-[CH 2 ] 6 -CH 2 -COOH 

321 17 98 1 

Vinylacetic Acid Oleic Acid 



CH 8 -C:CH-CH 2 -CH 2 -CH-CH 2 -CHO 

81 7684321 

Alcohol Citronellal 



_. Introduction 

-X. 

In the case of carbon chains interrupted by (ethers), NH (secondary amines), S (sulphides), 
etc., niimbering commences at the carbon atoms attached to the oxygen, nitrogen, sulphur, etc. 
Ejg., 

CH 3 -CH,-CH 2 -CH,-]m-CH 2 -CH 2 -CH 2 -CH 3 C1CH 2 -CH 2 -S-CH 2 -CH 2 C1 

4' 3' 2' 1' ** 1 2 3 4 2' 1' 12 

Dibutylamine 2 : S'-Dichlorodiethyl sulphide 

Homocydic and Heterocyclic Compounds. As stated above, no one system of orientation of ring 
compounds has been exclusively followed, and no new departures have been made from those 
already in use. Where there is any doubt numbers have been inserted in the constitutional formulae 
of the parent compounds. The numbering adopted for any particular ring system can therefore be 
readily ascertained by reference to the text. In the methylbenzenes (i.e. toluene and its deriva- 
tives) numbering begins in most cases at the carbon to which the methyl group is attached. 

In heterocyclic rings containing both oxygen (or sulphur) and nitrogen the lowest number is 
given to the oxygen (or sulphur). E.g., in the oxazoles (or thiazoles) numbering commences at the 
oxygen (or sulphur). 

Where there is a choice of numbering of polysubstituted compounds the lowest number is, 
wherever possible, assigned to the functional groups (OH, NF 2 , etc.). E.g., 5-Chloro-l-aminoanthra- 
quinone, not l-Chloro-5-aminoanthraquinone, such a compound being regarded as a chloro deriv- 
ative of aminoanthraquinone rather than an amino derivative of chloroanthraquinone. Similarly 
6-Bromo-3-hydroxybenzyl Alcohol, not 2-Bromo-5-hydroxybenzyl Alcohol. 

Aromatic-aliphatic (arallcyl) compounds. In the aralkyl compounds the general rule given above 
for the numbering of aliphatic chains has been departed from, the carbons in the aliphatic part 
of the molecule being designated by Greek letters in order to avoid confusion with the numbers 
of the rings. E.g., 

CHBr-COOH CH 2 <&E 2 C1 CH 2 C1 



./ \/ A/ V 

a-Bromophenylacetic Acid /3-Chloroethylbenzen a-Chloro-o-toluic Acid a-Chlorostilbone 

COCHBr<$B 3 




/3-Bromopropiophenone Diphenylmethane 2-[w-Aminoethyl]~mdolo 

The letters begin at the carbon attached to the ring except in the case of the aromatic-aliphatic 
acids, aldehydes, nitriles, or primary alcohols. In those cases lettering begins at the carbon csarry- 
ing the COOH, OHO, or ON group or at the carbon of the CH 2 OH group. E.g., 

CHICBrCHO CBrlCH-COOH 6H 2 -CH(NH 2 )-COOH 



a-Bromocinnamaldehyde /3-Bromocinnamic Acid a-Aminohydrooinnaxnio Acid 

In many aralkyl compounds, however, the aromatic radical can, from the point of view of tho 
name, be regarded merely as a substituent. In such cases the numbering of the parent aliphatic 
compound is retained provided no ambiguity is likely to result. Thus, 



C 6 H 5 -CH:CH-CH 2 -CH 2 -COOH CH 3 *CH 2 -CH(C 6 H 5 )-CH 2 6 H 5 (O e H 5 ),OH-O 

3- (not y -) Benzylidenebutyric Acid 1 : 2-(not a/3-) Diphenylbutano 2 : 2-(not $3-)Dipheuyl 

propionfa Acid 



Introduction xi 

General Remarks 

In the descriptive matter in the text the same order has been folio wed-in all cases, viz. : sources, 
where of interest ; physical properties (melting point, boiling point, solubility, density, refractive 
index, heat of combustion, optical rotation, etc.) : chemical properties (typical reactions, analytical 
tests, etc.). The data for derivatives then follow under separate sub-headings. 

As regards abbreviations, these have been used freely in the text, but all abbreviations and 
contractions, such as Me, Et, Ph, CO 2 H, etc., have been rigidly excluded from the constitutional 
formulae. 

As would be expected, the original literature reveals numerous instances of divergent and 
sometimes contradictory data for the same compound. As far as possible palpable inconsistencies 
have not been recorded, but where a choice could not be safely made the alternative data, e.g., 
melting and boiling points, densities, etc., are given in parentheses. In some cases the information 
given in the literature is so scanty and uncertain that it has been considered advisable to omit the 
compound altogether. Nevertheless, although in some instances the recorded facts regarding 
chemical and physical properties are very meagre, the compound has been included by virtue of 
other valuable information contained in the literature references, such as method of preparation or 
proof of constitution. 



TABLE OF ABBREVIATIONS 



A . Acid (A z , t> wo raols of acid). InsoL . 

A . Angstrom unit. (10~ s cm.). I-U. 

Abs. EtOH Absolute alcohol. Jap. P. 

AcOH . Acetic acid. k 

Ac 2 . Acetic anhydride. I 

AcOEt Ethyl acetate. Liq. . 

Add. . Additive. w 

Add. comp. Addition compound, molecular compound, Max. . 

adduct. Me 

Addn. . Addition. MeOH . 

A.G.F.A. Aktien-Gesellschaft fur Anilinfabrikation. Me 2 CO 

Ale. . Alcohol, alcoholic. Min. 

Ale. NH 3 Alcoholic ammonia. Misc. . 

Al.Hg. Aluminium amalgam. M.L.B. 

Alk. . Alkaline. mm. 

[a] . Specific rotation. Mod. . 

Amorph. Amorphous. Mol. 

Anhyd. Anhydrous. M.p. 

Aq. . Aqueous. ins 

as. . Asymmetric. MW 

Atm. . Atmosphere(s), atmospheric. mgm. . 

B . Base (1? 2 , two rnols of base). m/i 

Badische Badische Anilin und Sodafabrik. n 

Belg. P. Belgian Patent. WD 

B.D.C. British Dyestuffs Corporation. NaHg . 

Bibl. . Bibliography. NH 3 . 

B.p. . Boiling point. KH 3 .AgN0 3 

B.P. . British Patent. o 

c , . Concentration. Ord. 

Cp . Constant pressure. Org. 

C w . Constant volume. Ox. 

Cal. . Calories. p 

Can. P. Canadian Patent. P 

Col. . Colour, coloration. pH 

Comb. . Combustion. pK 

Comp. . Compound. Part. 

Cone, . Concentrated. Pet. ether 

Corr. . Corrected. PhN0 2 

Crit. . Critical. PhOH . 

Cryat. . Crystals, crvstalline, crystallise. Ppd. 

(COOH) 2 Oxalic acid." Ppt. . 

(CH 2 COOH) 2 Succinic acid. Pptn. . 

D . Density. Prac. . 

r> . Dextro-. Press. . 

d . Dextrorotatory. 

dl . Racemic. Optically inactive by external 

compensation. r 

Decpmp. Decomposed, decomposition. Red. . 

Deriv. . Derivative. Ref. 

Dil. . Dilute, dilution. Russ.P. 

Diss. . Dissolves, dissolved. S.C.I. . 

Diet. . Distil, distillation, 

D.R.P. German Patent. Sec. 

Et . Ethyl. Sol. 

Et 2 . Ether (diethyl ether). Spar. , 

EtOH Ethyl alcohol. Sp. gr. . 

Evac. . Evacuated. Sp. heat 

Fluor. . Fluoresces, fluorescence. Spp. . 

F.p. . Freezing point. SuppL . 

F.P. . French Patent. Sym. . 

Form. . Formation. Temp. . 

y . 10~ tt gm. or 10~ a mgm. (microgrammes). Tert. . 

gm. . Gramme(s). Undecomp. 

Hyd. . Hydrolyses, hydrolysed, hydrolysis. Unsym. 

t . OpticaUy inactive by internal compensation. UV. 

I.C.I. . Imperial Chemical Industries. Vac. 

I.G. . Intereesen Gemeinschaft Farbenindustrie Vap. . 

Aktien-Gesellfichaft. Vol. 



Insoluble. 

International Unit. 

Japanese Patent. 

Dissociation constant. 

Lsevorotatory. 

Liquid. 

Meta (position). 

Maximum. 

Methyl. 

Methyl alcohol. 

Acetone. 

Mineral (inorganic). 

Miscible. 

Meister, Lucius & Bruning. 

Millimetre (s). 

Moderately. 

Molecule, molecular, molar. 

Melting point. 

Meso (position). 

Molecular weight (formula weight) . 

Milhgramme(s). 

Millimicron(s). (10~ 7 cm.). 

Normal (chain). 

Refractive index (D line, etc.). 

Sodium amalgam. 

Ammonia, aqueous ammonia. 

Ammoniacal silver nitrate. 

Ortho (position). 

Ordinary. 

Organic. 

Oxidise, oxidation. 

Para (position). 

Patent. 

lgio hydrogen ion concentration. 

Iog 10 k (dissociation constant). 
Partly, partial. 

Petroleum ether. 

Nitrobenzene. 

Phenol. 

Precipitated. 

Precipitate. 

Precipitation. 

Practically. 

Pressure(s). 

Pseudo. 

Pyridine. 

Racemic. 

Reduce* reduction. 

Reference. 

Russian Patent. 

Socie'te* pour I'industrie cMraique 

Basle. 
Secondary. 
Soluble, solution. 
Sparingly, 
Specific gravity. 
Specific heat. 
Species. 
Supplement. 
Symmetrical. 
Temperature(e), 
Tertiary. 
Undecomposed. 
Unsymmetrical. 
Ultraviolet. 
Vacuum. 
Vaporisation* 
Volume. 



JOURNAL ABBREVIATIONS 

Journals not listed here are given their full titles in the text. 



Ada Chem. Scand. 
Ada Phytochim. 
Am. Chem. J. 
Am. J. Pharm. 
Am. J. Sci. 
Anales asoc. quim. 

Argentina 
Anales soc. espan. 

fis. quim. 
Angew. Chem. 
Ann. 

Ann. chim. 
Ann. chim. appli- 

cata 

Ann. chim. phys. 
Ann. pharm. frang. 
Ann. phys. 
Ann. Physilc 
Ann. JKev. Biochem. 
Ann. tici. Unw. 

Jassy 
Ann. Trop. Med. 

and Parasit. 
Arch. Biochew. 



. Bio- 



Arch. 

phi/s. 
Arch. Pharm. 



Arkiv Kemi, Mine* 

ral. Oeol. 
Atti accad. Lincei 



Ber. 



Bcr. deut. pharm. 

<hs. 
Ber. gee. Physiol. 

exptl. Pharmakol. 



Ifalumg till ft 
Vd.-Akad. 



Biochem. J. 
Biochem. %>. 
Biol. Zentr. 
Brit. Ghem. Ab- 

stracts 
lirit. J. Mxptl. Path. 

Brit. /. PharmacoL 
Bull. acad. sci. 

cr*tiJ8,& 

Bull. Chem. j$oc, 

Japan 

Bull. Imp. Inst. 
Bull. ln$t. Phys. 

Chem. Research, 

Tokyo 
Bull. sci. acad. roy. 

Bdg. 
. ci, pharmacoL 



Acta Chemica Scandinavica. 
Acta Phytochimica (Japan). 
American Chemical Journal. 
American Journal of Pharmacy. 
American Journal of Science. 
Anales de la Asociacion Quimica 

Argentina. 
Anales de la sociedad espanola de 

fisica y quimica. 
Angewandte Chemie. 
Annalen der Chemie. 
Annales de chimie. 
Annali di chimica apphcata. 

Annales de chimie et de physique. 

Annales Pharmaceutiques Fran9aise. 

Annales de physique. 

Annalen der Physik. 

Annual Review of Biochemistry. 

Annales scientifiques de I'Umversitc 

do Jassy. 
Annals of Tropical Medicine and 

Parasitology. 
Archives of Biochemistry (name 

changed to next in 1951). 
Archives of Biochemistry and Bio- 
physics . 
Archiv der Pharmazie (und Berichte 

der deutschon pharmazeutischen 

Gesellschaft). 
Arkiv fdr Komi, Mmeralogi och 

Geologi. 
Atti della reale accademia nazionale 

del Lincei. 

Berichte der deutschen chemischen 
Gosellschaft. Now Cheuiische 
Boriohto. 

Berichte der deutschen pharma- 
zeutischen Gesellschaft. 

Berichte uber die gesamte Physio - 
logie und oxporimentelle Pharm a- 
kologie. 

Bihang till KungUga Svcnaka 
Vctonskapsakademions li and- 
lingon. 

Biochemical Journal. 

Biochemische Zeitschrift. 

Biologisches Zentralblatt. 

British Chemical Abstracts. 

British Journal of Experimental 

Pathology. 
British Journal of Pharmacology 

and Chemotherapy. 
Bulletin of tho Academy of Sciences 

of the U.H.H.H. 
Bulletin of the Chemical Society of 

Japan. 

Bulletin of the Imperial Institute. 
Bulletin of the Institute of Physical 

and Chemical Besearch, Toyko. 

Bulletin do la clasae des sciences, 
academic royalo de Belgique. 

Bulletin des sciences pharmacolo- 
giquos. 



Bull. soc. chim. 

Bull. soc. chim. 
Belg. 

Bull. soc. chim. biol. 



Can. Chem. Met. 
Can. J. Research 
Chem. Abstracts 

Chem. Ind. 
Chem. Met. Eng. 

Chem. News 

Chem. Reviews 
Chem.-Tech. Rund- 



Chem. Trade J. 
Chem. Umschau 



Chem. Weekblad 
Chem. Zentr. 
Chem.-Ztg. 
Compt. rend. 



Compt. rend. acad. 

sci. U.R.S.S. 
Compt. rend. soc. 

biol. 
Color Trade J. 



Dingier s poly lech. J. 
Fettchem. Umschau 

Oazz. chim. ilal. 
Oiorn. chim. appli- 

cata 

Oiorn. chim. ind. 
Oiorn. chim. ind. 

applicata 

Helv. Chim. Acta 
Ind. Eng. Chem. 

Jahresber. Fortschr. 

Chem. 

Japan. J. Chem. 
J. Am. Chem. Soc. 

J. Am. Pharm. As- 

socn. 
J. appl, Chem. 



J. Applied Chem., 

U.S.S.R. 
J. Bact. 



Bulletin de la societe chimique de 

France. 
Bulletin de la societe chimique de 

Belgique. Now Bulletin des 

societes chimiques Beiges. 
Bulletin de la societe de chimie 

biologique. 

Canadian Chemistry and Metallurgy. 

Canadian Journal of Research. 

Chemical Abstracts (of the American 
Chemical Society). 

Die Chemische Industrie. 

Chemical and Metallurgical Engin- 
eering. 

Chemical News (and Journal of In- 
dustrial Science). 

Chemical Reviews. 

Chemische-Technische Rundschau. 

Chemical Trade Journal (and Chemi- 
cal Engineer). 

Chemische Umschau (auf dem Gebi- 
ete der Fette, Oele, Wachse, und 
Harze). Now Fettchemische Um- 
schau. 

Chernisch Weekblad. 

Chemisches Zentralblatt. 

Chemiker-Zeitung. 

Comptes rendus (hebdomadaires 
des seances de I'acad^mie des 
sciences). 

Comptes rendus de 1'Academie des 
Sciences de 1'U.R.S.S. 

Comptes rendus des seances de la 
societe* de biologia. 

Color Trade Journal and Textile 
Chemist. 

Dinglers polytechnisches Journal. 
Fettchemische Umschau. 

Gazzetta chimica italiana. 
Giornale di chimica applicata. 

Giornale di chimica industriale. 
Giornale di chimica industriale ed 
applicata. 

Helvetica Chimica Acta. 
IndustrialandEngineeringChemistry. 

Jahresbericht uber die Fortschritte 
der Chemie. 

Japanese Journal of Chemistry. 

Journal of the American Chemical 
Society. 

Journal of the American Pharma- 
ceutical Association. 

Journal of Applied Chemistry. 
Formerly Jcmrnal of the Society 
of Chemical Industry. 

Journal of Applied Chemistry 
U.8.S.R. 

Journal of Bacteriology. 



XIV 



Journal Abbreviations 



J. Biochem. Japan 
J. Biol Chem. 
J. Chem. Education 
J, Chem. Ind. Japan 

J. Chem. Physics 
J. Chem. Soc. 



J. Chem. Soc. Ab- 

stracts 
J. Chem. Soc. Japan 

J. chim. phys. 

J. Chinese Chem. 

Soc. 
J. Gen. Chem, 

U.S.S.R. 

J. gen. Microbiol. 
J. Indian Chem. Soc. 

J. Indian Inst. Sci. 

J. Inst. Petroleum 
J. Org. Chem. 
J. pharm. Belg. 
J. pharm. chim. 

J. Pharm. Soc. 

Japan 
J. Pharmacol. 

J. Pharm. Pharm- 

acol. 

J. Phys. Chem. 
J. prakt. Chem. 
J. Proc. Roy. Soc, 

N.S. Wales 

J. Russ. 

Chem. Soc. 
J. Soc. Chem. Ind. 

Now J. appl. 

Chem. 
J. Soc. Chem. Ind. 

Japan 
J. Soc. Dyers Col- 

ourists 



Journal of Biochemistry of Japan. 
Journal of Biological Chemistry. 
Journal of Chemical Education. 
Journalof Chemical Industry (Japan). 

Now J. Soc. Chem. Ind. Japan. 
Journal of Chemical Physics. 
Journal of the Chemical Society 

(London). 
Abstracts of the Chemical Society 

(London). 
Journal of the Chemical Society of 

Japan. 

Journal de chimie physique. 
Journal of the Chinese Chemical 

Society. 
Journal of General Chemistry, 

U.S.S.R. 

Journal of General Microbiology. 
Journal of the Indian Chemical 

Society. 
Journal of the Indian Institute of 

Science. 

Journal of the Institute of Petroleum. 
Journal of Organic Chemistry. 
Journal de pharmacie de Belgique. 
Journal de pharmacie et de 

chimie. 
Journal of the Pharmaceutical 

Society (Japan). 
Journal of Pharmacology and Ex- 

perimental Therapeutics. 
Journal of Pharmacy and Pharma- 

cology. 

Journal of Physical Chemistry. 
Journal fiir praktische Chemie. 
Journal and Proceedings of the 

Royal Society of New South 

Wales. 
Journal of the Russian Physical- 

Chemical Society. 
Journal of the Society of Chemical 

Industry. 

Journal of the Society of Chemical 

Industry (Japan). 
Journal of the Society of Dyers and 

Colourists. 



Mem. Coll. Sci., Memoirs of the College of Science, 

Kyoto Imp. Univ. Kyoto Imperial University. 
Monatsh. Monatshefte fur Chemie und ver- 

wandte Teile anderer Wissen- 

schaften. 



Naturwiss. 

Org. Chem. Ind. 

U.S.S.R. 

Pharm. Acta Helv. 
Pharm. J. 

Pharm. Weekblad 
Pharm. Ztg. 



Naturwissenschaften. 

Promlschlennosti Organitscheskoi 
Chimii, U.S.S.R. 

Pharmacoutica Acta Helvetiae. 
Pharmaceutical Journal and Phar- 

macist. 

Pharmaceutisch Weekblad. 
Die deutsche Pharmazeutische 

Zeitung. 



Pharm. Zentralhalle 
Phil. Mag. 

Physical Rev. 
Physiol. Rev. 
Proc. Acad. Sci., 

Amsterdam 
Proc. Chem. Soc. 

Proc. Imper. Acad. f 

Tokyo 
Proc. Ind. Acad. 

Sci. 
Proc. Indian Acad. 

Sci. 
Proc. Roy. Soc. 

Proc. Soc. Exptl. 
Biol. Med. 



Quart. J. Indian 

Chem. Soc. 
Quart. J. Pharm. 

Pharmacol. 

Rec. trav. chim. 

Rev. chim. ind. 
Rev. prod. chim. 

Sd. Papers Inst. 
Phys. Chem. Re- 
search, Tokyo 

Sci. Proc. Roy. Dub- 
lin Soc, 

Sci. reps. Nail. 
Tsinghua Univ. 

Sci. reps. Natl. 
Univ. Peking 

Sitzb. Akad. Wiss. 
Wien 

Svensk Farm. Tids. 

Svensk JKem. Tid. 

Trans. Faraday Soc. 
Trans. Roy. Soc. 

Trans. Roy. Soc. 
Canada 

Z. anal. Chem. 
Z angew. Chem. 



Z. anorg. allgem. 

Chem. 
Z. Chem. 
Z. Klektroclwrn. 

Z. ges. Naturwiss. 

Z. physik. Chem. 
Z. physiol. Chem. 



Pharmazeutische Zentralhalle 
Philosophical Magazine and Journal 

of Science. 
Physical Reviews. 
Physiological Review. 
Proceedings of the Royal Academy 

of Sciences of Amsterdam. 
Proceedings of the Chemical Society 

(London). 

Proceedings of the Imperial Acad- 
emy, Tokyo. 
Proceedings of the Indiana Academy 

of Science. 
Proceedings of the Indian Academy 

of Science. 
Proceedings of the Royal Society 

(London). 
Proceedings of the Society for 

Experimental Biology and Med- 

cme, Now York. 

Quarterly Journal of the Indian 

Chemical Society. 
Quarterly Journal of Pharmacy and 

Pharmacology. 

Recueil des travaux chimiques des 

Pays-Bas. 

Revue de chimie industrielle. 
Revue des produits chimiques. 

Scientific Papers of the Institute of 

Physical and Chemical Research 

(Tokyo). 
Scientific Proceedings of the Royal 

Dublin Society. 
Science Reports of the National 

Tsinghua University. 
Science Reports of the National 

University of Peking. 
Sitzungsberichte Akademie dor Wis- 

senschaften in Wien. 
Svensk Farmaceutiacho Tidaknft. 
Svensk Kemisk Tidskrift. 

Transactions of the Faraday Society. 
Transactions of the Royal Society 

(London). 
Transactions of the Royal Society of 

Canada. 

Zeitschrift fiir analytischo Chomic*. 
Zeitschrift fiir angewandto Cb curie. 

Later Angewandto Chemie, now 

Die Chemio. 
Zeitechrift ffir anorgamache und 

aUgemoino Chemie. 
Zeitechrift fiir Oliemie. 
Zeitschrift fiir Elektrochemie imd 

angewandte physikaKsche Chemie, 
Zeitschrift fiir die gesamto Natur- 

wissenschaft. 

Zeitschrift fiir physikalische Chonue. 
Zeitsohrift fttr phyaiologisoh Chemie 

(Hoppe-Seyler). 



LIST OF SUBSTITUENTS 

In the following table is given a list of the principal substituent groups as they 
are used in the dictionary. 



1 


F 


Fluoro 


54 


CH 2 1CH 2 ] 7 -CH 3 


Nonyl 


2 


01 


Chloro 


55 


CH 2 -[CH 2 ] 8 -CH 3 


Decyl 


3 


B r 


Bromo 


56 


CHo-[CH 2 ] 9 -CH 3 


Undecyl 


4 


I 


lodo 


57 


-CH;.[CH 2 ] 10 -CH 3 


Dodecyl 


5 


NO 


Nitroso 


58 


-CH 2 .[CH 2 ] 11 -CH 3 


Tridecyl 


6 


N0 2 


Nitro 


59 


CH 2 -[CH 2 ] 12 -CH 3 


Tetradecyl 


7 


N Nl>rN 


Azido, Triazo 


60 


-CH 2 *rCH. 2 j 13 *CH 3 


Pentadecyl 


8 


OH Hydroxy (folloived 


by OCH 3 Methoxy, 


61 


-CH 2 .[CH 2 ] 14 -CH 3 


Cetyl, Hexadecyl 




OC 2 H 5 Ethoxy, 


O-CH 2 -0 methyl- 


62 


-CH 2 -[CH 2 ] 16 -CH 3 


Heptadecyl 


enedioxy, OC 6 H 5 Phenoxy, 0'00-CH 3 , 


63 


CH 2 -[CH 2 ] 16 'CH 3 


Octadecyl 




Acetoxy. etc. in 


the order of the group 


64 


CH,-[CH 2 ] 18 -CH 3 


Eicosyl 


attached to the oxygen) 


65 


-CH 2 .[CH 2 ] ;9 -CH 3 


Heneicosyl 


9 
10 
11 
12 


SH 

SO 
S0 2 


Mercapto 
Thiony], Sulphenyl 
Sulphonyl 
Mesyl 


66 
67 

68 


CH 8 1CH 2 ] 24 -CH 3 Ceryl 
CH 2 -[CH 2 ] 28 -CH 3 Myricyl, Melissyl 
.CH a Cyclopropyl (followed by Cyclobutyl, 
CH<^ 1 Cyclopentyl, Cyclohexyl, Cyclo- 


13 


SON 


Thiocyano 




X CH 2 heptyl 


(Suberyl) in that order) 


14 
15 


=0 (m C CO C) 

>NH 


Keto 
Imino 


69 
70 


CH!CH 2 
CHICH-CHg 


Vinyl 
Propenyl 


16 




Isonitroso, Oximino 


71 


C(:CH 2 )-CH 3 


Isopropenyl 


17 


o 


Thio 


72 


CH 2 *CH,CH 2 


Ally! 


18 
19 
20 
21 
22 
23 
24 
25 


SO a H 
NH 2 
NH-C 6 H 5 
NH-C 6 H 4 -CH a 

NH-C(:NH)- 2 NH 2 
NH-OH 


Sulpho 
Amino 
Aniline, Phenylimino 
Toluidino 
Ureido 
Guanidino 
Hydroxylamino 
Hydrazino 


73 

74 
75 
76 
77 
78 
79 
80 


CH:CH-CH.j-CH 3 a-Butenyl 
CH 2 -CH:CH-CH 3 0-ButenyI, Crotyl 
CH 2 -CH2-CH:CH 2 y-Butenvl, Allylomethyl 
CH:CH-CH 2 -CH 2 -CH a a- (]8- etc.) Pentenyl 
CH:CH-[CH 2 VCH 3 a- (p- etc.) Hexenyl 
CH 2 -[CH 2 ] 7 -CH:CH-[GH 2 ] 7 -CH 3 Octadecenyl 
C-CH Ethynyl, Acetylenyl 
CH 2 -C:CH Propargyl 


26 


NH-NH 


Hydrazo 


81 


C a H 5 


Phenyl 


27 


N:N 




82 


C fl H 4 *CH 3 


Tolyl 


28 
29 


N:N] H X Diazomum, Diazo (X = OH, 01, etc.) 


83 

84 


CH 2 -CH 4 5 -OH (-0) 


Benzyl 
Salicyl 




~^ N "(T N ~) 


Azoxy 


85 
86 


CH a -C fl H 4 -OCH 3 (-p) 
CH 2 -CH 2 -C 6 H 5 


Anisyl 
Phenylethyl 


30 
31 


\ v/ / 

NH>N:N (open) 


Arseno 
Diazoamino 


87 
88 
89 


CH a -C 8 H 4 -CH 3 
CH 2 'G 10 H 7 


Xylyl 
Menaphthyl 
Cumyl 


32 
33 


NH-N:N (cyclic) 

CH 3 


Azimino 
Methyl 


90 
91 


-8;H 2 (CHS(^ 


i/r-Cumyl 
Mesityl 


34 
35 
36 


OH 2 OH Hydroxy methyl, Methylol 
O a H 8 Ethyl 
CH 2 -CH 2 -CH a n-Propyl 


92 
93 
94 


CH 2 -CH:CH-C e H B 


Styryl 
Cinnamyl 
Nanhthvl 


37 

38 
39 


-CH(CH 3 ) a 
nur nnf .r<w .^TPT 

- vJO, 2 *OO,2 vJPLg UJu,;) 
piur r*JP[.r i P[ OH. 


Isopropyl 
w-Butyl 
^ec.-Butyl 


95 
96 
97 


cJllJCeHs Biphenylyl, ^Xenyl 
CH(C e H 5 ) 2 Benzhydryl, Diphenylmethyl 
C 14 H 9 Anthryl, anthranyl 


40 
41 
42 
43 

44 

45 


CH 2 -CH(CH 3 ) 2 
C(CH S ) 3 
CH 2 -[OH 2 VCH 3 

CH 2 -GH a -OH(OH 3 ) 2 
CHX)H-CH(CH 8 ) 2 


Isobutyl 

n-Amyl 
sec.- Amyl 

Isoamyl 
sec.-Isoamyl 


98 
99 
100 
101 
102 
103 
104 


"1&' 

CH(CH 3 VCH 2 
-CH 2 -CH a -CH 2 


Phenanthryl 
Triphenylmethyl 
Ethylene, Dimethylene 
Propylene 
Tnmethylene 
Tetramethylene 
Isobutylene 




/CH, 




105 


CH 2 *[CH 2 ] 3 "CH 2 


Pentamethylene 


46 


GH 2 -C ^^ 


active Amyl 


106 
107 


CH a -[CH 2 ] 4 6 -CH 2 


Hexamethylene 
Heptamethylene 




yClia 




108 


CH 2 '[CH 2 ] e *CH 2 


Octamethylene 


47 


Cr-0H B 


tert.-Amyl 


109 


CH:CH - 


Vinylene 




x3H a 




110 


C.H, 


Phenylene 


48 
49 


~OH(CH 2 -CrL) 8 
OH 2 -[CH a ] 4 *CH 3 


Diethylmethyl 
w-Hexyl 


111 
112 




Tolylene 
Methylene 


50 


OHalCHaVCHfOH^ 


Isohexyl 


113 


=CH-CH 3 


Ethylidene 


51 


CH 2 *[OH a T F 'OH 3 


n-Heptyl, Oenanthyl 


114 


=CH-CH 2 -CH 3 


Propylidene 


52 


CH 2 f [CH )t l a *CH(CH a ) 2 


Isoheptyl 


115 


=C(CH 3 ) 2 


laopropylidene 


53 


OH 2 '[GH 2 ] 8 -CIf,, 


Octyl, Capryl 


116 


=CH-CH 2 -CH ? -CHj 


Butyhdene 






XV 









XVI 



List of Substitnents 



117 =CB>CH(CH 8 ) 2 


Isobutylidene 


146 


CO-C 8 H 4 -OCH a (-p) 


Anisoyl 


CIL CH 2V 




147 


CO'CH 2 *C 6 H 8 


Phenylacety] 


118 H 2 C/ \C= 
XJE 2 CH/ 


Cyclohexylidene 


148 
149 


~~~OO*OgJi 4 "OJtjLj 
CO'CH:CH-C 6 H 5 


Toluyl 
Cinnamoyl 


1 1Q - O'f^TT 
120 =CH*cfccH. 
121 CH 3 -CH.'CH-CH= 


Vinylidene 
Allylidene 
Crotylidene 


150 
151 
152 


CO-C 10 H 7 
CO-CO 
CO-CH 2 -CO 


Naphthoyl 
Oxalyl 
Malonyl 


122 CH*C 6 H 5 


Benzylidene 


153 


CO-CH 2 -CH 2 -CO 


Succinyl 


123 =CH-C fl H 4 -OH (-0) 


Salicylidene 


154 


CO-C^H.-CO 




124 CH*C 6 H 4 -OCH 3 (-7?) 


Anisylidene 


Phthaloyl, Isophthaloyl, Terephthaloyl 


125 =CH-C 6 H 4 *CH(CH 3 ) 2 (-p) 
126 =CH-CH;CH-C 6 H 5 
127 CH 2 -CO-CH 3 
128 CH 2 -CO-C 6 H 5 
129 CH 2 -CO-C 6 H 4 -CH S 


Cummylidene 
Cinnamylidene 
Acetonyl 
Phenacyl 
Tolacyl 

TP| ___ T 1 


155 

156 
157 
158 


__COOH ( CO-OCHg, CO'OC,H Bf etc.) 
Carboxy, (Carbomethoxy, Carbethoxy, etc.) 
CO-NH 2 Carbamyl 
>CO Carbonyl 
C(:NH)-NH 2 Guanyl 


wjrLg'L/rL'tiU'Ugiig 


JJesyl 


159 


ON 


Cyano 


131 CHO 


Aldehyde, Formvl 


160 


CO-CH 2 NH. 


Glycyl 


132 =CH 


Methynyl 


161 


CO-CH(NHj)-CH 3 


a-Alanyl 


133 CO-CHj 
134 CO-CH 2 'CH 3 


Acetyl, Aceto 
Propionyl 


162 
163 


CO-CH 2 *CH 2 NH 2 
CO'CH(NH t )-CH(OH 8 ), 


-Alanyl 
Valyl 


135 CO 'CHj'CHvCH* 


Butyryl 


164 


CO*CH(NH 2 )"CH 2 *CH(CH 3 


^ Leucyl 


136 ~-CO-CH(CH 3 ) 2 
137 CO-CH z '[CK 2 ] 2 -CH a 
138 ~CO<JH 2 'CH(CH 3 ), 
139 CO'CHjfCH 2 VCH, 
JJ? -^* C f 2 'f CH ^i3-CH 3 


Tsobutyryl 
Valeryl 
Isovaleryl 
Caproyl 
Palmityl 


165 
166 
167 
168 
169 


CO-CH 2 -NH-CO-C 6 FT 5 
C 4 H 3 
C 4 H 3 S 
CH 2 -C 4 H 3 


Hippuryl 
Furyl 
Thienyl 
Furfuryl 
Furfurylidene 


141 CO-CH a -[CH a ] 16 -CH 3 
142 CO-[OH,] 7 -OH:CH-[CHJ 7 -OH, 


Stearyl 
Oleyl 


170 
171 


CO-C 4 H 3 
C 4 H 3 ISrH 


Furoyl, Pyromucyl 
Pyrryl 


143 CO-COOH 


Oxalo 


172 


C 5 H 4 N 


Pyndyl 


144 CO-0 6 H S 


Benzoyl 


173 


C 5 H 10 N 


Piporidyl 


145 CO-C t H 4 -OH (-0) 


Salicyloyl 


174 


~NC 5 H 10 


Piperiduxo 



DICTIONARY OF ORGANIC COMPOUNDS 



Abadole. 

See 2-Aminothiazole. 
Abienol 

C 17 H 28 O MW, 248 

Viscous oil. B.p. 160/0-5 mm. [a] D +7-9 



in Et 2 0. D 20 0-9808. 



1-5326. Readily 



sol. most common org. solvents. Obtained by 
dehydration of abienol hydrate, isolated from 
turpentine of Abies pectinata. Probably an 
unsaturated tricyclic tert. alcohol, 

Wienhaus, Mucke, Ber., 1942, 75, 1830. 

J- Abietic Acid (Sylvic acid) 
HOOC CH 3 




CH(CH 3 ) 2 

MW, 302 

The name " abietic acid " has been applied 
indiscriminately to a number of "rosin" acids 
which consist of mixtures of Z-abietic acid with 
other isomeric acids. Many of the primary 
oleoresin acids are isomerised by heat or by 
treatment with mineral acids to Z-abietic 
acid. 

Isolated from American colophony (rosin). 
Plates. M.p. 170-4. [a] D - 102 in EtOH. 
Sol. MeOH, EtOH, Et 2 0, AcOH, Me 2 CO, CHC1 3 , 
C 6 H 6 . Insol. H 2 0. Forms additive compound 
with maleic anhydride. Dehydrogenation with 
selenium > retene. Absorption maximum at 
237-5 my. 

Krestinskil, Persiantseva, Novak, Chem. 

Abstracts, 1940, 34, 3277. 
Hasselstrom, McPhcrson, J. Am. Chem. 

Soc., 1939, 61, 2247. 
Buzicka, Sternbach, Helv. Chim. Acta, 

1938, 21, 565. 
Fieser, Campbell, J. Am. Chem. Soc., 

1938, 60, 159. 
Palkin, Harris, /. Am. Chem. Soc., 1934, 

56, 1935. 
Buzicka, de Graaf, Muller, Helv. Chim. 

Acta, 1932, 15, 1300. 
Buzicka, Ankersmit, Frank, Helv. Chim. 

Acta, 1932, 15, 1289. 
Levy, Z. angew. Chem., 1928, 41, 233 
(Ml). 

Diet, of Org. Convp. I, 



Baudnitz, Lederer, Kahn, Ber., 1938, 71, 

1273. 

Barton, Quarterly Reviews, 1949, III, 1. 
Simonsen, Barton, The Terpenes, Vol. Ill, 

374. (Cambridge University Press, 

1952). 

Abietinol (Abietyl alcohol) 
HOH 2 C CH 3 




C 20 H 32 MW, 288 

B.p. 169-72/0-2 mm. Dy 1-0345. < 
1-5487. Obtained by red. of an ester of abietic 
acid. 

Buzicka, Meyer, Helv. Chim. Acta, 1922, 
5, 581. 

Abrine (N-Methyltryptophane) 




NH-CH 






C 12 H U 2 N 2 MW, 218 

From seeds of Abrus precatorius. Prisms from 
BLO. Decomp. at 295. [a]ff + 444 in dil. 
TTO1 

B,HCl: needles. M.p. 221-5. 

B,HN0 3 : needles. M.p. 143 decomp. 

N-Nitroso : m.p. 121. 

N-Acetyl : cryst. from EtOH.Aq. M.p. 
286-7. 

Pier ate : red prisms from H 2 0, EtOH, or 
AcOH. Decomp. at 149 (194). 

Hoshino, Ann., 1935, 520, 31. 
Ghatak, Chem. Zentr., 1935, 1, 576. 

Acacetin (Apigenin 4:' -methyl ether, 5 : 7- 
dihydroxy-4: 1 -methoxyflavone) 

HO CO 

54 H 




C 16 H 12 S MW, 284 

Colouring matter of common acacia. Pale 
yellow needles from EtOH. M.p. 261. Sol. 

1 



Acaciabiuronic Acid 



AcenapMhene 



EtOH. Insol. Et 2 0. Sol. alkalis with pale 
yellow col. KOH fusion > phloroglucinol + 
2?-hydroxybenzoic acid. 

1-Acetyl : m.p. 203-8. 

Diacetyl : needles from EtOH. M.p. 203. 

Dibenzoyl : m.p. 201. 

Robinson, Venkataraman, J. Chem. Soc., 

1926, 128, 2344. 
Hattori, Acta Phytochim., 1925, 2, 99. 

Acaciabiuronic Acid (6-$-Glucuronisidoga~ 
lactose) 

EH OH H 

HOOC-6 9 9 () CH- 

OH H OH 

I Q 




H OH OH H 



C 12 H 20 12 



MW, 356 



Cryst. +2H 2 from aq. EtOH. M.p. 118- 
19. [a]^ +11-6 initial, 8-56 final, in H 2 0. 
Isolated from hyd. products of gum acacia. 

Heidelberger, Kendall, J. Bid. Chem., 

1929, 84, 639. 
Goebel, Reeves, J. Biol. Chem., 1938, 

124, 207. 



Acaciin 



HO 



C 12 H 21 8 - 
C 28 H 32 13 ,4H 2 




OOEL 



MW, 648 



From Eobina pseudacacia. Needles. Sinters 
250. M.p- 260 decomp. Sol. H 2 0, EtOH, 
CHC1 3 , alkalis. FeCl 3 > reddish-brown col. 
H 2 S0 4 > acacetin. 

Hepta-acetyl deriv. : m.p. 135-40. 

Hepta-benzoyl deriv. : m.p. 180-1. 

Hattori, Acta Phytochim., 1925, 2, 99, 



Aceanthrene 



H 2 C f 



Aceanthrenequinone (3 : 4:-Benzacenaph- 
thenequinone, I ; 9-oxalylanthracene) 



00, 




C 16 H 8 2 MW, 232 

Red prisms from C 6 H 6 . M.p. 270. Spar, 
sol. EtOH, AcOH. Readily sublimes. Forms 
bisulphite comp. Sol. cone. H 2 S0 4 with green 
col. CrO 3 in AcOH > anthracene-1 : 9-di- 
carboxylic acid + anthraquinone-1-carboxylic 
acid. 

Monoxime : yellow prisms from AcOH. M.p. 
251 decomp. 

Monophenylhydrazone : orange needles from 
C 6 H 6 . M.p. 203. 

Liebermann, Zsuffa, Ber., 1911, 44, 202. 

Aceconitic Acid. 

See Cyclopropane- 1 : 2 : 3-tricarboxylic Acid. 
Acenaphthanthracene. 
See JSTaphthacenaphthene. 
Acenaphthapyridine . 
See Pyridinoacenaphthene. 
Acena,phthaquinoline . 
See Pyridinoacenaphthene. 
Acenaphthazine 




C 26 H 12 N 2 MW, 352 

Deep red. M.p. 438. Spar. sol. OHOL, AcOH. 
Insol. EtOH. 

4 : orange. M.p. 286 decomp. 

Graebe, Gfeller, Ann., 1893, 276, 9. 
Schiedt, J. prakt. Chem., 1941, 157, 203. 



Acenaphthene 

H 2 C 





C 16 H 12 

Pale yellow plates from EtOH. M.p. 113. 
Picrate : dark red needles. M.p. 120. 

Liebermann, Zsuffa, Ber,, 1911, 44, 852. 
Fieser, Peters, J. Am. Chem. Soc., 1932, 
54, 4373. 



C 12 H 10 " " MW, 154 

Needles from EtOH. M.p. 96. B.p. 279. 
Sol. EtOH to 4% at 20, 40% at 70. Sol. 
MW, 204 CHCL, to 27% at 20. Sol. toluene to 24% 
at 20, 74% at 60, D" 1-024. < 1-6048. 
Heat of comb. C p 1521 Cal. K 2 Cr 2 7 > aoc- 
naphthyJene + acenaphthenequinono + naph- 
thalic anhydride. Pb0 2 >- acenaphthylono. 

Picrate : orange-red prisms from EtOH. 
M.p. 162. 



Acenaplithene~5-acryiic Acid 



AcenaplitIiene-5 : 6-disulplionic Acid 



1:3: 5-Trinitrobenzene add. comp. : yellow 
needles from EtOH. M.p. 168. 

Hahn, Holmes, 2nd. Eng. Chem., 1921, 

13, 822 (Bibl). 

Jones, J. Am. Chem. Sac., 1945, 67, 2127. 
Schonberg, Moubasher, Mostafa, J. Chem. 

Soc., 1946, 966. 

Acenaphtliene-5-acrylic Acid 




CHICH-COOH 
C 15 H 12 2 MW, 224 

Pale yellow needles from EtOH. M.p. 251-2 
decomp. 

Me ester : yellow cubes. M.p. 105. B.p. 
204 /6 mm. 

Fieser, Jones, /. Am. Chem. Soc. 9 1942, 
64, 1666. 

Acenaphthene-3-aldehyde 



HO 



C 13 H 10 MW, 182 

Pale yellow needles from Et 2 0-pet. ether. 
M.p. 99'5~10O5. 

Feiser, Hershberg, /. Am. Ghem. Soc., 
1940, 62, 49. 

Acenaphtliene-5-alde3iyde . 

Plates from EtOH.Aq. or pet. ether. M.p. 
87 (107-8). H 2 S0 4 > red sol. 

Oxime : needles from pet. ether. M.p. 126-5. 

Semicarbazone : needles from MeOH. M.p. 
234. 

Phenylhydrazone : orange needles from 
EtOH.Aq. M.p. 140. 

2 " 4;~Dinitrophenylhydrazone : scarlet needles 
from EtOH. M.p. 273. 

Anil ; orange needles from Et 2 0~pet. ether. 
M.p, 97. 

Hinkel, Ayling, Beynon, J. Chem. Soc., 
1936, 341. 

Acenaphthene-3-carboxylic Acid 




C 13 H 10 2 MW, 198 

Prisms from AcOH, M.p. 256-7. 
Chloride : tan needles. M.p. 110-11. 



Amide: needles from EtOH. M.p. 227-8. 

Fieser, Hershberg, /. Am. Chem. Soc. } 

1939, 61, 1272. 
Fieser, Cason, J. Am. Chem. Soc., 1939, 

61, 1740. 

AcenapMhene-5~carl)oxylic Acid. 

Needles from C 6 H 6 . M.p. 219. 
Amide: m.p. 198. 
Nitrile: m.p. 110-11. 

Liebermann, Zsuffa, Ber., 1911, 44, 207. 
Gattermann, Harris, Ann., 1888, 244, 58. 
Gattermann, Rossolymo, Ber., 1890, 23, 
1198. 

Acenaphtliene-3 : 8-dicarboxylic Acid 



HOOCZ V JiCOOH 



C 14 H 10 4 MW, 242 

Yellow needles from EtOH. M.p. 355 
decomp. 

Dziewonski, Spirer, Chem. Zentr., 1932, 1, 
939. 

AcenaphiJiene-5 : 6-dicarboxylic Acid. 

M.p. 293-4. Spar. sol. H 2 0, EtOH, Et 2 0, 
AcOH, CHC1 3 . Heat. > anhydride. KMn0 4 
>-naphthalene-l : 4 : 5 : 8-tetracarboxylic acid. 
H 2 S0 4 > yellow sol. with blue fluor. 

Anhydride: C 14 H 8 3 . MW, 224. M.p. 




Freund, Fleischer, Ann., 1913, 399, 223. 

Acenaphthene-3 : 8-disulphonic Acid 

Acenaphthene-fi-disulphonic acid) 



H0 3 S 



C 12 H 10 6 S 2 MW, 314 

Diamide : C 12 H 12 4 N 2 S 2 . MW, 312. Needles 
from H 2 0. M.p. 301 decomp. 

Dziewonski, Stolyhwo, Ber., 1924, 57, 
1531. 

Acenaphthene-5 : 6-disulphonic Acid 

(Acenaphthene-K-disulphonic acid). 

Di-Me ester : C 14 H 14 6 S 2 . MW,342. Needles 
from ligroin. M.p. 170-1. 

Diamide: needles from H 2 0. M.p. 282 
decomp. 

Dziewonski, Stolyhwo, Ber., 1924, 57, 
1531. 



AcenapMhenequinoue 

Acenaphtfoeaeqiiinone (Acenaphthaquinone) 
OCf iCO 




Zn 

Prisms 

cryst. 
cryst. 
decomp. Prolonged 

M.p. 223 



C 12 H 6 2 MW, 182 

Yellow needles from AcOH, M.p. 261. 
Sol. hot C 6 H 6 , hot toluene. Spar. sol. EtOH, 
AcOH. Sublimes. Gives bisulphite cpmp. 
K 2 Cr 2 7 in AcOH > naphthalic acid. 
AcOH -> acenaphthenone. 

Monoxime : exists in two forms, (i) 
from EtOH.Aq. M.p. 230. Acetyl: 
from EtOH. M.p. 247. (ii) Yellow 
from AcOH. M.p. 207 " 
heating in AcOH > (i). 

Dioxime : prisms from EtOH. 
decomp. 

Monosemicarbazone : prisms. M.p. 192-3. 

Disemicarbazone : plates from EtOH. M.p 
271. 

Monohydrazone: yellow prisms. M.p. 241. 

Monophenylhydrazone : orange needles from 
EtOH. M.p. 179. 

Di-phenylhydrazone : yellow 
AcOH. M.p.219. 

Mono-o-nitrophenylhydrazone : 
needles from AcOH. M.p. 249. 

Mono-m-nitrophenylhydrazone : yellow needles 
from AcOH. M.p. 229-30. 

Mono-p-nitrophenylhydrazone : 
needles from AcOH. M.p. 247. 

Mono--p-bromophenylhydrazone : yellow needles. 
M.p. 193. 

Mono-o-tolylhydrazone ; 
AcOH. M.p. 175. 

Mono-p-tolylhydrazone 
from AcOH. M.p. 163. 

Monoanil : yellow cryst. M.p. 189-90. 

Azine: C 12 H 6 N 2 . MW, 178. Yellow prisms. 
M.p. 164. 

Francesconi, Pirazzoli, Gazz. chim. ital., 

1903, 33, I, 42. 

Graebe, Gfeller, Ann., 1893, 276, 4. 
Buu-Hoi, Cagniant, Compt. rend., 1942, 

214, 315; Organic Syntheses, 1944, 

XXIV, 1. 
Schonberg, Moubasher, Mostafa, /. Chem. 

Soc., 1946, 966. 

Acenaphthene-3-sulphonic Acid 



4 o-[5-AcenapMhoyl]-tenzoic Acid 

Et ester: C 14 H 14 3 S. MW, 262. Needles 
from ligroin. M.p. 137-9. 

Chloride: C 12 H 9 2 C1S. MW, 252-5. M.p. 
113-14. 

Amide: C 12 H X1 2 NS. MW, 233. Needles 
from H 2 0. M.p. 196-9 (222-3). 

Dziewonski, Grunberg, Schoen, Chem. 

Zentr., 1931, I, 3684. 
Bziewonski, Galitzerowna, Kocwa, Chem. 

Zentr., 1926, II, 2816. 
Dziewonski, Stolyhwo, Ber., 1924, 1, 1531. 
Oliveri-Mandala, Atti accad. Lined, 1912, 
21, I, 779. 

AcenaphthenoL 

See Hydroxyacenaphthene. 
Acenaphthenone 



needles from 
orange-red 



orange-red 



red needles from 
orange-red cryst. 




MW 9 234 

Aniline salt : m.p. 284-6, 
Me ester : C 13 H 12 3 S. MW, 248. Needles. 
M.p. 122-3. 




C 12 H 8 MW, 168 

Colourless needles or plates. M.p. 121. Sol. 
EtOH, CHC1 3 , C 6 H 6 . Spar. sol. ligroin. Vola- 
tile in steam. Zn + HC1 > acenaphthylene. 
Hot aq. NaOH > naphthalic acid. 
Oxime : plates from EtOH. M.p. 175. 
Phenylhydrazone : cryst. from EtOH. M.p. 
90. 
Picrate : yellow needles. M.p, 113. 

Graebe, Jequier, Ann., 1896, 290, 198. 
Marquis, Compt. rend., 1926, 182, 1227. 
Buu-Hoi, Cagniant , Compt. rend., 1942, 
214, 315. 

13-Acenaphtho- (1 ,8-afo )-phenantlireae 
Ho 




C 23 H M " MW, 290 

Greenish yellow prisms, m.p. 266-7 oorr. 
Dipicrate : orange noodles. M.j>. 201 corr. 

Fieser, Hershborg, /. Am. Chem. Hoc,, 
1935,57, 1681. 

o- [5-Acenaph.tlioyl ]-benzoic Acid (5- [o - 
Carboxybenzoyl \ -acenaphthene) 




C 20 H 14 3 



"9 

COOH 



MW, 302 



Acenaphtliylene 



Acetaldeliyde 



M.p. 200. Sol. EtOH, Et 2 0, CHC1 3 . Spar, 
sol. C 6 H 6 . Insol. ligroin, CS 2 . 

Me ester : C 21 H 16 3 . MW, 316. M.p. 128. 
Picrate : m.p. 135. 

m ester : C 22 H 18 3 . MW, 330. M.p. 111. 
Picrate : m.p. 126. 

Graebe, Perutz, Ann., 1903, 327, 99. 

Acenaphthylene 

HC=CH 




C 12 H 8 ~ v MW, 152 

Yellow plates from EtOH. M.p. 92-3. 
E.p. 265-75 decomp. Sol. EtOH, Et 2 0, pet. 
ether. NaHg >- acenaphthene. Ox. >- 
naphthalic acid. Polymerised by strong acids. 

Picrate : yellow needles. M.p. 201-2. 

1:3: 5-Trinitrobenzene add. comp. : yellow 
needles. M.p. 221. 

1 : 2-Dibromide : I : 2-dibromoacenaphthene. 
M.p. 121-3. 

Dziewonski, Rapalski, Ber., 1912, 45. 
2491. 

Flowers, U.S.P., 2,390,363. (Chem. 

Abstracts, 1946, 40, 1543). 
Jones, /. Soc. Chem. Ind., 1949, 68, 225; 

J. appl Chem., 1951, 568. 
Kynaston, Jones, J. Soc. Chem. 2nd., 

1949, 68, 228. 
Kaufman, Williams, J. appl. Chem,, 1951, 

489. 

Aceuaphthylene Glycol. 

$ae 1 : 2-Dihydroxyacenaphthene. 
Aceritol. 

/Stefl 1 : 5-Anhydro-D-sorbitol. 
AcesaL 

flee under Diplosal. 

Acetal (Acctaldehyde diethyl acetal, ethylidene 
diethyl ether, 1 : I~diethoxyethane) 



C 6 H M 2 MW, 118 

B.p. 103-2/761 mm., 50-1/120 mm., 21/22 
mm. Sol. 18 vols. H 2 at 25. Misc. EtOH. 
DJ 0-8314. < 1-38193. Heat of comb. C^ 
930 Cal. Stable to alkalis. Acids > acetalde- 
hyde + C 2 H 6 OH. Ox. > acetic acid. Eeadily 
polymerises. 

Adkins, Nissen, Organic Syntheses, Col- 

lective Vol. I, 1. 
Patter, Monatsh., 1931, 58, 1. 
Voricat, Chem. Zentr,, 1,944, 1, 58. 



Acetajdehyde (Ethanal) 



Colourless fuming liq. M.p. 121. B.p. 21. 
Misc. H 2 0, EtOH, Et 2 aU proportions. D$ 
0-79509, DJJ 0-78761. n 1-3316. Heat of 
comb. Gp 281-9 Cal. Burns with luminous 
flame. Gives bisulphite comp. Gives Na deriv. 
Eeduces NH 3 .AgN0 3 . NaHg > ethyl alco- 



(i) 
mm. 



M.p. 
M.p. 



CH 3 -CHO 



MW, 44 



hoi. PC1 5 > CH 3 -CHC1 2 . Readily polymer- 
ises. 

Oxime : acetaldoxime. Needles. M.p. 47. 
B.p. 115. Sol. H 2 0, EtOH, Et 2 0. DJ 0-9656. 
< 4 142567. Me ether: Hq. B.p. 47-5. Sol. 
H 2 0, EtOH, Et 2 0. Et ether : liq. B.p. 71-1-5. 
Sol. EtOH, Et 2 0, Spar. sol. H 2 0. 

Semicarbazone : needles from H 2 or EtOH. 
M.p. 163. 

Thiosemicarbazone : cryst. M.p. 146. 

4-Phenylsemicarbazone : m.p. 151-2. 

o-Tolylsemicarbazone : m.p. 143-5. 

ip-Tolylsemicarbazone : m.p. 174-5. 

Phenylhydrazone : exists in two forms. 
Needles. M.p. 98-101. B.p. 236-7/21 
(ii) Needles. M.p. 57. B.p. 133-6/21 mm. 

p-Chlorophenylhydrazone : m.p. 98-9. 

p-Bromophenylhydrazone : yellow needles from 
ligroin. M.p. 87. 

p-Iodophenylhydrazone : m.p. 224. 

o-Nitrophenylhydrazone : m.p. 124 

w.'Nitrophenylhydrazone : yellow prisms. 
142. 

p-Nitrophenylhydrazone : yellow needles. 
128-5. 

2 : 4:-Dinitrophenylhydrazone : exists in two 
forms, (i) Yellow plates from EtOH. M.p. 
163-5-4-5. (ii) Orange cryst. M.p. 146. 

Diphenylhydrazone : plates or prisms from 
pet. ether. M.p. 60-1. B.p. 177-9/ll 
mm. 

$-Naphthylhydrazone : prisms from EtOH. 
M.p. 128-9. 

$-Naphthoylhydrazone : m.p. 109-10. 

Di-Me acetal: C 4 H 10 2 . MW, 90. B.p. 
64-5. Df 0-85015. < 1-3668. 

Di-Et acetal : see Acetal. 

Dipropyl acetal : C 8 H 18 2 . MW, 146. B.p. 
146-8-5. Df 0-8256. 4 1-3971. 

Di-isopropyl acetal : b.p. 82-4. Df 0-7855. 

< 1-3790. 

Dibutyl acetal : C 10 H 22 2 . MW, 174. B.p. 
197-8. D? 0-8312. < 1407L 
Di-isobutyl acetal : b.p. 168-9 

< 14021. 

Diamyl acetal : C 12 H 26 2 . 
114-16/16 mm. Df 0-8282. 

Di-isoamyl acetal : b.p. 211, 
14139. 

Cyanhydrin : see under Lactic Acid. 

Dimedone deriv. : cryst. from EtOH. M.p. 
141-2. 

Azine : acetaldazine. B.p. 95-6. Sol. H 2 0. 
B 17 0-832. 

Ammonia comp. : see 1-Aminoethyl Alcohol. 

Anil : see Ethylideneaniline. 



D5 4 0-8123. 
B.p. 



MW, 202. 
< 14169. 

Df 0-8278. 



Acetaldol 

AeetaldoL 

See Aldol. 

Acetamlde 

CH 3 -CONH 2 
C 2 H 5 ON MW, 59 

Hexagonal cryst. Odourless when pure. 
M.p. 82-3. B.p. 222. Df 1-159. Sol. H 2 
to 97% at 20. Sol. EtOH to 31 % at 20, 72% 
at 60. Sol. CHC1 3 , glycerol. Prac. insol. Et 2 0. 
Reacts neutral. < 14274. Jc (base) = 3-1 X 
1C- 15 at 25, 4-1 X 1C- 13 at 60. Heat of comb. 
288-0 Gal. Triboluminescent. Combines with 
metals and metallic salts. Combines with min. 
acids. P 2 5 > acetonitrile. Hyd. by acids 
or alkalis to acetic acid. 

B^HBr : needles. M.p. 138-9. 

B 9 HNO Z : m.p. 98. 

Picrate : m.p. 117. 

Eg salt : m.p. 196-7. 

N-Xanthydryl : m.p. 238-40. 

"E-Diphenyl : see under Diphenylamine. 

~N-Acetyl : see Diacetamide. 

N-Allyl : b.p. 215, 118/17 mm. Misc. all 
proportions H 2 0, EtOH, Et 2 0. D 15 0-9608. 

Coleman, Alvarado, Organic Syntheses, 
Collective Vol. I, 3. 

Acetamidine 



6 



NH 
C 2 H 6 lSr 2 MW, 58 

Unstable. Aq. sol. decomp. on warming >- 
acetic acid + NH 3 - Beacts strongly alkaline. 

B,HCl : prisms from EtOH. M.p. 166-7. 

B,HN0 3 : needles. M.p. 189. 

NN' '-Dimefhyl : plates from EtOH. M.p. 
218. 

ip-Toluenesulphonyl deriv. : m,p. 193. 

Picrate : m.p. 245. 

Dox, Organic Syntheses, Collective Vol. 

1,5. 
Barber, Self, B.P., 551,445, (Chem. 

Abstracts, 1944, 38, 1239). 

Acetanilide (Acetylaniline, N-phenylacetam- 
ide, Antifebrin) 

C 6 H S NH-CO-CH 3 

C 8 H 9 ON MW, 135 

Plates from H 2 0. M.p. 113-4. B.p. 304. 
Sol. 189 parts H 2 at 6, 5-55% at 100. Sol. 
MeOH to 41% at 20, 107% at 50. Sol. EtOH 
to 27% at 20, 87% at 60. Sol. CHC1 3 to 12% 
at 20, 31% at 50. Sol. Et 2 0. k (base) = 
4-1 x 10- u at 40. Dl 1-21. Heat of comb. 
1016-1 Call Forms N-Na deriv. Febrifuge and 
antipyretic. 

Acetanisidide. 

See under Anisidine. 
Acetarsone. 

See under 2-Ammoph,enol-4-arsonic Acid. 



Acetic Acid 

Acet-vy-cumidide . 
See under ^-Cumidine. 

Acetengenol (Acetyleugenol, eugenol acetate, 
l-altyl-3-methoxy'4:-acetoxybenzene) 




MW, 206 

Constituent of oil of cloves. Plates from 
EtOH. M.p. 30-1. B.p. 281-2/752 mm., 
163-4/13 mm., 146/8 mm. Sol. EtOH, Et 2 0. 
Insol. H 2 0, Dg 1-087. < 1-52069. Heat of 
comb. Gp 1498-5 Cal. 

Freyss, Chem. Zentr., 1899, I, 835. 

Erdmann, J. praTct. Chem., 1897, 56, 146. 

Acethy drazide . 

See under Acetic Acid. 

Acethydroxamic Acid (S-Acetylhydroxyl- 
amine, acethydroximic acid) 



or 

CHg-CO-KEOH 

C 2 H 5 2 N MW, 75 

M.p. anhyd. 87-8. Sol. H 2 0, EtOH. 
Insol. Et 2 0. k = 2-8 X 10- 8 at 25. Eeduces 
NHo.AgN0 3 . FeCl 3 ^ cherry-red col 

/t ether: C 4 H 9 2 N. MW, 103. Needles, 
M.p. 25-6. B.p. 59-60/13 mm. Sol. H 2 0. 

Acetyl deriv. : diacethydroxamic acid. 
Needles. M.p. 89. Sol. H 2 0. 

Benzoyl deriv. : cryst. from Et 2 0, M.p. 
69-70. 

Jones, Oesper, Am. Chem. J., 1909, 42, 
518. 



Acetic Acid 



CBL-COOH 



MW, 60 



"M.p. 16-7. B.p. 118-2, 109/560 mm,, 96/ 
360 mm., 73/160 mm., 48/60 mm., 30/31 mm. 
Misc all proportions with H 2 0, EtOH, Et 2 0, and 
sol. most org. solvents. Insol. CS 2 . BJ 1 -04922. 
ng> 1-36976. i 1-845x10* at 25, Sp. 
heat of Hq. at 17 0480. Latent Ixcat of 
vaporisation 85 Cal. per kilogramme at 118. 
Heat of comb, (liq.) 2094 Cal. Grit. temp. 
321*5. Molecular f.p. depression 39, molecular 
b.p. elevation 29-9. Dist. of Ca salt~>- 
acetone. Excellent solvent for organic com- 
pounds. Also dissolves sulphur, phosphorus , 
and halogen, acids. 

Anhydride : see Acetic Anhydride. 

Nitrile : see Acetonitrile. 

Anilide : see Acetanilide. 

Hudrazide : acethydraztide, acetylhydrassme, 
Needles from EtOH. M.p. 67, B.p. 129/18 



Acetic Anhydride 



Acetoacetic Acid 



mm. Sol. H 2 0, EtOH. Spar. sol. Et 2 0. Re- 
duces NH 3 .AgN0 3 . 

Acetic Anhydride 



MW, 102 

M.p. 73. B.p. 139-55, 81/105 mm., 68/ 
53 mm., 44/15 mm. Sol. to 2-7% in ELO at 
15. Sol. Et 2 0, C 6 H 6 , PhN0 2 . D 1-0850. 
4 1-39006. Sp. heat 0434. Latent heat of 
va,p. 66-1 Cal. per kilogramme at 137. Heat of 
comb. C p 460-07 Cal. Aq. sol. reacts neutral 
and is only very slowly hyd. to acetic acid. 
Heat of hydration to acetic acid 13-1 Cal. per 
gm.-mol. 

Orshansky, Bograchov, Chemistry and 
Industry, 1944, 382. 

Acetiminoether (Acetimidic acid ethyl ester) 



C 4 H 9 ON MW, 87 

B.p. 92-5. Unstable. DJ 9 0-8729. < 9 

140348. 
B,HCl : felted plates. Decomp. at 98-100. 

Hyd. by H 2 to ethyl acetate + NH 4 C1. Ale. 

KH 3 > acetamidine. 

Hill, Rabinowitz, J. Am. Chem. Soc., 

1926, 48, 734. 
McElvain, Nelson, J. Am. Chem. Soc., 

1942, 64, 1825. 
Acetin. 

See Monoacetin, Diacetin, and Triacetin. 
Acetiodoamide . 
See JV-Iodoacetamide. 
Acetnaplxthalide . 
See under Naphthylamine. 
Acetoacetaldehyde (Acetoacetic aldehyde, 
formylaceione, butanalone) 

C%CO-CH 2 -CHO 

or 

CH 3 -CO-CH:CH-OH 
C 4 H 6 2 MW, 86 

Very unstable. Isolated as Na deriv., sol. 
H 2 0. Cu(C4H 5 2 ) 2 , light blue needles, sol. 
H 2 0, Et a O, hot C H 6 . Spar. sol. ligroin. 

Benzoyl deriv. : cryst. from C 6 H 6 -ligroin. 
M.p, 92-3. 

Pock, U.S.P., 2,262,817, (Chem. Abstracts, 

1942, 36, 1331). 
Claisen, Stylos, Ber., 1888, 21, 1144. 

Acetoacetanilide (Acetoacetic anilide, aceto- 
acetylaniline) 



OioHiAN MW, 177 

Plates from ligroin. M.p, 86. Sol. EtOH, 

EtfcO, OHOlg, ligroin, hot CglL. Sol. acids and 

alkalis. Spar. sol. H 2 0. 3reCl0 > Tiolet col. 

Beduces NH 3 ,AgNO a , Diet. - > diphenylurea. 



Oxime : CH 3 -C(:N-OH)-CH 2 -CO-NH-C 6 H 5 . 
Needles from EtOH. M.p. 1 25. 

Phenylhydrazone : plates from EtOH. M.p. 
128 

Pfeiffer, J. prakt. Chem., 1925, 111, 240; 

1926,114,56. 
Eierz-Bavid, Ziegler, Helv. Chim. Acta 9 

1928, 11, 779. 

Williams, Krynitsky, Organic Syntheses, 
1941, XXI, 4. 

Acetoacetic Acid (2-Ketobutyric acid, acetone- 
carboxylic acid, 2-hydroxycrotonic acid) 

CH 3 -CO-CH 2 -COOH 



CH 3 -C(OH):CH-COOH 

C 4 H 6 3 MW, 102 

Syrup. Misc. H 2 all proportions. Un- 
stable. Heat ^ acetone + C0 2 . FeCl 3 > 
reddish- violet col. HN0 2 > isonitrosoacetone 



o-Chlorophenylhydrazone : cryst. from 
AcOH-H 2 0. M.p. 74-7. 

Me ester: C 6 H 8 3 . MW, 116. Liq. B.p. 
169-70, 73-4 /12 mm. Misc. H 2 0. D]? 1-0809, 
Dg 1-0724. ^ D 141964. FeCl 3 > deep red 
col. Boil. H 2 > acetone + CH 3 -OH + C0 2 . 
Semicarbazone ; cryst. from MeOH. M.p. 
151-2. 

Et ester : see Ethyl acetoacetate. 

Isopropyl ester: C 7 H 12 3 . MW, 144. B.p. 
185-7, 75-6/15 mm. Cu " 
from abs. EtOH. M.p. 174 

Isobutyl ester : C 8 H 14 3 . 
202-6. D 0-979, D^ 8 0-932. 



salt : green cryst. 
Sol. CHC1 3 . 
MW, 158. 



C9H 16 3 . 



172. 



MW, 142. 
n 14380. 



B.p. 
B.p. 
B.p. 



MW, 192. Oil. 

Vu salt : green cryst. 



Isoamyl ester : 
223. DJ? 0-954. 

Allyl ester : C 7 H 10 3 . 
66-5/14mm. Dg 1-0366. 

Benzyl ester : C U H 12 
B.p. 270, 162-4/16 mm. 
from CeH 6 . M.p. 156. 

Nitrtie : cyanoacetone. C 4 H 5 ON. MW, 83. 
Liq. Readily polymerises > yellow glassy 
mass, decomp. above 230. Phenylhydrazone : 
needles from EtOH. M.p. 101-2. o-Tolyl- 
hydrazone : needles from EtOH. M.p. 115. 
p-Totylhydrazone : yellow plates. M.p. 123. 

Amide : acetoacetamide. C 4 H 7 2 N. MW, 
101. Cryst. from Me 2 CO-pet. ether. M.p. 54. 
Sol. H 2 0, EtOH, AcOH. Insol. Bt a O. Forms 
green cryst. Cu salt. Phenylhydrazone : m.p. 
128. 

Anilide : see Acetoacetanilide. 

O'Chloroanilide : m.p. 105 

2 : 5-Dichloroanilide : m.p. 

^-Nitroanilide : m.p. 119 6 

o-Toluidide : m.p. 104. 

-p-Toluidide : m.p. 95. 

m-Xylidide : m.p. 89. 

o-Anisi&ide : m.p. 87. 



96 



Acetoacetic Ester 



8 



Aceto&romoglucose 



Acetoacetic Ester. 
See Ethyl acetoacetate. 
Acetoacetylene . 
See l-Butyne-3-one. 
2-AcetoacetyIpyridine 



(K-Aceioacetylpyrid- 



me] 



JJCO"CH 2 -CO-CH 3 

C 9 H 9 2 N MW, 163 

Needles or prisms from pet. ether. M.p. 50. 
B.p. 137-43/15 mm. Sol. EtOH, Et 2 5 CHC1 5 , 
C 6 H 6> hot ligroin. Insol. H 2 0. FeCl 3 in EtOH 
so l. _^. deep red col. Cone. KOH at 100 > 
picolinic acid + acetone. 

Monoxime : cryst. from C 6 H 6 -ligroin. M.p. 
78. 

Dioxime : red prisms from H 2 0. M.p. 146-7. 
Micko, Monatsh., 1896, 17, 442. 

3-Acetoacetylpyridine ( (3 -Acetoacetylpyrid- 
ine). 

Needles from ligroin. M.p. 85. B.p. 171 / 
15 mm. Sol. EtOH, Et 2 0, Me 2 CO, C 6 H. 



Spar. sol. H 2 0. FeCl 3 



deep red col. KOH 



. nicotinic acid + acetone. 

B,HCl: needles from EtOH-Et 2 0. M.p. 
92 

B,HgCl 2 : needles from EtOH. M.p. 107-10. 

,HCl.HgCl 2 : cryst. from dil. HCL M.p, 
123-5 decomp. 

B 2) H 2 PtOl B : reddish-yellow cryst. from dil. 
HC3. M.p. 173-5 decomp. 

Dioxime : cryst. from EtOH. M.p. 79. 
Sol. H 2 0. 

Picrate : m.p. 155. 

Ferenczy, Monatsh., 1897, 18, 673. 

4-Acetoacetylpyridine (y-Acetoacetylpyrid- 
ine). 

Needles from ligroin. M.p. 62. B.p. 145- 
7/18 mm. Sol. EtOH, Et 2 0, C 6 H 6 . Spar, 
sol. H 2 0. Sol. HC1 with greenish-yellow coL 

B^HJPtCl* : reddish-brown plates. Decomp. 
at 228. 

Monoxime : cryst. from EtOH. M.p. 165. 

Monoanil : yellow plates from ligroin. M.p. 
103-4. 

Tscherne, Monatsh., 1901, 22, 616. 

4-Acetoacetylquinoline (y-Acetoacetylguino- 
line) 

CO-CH 2 -CO-CH 3 




C 13 H U 2 N MW, 213 

Needles from ligroin. M.p. 64-5. B.p. 205- 
7/17 mm. Sol. EtOH, Et 2 0, C H 6 . Spar, 
sol. cold ligroin. 



B.HCl : yellow needles from dil. HCL M.p. 

180-1. 

B 2 ,H 2 PtClfi : orange-yellow needles from HCL 
M.p. 192-3 decomp. 

S t (OOOH) 2 : needles from EtOH. M.p. 
166-7. 

Monoxime : m.p. 171. 

Methiodide : (+1H 2 O), reddish-yellow needles. 
M.p. 189-91 decomp. 

Monoanil : yellow needles from C 6 H 6 . M.p. 
129-5. 

Weidel, Monatsh., 1896, 17, 402. 

2-Acetoacrylic Acid 

CH 3 -CO-CH:CH-COOH 
C 5 H 6 3 MW, 114 

Needles or plates from CHC1 3 or C 6 H 6 . M.p. 
125. Sol. 15 parts cold H 2 0. Sol. EtOH, 
Bt 2 0, hot H 3 0, hot CHC1 3 . Insol. CS 2 , ligroin. 
Sublimes. Bed. > levulinic acid. Br > 
1 : 2-dibromolevulinic acid. 

Oxime : exists in two forms, (i) M.p. 206 
decomp. Acetyl deriv. : m.p. 155. (ii) M.p. 
189 decomp. Boil. H 2 > (i). Acetyl de- 
riv. : m.p. 143. 

Phenylkydrazone : yellow needles from. H 2 0. 
M.p. 169 (158). 

Me ester: C 6 H 8 3 . MW, 128. Plates. M.p. 
60-5. B.p. 197, 85/14 mm. DJ 8 1-046. n% 
1-43392. Oxime: needles from pet. ether. 
M.p. 100. Semicarbazone : m.p. 196. PJwnyl- 
hydrazone : yellow cryst. from toluene. M.p. 
156. p-Nitrophenylhydrazone : needles. M.p. 
227-8. 

Et ester : C 7 Hn0 3 , MW, 142. B.p. 206-7. 
D 1-057. Phenylhydrazone : yellow platen from 
EtOH. M.p. 117-5, tiemicarhazone : m.p. 
205-7. 

Konigs, Wagstaffe, Ber., 1893, 26, 555. 
Binkes, van Hasselt, G/iem. Zentr., 1917, 
I, 208. 

4-Aceto-n-amyl Alcohol. 

See 3-Methyl-6-hexanolone-2. 
Acetoanisole. 

See under Hydroxyacetophenorio. 
co-Acetoanisole . 
See Phenoxyacetone, 
Acetobenzoic Acid. 
See Acetophenone-carboxylic Acid. 
Acetobroraoamide . 
See ^-Bromoacetamide. 
Acetobromoglucose (l-^omo-2 : 3 : 4 ; 6- 
tetra- acetylglucose) 




MW, 



2-Acetobutane 



Acetochloroanilide 



d-. 

a-Form : prisms from ligroin. M.p. 79-80. 

$-Form: needles from Et 2 0. M.p. 88-9. 
Spar. sol. H 2 0. [o& 9 + 198 in CHC1 3 . Hyd. 
by H 2 0. Reduces hot Fehling's. 

Needles from Et 2 0. M.p. 88. [a]J> 7 * 5 192-7 
in Et 2 0. 

(B-. 

Needles from Et 2 0. M.p. 85. 

Karrer, Nageli, Smirnoff, Helv. Chim. 

Acta, 1922, 5, 141. 

Fischer, Armstrong, Ber., 1901, 34, 2885. 
Fischer, Ber., 1911, 44, 1898. 
Redemann, Niemann, Organic Syntheses, 

1942, XXII, 1. 
McCloskey, Pyle, Coleman, J. Am. Chem. 

Soc., 1944, 66, 349-50. 
Nichols, Smith, Nature, 1948, 161, 349. 

2-Acetobutane . 

See Methyl sec.-butyl Ketone. 
Acetobutyl Alcohol (Methyl 4:-hydroxybutyl 
ketone, l-hexanolone-5) 

CE 3 'CO'[CH 2 ] 3 -CH 2 OH 

C 6 H 12 2 " MW, 116 

B.p. 227, 1717177 mm., 1577100 mm., 

112715 mm. Sol. H 2 0, EtOH, Et 2 0. DJ 5 5 

0-9895. n a 1*44937. Spar, volatile in steam. 
Acetyl: b.p. 114-16712 mm. Df s 1-002. 

< >e 1-4336. 

Lipp, Awn., 1896, 289, 182. 

Aceto-sec.-n-butyl Alcohol. 

See 2-Ho3canolone-5 and 3-Hexanolone-5. 
4- Acetobutyl bromide. 
See Methyl 4-bromobutyl Ketone. 
Acetobutylene . 

See Hoxonono and Mcthylpentenone. 
1-Acetobutyric Acid (l-E/thylacetoaceticacid) 



C 6 H 10 3 

Me ester: 
D M 0-995. 
JSt ester : 



MW, 130 
C 7 H 12 3 . MW, 144. B.p. 190. 



C 8 H M 0- 
96716 mm., 83712 



MW, 158. B.p. 198, 
mm. Df 0-9754. < 

142256. Sol. EtOH, Et 2 0. Mod. sol. H 2 0. 
Gives Na deriv. Semicarbazone : cryst. M.p. 

154 decomp. 

C 10 H 18 3 . MW, 186. 



B.p. 



MW, 200. B.p. 



Isobutyl ester : 

211-5. 

Isoamyl ester : ( 
233-6, D?? 0-937. 

Amide : 6 H n 2 N. MW, 129 Needles from 
BLO. M.p. 95-6. Sublimes. Sol. H 2 0, 
McOH, EtOH. Mod. sol pet. ether. 

Nitrile: 6 H 9 ON. MW, 111. B.p. 80713 
ram. I) 19 0*9555. Sol. dil. alkalis. Semi- 
carbazone : needles from MeOH. M.p. 160. 



C 6 H 10 3 



PhenyThydmzone : prisms from EtOH. M.p. 
73-4. 

Eobinson, J. Chem. Soc., 1916, 109, 1044. 

Michael, J. pralct. Chem., 1905, 72, 553. 

2-Acetobutyric Acid (2-Mettyl-Uvulinic 
acid) 

CH 3 -CO-CH(CH 3 )*CH 2 'COOH 

MW, 130 

M.p. 31-5. B.p. 241-2, 140-1 714 mm. Sol. 
H 2 0, EtOH. Di 7 1-0932. < 1-4443. Very 
hygroscopic. Oxidises in air. 

Me ester: C 7 H 12 3 . MW, 144. B.p. 200, 
82-3710 mm. Df 1-022. wg 1-4052. Phenyl- 
hydrazone : m.p. 88. p-Nitrophenylhydrazone : 
m.p. 147. 

Et ester: C 8 H 14 3 . MW, 158. Oil. B.p. 
206, 110730 mm. DJ 0-987. 

Semicarbazone : needles. M.p. 197 decomp. 
(179). Spar. sol. H 2 0. 

Phenylhydrazone : m.p. 125. 

p-Nitrophenylhydrazone : m.p. 168-9. 

Pauly, Gnmour, WiU, Ann., 1914, 403, 

149. 
Blaise, Bull soc. chim. } 1900, 23, 920. 

3-Acetobutyric Acid (4c-Ketocaproic acid) 

CH 3 -CO-CH 2 -CH 2 -CH 2 -COOH 
C 6 H 10 3 MW, 130 

M.p. 13-4. B.p. 275 slight decomp,, 196- 
200765 mm., 180720 mm. Sol. H 2 0, EtOH, 
Et 2 0. Cryst. in prisms from. H 2 0, with 1H 2 0, 
m.p. 38. k = 2-2 x 10~ 5 at 25. Hot dil. 
HN0 3 > succinic acid. NaOEt ^ dihydro- 
resorcino]. Small amount H 2 > hydrate, 
m.p. 34-6. 

Et ester: C 8 H 14 3 . MW, 158. B.p. 222, 
110-5712 mm. 

Amide : C 6 H n 2 N. MW, 129. Cryst. from 
CHC1 3 . M.p. 114. Sol. H 2 0, EtOH. Mod. 
sol. Et 2 0. 

Oxime : prisms from C 6 H 6 . M.p. 104-5. 

Semicarbazone : plates from H 2 0, with 1H 2 0. 
M.p. 175 decomp. 

p-Toluidide : leaflets from H 2 0. M.p. 123. 
Bentley, Parkin, J. Chem. Soc., 1896, 69, 

1511 

Hopff, Rapp, U.S.P., 2,265,165, (Chem. 
Abstracts, 1942, 36, 1615). 

5-Acetocaproic Acid. 

See 6-Keto-ri-caprylic Acid. 
7-Acetocaprylic Acid. 
See 8-Ketocapric Acid. 
Acetocatechol. 

See 2 : 3-Dihydroxyacetophenone and 3 : 4- 
Dihy dr oxy acetophenone . 
Acetochloroamide . 
See JV-Chloroacetamide. 
Acetochloroanilide . 
See j^-Chloroacetamlid. 



Acetocinnamone 



10 



Acetocymene 



Acetocinnamone . 

See Benzylideneacetone. 
3-Acetocoumarin 

CH 




C n H 8 3 MW, 188 

Needles from EtOH. M.p. 124. SoLEtOH, 
AcOH, CHC1 3 , hot C 6 H 6 , hot ligroin. Insol. cold 
H 2 0. 

Oxime: cryst. from EtOH. M.p. 206. 

Phenylhydrazone : orange-yellow needles from 
EtOH. M.p. 186. 

Semicarbazone : needles from EtOH. M.p. 
231. 

Picrate : yellow needles. M.p. 75. 
Knoerenagel, Ber., 1898, 31, 732. 



2-Acetocoumarone 



A fi 

Vy c ' C(>l 



CH, 



C 10 H 8 2 MW, 160 

Plates from EtOH.Aq. M.p. 75-6. Sol. 
most org. solvents. Mod. sol. H 2 0. Volatile in 
steam. 

Oxime : m.p. 150. 

Stormer, Ber., 1897, 30, 1711. 

Acetocresol. 

See Hydroxy-methylacetophenone. 

Acetocumene . 

See Isopropylacetophenone. 

5-Aceto-y-cuxnene . 

See 2:4: 5-Trimethylacetophenone. 

Acetocyclobutane (Methyl cydobutyl ketone) 



C 6 H 10 MW, 98 

B.p. 137-9. Spar. sol. H 2 0. Df 0-9020. 
n lQ3 14322. Forms bisulphite comp. 

Oxime : prisms from IL>0. M.p. 61. B.p. 
194-5. 

Semicarbazone : m.p. 148-9 corr. 

Zelinsky, Gutt, Ber., 1908, 41, 2432. 
Kishner, Ghem. Zentr., 1913, II, 2132. 

Acetocyclohexane (Hexahydroacetophenone, 
methyl cyclohexyl ketone) 



C 8 H 14 " " MW, 126 

B.p. 180-1, 72/25 mm., 68712 mm. Di 8 

0-9254. w# 145652. Alk. KMn0 4 5^ adipic 

acid. Forms bisulphite comp. 

Oxime : plates from Et 2 0. M.p. 60. B.p. 

145-50720 mm. 



Semicarbazone : cryst. from MeOH. M.p. 177. 
p-Nitrophenylhydrazone : reddish-violet cryst. 
from EtOH. M.p. 154. 

JSTenitzescu, Cioranescu, Ber., 1936, 69, 

1821. 

Hell, Schaal, Ber., 1907, 40, 4163. 
Darzens, Eost, Compt. rend., 1911, 153, 

773. 

Walker, Hauser, J. Am. Chem. Soc., 1946, 
68, 1386. 

1-Acetocycloliexene (Tetrahydroacetophen- 
one) 



C 8 H 12 MW, 124 

B.p. 201-2. Df 0-9655. < 14881. 
Oxime : cryst. from C 6 H 6 -ligroin. M.p. 99. 
Semicarbazone : m.p. 221 decomp. 

Euzicka, Koolhaas, Wind, Helv. Chim. 
Acta, 1931, 14, 1157. 

Acetocyclopeaatane (Acetylpentamethylene, 
methyl cyclopentyl Jcetone) 



C 7 H 12 MW, 112 

B.p. 158-9-5, 75-6.5720 mm. D$ 0-9269, 
D?S 0-918. <1444. 

Semicarbazone : cryst. from Me 2 CO. M.p. 
145. 

Goldsworthy, J. Chem. Soc., 1934, 378. 
Nenitzescu, Cantuniari, Ber., 1932, 65, 

810. 

KTenitzescu, Cioranescu, jBer,, 1936, 69, 
1820. 

Acetocyclopropane (Aeetyltrimethylene, 
methyl cyclopropyl ketone) 



C 5 H 8 MW, 84 

Oil with camphoraceous odour. B.p, 114. 
DJ 0-89839. < 142514. Sol H0. Poly- 
merises readily. KMn0 4 > cyolopropano- 
carboxylic acid. 

Oxime : prisms from C BT0. M.p, 50-1. 

Semicarbazone : plates from MoOH. M.p. 
118-20 (110-12). 

Hydrazone : b.p. 173-57752 mm., 63-575-6 
mm. 

Methylhydrazone : b.p. 85~7/25 mm. DJ 
0-9692. < 1-5124. 

Marshall, Parkin, /. Chem. Soc, y 1801, 59, 

860. 
Idzkowska, Wagner, Chem. Zentr. t 1898* 

II, 474. 

Acetocymene . 

See Methylisopropylaoetophonone. 



2-Acetodiplienyl 



11 



2-Acetoliydiindene 



2-Acetodiplienyl (o-Phenylacetophenone) 




C 14 H 12 MW, 196 

B.p. 104-5/l mm. 
Semicarbazone : m.p. 197. 
2 : 4-Dinitrophenylhydrazone : m.p. 169-70. 

Campaigne, B,eid, J. Am. Chem. Soc., 
1946, 68, 1663. 

3-Acetodiphenyl (m-Phenylacetophenone). 
B.p. 148-51 /! mm. 

Semicarbazone : m.p. 222-3. 

2 : A-Dinitrophenylhydrazone : m.p. 191-2. 

Campaigne, Beid, J. Am. Chem. Soc., 
1946, 68, 1663. 

4-Acetodiphenyl (p-Phenylacetophenone) . 

Cryst. from EtOH or Me 2 CO. M.p. 120-1. 
B.p. 325-7. KMn0 4 > diphenyl-4-carboxy- 
Jic acid. Cu chromite red. > ethylcyclohexyl- 
benzene. 

Oxime : m.p. 184-6. 

Gull, Turner, J. Chem. Soc., 1929, 498. 
Grieve, Hey, /. Chem. Soc., 1933, 970. 
Long, Henze, J. Am. Chem. Soc., 1941, 
63, 1939, 

4-Acetodiph.enyl Ether. 

See under ^-Hydroxyacetophenone. 

Acetoevernone , 

See under 4 : 6-Dihydxoxy-2-methylaceto- 
phonone. 

2-Acetofurone (2-Acetylfuran, methyl u.-furyl 
Jcetone) 



C 6 H 6 2 MW, 110 

Cryst. from ligroin. M.p. 33 (29). B.p. 
173, 67/10 mm. D 20 1-098. < 1-5017. 

Oxime : prisms from Et 2 0~pet. ether, M.p. 
104 (92). Spar. sol. EtOH. Acetyl : needles 
from Et 2 0. M.p. 96. B.p. 135/10 mm. 
Benzoyl : needles from MeOH. M.p. 97-8. 

Semicarbazone : plates from MeOH. M.p. 
180. 

Phenylhydrazone : yellow plates from 
EtOH.Aq. M.p. 86-5, 

p*Nitrophenylhydrazone : red needles from 
EtOH.Aq. M.p. 185-6. 

Hartough, Kosak, /. Am. Chem. Soc., 

1947, 69, 1012. 
Reichstem, Helv* Ghim, Acta, 1930, 13, 

356. 

Asahina, Murayama, Arch, Pharm., 1914, 
252, 443. 



3-Acetofurone (3-Acetylfuran, methyl $-furyl 
Jcetone). 

B.p. 84/21 mm. 
Semicarbazone : m.p. 150. 

Gilman, Woolley, Wright, J. Am. Chem. 
Soc., 1933, 55, 2609. 

1-Acetoglutaric Acid 

CH 3 -CO-9H-COOH 

9 H 2 

CH 2 -COOH 

C 7 H 10 5 MW, 174 

M.p. anhyd. 102. B.p. 205/12 mm. 
Di-Et ester: C n H 18 5 . MW, 230. B.p. 
271-2 sHght decomp., 169-71/22-25 mm., 
162/llnim. Df 1-07115. 

Adkins, Isbell, Wojcik, Organic Syntheses, 

1934, XIV, 39. 
Kiister, Weller, Z. physioL Chem.., 1917, 

99, 235. 

2-Acetoglutaric Acid 



C 7 H 10 5 



MW, 174 



Leaflets. M.p. 58. Sol. H^O, EtOH. Mod. 
sol. Et 2 0, CHC1 3 . Insol. ligroin. Easily forms 
anhydride. 

Me ester: C 8 H 12 5 . MW, 188. Needles. 
M.p. 99. 

Di-Me ester: C 9 H 14 5 . MW, 202. B.p. 
144/12 mm. DJ 1-441. Phenylhydrazone : 
needles from dil. AcOH. M.p. 83. 

Di-Et ester: C n H 18 5 . MW, 230. B.p. 
154/12 mm. DJ 1-0798. 

Mono-amide : C 7 H n 4 N. MW, 173. Needles 
from EtOH-Et 2 0. M.p. 141-2. Sol. H 2 0. 
Spar. sol. EtOH, Et 2 0, CHC1 3 , ligroin. 

Eittig, Eoth, Ann., 1901, 314, 21. 

2-Acetoliepta,n . 

See 3-Methyloctanone-2. 
6-Aceto-ra-heptylic Acid. 
See 7-Ketopelargonic Acid. 
co-Acetohexahydrostyrene . 
See Hexahydrobenzylideneacetone. 
2-Acetolxydrindene (Methyl Z-hydrindyl 
Jcetone) 



CO-CH^ 



C U H 12 

B.p. 175-7/80 mm,, 164~8/47 mm. 
1-0685. 

Oxime : prisms from MeOH. M.p. 125-6 

Semicarbazone : m.p. 178. 

Ssolonma, Chem. Zentr. t 1905, 1, 343. 



MW, 160 



-Acetolaydrociimamic Acid 



12 



Acetoisopropyl Alcohol 



a-Acetohydrocinnamic Acid. 

See 1-Benzylacetoacetie Acid. 

Acetohy droquinone . 

See Quinacetophenone. 

Acetoin (Methylacetylcarbinol, Mmeihylkelol, 
methyl l-hydroxyethyl ketone, 2-butanolone-3) 

CH 3 -CH(OH)-CO'CH 3 
C 4 H 8 2 MW, 88 

M.p. 15. B.p. 148 (142). Misc. H 2 0. Sol. 
EtOH. Prae. insol. Et 2 0. Df 0-9972. < 
1 41 90 . Forms bisulphite comp . Reduces Feh- 
ling's. Dist. > diacetyl. Polymerises to 
C 8 H 16 4 , m.p. 95 (another form has m.p. 85), 
depolymerised by heat or treatment with Et 2 0. 
Catalytic dehydration > methyl vinyl ketone, 

Acetyl : b.p. 169-73. D} 7 1-033. 1% 14153. 
Semicarbazone: plates from EtOH. M.p. 161. 

Benzoyl : b.p. 140-1 /8 mm. D 18 1-104. 

Me ether: C 5 H 10 2 . MW, 102. B.p. 114 / 
727 mm. Spar. sol. H 2 0. 

Et ether: C 6 H 12 2 . MW, 116. 



727 mm. 
Propyl 



148-9/727 mm. 



ether : C 7 H 1A 



'7-U.14V/2- 



C 10 H 12 2 . 



MW, 
MW, 



B.p. 
130. 



164. 



i28y 

B.p. 
B.p, 



Phenyl 
235-40. 
Semicarbazone : 
Bergmann, 

173. 
Lowry, Baldwin, J. Chem. Soc., 1935, 704. 



m.p. 202 (185). 
Ludewig, Ann. 3 



1924, 436, 



3-Acetoindazole (Methyl %-indolyl Jcetone) 



NH 

C 9 H 8 ON 2 MW, 160 

Yellow leaflets from AcOH. M.p. 182. Sol. 
EtOH, Et 2 0, AcOH. Spar. sol. H 2 0, C 6 H 6 , 
ligroin. 

N-Acetyl: needles from AcOH. M.p. 123. 

Oxime : needles from CJEL-EtOH. M.p. 
222. 

2 : 4:-Dinitrophenylhydrazone : red needles from 
nitrobenzene. Does not melt below 320. 

Meisenheimer, Diedrich, Ber., 1924, 57, 
1720. 

3-Acetoindole 




C 10 H 9 ON MW, 159 

Needles from C 6 H 6 , M.p. 190-1. Sol. 
EtOH. Spar. sol. H 2 0, C 6 H 6 . Sublimes. 

Oxime : needles from H 2 0. M.p. 144-7. 

*N-Acetyl : needles from C H 6 -pet. ether. 
M.p. 151. Sol. hot H 2 0. Sublimes. 

Picrate : yellow cryst. from pet. ether. M.p. 
183. 



Oddo, Sessa, GCKSZ. chim. ital, 1911, 41, 1, 

237. 
Zatti/jBer., 1889, 22, 662. 

3-Acetoisobutylene . 

See 2-Methyl-l-pentenone-4. 
1-Acetoisobutyric Acid (1 : l-Dimethylaceto- 
acetic acid) 

CH 3 -CO\ 

CH 3 )C-COOH 



C 6 H 10 3 MW, 130 

Very hygroscopic. Decomp. readily at ord. 
temps, to methyl isopropyl ketone and C0 2 . 

Me ester : C 7 H 12 3 . MW, 144. B.p. 175-6, 
74 /15 mm. DJ 4 1-0002. rig 1-418. p-Bromo- 
phenylhydrazone : colourless prisms from EtOH. 
M.p. 90. Unstable. 

Et ester: C 8 H 14 8 . MW, 158. Oil. B.p. 
184. Sol. EtOH, Et 2 0. Spar. sol. H 2 O. DH 
0-9773. n$ 1-418. Semicarbazone: cryst. from 
H 2 0. M.p. 183-7 decomp. 

Amide : C 6 H n 2 N. MW, 129. Cryst. from 
H 2 0. M.p. 121. Sol. HoO. Spar. sol. EtOH, 
C 6 H 6 . Oxime : prisms from EtOH. M.p. 162- 
4 decomp. 

Nitrite: C 6 H 9 ON. MW, 111. Yellow liq. 
B.p. 163-4. Insol. H 0. D 13 1-008. Oxime : 
cryst. from ligroin. M.p. 99-100. B.p. 230 
decomp. 

Oxime : cryst. from Et 2 0. M.p. 96-7 de- 
comp. Unstable. 

Folkers, Adkins, J. Am. Chem. Soc., 193J , 

53, 1416. 
Meyer, jjfonatsh., 1906, 27, 1088, 

2-Acetoisobutyric Acid (l*Methyl-l?,mdiiiic 
acid) 

OH 8 -00-OH 8 -OH(OH 8 )-OOOIl 

C 6 H 10 3 MW, 130 

Hygroscopic oil. B.p. H>5/40 mm,, 153- 
6/3 mm. Sol. H 2 0, EtOH, E1 2 0. 30% KOH 
> acetone + x)yruvic acid. 

2 : 4:-Dintirophenylhydrazone : m.p. 130. 

Et ester: C 8 H 14 3 . MW, 158. B.p. 206-8. 
Insol. H 2 0. 

March, Corrupt, rend., 1902, 134, 180, 
Ajello, Cusmano, Qazz. Mm. itaL, 1940, 

70, 755. 

Acetoisopropyl Alcohol ( Mathylacdonyl 
carbinol, methyl 2-hydroxypropyl ketone 9 4*penf- 
anolone-2) 

CH 3 'CH(OH)-CH 2 -CO'CH 3 
C 5 H 10 2 MW 102 

B.p. 177, 77/28 mm., 62-4/12 mm. MIHO. 
with H 2 0, EtOH, Et 2 0, CHOI,. Df 1*0071, 
< 144146. Heat to 250, or with Ao fi O > 
ethylidenoaootone, OH-,-OH:OH-CO-CH 8 . 

Oxime ; b.p. 123-4 /1 3 mm, 

Pfaenylhydrazone : m,p. 102~3 



p-Acetoisopropylfoenzene 



13 



Acetone 



Acetyl : b.p. 84/12 mm. Phenylhydrazone : 
plates from EtOH. M.p. 115 corr. 
Claisen, Ann., 1899, 306, 324. 
Winthrop Chem. Co., U.S.P., 1,714,378, 
(Chem. Abstracts, 1929, 23, 3477). 

p- Acetoisopropylfoenzene . 

See 2-Phenylpentanone-4. 

3-Acetoisovaleric Acid. 

See 2-Methyl-3-acetobutyric Acid. 

AcetoL 

See Hydroxy acetone. 

Acetomalonic Acid 

CH 3 -CO-CH< COOH 



MW, 146 

C 6 H 8 5 . MW, 160. NitriU: 
M.p. 46-7. B.p. 130/40 
Et 2 O. Insol. H 2 0. * = 



C 5 H 6 5 

Mono-Me ester ; 
needles from Et 2 0. 
mm. Sol. EtOH, 
8-5 X 10~ 4 at 25. 

Mono-Et ester: C 7 H X0 5 . MW,174. NitriU: 
colourless needles. M.p. 26. B.p. 195-7, 
130~-2/35 mm. Sol. EtOH, Et 2 0, CHC1 3 , 
CS 2 , C 6 H 6 . Spar. sol. H 2 0. DJ 1-1107. < 
14710. k = 6-5 X 10- 4 at25. Amide : prisms 
fromAcOH. M.p. 110. Anilide : prisms from 
EtOH. M.p. 57-8. Spar. sol. H 2 0. Oxime : 
needles from dil. EtOH. M.p. 148. 

Di-Et ester : C 9 H M 6 . MW, 202. B.p. 1257 
20 mm. Exists as mixture of keto and enol 
forms, about 64% enol. Sol. dil. alkalis. Df 
1-099. rig 14460. FeCl 3 > dark red col. 
Acetyl: b.p. 154-6715 mm. DJ 5 1-1161. < 6 
Propionyl : b.p. 154-5/10 mm. D} 9 
MX? 1-452. Semicarbazone: m.p. 106- 
: A-Dinitrophenylhydrazone : m.p. 147. 
124. 
ester : C 8 H 12 5 . 



1-451. 
1-0984. 

7. 2 

Cu comp. : m.p. 
Mono-propyl 



MW, 188. 
M.p. 35-6. 



10 H 1 







MW, 216. 
1-0328. < 



127. Anilide 



Nitrite : needles from pet. ether. 

B.p. 133 /25 mm. k = 6-0 X 10" 4 at 25 

Mono-isdbutyl ester: C 9 H 14 5 . MW, 202. 
NitriU : b.p. ]43/32 mm. k = 7-0 x 10 4 at 
25. 

Mono-isoamyl ester : 
NitriU: b.p. 167/44 mm. 
14676. k = 6-8 X KH at 25 

NitriU : 5 H AN. MW, 
needles from EtOH. M.p. 145. o-Toluidide : 
needles. M.p. 110. p-Toluidide : needles. 
M.p. 176. 

Nef,4m., 1891, 266, 105. 
Guinchant, Ann. chim., 1918, 9, 70- 

Acetomesitylene . 

See 2:4: 6-Trimethylacetophenone. 
Acetomethylthienone (2-Methyl-5-acetyl* 

thiophene, methyl methylthienyl ketone) 
HG OH 



H 3 



O 7 H S OS 



Y 



M.p. 25. B.p. 232-3. Volatile in steam. 
Oxime : m.p. 125. 

Einkes, Rec. trav. chim., 1932, 51, 1134. 
Demuth, er., 1886, 19, 1859. 

Acetona,phthol . 

See Hydroxyacetonaphthone. 
1-Acetonaphthone (Methyl a-napTithyllcetone, 
1 -acetylnaphthalene) 



CO'CH., 




MW, 140 



C 12 H 10 ' " MW, 170 

M.p. 34. B.p. 167-70713 mm. Sol. com- 
mon org. solvents. Insol. H 2 O. D 1-1336. 
< 7 1-622. KMn0 4 (cold) ^ 1-naphthoyl- 
formic acid. KMn0 4 (hot) ^ 1-naphthoic 
acid. 

Oxime : cryst. from EtOH.Aq. M.p. 136. 

Semicarbazone : m.p. 235-7 (205). 

P^crate : yellow needles from EtOH. M.p. 
116 (118-19). 

1:3: 5-Trinitrobenzene add. comp. : yellow 
needles. M.p. 112. 

Froschl, Harlass, Monatsh., 1932, 59, 279. 
Caille, Compt. rend., 1911, 153, 393. 
Nunn, Henze, /. Org. Chem., 1947, 12, 
540. 

2-Acetonaphthone (Mefhyl^-naphthyl "ketone, 
2-acetylnapMfialene) . 

Needles from ligroin. M.p. 56. B.p. 301- 
3, 171-3/17 mm. Dil. HN0 3 > 2-naphthoic 
acid. 

Oxime : m.p. 145. 

Semicarbazone : m.p. 235-7. 

Phenylhydrazone : m.p. 176-7. 

Picrate : m.p. 85 (82). 

Barbot, Bull. soc. chim., 1930, 47, 1318. 
Immediata, Day, J. Org. Chem., 1940, 5, 
512. 

Acetone (Dimethyl ketone, propanone) 

CH 3 -CO-CH 3 
C 3 H 6 MW, 58 

M.p. -94. B.p. 562. D 0-8186, Df 
0-7899. Misc. H 2 0, EtOH, Et 2 0. Salted out 
from H 2 with CaCl 2 or K 2 C0 3 . wjf 1-36157. 
Heat of comb. liq. C w 426-3 Cal., vapour C^ 
437*25 Cal. Grit. temp. 246-1. Mol. elevation 
of b.p. 17-1. Forms add. comps. at low temps, 
with HF, HBr, HC1, HN0 3 . Gives bisulphite 
comp. Iodine + KOH > iodoform. NH 3 
> di- and tri-acetonamine. H + Ni at 125 
> isopropyl alcohol. H 2 S0 4 > mesityl 
oxide and phorone. 

Oxime: acetoxime. M.p. 59 (61). B.p. 
134-5/730 mm. Sol. H 2 0, EtOH, Et 2 0, ligroin. 
D| 0-97. < 141560. Me ether: b.p. 73. 
Sol. H 2 0, m ether: b.p. 91-2. 



Acetone-chloroform 



Acetonylacetone 



Hydrazone : oil. B.p. 124-5. 

Phenylhydrazone : m.p. 42. B.p. 140/16 
mm. 

Diphenylhydrazone : leaflets from ligroin. 
M.p. 148. 

MethylpJienylhy&razone : b.p. 215-16. 

o-Nitrophenylhydrazone : m.p. 70. 

p-Nitrophenylhydrazone : yellow needles from 
EtOH. M.p. 149. 

2 : 4^'DimtropJienylhydrazone : yellow needles 
from EtOH. M.p. 128. 

p-Bromophenylhydrazone : plates from ligroin. 
M.p. 98-9 (93). 

p-Iodophenylhydrazone : cryst. from EtOH-H 2 0. 
M.p. 214-15. 

1-Naphthylhydrazone : cryst. from ligroin. 
M.p. 74. 

2-Naphthylhydrazone : yellow prisms from 
ligroin. M.p. 65-5. 

1-Naphthoylhy 'drazone : m.p. 145-6. 

Semicarbazone : needles from H 2 or Me 2 CO. 
M.p. 190-1 decomp. 

2-Phenylsemicarbazone : needles from EtOH. 
M.p. 140. 

4:-Phenylsemicarbazone : needles. M.p. 160-1 . 

4 : 4:-Diphenylsemicarbazone : needles from 
Et 2 0. M.p. 119. 

4:-m~Nitrophenylsemicarbazone : m.p. 210-11. 

4^-p-Nitrophenylsemicarbazone : m.p. 235-6. 

^--p-Bromophenylsemicarbazone : m.p. 174. 

4;-o-Tolylsemicarbazone : cryst. from EtOH.Aq. 
M.p. 154-6 decomp. (142-3). 

i-p-Tolylsemicarbazone : needles from EtOH. 
M.p. 174-5. 

Thiosemicarbazone : cryst. from H 2 0. M.p. 
179. 

2-Phenylthiosemicar bazone : needles. M.p. 135. 

4:-Phenylthio$emicarbazone : m.p. 128. 

4-Q-TotylMosemicarbazone : m.p. 182. 

4t-p~TotylMosemicarbazone : m.p. 142. 

Semioxamazone : needles from Me 2 CO. M.p. 
147. 

Cyanhydrin : see under 1-Hydroxyisobutyric 
Acid. 

Anil : isopropylideneaniline. B.p. 227-9. 
^-Me acetal : 2 : 2-dimethoxypropane. 
C 5 Hi 2 2 . MW, 104. B.p. 83. 

Di-Et acetal: 2 : 2-diethoxypropane. C 7 H 16 2 . 
MW, 132. B.p. 114. 

Acetone-cMor of orm . 
See Chloretone. 
Acetone-diacetic Acid. 
See 3-Ketopimelic Acid. 
Acetone-dicarboxylic Acid (%-Ketoglutaric 
acid) 



acids or alkalis to acetone + 00 2 . EeCl 3 > 
violet col. Ic = 7-9 x 10- 4 at 25. NaHg ^ 
2-hydroxyglutaric acid. 

Di-Me ester: C 7 H 10 5 . MW, 174. B.p. 
150/25 mm., 128/12 mm. 

m ester: C 7 H 10 5 . MW, 174. Amide: 
needles. M.p. 86. Sol. EtOH. Mod. sol. 
CHC1 3 . Spar. sol. cold H 2 0, EtOH. Anilide : 
needles from H 2 0. M.p. 75-6. Sol. EtOH, 
Et 2 0, C 6 H 6 . Spar. sol. ligroin. 

Di-Et ester: 9 H 14 5 . MW, 202. Oil. B.p. 
250, 140/13 mm. DJ 1-113. Misc. EtOH. 
Spar. sol. H 2 0. Semicarbazone : cryst. from 
EtOH. M.p. 94-5. 

Di-isobutyl ester : C 13 H 22 5 . MW, 258. B.p. 
220/120 mm. 

Di-anihde : needles from EtOH. M.p. 155. 
Spar. sol. Et 2 0, CHC1 3 , C 6 H 6 . 

Oxime : m.p. 53-4. 

Adams, Chiles, Eassweiler, Organic Syn- 

theses, Collective Vol. I, 9. 
Jerdan, /. Ohem. Soc., 1899, 75, 809. 
Ruggli, Doebel, Helv. Chim. Ada, 1946, 

29, 600. 

Acetone dichloride. 

See 2 : 2-Dichloropropane. 

Acetone diethylsulphone. 

See Sulphonal. 

Acetone-dioxa,lic Acid. 

See Triketopinaelic Acid. 

Acetone-dipropionic Acid. 

See 4-Ketoazelaic Acid. 

Acetone-oxalic Acid. 

See Acetopyruvic Acid. 

Acetonic Acid. 

See 1-Hydroxyisobutyric Acid. 

Acetonitrile (Methyl cyanide, cyanonwtfime) 



C 5 H 6 6 MW, 146 

Needles from EtOAc. M.p. 135 decomp. 

Sol. H 2 0, EtOH. Mod. sol. Et 2 0, EtOAc. Insol. 

CHC1 3 , C 6 H 6 , ligroin. Decomp. by hot H 2 0, 



C 2 H 3 N MW, 41 

M.p. -44-9. B.p. 81-6. 1)J 0-7828. Misc. 
with H a O. < 1-34423. Heat of com!), of 
vapour C^ 312-14 Gal., liq. 304-0 Oal. Burns 
with luminous flame. Good solvent for iaorg. 
salts. H 2 at 100 ^ acetamido. Rod. 
-> ethylamine. H 2 S > thioaootainido. 
Benzoic acid at 280 > bonzonitrile -| acotic 
acid. 

Walden, Ber., 1907, 40, 3215. 

van Epps, Reid, /. Am. Ohem. Soo. 9 

38, 2130. 
Yeo-Scin. Qwan, J, Indian Chew, 

1941, 18, 164, (Ghem. Abstracts, 

40, 2782). 

Acetonylacetone (1 : 2Dia>cetylethane y 
dione-2 : 5, 2 : fr-MJcetohexane) 



C 6 H 10 2 MW, 114 

M.p. -9. B.p. 194 /754 mm-, 1377150 



Acetonyl Alcohol 



15 



9-Acetophenanthrene 



mm. Df 0-97370. vSS 1-449. Msc. all pro- 
portions H 2 O, EtOH, Et 2 0. 

Monoxime : b.p. 130/11 mm. 

Dioxime : plates from C 6 H 6 . M.p. 137. 
Sol. H 2 0. Red. >- dimethylpyirolidine. 

Di-phenylhydrazone : plates from EtOH. M.p. 
120. 

Di-p-nitrophenylhydrazone : red needles from 
EtOH. M.p. 210-12. 

Di-2 : 4-dinitrophenylhydrazone : m.p. 257. 

Disemicarbazone : m.p. 223-4. 

Knorr, JBer., 1900, 33, 1219. 

Justoni, Gazz. chim. ital., 1941, 71, 375. 

Acetonyl Alcohol. 

See Hydroxy acetone. 
Acetonylbenzene . 
See Methyl benzyl Ketone. 
Acetonylbenzoic Acid. 
See Methyl benzyl ketone carboxylic Acid. 
Acetonylca,rbinol . 
See 3-Keto-^-butyl Alcohol. 
Acetonylf ur an . 
See Methyl furfuryl Ketone. 
2- Acetonylheptane . 
See 4-Methylnonanone-2. 
2- Acetonylhexane . 
See 4-Methyloctanone-2. 
Acetonylmalonic Acid (2-J3utanone-4: : 4- 
dicarboxylic acid) 



C 6 H 8 6 MW, 160 

Plates from Et 2 0. M.p. 150 decomp. Very 
sol. H 2 0. Spar. sol. Et 2 0. Heat > levulinic 
acid + C0 2 . 

Semicarbazone : cryst. from H 2 0. M.p. 170 
decomp. 

M e ester nitrile : C 7 H 9 2 N. 
159~60/26 mm. D l4 1 -148. 
needles. M.p. 137-8. 

Et ester nitrile : CgHiiOaN. 

D^T-r 



MW, 139. B.p. 

Phenylhydrazone : 



161~71/24 mm. 



-10. 



MW, 153. B.p. 
Phenylhydrazone : 



noodles from BtOH. M.p. 144 

Perkin, Simonsen, J. Chem. Soc., 1907, 
91, 821. 

2-Acetonylpiperidine . 

See Isopelletierine. 
2V-Acetonylpiperidine . 
See Piporidinoacetone. 
Acetonyltoluene 
See Tolylacetone. 
2-Aceto-octane . 
See 3-Methylnonanone-2. 
1 - Aceto-1 -octene . 
See Methyl 1-octenyl Ketone. 
8-Acetopelargonic Acid. 
See 9-Kctoundeoylic Acid. 
1- Aceto-1 : 3-pentadiene. 
See 2 ; 4-Hptadieiione-6. 



2-Acetopentane . 

See 3-Methylhexanone-2. 

3-Acetopentane . 

See 3-Ethylpentanone-2. 

2- Aceto-3-pentanol . 

See 3-Methyl-4-hexanolone-2. 

1-Aceto-l-pentene . 

See 3-Heptenone-2. 

4- Aceto-1 -pentene . 

See 4-Methyl- 1 -hexenone-5 . 

5-Aceto-l-pentene . 

See l-Heptenone-6. 

l-Aceto-2-pentene . 

See 3-Heptenone-6. 

2-Aceto-2-pentene . 

See 3-Methyl-3-hexenone-2. 

5-Aceto-2-pentene . 

See 2-Heptenone-6. 

1-Acetophenanthrene 



CO-CH, 




C 16 H 12 O MW, 220 

Plates from EtOH. M.p. 112-3. 

Bachmann, Boatner, J. Am. Chem. Soc., 
1936, 58, 857, 2097. 

2-Acetophenanthr ene . 
Needles from MeOH. M.p. 143. Sol. EtOH, 
C 6 H 6 . 

Semicarbazone : leaflets from EtOH. M.p. 
260. Solidifies and remelts at 297-9. 
Phenylhydrazone : m.p. 187-8. 

Mosettig, Van de Kamp, /. Am. Chem. 

Soc., 1930, 52, 3704. 
Biegel, Gold, Kubico, /. Am. Chem. Soc. 9 

1942, 64, 2221. 

3-Acetophenanthrene . 

Needles from MeOH. M.p. 72. Sol. MeOH, 
EtOH, AcOH, C 6 H 6 . Spar. sol. pet. ether. 
Oxime : needles from MeOH. M.p. 143-4. 
Semicarbazone : needles. M.p. 228-30. 
Phenylhydrazone : m.p. 193-4. 
Picrate : m.p. 125-6. 

Mosettig, van de Kamp, /. Am. Chem. 
Soc., 1930, 52, 3704. 

4- Acetophenanthrene . 

Clusters of plates. M.p. 90. 
Picrate : yellow needles from MeOH. M.p. 
129-30. 

Fieser, Eieser, Hershberg, J. Am. Chem. 
Soc., 1936, 58, 2322. 

9-Acetophenanthrene . 
Needles from MeOH. M.p. 74-6. 
Oxime : needles from MeOH. M.p. 154-5. 
Semicarbazone : plates from MeOH. M.p. 
199-201. 



Acetopkenine 



16 



Acetophenone-co-dicarboxylic Acid 



M.p. 
M.p. 



Picrate : yellow needles from MeOH. M.p. 
107-8. 

Bachmann, Boatner, J. Am. Chem. Soc., 

1936, 58, 2097. 

Mosettig, van de Kamp, J. Am. Chem. 
Soc., 1933, 55, 3442. 

Acetophenine. 
See 2:4: 6-Triphenylpyridine. 
Acetophenol. 
See Hydroxyacetophenone. 
Acetophenone (Methyl phenyl Jcetone, Hyp- 
none) 

C 6 H 5 -COCH 3 

C 8 H 8 MW, 120 

Plates. M.p. 20-5. B.p. 202, 83~5/12 
mm. Sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . Insol. 
H 2 0. Sol. cone. H 2 S0 4 with orange col. Df 
1-0236. n% 1-53418. Soporific. Cr0 8 > 
benzoic acid. Alk. KMii0 4 > benzole acid. 
H 2 2 in H 2 S0 4 > benzoylcarbinol. Na + 
EtOH or Al 2 3 /Cu 2 > methylphenylcarbinol. 

Oxime : needles from H 2 0. M.p. 60. B.p. 
245, 119/20 mm. Mod. volatile in steam. 
Me ether : b.p. 214-16 decomp. 

Hydrazone : cryst. from pet. ether. 
22. B.p. 255. Decomp. by H 2 0. 

Phenylhydrazone : needles from EtOH. 
106. 

o-Nitrophenylhydrazone : m.p. 138. 

m-Nitrophenylhydrazone : m.p. 163. 

-p-Nitrophenylhydrazone : orange -red needles. 
M.p. 184-5. 

2 : 4c-Dinitrophenylhydrazone : m.p. 237. 

p-Bromophenylhydrazone : m.p. 111-12. 

p-Iodophenylhydrazone : m.p. 212. 

o-Tolylhydrazone : m.p. 101. 

m-Tolylhydrazone : m.p. 81. B.p. 214-23 / 
12 mm. 

p-Tolylhydrazone : needles from pet. ether. 
M.p. 125. 

Methylphenylhydrazone : m.p. 49-50. 

Diphenyl-hydrazone : cryst. from EtOH. M.p. 
97-8. 

$-Naphthylhydrazone : needles from EtOH. 
M.p. 157-8. 

Semicarbazone : plates from EtOH. M.p. 
203 decomp. 

2-Phenylsemicarbazone : 
M.p. 122. 

4-Phenylsemicarbazone : 
M.p. 187-8. 

i'O'Tolylsemicarbazone : 
M.p. 211-12 decomp. 

i~p-Tolylsemicarbazone : 

$-Naphthylsemicarbazone : 
EtOH. M.p. 201-2. 

TMosemicarbazone : cryst. from C JEL, M.p. 
108 

Anil: cryst. M.p. 41. B.p. 310, 166-7/12 
mm. 



cryst. from EtOH. 
needles from EtOH. 
needles from EtOH. 



needles. M.p. 192. 
needles from 



Semioxamazone : needles from EtOH. M.p. 
214. 

Picrate : m.p. 53. 

Di-Et acetal : b.p. 212-6 part, decomp., 
103~4/23 mm. D 0-9266. 

Bouveault, Bull. soc. chim., 1897, 17, 

1020. 

Nencki, Stoeber, Eer., 1897, 30, 1769. 
Senderens, Ann. chim., 1913, 28, 312. 
Williams, Dickert, Krymtsky, J. Am. 

Chem. Soc., 1941, 63, 2510. 
Berlin, J. Gen. Chem. U.S.S.R., 1944, 14, 
1096, (Chem. Abstracts, 1946, 40, 4054). 
Salmi, Vaihkonen, Chem. Abstracts, 1947, 
41, 5481. 

Acetophenone-acetone . 
See Phenacylacetone. 
Acetophenone Alcohol. 
See Phenacyl Alcohol. 

Acetophenone-o-carboxylic Acid (o- Aceto- 
benzoic acid, methyl o-carboxyphenyl Jcetone) 

CO-CH 3 
300H 

C a H 8 3 " MW, 164 

Cryst. from H 0. M.p. 114-15. 
Et ester : C U H 12 3 . MW, 192. B.p. 279. 
Amide : C 9 H 9 2 N. MW, 163. Prisms from 
H 2 0. M.p. 116-5. N-Et : plates from H 2 0. 
M.p. 93-4 decomp. Spar. sol. H 2 0. 

Gabriel, Michael, Ser. 9 1877, 10, 1551. 
De Benneville, J. Org. Chem., 1941, 6, 

462. 
Yale, J. Am. Chem. Soc., 1947, 69, 1547. 

Acetophenone-m-carboxylic Acid (m- 

Acetobenzoic acid, methyl m-carboxyphe.nyl ketone). 

Needles from H 2 0. M.p. 172*. Sol EtOH, 
Et 2 0, hot H 2 0. Spar. sol. OHCL,, ir G . 

Nitrile : m-cyanoacotoi)henono. <\,1I 7 ON, 
MW, 145. Needles from EtOH. M.p. 98 -9. 
Bupe, Majewski, Eer. 9 1900, 33, 3408. 




Acetophenone-jp-carboxylic Acid ( 
benzoic acid, methyl p-carboxyphenyl ketone). 

Needles from H,>0. M.p. 208. Sol hot 
H 2 0. Spar. sol. EtOH, Et a O. SublimoH. 

Phenylhydrazone : m.p. 234. 

Semicarbazone : m.p. 269. 

Me ester: 10 H 10 S . MW, 178. Noodlos 
from H 2 0. M.p. 92 e , Sublimes. 

Et ester: n H ia 8 . MW, 192. Needles 
fromH 2 0. M.p. 57\ 

Nitrile : jp-cyanoacetophonono NoodloB from 
EtOH. M.p. 60-1. Sol. KtOH, KtfeQ. Inaol. 
H 2 0. Oxime : plates from H 2 0. M.p. 160, 

Meyer, Ann., 1883, 219, 260. 

Acetophenone-oo-dicarboxylic Acid. 

See Bonzoylmalonic Acid. 



Acetopiperone 



17 



3- Acet o (Tuinaldine 



Acetopiperone (3 : 4:-Methylenedioxyaceto- 
phenone) 



CO-CH, 




C 9 H 8 3 " MW, 164 

Leaflets from EtOH.Aq. M.p. 88. Sol. 

EtOH, Et 2 0, Me 2 00, CHC1 3 , C 6 H 6 . Insol. pet. 

ether. Does not give bisulphite comp. 
Oxime : needles from H 2 O. M.p. 156-7, 
Phenylhydrazone : plates from EtOH. M.p. 

114. 

Mameli, Gazz. chim. ital., 1909, 39, II, 165. 

Acetopivalic Acid. 

See Mesitonic Acid. 
2- Acetopropane . 
See Methyl isopropyl Ketone. 
2- Acetopr opioiialdehyde . 
See Levulinic Aldehyde. 
1-Acetopropionic Acid. 
See 1-Methylacetoacetic Acid. 
2-Acetopropionic Acid. 
See Levulinic Acid. 
1-Acetopropyl Alcohol. 
See 3-Pentanolone-2. 

2-Acetopropyl Alcohol (2-Methyl-l~butanol- 
one-3) 



C K H 10 2 



CH 3 -CO-CH-CH 2 OH 



MW, 102 

B.p. 90-5/15 mm. H 3 P0 4 dehydration > 
methyl isopropenyl ketone. 
Oxime : b.p. 144/20 mm. 

Decombe, Compt. rend., 1936, 202, 1685. 
Bayer, D.R.P. 223,207 (Chem. Zentr., 

1910, II, 347). 
Colemoro Adhesives, White, B.P. 551,219, 

(Chem. Abstracts, 1944, 38, 2350). 
Dreyfus, Drewitt, TJ.S.P., 2,378,988, 

(Chem. Abstracts, 1945, 39, 4626). 
Lincoln, Drewitt, U.8.P., 2,395,414, 

(Chem. Abstracts, 1946, 40, 3127). 
Landau, Irany, J. Org. Chem., 1947, 12, 
422. 

3-Acetopropyl Alcohol (Methyl 3~hydroxy. 
propyl ketone, levulinic alcohol, i-pentanolone-ty 

CH 3 -CO-CH 2 -CH 2 -CH 2 OH 
C,H 10 2 MW, 102 

B.p. 208/730 mm. decomp., 144~5/100 mm., 
116-18/33 mm. Cyclised by dist. at atm. press. 
>. dihydromethylfuran. Misc. with H 2 0. 
SoLEtOII,Et 2 0. Df 1-0071. < 1-4436. Steam 
volatile. KeducesNH 3 .AgN0 3 . Forms bisulphite 
comp, Or0 3 > levulinic acid. Electrolyiic 
re d. >. w-amyl alcohol. 

Aeetyl: b.p. 211-3, 91/12 mm. D a 4 1-0181. 
< 142677. 

Semicarbazone : m.p. 156-7. 

Diet, of Org. Comp, 1 I. 



PJienyl ether : C U H 14 2 . MW, 178. Plates 

from pet. ether. M.p. 55. Oxime : m.p. 78. 

Semicarbazone : plates from EtOH. M.p. 144. 

Possanner, Ehrenthal, Monatsh., 1903, 

24, 352. 

Paul, Bull. soc. chim., 1933, 53, 417; 
Chem. Abstracts, 1944, 38, 2334. 

y-Acetopropylbenzene . 

See l-Phenylpentanone-4. 
p-Acetopropylbenzene . 
See jp-Propylacetophenone. 
Acetopyridine . 
See Methyl pyridyl Ketone. 
Acetopyrine. 
See under Antipyrine. 
Acetopyrocatechol. 
See 3 : 4-Dihydroxyacetophenone. 
4- Acet opy r og-allol . 
See Gallacetophenone. 
5- Acetopy rogallol . 
See 3:4: 5-Trihydroxyacetophenone. 
Acetopyrotartaric Acid. 
See Methylacetosuccinic Acid. 
2-Acetopyrrole . 
See Methyl 2-pyrryl Ketone. 
Acetopyruvic Acid (1 : 3-Diketo-u-valeric 
acid, acetonylglyoxylic acid, acetone-oxalic acid) 

CH 3 -CO-CH 2 -CO-COOH 

C 5 H 6 4 MW, 130 

Prisms from C 6 H 6 . M.p. 101. B.p. 130/37 
mm. Sol. H 2 0, EtOH, Et 2 0, Me 2 CO, AcOEt, 
CHC1 3 , C 6 H 6 . Insol. pet. ether. Sublimes with 
part, decomp. Heat with alkalis > acetone + 
oxalic acid. 

Me ester : C 6 H 8 4 . MW, 144. Cryst. from 
C 6 H 6 . M.p. 63-4. B.p. 93-7/12 mm. D?J 
1-1536. Enolises. 

Et ester: C 7 H 10 4 . MW, 158. M.p. 18. 
B.p. 213-15, 134-5/40 mm., 111-12/16 mm. 
Di 7 1-12879. < 1-475699. Enolises. 

Amide : C 5 H 7 3 K. MW, 129. Cryst. from 
EtOH. M.p. 131-2 decomp. Easily sol. H 2 0. 
Sol. Me 2 CO, AcOH, AcOEt. Spar. sol. Et 2 0. 
Insol. pet. ether. PeCl 3 > red col. 

Mumm, Bergell, Ber., 1912, 45, 3045. 
Breusch, Keskin, Enzymologia, 1945, 11, 
356, (Chem. Abstracts, 1946, 40, 5702). 
Lehninger, Witzemann, 7. Am. Chem. 
Soc., 1942, 64, 874. 

3-Acetoquinaldine (2-Methyl-3~acetylquinol- 
ine) 




C 12 H U ON MW, 185 

Needles from ligroin. M.p. 78-9. B.p. 306. 

Cryst. as hydrate from EtOH.Aq., m.p. 57-5. 
Oxime : cryst. + 1JH 2 from EtOH.Aq. 

M.p. 118-20, anhyd. 146. 

2 



6-Acetoonainaldin,e 



18 



Acetovanillone 



Semicarbazone : needles from EtOH. M.p. 208. 

Phenylhydrazone : needles from C 6 H 6 . M.p. 
130. Unstable. 

2 : 4:-Dinitrophenylhydrazone : yellow, m.p. 
216-7. 

Picrate : yellow, m.p. 233-4. 
Stark, Ber. 3 1907 3 40, 3427. 

6-Acetoquinaldine (2-Methyl-6-acetylquinol- 
ine). 

Needles from H 2 0. M.p. 92. B.p. 318-20. 
Spar. sol. cold H 2 0. 

Phenylhydrazone : reddish-yellow needles from 
EtOELAq. M.p. 193. 

Picrate : yellow needles from H 2 0. M.p. 
208-11. 

Berend, Thomas, Ber., 1892, 25, 2548. 

Acetoresorcinol . 

See Dihydroxyacetophenone and Resaceto- 
phenone. 

Acetosuccinic Acid 

CH 3 -CO"9H-COOH 
CH 2 -COOH 

C 6 H 8 5 MW, 160 

Di-M ester: C 10 H 16 5 . MW, 216. B.p. 
254-6 decomp., 239~40/330 mm., 180-3/50 
mm., 140-2/15 mm. DJjj 1-08809. < 1438. 
Boiling ale. KOH ^ acetic + succinic acid. 
Ba(OH) 2 > levulinic acid + C0 2 . 

Fittig, Spenzer, Ann., 1894, 283, 67. 

2-Acetothienone (Methyl 2-thienyl ketone, 2- 
acetylthiophene) 



C 6 H 6 OS 
M.p. 9. 



HO. C-CO-CH, 



Y 



MW, 126 

B.p. 213-14, 94-5-6-5713 mm. 
D 24 1467. < 1-5667. KMn0 4 > thiophene- 
2-carboxylic acid. H 2 S0 4 + isatin >- blue 
col. 

CQH 6 OS,H Q PO^: cryst. M.p. 92-6. Mod. 
sol. Et 2 0. 

Oxime : m.p. 81. 

Semicarbazone : plates from C 6 H 6 . M.p. 
190-1. 

Phenylhydrazone : yellow needles from EtOH. 
M.p. 96. 

p-Nitrophenylhydrazone : red cryst. from 
EtOH. M.p. 181-2. 

Benzoylhydrazone : cryst. from toluene. M.p. 
187-8. 

Hartough, Kosak, /. Am. Chem. Soc., 

1947, 69, 1012. 
Johnson, ibid., 150. 
Hartough, Kosak, /. Am. Chem. Soc., 

1946, 68, 2639. 

Mowry, Renoll, Huber, ibid,, 1105. 
Stadnikoff, Rakowski, Ber., 1928, 61, 268. 
Bradley, Ber., 1886, 19, 2115. 



o-Acetothiophenol . 
See o-Mercaptoacetophenone. 
1-Aceto-n-valeric Acid (l-Propylacetoacetic 
acid) 

CH 3 -CH 2 -CH 2 -9H-COOH 



C 7 H 12 3 



MW, 144 

Et ester : C 9 H 16 3 . MW, 172. B.p. 210-12 / 
749 mm., 105-7/13 mm. D2 0-981. 

Isobutyl ester: C n H 20 3 . MW, 200. B.p. 
115-16/13 mm. D 0-954. 

Amide : C 7 H 13 2 N. MW,143. Needles from 
EtOHEt 2 0. M.p. 105-6. Sol. H 2 0. FeCl 3 
>- blue col. 

Burton, Am. Chem. /., 1881, 3, 385. 

3-Aceto-n-valeric Acid 

CH 3 -9H-CH 2 -CH 2 -COOH 
CO-CH 3 

C 7 H 12 3 MW, 144 

B.p. 168-9/22 mm. DS 1-114. 
Et ester : b.p. 117-48723 mm. D2 1-004. 
March, Ann. chim. phys., 1902, 26, 337. 

4-Aceto-n-valeric Acid (<*>-Aceto-n-valeric 
acid, 6-ketO'iL-heptylic acid) 

CH 3 -CO-CH 2 -CH 2 -CH 2 -CH 2 -COOH 

C 7 H 12 3 MW, 144 

M.p. 40-2 (31-2). B.p. 250-3/280 mm. 
Sol. H 2 0, EtOH, Et 2 0. 

Et ester : b.p. 120-5/ll mm. Semicarbazone : 
cryst. from EtOH. M.p. 107 (100-4). 

Semicarbazone : cryst. from AcOH. M.p. 
144-6. 

Blaise, Kohler, Compt. rend., 1909, 148, 

490. 
Polgar, Robinson, J. Chem, Soc,, 1945, 

389. 

Acetovanillone (4-Hydroxy~3~methoxyace(o- 
phenone, Apocynin) 

CO-CH 3 



C 9 H 10 3 




MW, 166 



Prisms from hot H 2 0. M.p. 115. B.p. 295- 
300, 233~5/15-~20 mm, Sol. EtOH, Et 2 0, 
CHGU CeH 6 , hot H 2 0. Spar, sol ligroin, Spar. 
volatile in steam. FeCl 3 > bluish-violet coL 
Me ether : see Acetoveratrone. 
Et ether: C n H 14 O a . MW, 194. Noodles 
from EtOH.Aq. M.p. 78. Sol EtOH, 'KU>, 
CHCJ 8 , C 6 H 6 . Oxime : prisms from EtOlLAq* 
M.p. 116-18*. 

Acetyl : needles from EtOH.Aq. M.p. S8 
Benzoyl : needles from EtOH.Aq, M.p, 
Oxime : cryst. from C 6 H . M.p, 95. 



Acetoveratrone 



19 



Acet-o-toluidide 



Semicarbazone : prisms from EtOH.Aq. M.p 
166. H * 



cryst. from H 2 0. M.p. 
Chim. Acta } 1927, 10, 

(3 : 4b-Dimethoxyacetophen- 
CO-CH 




Phenylhydrazone : 
125. 

Reichstein, 
392. 

Acetoveratrone 

one) 



G ioH 12 3 MW, 180 

Prisms from EtOH.Aq. M.p. 51 (49). B.p. 
286-8, 205-7/10-15 mm. Sol. EtOH, Et 2 0, 
CHC1 3 , C 6 H 6 , hot H 2 0. Spar, volatile in steam. 
HN0 3 + H 2 S0 4 > 6-nitro deriv. 

Oxime : cryst. from EtOH.Aq. M.p. 140. 

Semicarbazone : cryst. from EtOH.Aq. M.p. 
218. 

Phenylhydrazone : m.p. 131. 

p-Nitrophenylhydrazone : m.p. 227. 

Ploeg, Rec. trav. chim., 1926, 45, 342. 

Acetoxime 

See under Acetone. 

Acetoxyacetic Acid (Acetylglycollic acid) 

CH 3 *CO-OCH 2 -COOH 
C 4 H 6 4 MW, 118 

Needles from C 6 H 6 . M.p. 66-8. B.p. 145 / 
12 mm. Sol. H 2 and most org. solvents. 



Et ester: C 6 H 10 4 . MW, 146. B.p. 179. 
D 17 1-0993. 
Anilide : needles from H 2 0. M.p. 89-90. 

Anschiitz, Bertram, Ber., 1903, 36, 466. 

Acetoxyacetone (Acetol acetate, acetylhydr- 
oxyacetone) 

CH 3 -CO-CH 2 0-CO-CH 3 
C 5 H 8 3 MW, 116 

B.p. 174~5 / 138/230 mm., 74/18 mm., 66/ 
12 mm. Sol EtOH, Et 2 0. Hyd. by H 2 0. 
Df 1-0749. < 14150. 

Oxime : b.p. 144 /20 mm. 

Semicarbazone : needles from MeOH. M.p. 
145. 

Phenylhydrazone : plates from Et 2 O . Decomp . 
at 60. 

j)-Bromophenylhydrazone : cryst. from EtOH. 
M.p. 137-8. 

-p-Nitrophenylhydrazone : yellow cryst. from 
C 6 H . M.p. 144. 

Nef, Ann., 1904, 335, 260. 

Acetoxybenzoic Acid, 

See Acetylsalicylic Acid and under Hydroxy- 
benzoic Acid. 
Acetoxycapric Acid. 
See under Hydroxycapric Acid. 



Acetoxycaprylic Acid. 

See under Hydroxycaprylic Acid. 

Aceto-xylene. 

See Dimethylacetophenone. 

a-Acetoxyphenylacetic Acid. 

See under Mandelic Acid. 

1-Acetoxypropionaldehyde 



C 5 H 8 3 MW, 116 

B.p. 52-5 /15 mm. 
Semicarbazone : m.p. 163. 
Nef, Ann., 1904, 335, 266. 
Greaham, Brooks, U.S.P., 2,402,133, 
(Chem. Abstracts, 1946, 40, 6093). 

1-Acetoxypropionic Acid (Acetyl-lactic 
acid) 



C 5 H 8 4 MW, 132 

M.p. 57-60 (39-40). B.p. 167-70/78 mm., 
127 /11 mm. Sol. EtOH, C 6 H 6 . Ba salt sol. 
H 2 O. 

Et ester: C 7 H 12 4 . MW, 160. B.p. 177 / 
730 mm. Insol. H 2 0. D 17 1-0458. 

Chloride : C 6 H 7 3 C1. MW, 150-5. B.p. 150 
part, decomp., 56711 mm. DJ 7 1-1920. n$ 
1-4241. Hyd.byH 2 0. 

Nitrite : C 5 H 7 2 N. MW, 113. B.p. 172-3, 
73/8 mm. Sol. H 2 to 4% . Sol. EtOH, Et 2 O, 
AcOH. D 14 1-032. 

Auger, Compt. rend., 1905, 140, 938. 
FilacMone, Fisher, U.S.P. 2,399,395, 
(Chem. Abstracts, 1946, 40, 4394). 

Acetoxysuccinic Acid (Acetyl-l-malic acid) 

9H 2 -COOH 
CH 3 -CO-OCH-COOH 

MW, 176 

M.p. 139 (132). Hyd. by H 2 0. Heat ^ 
maleic + acetic acids. 

Di-Me ester: C 8 H 12 6 . MW, 204. B.p. 
157/35 mm., 132/12 mm. DJ 1-1983. [og? 
22*9 

Di-Et ester: C 10 H 16 6 . MW, 232. B.p. 
2667730 mm., 141/13 mm. Df 1-1168. < 
1-4295. [ag - 22-5. 

AnscMitz, Bennert, Ann., 1889, 254, 165. 

Acetphenetidide . 

See under Phenetidine. 

Acet-o-toluidide (Acetyl-o-toluidine,I-methyl- 
%-acetylaminobenzene) 

CH 3 
/\NH-CO-CH 3 

C 9 H H ON MW, 149 



C 6 H 8 6 



Acet-m-toluidide 



20 



Acetylamidrazone 



Needles. M.p. 110. B.p. 296. 1000 parts 
H 2 dissolve 8 -6 parts at 19. Heat of comb. G p 
1174-6 Cal. KMn0 4 > o-acetylaminobenzoic 
acid. 

N-CMoro : ni.p. 43. Sol. CHC1 3 , C 6 H 6 . At 
160 > 5-chloro-acet-o-toluidide. 

N-JSromo : m.p. 100-6. 

N- M & : see under j^-Methyl-o-toluidine. 

IS-fit : see under ^-Ethyl-o-toluidine. 
Kaufmann, Ber., 1909, 42, 3481. 
loffe, Chem. Abstracts, 1945, 39, 3786. 

Acet-m-toltddide (Acetyl-m-toluidine, 1- 
methyl-%-acetylaminobenzene) . 

Needles. M.p. 65-5. B.p. 303, 182-3 / 
14 mm. Sol. EtOH, Et 2 0. 1000 parts H 2 
dissolve 44 parts at 13. Heat of comb. Op 
1174-7 Cal. 

N-Jfe : see under JV^-Methyl-w-toMdine. 

N-Et : see under j/V-Ethyl-w-toluidine. 

Beilstein, Kuhlberg, Ann., 1870, 156, 83. 

Acet-p-toluidide (Acetyl-p~toluidine, 1- 
methyl-4c-acetylaminobenzene) . 

Cryst. from EtOH.Aq. M.p. 155 (146). 
B.p. 307. Spar. sol. H 2 0. Sol. to 10% in 
EtOH at 25. D 15 1-212. Heat of comb. G p 
1174-3 Cal. KMn0 4 > p-acetylaminobenzoic 
acid. Sublimes. 

N-Chloro : m,p. 91-2. Heat > 3-chloro- 
acet-jp-toluidide. 

N-J?romo : m.p. 94-5. At 95 > 3-bromo- 
acet-^-toluidide. 

18 -Me : see under ^V-Methyl-j?-toluidine. 

Dehn, /. Am. CTiem. Soc., 1912, 34, 1405. 
loffe, Chem. Abstracts, 1945, 39, 3786. 
Sanford et al, J. Am. Chem. Soc., 1945, 
67, 1941. 

Aceturic Acid. 

See Acetylglycine. 
Acet-xyHdide. 
See under Xylidine. 
Acetyl^cetonamine (Aminopentenone) 



CH 3 -CO-CH: 
or 



Acetylacetone (Diacetylmethane, pentandi - 
one-2 : 4, 2 : k-diketopentane) 

CH 3 -CO-CH 2 -CO-CH 3 



C 6 H 9 ON 

M.p. 43 
dil. acids - 




MW, 99 
HotH 2 Oor 



B.p. 209. Sol! 
> acetylacetone + ! 

N-J3enzoyl : prisms from MeOBT. M.p. 82. 
Sol. EtOH, Me 2 CO, CHC1 3 , C 6 H 6 . Spar. sol. 
Et 2 0, AcOH. InsoL pet. ether. Phenylhydr- 
azone : yellow needles from MeOH. M.p. 130. 
TS-Me: acetylacetone metltylimide. C0H 1X ON. 
MW, 113. Plates. M.p. 45. B.p. 200. 
TN-Pkenyl : see under Acetylacetone. 

Combes, Combes, Bull, soc. chim,, 1892, 7, 
779. 



C 5 H 8 2 



^ 

CH 3 -CO-CH:C(OH)-CH 3 



M.p. 23. B.p. 139/746 mm. 
to 15% at 30, 34% at 80. Sol. 



MW, 100 

Sol. H 2 
dil. HC1. 

Misc. EtOH, Et 2 0, CHC1 3 all proportions. Df 
0-9721. < 1-45409. ^ = l-5xlO- 6 at 25. 
Heat of comb. C v 616-3 Cal. Forms salts with 
many metals. Ox. >- acetic acid. KOH > 
acetone + acetic acid. FeCl 3 > red col. 

Dioxime : prisms from Et 2 0. M.p. 149-50. 
Keduces Fehling's in cold. 

Monoanil : N - phenylacetylacetonamine. 
Plates from ligroin. M.p. 51-3. B.p. 285-6. 

Mono-methylphenylhydrazone : m.p. 98 B.p. 
165/12 mm. 

Enolform : 

M.p. 9. fli 5 1-4609. Eeadily passes into 
equilibrium mixture. 
Me ether: b.p. 58-9/10 mm. Df 0-9740. 

< 1-470. 

Et ether: b.p. 69-70/10 mm. Dl 6 0-9477. 

< 1-466. 

Acetyl: b.p. 95-6/20 mm Df 1-0483. < 
1-4507. 

Hippuric ester : plates from CHC1 3 . M.p. 
109. 

Knorr, Ber., 1911, 44, 2771. 
Claisen, Ann., 1893, 277, 168. 
Adams, Hauser, /. Am. Chem. $oc. ? 1944, 
66, 1220. 

Acetylacetonylguanidine . 

See 2-Amino-4 : 6-dimethylpyrimidinc. 
Acetylacetophenone. 
See Diacetobenzeno. 
Acetylacetylene . 
See l-Butyne-3-ono, 

Acetyl-di-alanine (Inactive acfityl-l-amino~ 
propionic acid) 



C 5 H 9 3 N MW, 131 

Needles or plates from H 2 0, M.p. 137-8. 

Sol. HnO, EtOH. InsoL MtjO. Hyd. by aoicb 

or 0/lkalis. 

B,HNO% : needles. M.p. 64-6. 
NH^ salt : needles + H 2 0, M.p. 100, 
Et ester: C^^N. MW, 169. Noedlos. 

M.p. 39^0, 
Amide : C 5 H, 02]Sr 2 . MW, 130. Cryst from 

H 2 0. M,p. 15/V. 
NtorO*: OJS.ON,. MW, 112. Leaflets. 

M.p. 102. Sol H 2 0, EtOH, Et 2 0, 

Fischer, Otto, Ber., 1903, 36, 2116, 

Acetylamidrazone , 
See Phenylhydrazidine. 



Acetylaminocarfoinol 



21 



Acetyl bromide 



Acetylaminocarbinol . 

See JV-Hydroxymethylacetamide. 

Acetylaminometliyl Alcohol. 

See ^-Hydroxymethylacetamide. 

p-Acetylaminoplienyi salicylate (Salopheri) 

NH-CO-CH.* 




C 15 H 13 4 N MW, 271 

White leaflets. M.p. 187-8. Sol. EtOH, 
Et 2 0, dil. alkalis. Alk. sol. turns blue on warm- 
ing. EeCl 3 > violet col. Odourless, taste- 
less. Analgesic and antipyretic. Tribolumin- 
escent. 

Brewster, J. Am. Chem. Soc. } 1918, 40, 
1136. 

Acetylanisoyl (Methyl p - methoxyphenyl 
diketone, methyl-p-methoxyphenylglyoxal) 



C 10 H 10 3 MW,178 

Yellow needles. M.p. 48 (45). Sol. EtOH, 
hot H 2 0. Volatile in steam. 

a-Oxime : needles from MeOH. M.p. 153. 

Dioxime : exists in two forms, (a) Needles 
from EtOH. M.p. 206. Diacetyl : needles from 
EtOH. M.p. 104. (b) Prisms. M.p. 125. 
Diacetyl : needles from EtOH. M.p. 89. 

Disemicarbazone : m.p. 235-6 decomp. In- 
sol. EtOH. 

Borschc, Ber., 1907, 40, 742. 

Acetylanthranil (Acetanthranil) 
CO 




C H 7 2 N MW, 161 

Cryst. from ligroin-EtOH. M.p. 79-80. 
B.p. 148-9/13 mm. DI 8 1-2034. %> 1-5686. 
Hyd, _^ acetylanthranilic acid. 

Brcdt, Hof, Bar., 1900, 33, 29. 
Lothrop, Goodwin, J. Am. Chem. Soc,, 
1943, 65, 363. 

Acetylanthranilic Acid (Acetyl-o-amino- 
benzoic acid, lappaconitic acid) 

/NcooH 

IJNH'CQ'CH 3 

C H O a N MW, 179 

Needles from AcOH. M.p. 186, Sol. Et.0, 

OflHfi, hot H 2 0, hot EtOH, Easily hyd. by dil. 

acids, k 2-3 X lO^ 4 at 25. 

Me ester : O lo H n O a N. MW, 193. Needles 
from EtOH. M.p.TOl . 



Et ester: CnH^OjN. MW, 207. Needles 
from EtOH. M.p. 64-5. 

Amide: C 9 H 10 2 N 2 . MW, 178. Needles 
from EtOH. M.p. 177. 

Methylamide : prisms from EtOH. M.p. 
171-2. 

Ethylamide : plates from EtOH. M.p. 140. 

Anilide : needles from EtOH. M.p. 167-8. 

Nitrile: C 9 H 8 ON 2 . MW, 160. Needles from 
H.O. M.p. 133. Volatile in steam. 

N-Jfe: C 10 H n 3 N - ^^^ 193 - Needles - 
M.p. 192-3. Amide : C 10 H 12 2 N 2 . MW, 192. 
Needles from EtOH. M.p. 155. 

T$-Acetyl : diacetylanthranilic acid. Prisms 
from EtOH. M.p.dSO . 

Kauffmann, Ber., 1909, 42, 3482. 
Bedson, King, J. Chem. Soc., 1880, 37, 762. 

Acetylarsan. 

See under 2-Aminoplienol-4-arsonic Acid. 
Acetylbenzoyl (Methyl phenyl di&etone, 
methylphenylglyoxal) 



CH 3 -CO-CO-C 6 H 5 

j8 ot 



MW, 148 



C 9 H 8 2 

Yellow oil. B.p. 222 (217-18), 164/116 
mm.,102/12mm. Df 1-0065. 4 1-537. Sol. 
in 380 parts H 2 at 20. Volatile in steam. 
Forms bisulphite comp. 

x-Oxime : oc-phenyl-a-isonitrosoacetone, phenyl 
acetyl ketoxime. Yellow needles from AcOH. 
M.p. 166-7. Acetyl : leaflets from EtOH.Aq. 
M!p!61-2. Benzyl ether: m.p. 62. 

$-Oxime : a-isonitrosopropiophenone, methyl 
benzoyl ketoxime. Needles from H 2 0. M.p. 

114-5*. ._ _. 

Dioxime : methylphenylglyoxime. JNeedles 
from EtOH.Aq. M.p. 238-40. a-Benzyl ether : 
leaflets. M.p. 157-8. Dibenzyl ether : needles. 
M.p. 55-6. 

u-Phenylhijdrazone : yellow needles from 

EtOH. M.p. 143-5. o 

Osazone : yellow cryst. M.p. 104-5 . Q 
Di-jt-nifrophenylhydrazone : m.p. 256-7 . 
x-Semicarbazone : m.p. 213. 
Disemicarbazone: m.p. 229-32. Spar. sol. 

most solvents. 

Borsche, Ber., 1907, 40, 740. 

Hartman, Boll, Organic Syntheses, XXIII, 

Wegmann, Dahn, Helv. Chim. Acta, 1946, 
29, 1247. 

Acetylbenzoylethane . 
See Phenacylacetono. 
Acetylbenzoylmetlxane . 
See Benzoylacetone. 
Acetyl bromide 

CH 3 'COBr 
C 2 H 3 OBr MW, 123 



Acetylbutyryl 



22 



Acetylene 



Colourless fuming liq. M.p. 96. B.p. 
81, 71/746 mm. DJ 6 1*6625. rig 145376. 

Gal, Ann., 1864, 129, 53. 
Burton, Degering, J. Am. Chem. Soc., 
1940, 62, 227. 



diketone, 



Acetylbutyryl (Methyl propyl 

methylpropylglyoxal, hexandione-2 : 3) 

CH 3 'CO-CO-CH 2 -CH 2 'CH 3 

C 6 H 10 2 " 3 MW, 114 

B.p. 128. Di 9 0-934. 

3-Oxime : methyl isonitrosobutyl ketone. 
Cryst. from EtOH. M.p. 60 (49-5). 

Dioxime : methylpropylglyoxime. Needles 
from Et 2 0. M.p. 175. Ni deriv. : orange 
needles from EtOH or C 6 H 6 . M.p. 159-60 
(144). Sol. EtOH, CHC1 3 , C 8 H 6 . 

2-Phenylhydrazone : cryst. from C 6 H 6 -ligroin. 
M.p. 113-14. 

3-Phenylhydrazone : m.p. 108-9. 

Osazone : yellow needles from CH fi . M.p. 
137-8. 

Dufraise, Moureu, Bull. soc. chim., 1927, 
41, 1370. 

Acetylbutyrylmethane . 

See Butyrylacetone. 
3-Acetylcamph.or 




CO-CH 3 

MW, 194 

Colourless oil, turning yellow in air. B.p. 
127-8/15 mm., 118-19^/11 mm. DJ 9 1-0314. 
< 1-49387. Sol. dfl. alkalis. FeCl 3 ^bluish- 
red col. 

Oxime : needles. M.p. 164. 
Cu deriv. : Cu(C 12 H 17 2 ) 2 . Dark green cryst. 
M.p. 200-2. Sol. org. solvents. 

Briihl, er. 9 1904, 37, 762. 

Acetylcaproyl (Methyl n-amyl diketone, 
methyl-n~amylglyoval, octandione-2 : 3, % 2 : 3-di- 
Jceto-octane) 

CH 3 -CO-CO"CH 2 -[CH 2 ] 3 -CH 3 
C 8 H 14 2 MW, 142 

B.p. 172-3 /733 mm. 

2-Oxime : isonitrosoethyl n-amyl ketone. M.p. 
39. B.p. 139/16 mm. 

%-Oxime : methyl isonitrosohexyl ketone. 
M.p.^59 (54). B.p. 133/11 mm. 

Dioxime : methyl-n-amylglyoxime. Needles 
from EtOHAq. M.p. 173. 

2~Phenylhydrazone : plates from EtOH. M.p. 
103-4. 

Osazone : yellowish-brown prisms from EtOH. 
M.p. 117-18. 

Ponzio, Gazz. chim. ital, 1901, 81, i, 406. 



Acetylcaproylmetiiane . 

See Caproylacetone. 

Acetylcarbinol. 

See Hydroxyacetone. 

Acetyl chloride 

CHg-COCl 
C 2 H 3 OC1 MW, 78-5 

Colourless fuming liq. M.p. 112. B.p. 
51-2. Sol. Et 2 0, C 6 H 6 , CHC1 3 , CS 2 . DJ 
1-1051. < 1-38976. H 2 > acetic acid + 
HC1. NH 3 .Aq. > acetamide. K 2 S > di- 
acetyl sulphide. CaI 2 $~ acetyl iodide. Na 
acetate > acetic anhydride. Alcohols > 
acetic esters. C 6 H 6 + A1C1 3 >- acetophenone. 
Aniline > acetanilide. 

Aschan, Ber., 1898, 31, 2346. 

Acetylcholine 

OH 

(CH 3 ) 3 N : CH 2 -CH 2 0-CO-CH 3 
C 7 H 17 3 N MW, 163 

Occurs in blood, spleen, ergot, and plants. 
Present as complex in brain. More sensitive 
than choline to dil. alkalis. Easily hyd. Physio- 
logical activity 1000 times greater than that 
of choline. 

Bromide : prisms from EtOH.Aq. M.p. 143. 
C^H^OzNCltAuClz : m.p. 166-8. 
2G 7 H lB 0<>NCl } PtCL : yellow needles from 
H 2 0. M.p. 242-4. 

Baeyer, Ann., 1867, 143, 325. 
Nothnagel, Arch. Pharm., 1894, 232, 266. 
Ewins, Biochem. J., 1914, 8, 44. 
Fourneau, Page, Bull. soc. chim., 1914, 

15, 550. 

Dudley, Biochem. J., 1929, 23, 1064. 
Gaddum, Annual Review of Biochemistry, 
1935, 4, 311. 

Acetylcoumaric Acid. 

See under Coumaric Acid, 
Acetyl cyanide. 
See under Pyruvio Acid. 
Acetyldibenzoylmethane . 
See 1 : 1-Dibenzoylacetono, 
Acetyldimethyl Ether. 
See Methoxyacetone. 
Acetyl disulphide. 
See Diacetyl disulphido. 
Acetylene (Mhine, ethyne) 

CH:CH 
C 2 H 2 MW, 26 

Colourless gas. B.p. 84. H 2 dim, 1 vol. 
at 18. Me 2 CO dies. 25 vols. at 15 and 760 
mm., 300 vols. at 12 atm., 2000 vols, at 80, 
EtOH dies. 6 vols., C 6 H 4 vole., AcOH 6 vole. 
at 18. Sol. CHC1 3 Vapour press, of liq, 
11 atm. at 23, 22 atm. at 0, 103 atm, at 
31. Sp. gr. (liq.) at 0, 0*451 ; solid at - 715, 
0-73. Heat of form. 50 Cal. Heat of comb. 



Acetylenecarboxylic Acid 



23 



Acetylene fltiorochloride 



C p 312-9 Cal. Crit. temp. 37. Crit. press. 
61-5 atm. Adds halogens to give di- and 
tetra-halogen comps. HOC1 > CHC1 2 -CHO. 
H 2 (+ catalyst) > CH 3 -CHO. Se0 2 > 
glyoxal. 

Na deriv. : C 2 HNa. Decomp. at 210-20. 
Insol. Et 2 0, C 6 H 6 . 

Cu deriv. : Cu 2 C 2 . Explodes at 120. Insol. 



H 2 0. 



Nieuwland, Vogt, The Chemistry of 
Acetylene, (Am. Chem. Soc. Monograph 
No. 99). 

Acetylenecarboxylic Acid. 

See Propiolic Acid. 

Acetylene chlorobromide (1 - Chloro - 2 - 
bromoethylene) 

CHCKCHBr 
C 2 H 2 01Br MW, 141-5 

B.p. 81-2. D 1-8157. 

Plimpton, J. Chem. Soc., 1882, 41, 393. 
Nesmeyanov, Bonsov, Chem. Abstracts, 
1946, 40, 2123. 

chloroiodide (l-Chloro-2-iodo- 



C 2 H 2 C1I 



Acetylene 

ethylene) 

CHCL'CHI 

MW, 188-5 

B.p. 119. D 2-2298. 

Thiole, Haakh, Ann., 1909, 369, 135. 
Nesmeyanov, Borisov, Chem, Abstracts, 
3946,40,2123, 3451. 



Acetylene 

ene) 

C 2 H 2 Br 2 



dibromide (&jm..-Dibromoethyl- 
CHBr.'CHBr 



MW, 186 

Cis : 

M.p. - 53. B.p. 112-5. Df B 2-2846. < <B 
] -54312. Reacts with ale. KOH 125 times more 
rapidly than trans isomer > bromoacetylene. 

Trans : 

M.p. - 6-5. B.p. 108. D} 7 ' 5 2-2667. rig* 
1-55054. 

van do Walle, Bull. sac. chim. Belg., 1913, 
27, 211. 



Di-Et ester : C 8 H 10 4 . MW, 170. B.p. 184 / 
200 mm., 107-8/13 mm. wjf 1-4405. Heat of 
comb. C, 5634 Cal. 

Diamide: C^O^Ng. MW, 112. Micro- 
cryst. powder. Decomp. at 294. Spar. sol. 
H 2 0, EtOH, Et 2 0, AcOH, CHC1 3 . 

Dinitrile: C 4 N 2 . MW, 76. Needles. M.p. 
21. B.p. 76/753 mm. Sublimes readily. D 



0-9703 
Cal. 



1-46471. Heat of comb. C, 6790 

Moureu, Bongrand, Ann. chim., 1920, 14, 

9. 

Musante, Gazz. chim. ital, 1935, 65, 199. 
Oilman, Haubein, J. Am. Chem. Soc., 

1945, 67, 1420. 

Acetylene dichloride (sym.-Dichloroethylene 
Dioform) 

CHC1ICHC1 
C 2 H 2 C1 2 MW, 97 

Cis: 

M.p. 80. B.p. 60. Df 1-2913 (1-2896). 
njf 1-45189. Reacts with KOH 20 times quicker 
than trans isomer > chloroacetylene. 



Acetylene-dicarboxylic Acid 

HOOC-C-C-COOH 
C 4 H 2 4 MW, 114 

Cryst. + 2H 2 from aq. Et 2 0. M.p. (anhyd.) n -p. .^ 
179. Sol. H 2 6, EtOH, BtgO. Very powerful ^W- 
acid. Metallic salts decomp, by hot H 2 0. B.p. 36 
NaHg, or Zn + AcOH > succinic acid. I 
-> di-iodofumaric acid. HC1, HBr, HI >- 
chloro-, bromo-, and iodo-fumarie acids. Hot 
H 2 > propiolic acid + C0 2 . 

DiMe ester; C e H e 4 , MW, 142. B.p. 195-8 
part, decomp. 98/20 mm. DJ M564. < 
1-4434. C 2 H 2 FC1 



M.p. 50. B.p. 48. D 1 / 1-2651. n% 
1*44903. 

Chavanne, Compt. rend. 3 1912, 154, 776. 
Ott, Ber., 1942, 75, 1517. 

Acetylene di-iodide (sym.-Di-iodoethylene) 

CHL'CHI 
C 2 H 2 I 2 MW, 280 

Ois: 

Colourless liq. M.p. 14. B.p, 188 de- 
comp., 72-5/16 mm. D 20 3-0625. Reacts with 
1% ale. KOH 200 times qiiicker than trans 
isomer > iodoacetylene. KCN in EtOH >- 
maleic acid. 

Trans : 

Prisms from EtOH. M.p. 78 (73). B.p. 
192, 77/16 mm. Sublimes. Volatile in steam. 
D 21 3-303. KCN in EtOH > fumaric acid. 

Keiser, Am. Chem. J., 1899, 21, 265. 
Gaade, Mec. trav. chim., 1946, 65, 823. 

Acetylenediurene. 
See Glycoluril. 

Acetylene fluorobromide 
bromoethylene) 

CHBr.'CHF 



(aym.-Fluoro- 



MW, 125 



D 16 ' 5 1-6939. 



Swarts, Chem. Zentr., 1909, II, 1414 : 
Bull soc. chim., 1919, 25, 153. 



Acetylene 

chloroethylene) 



fluorochloride 
CHC1ICHF 



(aym.-Fluoro- 



MW, 80-5 



Acetylene tetrabromide 



24 



Acetylisocaproyi 



B.p. 10-11. Sol. EtOH. Insol. H 2 0. 

Swarts, Chem. Zentr., 1903, I, 13 ; Bull 

soc. chim., 1919, 25, 153. 
Lamb, Mast, U.S.P., 2,377,297, (Chem. 

Abstracts, 1945, 39, 4081). 

Acetylene tetrabromide. 
See 52/m.-Tetrabromoethane. 
Acetylene tetrachloride. 
See st/m.-Tetrachloroethane. 
Acetylenylbenzene . 
See Phenylacetylene. 
Acetylenylcarbinol . 
See Propargyl Alcohol. 
Acetylenylf Tiran . 
See Eurylacetylene. 
2-Acetylenylisolmtyric Acid 
See l-Pentyne-4-carboxylic Acic 



oee i-jreniyue-^-ua.ruoAyj.iu AUIU. 
l-Acetylenyl-3-propynylethane . 
See 1 : 5-Heptadi-yne. 
Acetyl fluoride 

CH 3 -COF 
C 2 H 3 OF MW, 62 

Colourless liq. B.p. 20-1. D 1-032. Sol. 
EtOH, Et 2 0, AcOH, CHC1 3 , C 6 H 6 . Spar. sol. 
CS 2 . D 15 1-002. Decomp. by H 2 0. Reacts 
similarly to CH 3 COC1 but less vigorously. 

Meslans, Compt. rend., 1892, 114, 1020. 

Mashentsev, J. Applied Chem. U. S.S.It., 
1941, 14, 816, (Chem. Abstracts, 1943, 
37, 1990) : 1946, 16, 203, (Chem. 
Abstracts, 1947, 41, 706). 

Acetylglycine (Acetylaminoacetic acid, 
aceturic acid, acetylglycocoll) 

CH 3 -CO-NH-CH 2 -COOH 
C 4 H 7 3 N MW, 117 

Cryst. from H 2 0. M.p. 206. Sol. H 2 to 
2-7% at 15. Mod. sol. EtOH, Spar. sol. 
Me 2 CO, CHC1 3 , AcOH. Insol. Et 2 0, C*H 6 . 
Hyd. by acids or alkalis, k = 2-3 X 10~* at 
25. Cu, Ag, and Ba salts sol. H 2 0. 

Me ester : C 5 H 9 3 N. MW, 131. M.p. 58-9. 
B.p. 254/712 mm. Sol. H 2 0, EtOH, CHC1 3 ,C 6 H S . 

fit ester : C 6 H U 3 1S[. MW, 145. Leaflets from 
Et 2 0. M.p. 48*. B.p. 260/712 mm., 145/14 
mm. Sol. H 2 0, EtOH, Et 2 0, CHC1 3 , C 6 Hj. 

Chloride: C 4 H 6 2 NC1. MW, 135-5. Plates 
from acetyl chloride. Decomp. at 115-18. 

Amide : C 4 H 8 2 N 2 . MW, 116. Plates from 
H 2 0. M.p. 137. Sol. H 2 0, EtOH. Insol. 
Et 2 0. Hyd. by hot H 2 0. 

Hydrazide : prisms from EtOH-Et 2 0. M.p. 
115. B,HCl: m.p. 177. 

"N-Phenyl : see under Phenylglycine. 

Kadenhausen, J. prakt, Chem., 1895, 52, 
437. 

Acetylgly collie Acid. 

See Acetoxyacetic Acid. 



Acetylhydroperoxide . 
See Peracetic Acid. 
Acetyliminodiacetic Acid 



MW, 175 
MW, 203. M.p. 



C 6 H 9 5 N 

Di-Me ester: C 8 H 13 5 ]Sr. 
84. B.p. 184 /15 mm. 

Diamide: C B IL^O^. MW, 173. Needles 
from MeOH. Decomp. at 203. Sol. hot H 2 0. 

Di-nitrile : oil. B.p. 227/16 mm. Acids or 
alkalis > acetic + iniinodiacetic acids. 

Jongkees, Rec. trav. chim., 1908, 27, 310. 

Acetyl iodide 

CH 3 -COI 
C 2 H 3 OI MW, 170 

Colourless liq. B.p. 108, 36 /50 mm. D 17 
1*98. Fumes strongly in air, and turns brown 
with pptn. of iodine. H 2 > acetic acid + HI. 
Thiele, Haakh, Ann., 1909, 369, 145. 

Acetylisoamylmethane . 

See Isoamylacetone. 

Acetylisobutyryl (Methyl isopropyl diketone, 
methylisopropylglyoxal, 2-methylpentandione~3 : 4) 

CH 3 -CO-CO-CH(CH 3 ) 2 

C 6 H 10 2 4 $ MW, 114 

Yellow liq. B.p. 115-16. Spar. sol. H 2 0. 

DJ 1 0-9215. 
3-Oxime : methyl isonitrosisobutyl kotone. 

Plates from EtOH. M.p. 75. 



4-Oxime : isonitrosoethyl isopropyl ketono. 
Teedlep ^v-^w TT A TVT^ o/<" \7^i4.^i^ ; 

steam, 



Needles from H 2 0, M.p. 



Volatile in 



Dioxime : methylisopropylglyoximo. Noodles 
from C 6 H 6 . M.p. 155-8. 

Osazone : yellow needles from EtOH. M.p 
117. 

Pauly, Lieck, Ber., 1900, 33, 503. 
Adams, Buls, U.S.P., 2,393, 593, (Chem. 
Abstracts, 1946, 40, 2466). 

Acetylisobutyrylmethane . 

See Isobutyrylaeetone. 

Acetylisocaproyi (Methyl isoamyl diketone, 
methylisoamylglyoxal, Z-methytheptandione-ft : 6) 

CH 3 -CO-CO-CH 2 "CHj-CH(CH 3 ) 2 
C 8 H u O a 6 " MW, 142 

Dl 0-8814. 

isonitrosoisoamylacetono. Cryst, 
from pet. ether. M.p. 32-3. B.p. 1JJ8 / 
18 mm, 

Dioxime : methylisoamylglyoxime. Needles 
from EtOH.Aq. M.p. 172-3 8 (n7-8). 

B-Phenylhydrazone : needles from EtOH, 
M.p. 92-3. 

ft-Phenylhydrazone : needles froM OgH^** 
ligroin. M.p, 99-100. 



B.p. 163 



Acetylisovaleryl 



25 



Acetylsalicylaldeliyde 



Osazone : needles from EtOH.Aq. M.p. 114. 
Otte, v. Pechmann, Ber., 1889, 22, 2123. 

Acetylisovaleryl (Methyl isobutyl diketone, 
methylisobutylglyoxal, 2-methylhexandione-4: : 5) 

CH 3 -CO-CO-CH 2 -CH(CH 3 ) 2 
C 7 H 12 2 4 MW, 128 

B.p. 138. Df 0-908. 

4-Oxime : methyl isonitrosoisoamyl ketone. 
Leaflets. M.p. 42. Sol. EtOH, Et 2 0, alkalis 
with intense yellow col. Spar. sol. cold H 2 0. 
Sublimes. 

5-Oxime : isonitrosoethyl isobutyl ketone. 
Needles from EtOH.Aq. M.p. 64-5. 

Dioxime : methylisobutylglyoxime. Leaflets 
from EtOHAq. M.p. 171-2. Ni deriv.: 
orange needles. M.p. 160. 

4:-Phenylhydrazone : yellow needles. M.p. 
94. 

5-Phenylhydrazone : m.p. 98. 

Osazone : needles. M.p. 116-17. 

v. Pechmann, Ber., 1889, 22, 2122. 

Acetylmesityl oxide (2-Methylheptene-2- 
dione-4: : 6, 4 : 6-diketo-2-methylheptene-2) % 

(CH 3 ) 2 C:CH-CO-CH 2 -CO-CH 3 
C 8 H 12 2 MW, 140 

B.p, 204-6. Sol. alkalis. Ale. FeCl 3 > 
red col. 

Cu deriv. : olive-green powder. M.p. 123. 
Sol. Et 2 0, C e H 8 , ligroin, hot EtOH. 

Claisen, Ehrhardt, Ber., 1889, 22, 1013. 

Acetyl nitrate 

CH 3 -CO-ON0 2 
C 2 H 3 4 N MW, 105 

Colourless, hygroscopic fuming liq. B.p. 22 / 
70 mm. D 16 1-24. Explodes violently if sud- 
denly heated. Hyd. by H 2 to acetic and nitric 
acids. Powerful nitrating agent. Toluene > 
o- and some jp-nitrotoluene. Acetanilide >~ 
o-nitroacetanilide. 

Pictet, Khotinsky, Ber., 1907, 40, 1164. 

Acetyl peroxide (Diacetyl peroxide) 

CH 3 -CO-0-0-CX>CH 3 
C 4 H 4 MW, 118 

Oryst. M.p. 26-5 (30). B.p. 63/21 mm. 
Exceedingly explosive. Very pungent odour. 
Aq. sol, slowly evolves 2 . 

Walker, /, Chem. Soc., 1928, 2041. 
D'Ans, Friedrich, Z. anorg. allgem. Chem,, 
1912, 73, 357. 

Acetylphenanthrene . 

See Acetophenanthrene. 

Acetylphenol. 

See Hydroxyaoetophenone. 

Acetylphenylenediamine . 

See Aminoacetanilide. 



Acetyl phosphate 

CH 3 -CO-0-PO(OH) 2 

C 2 H 5 5 P MW, 140 

Decomp. m sol. Isolated as Ag salt. 

Lynen, Ber., 1940, 73, 367. 

Lipmann, Tuttle, J. Biol. Chem., 1944, 

153, 571. 
Bentley, J. Am. Chem. Soc., 1948, 70, 

2183. 

Acetyl phosphite 

CH 3 CO-0-P(OH) 2 
C 2 H 5 4 P MW, 124 

Small plates. M.p. approx. 110 decomp. 
Sol. H 2 0, EtOH. 

Wedenski, J. Euss. Phys. Chem. Soc., 
1888, 20, 31. 

Acetylpropionyl (Methyl ethyl diketone, 

methylethylglyoxal, 2 : 3-diketopentane, pentane- 
dione-2 : 3) 

CH 3 -CO-CO-CH 2 -CH 3 



C 5 H 8 2 



108 



MW,100 

Sol. 15 parts H 2 O 
Zn+H 2 S0 4 



Leaflets. 



YeUow liq. B.p. 
at 15. DJ 9 0-9565. n$ 140135. 
> methyl ethyl ketol. 

2-Oxime : isonitrosodiethyl ketone. 
M.p. 69-71 (60-2). 

3-Oxime : methyl isonitrosopropyl ketone. 
Leaflets. M.p. 58-9 (54-5). B.p. 183-7 part. 
decomp. Sol. EtOH, Et 2 0, CHC1 3 , alkalis 
(yellow sols.). 

Di-Me acetal : b.p. 162-3. DJJ 0-973. 
Dioxime : methylethylglyoxime. Needles 
from EtOH. M.p. 172-3 part, sublimation. 
Sol. EtOH. 

2-Phenylhydrazone : m.p. 102-3. 
$-Phenylhydrazone : m.p. 116-17. 
Bis-2 : 4-dinitrophenylhydrazone : m.p. 280-1. 
Osazone : yellow needles from C 6 H 6 . M.p. 
166-7. 

Manasse, Ber., 1888, 21, 2177. 

Adams, Buls, U.S.P., 2,393,532, (Chem. 

Abstracts, 1946, 40, 2466). 
Hearne, Adams, Buls, B.P., 586,754, 
(Chem. Abstracts, 1947, 41, 6894). 

unsym . - Acetylpropionylethane 

See Methylpropionylacetone. 
Acetylpr opionylmethane . 
See Propionylacetone. 
Acetylsalicylaldehyde 

CHO 

/\0-CO-CH 3 

C 9 H 8 3 MW, 164 

Needles from pet. ether or EtOH. M.p. 38- 
9. B.p. 253, 142/18 mm. Sol Et 2 0, EtOH. 
> ptirple col. Forms bisulphite comp. 



Acetylsalicylic Acid 



26 



Aconitic Acid 



Semicarbazone : powder from Me 2 CO. M.p. 
167. 

Phenylhydrazone : plates from EtOH. M.p. 
141-2. 

o-Nitrophenylhydrazone : red needles from 
EtOH. M.p. 160. 

m-Nitrophenylhydrazone : red needles from 
EtOH. M.p. 165. 

p-NitropJienylhydrazone : red needles from 
EtOH or AcOH. Yellow needles + iC 6 H 6 from 
C 6 H 6 ~ligroin. M.p. 185-6. 

o-Tolylhydrazone : yellow needles from 
EtOELAq. M.p. 111. 

o-Bromophenylhydrazone : needles from. EtOH. 
M.p. 114. 

p-Bromophenylhydrazone : plates from EtOH, 
C 6 H 6 , or ligroin. M.p. 137-8. 

Perkin, Ann., 1868, 148, 203. 
Rivals, Compt. rend. } 1897, 124, 369. 

Acetylsalicylic Acid (o-Acetoxybenzoic acid, 
Aspirin) 

COOH 

^0-CO-CH, 



MW, 180 

White cryst. M.p. 135 (rapid heat.). Liq. 
solidifies at 118. Sol. EtOH to 20%. Sol. 
Et 2 0, CHC1 3 . Sol. 100 parts H 2 at 37. 
Slowly hyd. by H 2 0. Gives no col. with FeCl 3 . 
k = 3-27 x 10- 4 at 25. Analgesic and anti- 
pyretic. 

Me ester: C 10 H 10 4 . MW, 194. Colourless 
cryst. M.p. 49 6 . Sol. EtOH. Insol. H 2 0. 

Et ester: C,,H 12 4 . MW, 208. Colourless 
iiq. B.p. 272. 

Phenyl ester : C 15 H 12 4 . MW, 256. Acetyl- 
salol. M.p. 97. B.p. 197-8/ll mm. 

Benzyl ester: C 16 H 14 4 . MW, 270. Cryst. 
M.p. 25-6. 

Kaufmann, Ber., 1909, 42 5 3482. 

Ciusa, Sollazzo, Chem Zentr., 1943,11, 615. 

Acetyl sulpMde. 
See Diacetyl sulphide. 
Acetyltartaric Acid. 
See under Tartaric Acid. 
Acetylthiopliene . 
See Acetothienone. 
Acetylvalerylmethane . 
See Octandione-2 : 4. 
AcidoL 

See under Betaine. 
Aconic Acid 



MW, 128 

..-- --B . . M.p. 164. Sol. 

5-6 parts H 2 at 15. Salts are sol, H 2 0. HC1 
or HBr > chloro- or bromo-itaconic acid. 



Cryst. from H 2 or EtOH. 



Me ester: C 6 H 6 4 . MW, 142. Prisms. 
M.p. 85. Sol. EtOH, Et 2 0. 

Tittig, Ann., 1883, 216, 91. 

Aconine 

C 21 H 25 0(OCH 3 ) 4 (OH) 4 N 
C 25 H 41 9 N MW, 499 

Hyd. product of aconitine. Amorph. Sol. 
H 2 O, EtOH, CHC1 3 . Prac. insol. Et 2 O, pet. 
ether. Dextrorotatory. 

B,HCl,2H 2 0: decomp. at 169-70. [a] 

3-70 in H 2 0. 

Tetra-acetyl deriv. : decomp. at 240-1. [a]| 

32-5 in CHC1 3 . 

Majima, Suginom6, Morio, Ber., 1924, 57, 

1456. 
Craig et al } J. Biol Chem., 1944, 154, 293. 

y-Aconine (Pseudaconine) 

C 20 H 22 (OCH 3 ),(OH) 4 NCH 3 
C 25 H 41 8 N MW, 483 

Hyd. product of ^-aconitine, Colourless 
cryst. + !Me 2 CO from Me 2 CO. M.p. 93-4. [og? 
+ 38-7 in H 2 0. 

Tetra-acetyl deriv. : m.p. 228. [a]J> 8-1 in 
EtOH, 

Henry, Sharp, /. Chem. Soc., 1928, 1105. 

Aconitic Acid (Propylene-1 : 2 : 3-tricarb- 
oxylic acid) 



H 900H 



900H 900H 



COOH CH 2 -COOH 



C 6 H 6 6 



__p 

. _^ 

H CHa'COOH 

MW, 174 

Trans- (I) : 

Leaflets from H 2 0. M.p. 194-5. Hoi. 6-5 
parts H 2 at 33, 2 parts 88% EtOH at 12. 
Spar. sol. Et 2 0. Bocomp. at the m.p. or by 
heat, with H 2 at 180 to itaoonic acid | (K)l. 
k (first) = 1-58 x 10- 3 at 25 (1-30 X 10 3 at 
25); k (second) = 3-5 X KH at 25. Heat of 
comb, a 481-32 Cal. (476-3), O p 475-4 CaL 
NaHg > tricarballylic acid. Jllk at H)() n 
>- bromotricarballylic acid. Brown eliorry- 
red col, changing to fusohin rod, with A a 6/ 

Me esters: C 7 H 8 . MW, 188, The throe 
possible esters hare been prepared, a. Prinmn 
from Me 2 CO~-C 6 H 6 . M.p. 136-7. p. 
from Me 2 CO-CeH 6 . M.p. 144-5. y. 
from MegOO-CgHfl. M.p. 154-5, 

Tri-Me ester: C 9 H 12 . MW, 2 IB, B.p. 
270, 170-80/20 mm., 16l/14 mm. <>l 
EtOH, EtgO. 

Tri-M "eater : C l2 H 18 O r MW 5 258, Oil, 
B.p. 275 decamp., 250-3 /2GO mm., l74-5/22 
mm., 184r-6/12 mm, Df 1-1064, < 1 -45502. 

Tripropyl ester : C 16 H 24 @ . MW, 300. B.p. 
195/13mm. 



Aconitine 



27 



Acridiae 



Adds Br more 



Trichloride: C 6 H 3 3 CL. MW, 229-5. B.p. 
155-7/20mm. * 

Triamide: C 6 H 9 O 3 N 3 . MW, 171. Needles. 
Turns brown at 250. Sinters without melting 
at about 260. Sol. hot BLO. Insol. EtOH, 
Et 2 0, CHC1 3 . 

Anhydride : m.p. 134-5. 

Cis- (II) : 

M.p. 125. Heat. ^ tram. 
easily than trans. 

Me esters : a. Prisms 
M.p. 101-2. (3. Prisms 
M.p. 102-4. y. Prisms 
M.p. 126-7. Irradiation 
trans- esters. 

Anhydride : m.p. 74. 

Monoanilide : (-CH 2 -CO-NH-C 6 H 5 ). Pale 
yellow prisms from EtOH. M.p. 170 decomp. 

Dianilide : may be from I or II. (1) Needles 
from EtOH. M.p. 188-9. (2) Needles from 
EtOH. M.p. 199-200. 

Malachowski, Maslowski, Ber., 1928, 61, 
2521, 2525. 



from Me 2 CO-C 6 H 8 . 
from Me 2 CO~C 6 H 6 . 

Me 2 CO-C 6 H 6 . 

corresponding 



from 

gives 



Aconitine 



(OH) 3 

(OCH 3 ) 4 

0-COCH 3 

0" 



CWH 47 U N MW, 647 

Principal alkaloid of Aconitum napellus, Linn, 
(monkshood) and other species. Colourless 
cryst. M.p. 204. [a] D + 17-3 in CHC1 3 . Aq. 
sol. alk. to litmus. 

B,HCl: cryst. Decomp. at 170-2. [oc] D 
- 29-2 in H 2 0. 

J3,Hr: m.p. 176-80. [a] D -29-1 in 
H 2 0. 

JB,HAu(\: m.p. 157-8, 136 (air-dried), 
151-2 (dried at 100), 138-40 (from Me 2 CO), 
177 (from CHC1 3 ). 

Styphnate : m.p. 120. 

Majima, Proc. Imper. Acad. Tokyo, 1929, 
5, 415. 

v|/-Aconitine (Pseudaconitine, nepaline, acetyl 
veratroyl-t//~aconine) 

C 29 H 28 4 (OCH 3 ) 6 (OH) 2 NCH 3 
C 36 H 51 12 N MW, 689 

From Aconitum deinorrhizum, Stapf., and A. 
JBalfourii, Stapf. Needles from Et 2 0. M.p. 
214 slight decomp. Sol. EtOH, Et 2 0. Prac. 
insol ILO- [a] B + 17-06 in EtOH, + 22-75 
in CHC10. Hyd. > ^-aconine + acetic and 
veratric *acids. 



H 2 0. 



m.p. 179-82, 
m.p, 199. 



[ag> - 18-1 in 
al?? - 18-5 



O: m.p. 230. 

Hcf) : m.p. 198. [a]? - 17-95 in 
H 2 0. 

B.HAuCl^: m.p. 233. 
B,HC10 4 : m.p. 239. 
Oxalate: m.p. 216. 
Picrate : m.p. 196. 

Henry, Sharp, J. Chem. Soc., 1928, 1105. 
Marion, Edwards, J. Am. Chem. 8oc. t 
1946, 68, 2565. 



C 36 H 51 12 N 



c-y- Aconitine 

MW, 689 

From Aconitum napellus. Colourless prisms 
from Et 2 or MeOH. M.p. 205-6 decomp. 
[a]ff +24-7 in CHC1 3 . Hyd. > ,/r-aconine + 
acetic and veratric acids. 

B,HI: needles from MeOH-Et 2 0. M.p. 
220. 

B.HCIO^ : plates from MeOH, Me 2 CO. M.p. 
246 decomp. 

Marion, Edwards, J. Am. Chem. Soc. 3 
1946, 68, 2565. 

Acorone 
C 15 H 24 2 MW, 236 

Sesquiterpene diketone present in essential oil 
of sweetflag (Acorus calamus, Linn.). M.p. 100. 
[a]Jf + 139-5 in EtOH. 

Di-semicarbazone : m,p. 205-7 decomp. [oc]JJ 
+ 437 in Py. 

Sorm, Herout, Chem. Abstracts, 1949, 43, 
3808 ; 1950, 44, 9384. 

Acr aldehyde. 

See Acrolein. 
Acrichine. 

See Atebrin. 

Acridan (5 : I0-Dihydroacridine } niB-dihydro- 
acridine) 

CH, 




C 13 H n N MW, 181 

Prisms from EtOH. M.p. 169. Sol. Et 2 0, 
hot EtOH. Insol. H 2 0. Sublimes. Does not 
form salts. Cr0 3 > acridine. 

Graebe, Caro, Ann., 1871, 158, 278. 

Acridine 




n 



C 18 H 9 N 1N MW, 179 

Needles or prisms. M.p. 111. Boils above 
360. Sublimes at 100. Sol. EtOH, Et 2 0, 



Acridme-5-aldebyde 



28 



a-Acritol 



CS 2 . Spar. sol. hot H 2 0. Sols, show blue fluor. 
Volatile in steam. KMn0 4 > acridinic acid. 
NaHg > acridan. 

(E,HCl)zHgCl 2 : yellow needles. M.p. 235. 

B,CHgCOCl: yellow needles. M.p. 236. 

Acid oxalate : cryst. from H 2 0. M.p, 162 
decomp. 

sym. - Trinitrobenzene add. comp. : yellow 
needles from EtOH. M.p. 115. 

Note.~ The following numbering of the acridine 
ring is also employed, particularly in German 
literature : 



CO 




Meyer, Hofmann, Monatsh., 1916, 37, 698. 
Ullmann, Ber., 1907, 40, 2521. 

Acridine-5-aldeh.yde 

3HO 





C U H 9 ON 1N MW, 207 

Yellow needles from EtOH. M.p. 139-40. 
Sol. EtOH, Et 2 0, C 6 H 8 . Spar. sol. H 2 0. 

o-Nitrophenylhydrazone : yellow, m.p. 191. 

2 : 4^-Dinitrophenylhydrazone : yellow, m.p. 
235. 

Bernthsen, Mnhlert, Ber., 1887, 20, 1547. 
Acridine-l-carboxylic Acid 



OOH 



C M Hg0 2 N MW, 223 

Yellow cryst. from EtOH.Aq. M.p. 189-90. 

Albert, Goldacre, /. Chem. Soc., 1946, 706. 

Acridine-3-carboxylic Acid. 

Buff cryst. from aq. cellosolve. Decomp. 
without melting at 270. 

* Albert, Goldacre, /. Chem. Soc., 1946, 706. 

Acridme-5~carboxylic Acid. 

Yellow needles. Unchanged at 300. Sol. 
EtOH. Spar. sol. H 2 0. Dil. alk. sol. > blue 
fluor. Heat, above 300 >- acridine and C0 a . 

Me ester: C 15 H n 2 N. MW, 237. M.p. 

127-8. 

Bernthsen, Muhlert, Ber., 1887, 20, 1549. 
Eisleb, Chem. Zentr., 1937, 1, 604. 
Braz, Gortinskaya, Chem. Abstracts, 1941, 
35, 4025. 

Acridinic Acid. 

See Quinoline-2 : 3-dicarboxylic Acid. 




Acridone 



NH 

C 13 H 9 ON MW, 195 

YeUow leaflets from EtOH. M.p. 354. Sol. 
hot EtOH, hot AcOH, ale. KOH. Insol. Et 2 O, 
C 6 H 6 , CHC1 3 . EtOH sol. fluor. blue. Distils 
undecomp. Sol. warm cone. H 2 S0 4 , cryst. on 
cooling, or ppd. unchanged by H 2 0. Insol. aq. 



acridine. PCL 



5- 



alkalis. Zn dust 
chloroacridine. 

N-Jfe: 14 H 1X ON. MW, 209. YeUow 
needles from EtOH. M.p. 203-5. Anil : yel- 
low needles from EtOH.Aq. M.p. 162-3, 

N-JW : C 15 H 13 ON. MW, 223. Prisms from 
EtOH. M.p. 159. 

TS-Phewyl: Ci 9 H 13 0]Sr. 
from toluene. MT.p. 276. 

Bamberger, Ber., 1909, 42, 1707. 
Allen, McKee, Organic Syntheses, 1939, 
XIX, 7. 



MW, 271. Cryst. 



Acrifla,vine (Trypaflavine) 




C 14 H 15 N 3 C1 2 MW, 296 

Red needles or prisms ; orange noodles from 
EtOH. Sol. H 2 0, MeOH, EtOH. Dil. aq. sol 
yellow with green fluor. H 2 S0 4 >- yellow sol. 
with blue-green fluor. Used as disinfectant for 
wounds and has a trypanocidal action in sleeping 
sickness. Commercial product usually contains 
a proportion of the unmethylatod base (hydro- 
chloride of the 2 : 8-diaminoacridino), 

Benda, Ber., 1912, 45, 1787. 

Grandmougin, Simonis, Ber., 1913, 46, 
3425. 

Acrifoline (Alkaloid 27) 

C 16 H 23 2 N MW, 261 

Alkaloid from Lycopodium acrifolium, (Iforu.), 
N. Comb. (L. annotinum yar. acrifolium, Fern.). 
M.p. 97. 
B,HCIO^ : m.p. 266. 

Manske, Marion, J, Am. Chem. tioc, 9 1947, 
69, 2126. 

Acriquine. 
See Atebrin. 
a-Acritol (dl-Mannitol) 

H H OH OH 
HOOH a -6 6 fi (J)-CH a OH 

OH OK H H 
C,H M S MW, 182 



Acrolein 



29 



Acrylic Acid 



M.p. 168. Sol. hot H 2 0. Spar. sol. EtOH. cc-Acrosone (Sl-Glucowne) 



Dil. HNQ 



- ^-mannose. 



Lespieau, Wiemann, Compt. rend., 1932. 

194, 1946. 
Fischer, Ber., 1890, 23, 383. 

Acrolein (Acrylic aldehyde, acraldehyde, 
propenal) 

CH 2 :CH-CHO 
C 3 H 4 MW, 56 

M.p. 87. B.p. 52. Unstable. Polymer- 
ises to disacryl, a white translucent solid. Sol. 
2-3 parts H 2 0. DJ 0-8410. < 1-39975. Be- 
duces NH 3 .AgN0 3 . HC1 >- 2-chloropropion- 
aldehyde. PC1 5 > CH 2 :CH-CHC1 2 , 

Di-M acetal: b.p. 123-4. Spar. sol. H 2 0. 
D 16 0-8543. 

Cyanhydrin : vinylglycollic nitrile. B.p. 94/ 
17 mm. DJ 5 1-009. Sol. H 2 0. Insol. pet. 
ether. 

Oxime : b.p. 35/9 mm. D 15 0-996. 

Semicarbazone : cryst. from EtOH-Et 2 0. 
M.p. 171. 

2 : 4:-Dinitrophenylhydrazone : reddish -orange 
cryst. from EtOH. M.p. 165. 

Benzoylhydrazone : cryst. from EtOH-Et 2 O. 
M.p. 175-7. 

Doebner, Ber., 1902, 35, 1137. 
Bremner, Jones, Beaumont, /. Chem. $oc., 

1946, 1018. 

Wilson, B.P., 569,625, (Ohem. Abstracts, 

1947, 41, 6275). 

Acrolein dibromide. 

See 1 : 2-Dibromopropionaldehyde. 
Acronycidine 

C 15 H 15 6 N MW, 289 

Alkaloid from the bark of Melicope fareana. 
Needles. M.p. 136-5-137-5 . 

Hughes, Lahey, Price, Webb, Nature, 

1948, 162, 223. 

ot-Acrose (dl-Fructose, methose) 




GBLOH 



>H H 



C 6 H 12 6 MW, 180 

Syrup. Reduces Fehling's. NaHg > a- 
aciitoL 

Qsazone : acrosazone, ^Z-phenylglucosazone. 
Yellow needleB from EtOH.Aq. M.p. 205. 
Insol. H 2 0. HC1 > glucosone. 
Fischer, Ber., 1890, 28, 387. 

p-Acrose. 

See Sorbose. 



90 




H'9OH 

H-9 

CH 2 OH 
C 6 H 10 6 MW, 178 

Syrup. Sol. hot EtOH. Zn + AcQH >. 
a-acrose. H 2 at 140 > furfural. 

l-Benzoyl-3 : 4 : Q-triacetyl : cryst. from EtOH. 
M.p. 116. [a]*? + 144-3 in CHC1 3 . 

1-Acetyl-S : 4 : 6-tribenzoyl : cryst. from 
EtOH. M.p. 131-2. [a] D + 29-5 in Py. 

Eischer, Tafel, Ber., 1889, 22, 98. 



Acrylic Acid (Vinylformic acid) 



MW, 72 
with H 2 aU 



B.p. 101. 
114. B.p. 



CH 2 :CH-COOH 
C 3 H 4 2 

M.p. 13. B.p. 141. Misc. 
proportions. Polymerises at b.p. DJ 6 1-0621. 
< 1-4224. Jc = 5-6 X 10~ 5 at 25. Heat of 
comb, (solid) 326-6 Gal. NaHg or Zn + H 2 S0 4 
> propionic acid. HBr, HC1 > 2-halo- 
genopropionic acid. KOH fusion > acetic + 
formic acids. 

Me ester : C 4 H 6 2 . MW, 86. B.p. 85. D 
0-977. TI$ 1-3984. Polymerises on long stand- 
ing. 

Et ester: C 5 H 8 2 . MW, 100. 
D 0-9252. 

Propyl ester: C 6 H 10 2 . MW, 
123. D 0-92. 

Isopropyl ester : b.p. 108-12. 

n-Butyl ester: C 7 H 12 2 . MW, 128. B.p. 
39/10 mm. 

Isobutyl ester : b.p. 130--4 . 

Allyl ester : C 6 H 8 2 . MW, 112. B.p. 120-4. 

Phenyl ester : C 9 H 8 2 . MW, 148. B.p. 202- 
3, 105 /20 mm. 

Benzyl ester: C 10 H 10 2 . MW, 162. B.p. 
228, 110-18 /8 mm. 

Chloride: C 3 H 3 OCL MW, 90-5. B.p. 75. 
D 1-14. < 1-4343. 

Amide : C 3 H 5 ON. MW, 71. Leaflets from 
C 6 H 6 . M.p. 85. Sol. H 2 0, EtOH, Et 2 0, 
CHCL. Polymerises on heating. 

Anhydride: C 6 H 6 3 . MW, 126. B.p. 
35mm. D 1-094. 

N-Methylamide : C 4 H 7 ON. MW, 85. 
220 decomp., 127-9/30 mm. D 1-018. 

TS-Ethylamide : C 5 H 9 ON. MW, 99. 
128-30 /25 mm. D 0-978. 

N-Diethylamide : C 7 H 13 ON. MW, 127. 
101-7 /10 mm. 

Nitnle: vinyl cyanide, cyanoethylene. C 3 H 3 N. 
MW,53. B.p. 78. Sol.H 2 0. Forms constant 



97 / 
B.p. 
B.p. 
B.p. 



Acrylic Acid Oxide 



30 



Actinodaplmine 



boiling mixture with H 2 0, containing 12-5% 
H 2 0. 

Anilide : m.p. 104-5. 

o-Toluidide : m.p. 109-10. 

p-Toluidide : m.p. 141. 

Fisher, Batchford, Smith, Ind. Eng. 

Chem., 1944, 36, 229. 
van der Burg. Eec. trav. chim., 1922, 41, 

21. 
Wohlk, J. praU. Chem., 1900, 61, 212. 

Acrylic Acid Oxide. 

See Glycidic Acid. 

Acrylic Aldehyde. 

See Acrolein. 

Acrylophenone (Vinyl phenyl ketone) 

C 6 H 5 -CO-CH:CH 2 
C 9 H 8 MW, 132 

Oil. B.p. 115/18 mm. Decomp. on heating 
at atm. press. Volatile in steam. Phenyl- 
hydrazine > 1 : 3-diphenylpyrazoline. 

Norris, Cough, J. Am. Chem. Soc., 1920, 
42, 2331. 

A . C . T .H . (Adrenocorticotrophin, cortico- 
trophin, adrenocorticotropic hormone). 

Hormone of the anterior pituitary gland, used 
in rheumatoid arthritis therapy. The natural 
material is, or is closely associated with, a 
protein, but highly active material of poly- 
peptidic nature can be prepared by controlled 
hyd. of the protein-like material. 

Protein. Isolated from pig and sheep 
pituitaries. MW, 20,000 (from sedimentation 
and diffusion data). Isoelectric point (by mov- 
ing boundary electrophoresis), pH 4-65-4-70 
(4.7-4-8). Sedimentation rate at 20, 2-08 X 
10- 13 (2-04-2-11 x 10" 13 ) cm./sec./dyne. Dif- 
fusion const, at 20, 10-4 x 10~ 7 cm. 2 /sec. Di- 
symmetry const. (f/f ), 1-1. Contains no phos- 
phorus, carbohydrate or cysteine. Contains 
tryptophan (1-0%), tyrosine (4*5%), methionine 
(1-93%), cystine (7-19%). Very sol. H 2 0. 
Pptd. by 2-5% trichloroacetic acid, 20% 
sulphosalicylic acid, 5% lead acetate. In- 
activated by CH 2 :C:0, HN0 2 , H-CHO, Ac 2 0, 1 2 
and esterification. Heat-stable. Inactivated in 
30 mins. at 100 by 0-llf/NaOH. Stable for 60 
mins. in boiling 0-1J//HC1. 

Low MW material. Obtained by hyd. of the 
protein (18% cleavage by trypsin, 50% cleavage 
by pepsin or 30% cleavage by HC1 at 37-4). 
Highly active material contains 7-9 amino- 
acid residues. Very highly active material has 
MW, 2,500-10,000. 

Li, Evans, Vitamins and Hormones, 1947, 
5, 198 (Bibl). 

Astwood, Tyslowitz, Federation Proceed- 
ings, 1942, 1 (Pt. 2), 4. 

Li, Evans, Simpson, Science, 1942, 96, 
450; J. Biol Chem,, 1943, 149, 413. 



Sayers, White, Long, Proc. Soc. Exptl. 

Biol. Med., 1943, 52, 199; J. Biol. 

Chem., 1943, 149, 425. 
Wilhelmi, Sayers, J. BioL Chem., 1948, 

176, 175. 
Burtner, J. Am. Chem. Soc., 1943, 65, 

1238. 
Li, Federation Proceedings, 1945, 5 (Pt. 

2), 144. 
Smith, Brown, Ghosh, Sayers, J. Biol. 

Chem., 1950, 187, 631. 
Li, J. Am. Chem. Soc., 1951, 73, 4146. 
Hess, Harris, Carpenter, Li, ibid., 5918. 

Actidione 



CH 3 -CH 



CO 



9H-OH 

9H 2 

CH 




O 

C^H^N NH MW, 281 

Antibiotic from Streptomyces griseus. M.p. 
119-5-121. [a]f? - 3-38 in EtOH. 
Acetyl : m.p. 150-2. 
p-Nitrobenzoyl : m.p. 215-20 decomp. 
Semicarbazone : cryst. + 1H 2 0. M.p. 187-8. 
Kornfeld, Jones, Parke, /. Am. Chem. 

Soc., 1949, 71, 150. 

Leach, Ford, Whiffen, J. Am. Ohem. Soc. f 
1947, 69, 474. 

Actiniasterol 
C 27 H 44 MW, 384 

Isolated from non-saponifiablo portion of 
sea-anemones (Anemonia sulcata). Leaflets 
fromMeOH. M.p. 145-6. [a]^ 42-5. Corn- 
tains 2 ethylenic linkages. Gives no m.p. 
depression with cholesterol. 

Acetyl : cryst. from MoOH or AcOEt. M,p- 
126-7. 

Klenk, Diebold, Z. physiol Ghem., 1935, 
236, 141. 

Actinodaplmine 




C 18 H 17 4 N 



Suggested structure 



MW, 311 



Actinomycin 



31 



Adenosine 



Constituent of bark of Actinodaphne hookeri. 
Needles from EtOH. M.p. 210-11. Sol. 
EtOH, Me 2 CO, CHC1 3 , C 6 H 6 . Mod. sol. Et 2 O. 
Insol. H 2 O. [a]* + 32-77 in EtOH. H 2 S0 4 
>. red > -purple col. 

B,HCl: needles from EtOH~Et 2 0. M.p. 
280-1 decomp. [aft + 8-75 in H 2 0. 

B,HI : needles from EtOH. M.p. 264-5 
decomp. 

B 2 ,H 2 S0 4 : needles + 3H 2 O from EtOH.Aq. 
M.p. (anhyd.) 249-50 decomp. 

Methiodide : cryst. from EtOH-Et 2 0. M.p. 
243-4. 

Acetyl deriv. : prisms from AcOEt. M.p. 
229-30. 

Benzoyl deriv. : m.p. 232-3. 

Picrate : needles + H 2 from EtOH.Aq. De- 
comp. at 220-2. 

Ghose, Krishna, Schlittler, Helv. Chim. 

Acta, 1934, 17, 919. 

Krishna, Ghose, /. Indian Chem. Soc., 
1932, 9, 429. 

Actinomycin 

C 41 H 58 O n N 8 MW, 838 

Pigment of Actinomycetes. Bed prisms 
+ 5H 2 from MeOH, EtOH or AcOEt-light 
petroleum. M.p. 255. [0$ -367. Shows 
ultraviolet absorption max. at 237-240 (E 
238) and 442-444 m^ (EJ 161). Very sol. 
Me 2 CO, CeH*, CHC1 3 , AcOH. Mod. sol. AcOEt, 
MeOH, EtOH, %-butyl alcohol. Spar. sol. 
Et 2 0, H 2 0. Insol. light petroleum. Sol. dil. 
min. acids. Insol. alkalis. EtOH-KOH > 
sol. with dark violet col. which fades. Hyd. > 
threonylproline + Z-threonine + sarcosine + d~ 
valino + Z-methylvaline + Z-proline. 

Dalgleiish, Johnson, Todd, Vining, J. 

Chem. Soc., 1950, 2946. 
Lehr, Berger, Arch. Biochem., 1949, 23, 

503. 

Actinorhodine 

C 23 H 20 10 _ MW.456 

Quinonoid pigment from Actinomycetes. Red 
noodles. Sol. Py, tetrahydrofuran, dioxan. 
Sol. alkalis with blue col. H 2 S0 4 > deep blue 
col, with H 3 B0 3 > reddish- violet col. Ab- 
sorption max. iii butyl alcohol at 571 and 553 
nx|ju 

Triacetyl deriv. : yellow needles. M.p. 260 
decomp. 

Brockmann, Pinni, Naturwiss., 1947, 34, 
190. 

Activin. 

See Ohloramiao-T. 

Adalin (l-Bromo-l-ethylbutyrylurea, bromod^- 
ethylacetyturea, Uradal) 

(C 2 H 5 ) a CBr-CO-NH-CONH 2 
r MW, 237 



Exists in two crystalline forms, both stable at 
room temp. Rhombic modification changing to 
the monoclinic at 70, m.p. 117. Cryst. from 
MeOH, EtOH, Me 2 CO, C 6 H 6 or ligroin. M.p. 
115-6. Sol. EtOH, Me 2 CO. Spar. sol. H 2 0. 
Heat, with H 2 O > diethylhydantoin. Hyp- 
notic and sedative. 

Bayer, D.R.Ps., 225,710, 240,353, 243,233, 
249,906, 253,189, 271,682. 

Beckmann, D.R.P., 262,048. 

Adamantane 




C 10 H 16 MW, 136 

M.p. 268 (252-3). D 1-07. n D 1-568. 
Camphor odour. 

Landa, Machacek, Chem. Abstracts, 1933, 

27, 2792. 
Prelog, Seiwerth, Ber., 1941, 74, 1769. 

Adamsite. 

See 10-Chloro-5 : 10-dihydrophenarsazine. 
Adenine (6-Aminopurine) 

rC-NH 2 HN 9INH 

J " " ~ 

I 

C 5 H 5 N 5 MW, 135 

Needles + 3H 2 from H 2 0. M.p. (anhyd.) 
360-5 decomp. (rapid heat.). Sol. hot H 2 0. 
Spar. sol. EtOH. Insol. Et a O, CHC1 3 . Sub- 
limes at 220. HN0 2 > hypoxanthine. 
FeCl 3 > red col. 

Acetyl deriv. : leaflets from H 2 0. Yellow at 
260. 

Di-acetyl : m.p. 195 decomp. 
Monochloroacetyl deriv. : m.p. 163 decomp. 
Monobenzoyl deriv. : m.p. 234-5. 
Picrate : decomp. 279-81. 

Traube, Ann., 1904, 331, 64. 
Todd et al, J. Chem. Soc., 1943, 386. 
Hoffer, Jubilee Vol. Emil Barrell, 1946, 
428, (Chem. Abstracts, 1947, 41, 4108). 

Adenosine 



CH 2 OH 




C 10 H 13 4 N 6 



MW, 267 



Adenosine diphosphate 



32 



Adenylic Acid b 



Occurs in heart muscles, etc. Cryst. from Adenylic Acid (Muscle adenylic acid, adeno- 
H 2 0. M.p. 229. [a] 63*3. sine & -phosphate) 

Triphenylmethyl ether: m.p. 259-60. [a]| 
- 8-8 in GHC1 3 . 

Picrate : m.p. 182. 

Levene, Tipson, J. Biol Chem., 1932, 97, 
491. 

Szent-Gyorgyi, Drury, Journal of Physio- 
logy, 1930, 68, 213. 

Embden, Zimmermann, Z. physiol. Chem., 
1927, 167, 114. 

Davoll, Lythgoe, Todd, J. Chem. Soc., 
1948, 967. 

Adenosine diphosphate (Adenosine pyro- 
phosphate) 





P. P. 

3 CH 2 0-P'0-P'OH 

OH 6H 



C 10 H 14 7 N 5 P MW, 347 

RTucleotide isolated from muscle. Needles 
from H 2 or EtOBLAq. M.p. 195, [a]?, 
41-78inH 2 0. 

Ostern, Biochem. Z., 1932, 254, 66. 
Lohmann, ibid., 381. 

Steudel, Z. physiol. Chem., 1933, 216, 77. 
Klimek, Parnas, Biochem. Z., 1932, 252, 

392. 
Baddiley, Todd, J. Chem. Soc., 1947, 648. 

Adenylic Acid a (Adenosine %' -phosphate) 
-0- 




I-CBLOH 



C 10 H 14 6 N 4 P 



MW, 347 



C 10 H 15 10 N 5 P 2 MW, 427 

Degradation product of cozymase and aden- 
osine triphosphate. 

Acridine salt : yellow prismatic needles. M.p. 
215 decomp. 

Lohmann, Biochem. Z., 1935, 282, 109, 
Gulland, Walsh, /. Chem. Soc., 1945, 

169. 

Lythgoe, Todd, Nature, 1945, 155, 693. 
Baddiley, Todd, /. Chem. Soc., 1947, 648. Isolated from yeast ribonucleic acid. Amor- 
phous. Turns brown at 170-80. M.p. 205-15 
decomp. 

Di-brucine salt : needles from H 2 0. M.p. 
165-75. 

Acridine salt : yellow needles from EtOH.Aq. 
M.p. 215 decomp. 

Carter, Cohn, Federation Proceedings, 

1949, 8, 190. 

Brown, Haynos, Todd, J. Chem. Soc., 

1950, 3299. 

Brown, Todd, /. Chem. Soc,, 1952, 44. 

Adenylic Acid b (Yeast adenylic acid, adeno- 
sine B' -phosphate) 

. . Q. 



Adenosine triphosphate (A.T.P.) 




Isolated from muscle extracts. 

Tri-acridine salt : egg-yellow needles. M.p. 
208-9 decomp. 

Acridine salt : (ATP) 2 (acridine) 5 : lemon- 
yellow crystals. M.p. 218. 

Lohmann, Naturwiss., 1929, 17, 624; 

Biochem. Z., 1931, 233, 460 ; 1932, 254. 

381 ; 1935, 282, 120. 
Fiske, Subbarow, Science, 1929, 70, 381. 
Baddiley, Michelson, Todd, J". Chem. Soc. f 

1949, 582. 




OHjOH 



MW, 347 



Adermin 



Adipic Acid 



Isolated from yeast ribonucleic acid. Bods 
from hot H 2 O. M.p. 194. 

Di-brucine salt : rods from H 2 O. M.p. 177. 
Decomp. at 225. 

Monoacridine salt : yellow needles. M.p. 
175 decomp. 

Di-acridine salt : m.p. 184. 

Tipson, J. Biol. Chem., 1937, 120, 621. 
Levene, Harris, J. Biol. Chem., 1932, 98, 

9. 
Brown, Todd, J. Chem. Soc., 1952, 44. 

Adermin (Vitamin B 6 , 2-methyl-3-hydroxy- 
4 : 5>~di-(hydroxymethyl)-pyridine, pyridoxin, 3- 
hydroxy-4 : 5-dimethylol-a.-picoline) 

CH 2 OH 
HOCI 



C 8 H n 3 N 




MW, 169 



Part of vitamin B complex which prevents 
or cures acrodynia-like dermatitis in young 
rats. Best source is rice husks but cane mol- 
asses, yeast, wheat germ and cod liver oils are 
good sources. Needles from Me 2 CO. M.p. 160. 
Sublimes readily. FeCl 3 > reddish-brown col. 
Silicotungstate and reineckate crystallise well. 

B,HCl: cryst. from EtOH-Me 2 CO. M.p. 
206-8, 

3-Jfe ether : C 9 H 13 3 N. MW, 183. Needles 
from CHCL-pet. ether. M.p. 89-5-90. ,HCl : 
m.p. 150. 

4:~M ether : Ci H 15 3 N. MW,197. M.p. 134. 

Triacetyl : viscous oil. B.p. 145~5070-2 mm. 

Tribenzoyl : m.p. 121-2. 

Picrate : m.p. 156. 

Kuhnetf al., Naturwiss., 1939, 27, 469; 

Ber. 9 1939, 72, 305, 309, 310. 
Harris, Folkors, /. Am. Chem. Soc., 1939, 

61, 1245, 3307. 

Greene, /. Biol. Chem., 1939, 130, 513. 
Todd, </. Chem. Soc., 1941, 429. 
Mowatt et al., J. Am. Chem. Soc., 1943, 

65, 954. 
Hoffcr, U.S.P., 2,410,938, (Chem. Abstracts, 

1947,41, 1395). 
Szabo, U.S.P., 2,410,531, (Chem. Abstracts, 

1947, 41, 1714). 

Adipaldehydic Acid (Adipic semialdehyde, 
%-formylvaleric acid) 

CH 2 -CH 2 -CHO 
CH 2 -CH 2 -COOH 
C H 10 3 MW, 130 

B.p. 151-3V20 mm., 144 /8 mm. D 15 1-15. 
n?) 1 " 6 1-4489. rolymerises on, standing to trimer, 
m.p. 131. 

M ester : b.p. 97-8/10 mm. < 1-4280. 

Semicarbazone : m.p. 159-60. 

Diet, of Org. Oomp. I. 



MW, 146 

HN0 3 . M.p. 
mm., 244/50 



p-Nitrophenylhydrazone : m.p. 134. 

2 : 4-Dinitrophenylhydrazone : m.p. 1401. 

Harries, Neymann, Ber., 1908, 41, 3557. 

Treibs, Ber., 1939, 72, 1194. 

Baer, J. Am. Chem. Soc., 1942, 64, 1416. 

Adipamic Acid. 

See under Adipic Acid. 

Adip amide. 

See under Adipic Acid. 

Adipic Acid (Butane-l : 4:-dicarboxylic acid) 

9H 2 -CH 2 -COOH 
CH^CH 2 -COOH 
C 6 H 10 4 

Monoclinic cryst. from liot 
149-50 (153). B.p. 265/100 
mm., 216/15 mm., 205/10 mm. Sol. H 2 0' to 
1-5% at 15. Sol. EtOH. Spar. sol. Et 2 0. 
Jc (first) = 3-76 x 10- 5 at 25 ; k (second) = 
2-4 x 10- 6 at 25. Sublimes. Heat, of comb. 
C v 668-6 Cal. Metallic salts mostly sol. H 2 0. 
Dist. Ca salt >- cyclopentanone. 

Me ester: C 7 H 12 4 . MW, 160. M.p. 3. 
B.p. 162/10 mm. 

Di-Me ester : C 8 H 14 4 . MW, 174. Freezes 
at 0. M.p. 8. B.p. 112/10 mm. 

Et ester : C 8 H 14 4 . MW, 174. M.p. 28-9. 
B.p. 169-70 111 mm. 

Di-Et ester: C 10 H 18 4 . MW, 202. B.p. 
245, 130/14 mm. 

Dipentyl ester : m.p. 14. 

Dihexyl ester : m.p. 9 to 7. 

Diheptyl ester : m.p. 3-8-4-5. 

Dioctyl ester : m.p. 9-5-9-8. 

Dinonyl ester : m.p. 21-6. 

Didecyl ester : m.p. 27-4. 

Diundecyl ester : m.p. 34-7. 

Didodecyl ester : m.p. 39*3. 

Ditridecyl ester : m.p. 45*9. 

Ditetradecyl ester : m.p. 49-4. 

Dipentadecyl ester : m.p. 55. 

Dihexadecyl ester : m.p. 57 '3. 

Diheptadecyl ester : m.p. 61-8. 

Dioctadecyl ester : m.p. 63*4. 

Di-phenyl ester : C 16 H 18 4 . MW,274. Plates 
from EtOH.Aq. M.p. 105-6. 

p-Nitrobenzyl ester : cryst. M.p. 106. 

Phenacyl ester : cryst. from EtOH. M.p. 88. 

p-Bromophenacyl ester ; cryst. from AcOH. 
M.p. 153. 

p~Phenylphenacyl ester : cryst. from Me 2 CO. 
M.p. 148. 

Bichloride : C 6 H 8 2 C1 2 . MW, 183. B.p. 
130-2/18 mm., slight decomp. 

Amide : adipamic acid. C 6 H n 3 N. MW, 
145. Needles from H 2 0. M.p. 125-30. 

Diamide : adipamide. QgH 12 2 N 2 . MW, 
144. M.p. 220. Ac 2 or P0 > dinitrile. 

Di-'N-methylamide : 

Di-'N-dimethylamide : 
M.p. 85. 




M.p. 152-3. 
Cryst. 



Adipic-dialdeliyde I 

Anhydride: C 6 H 8 3 . MW, 128. M.p. 22, 
B.p. 98-100/0-l mm. Polymerises with trace 
of H 2 0. 

Di-nitrile : I : 4-dicyanobutane. C 6 H 8 N 2 . 
MW, 108. M.p. 0-1. B.p. 295, 181/20 
mm. Sol. EtOH, CHC1 3 . Insol. H 2 0, CS 2 , 
Et 2 0. D$ 0-951. < 1-4597. 

Anilide : needles from H 2 0. M.p. 151-3. 

Di-anilide: needles from EtOH. M.p. 240-1, 

Mannich, Hancu, Ber., 1908, 41, 575. 

Feagan, Copenhaver, /. Am. Chem. Soc., 
1940, 62, 869. 

du Pont, U.S.P., 2,220,734, (Chem. Ab- 
stracts, 1940, 34, 6302) ; B.P., 494,236, 
(Chem. Abstracts, 1939, 33, 2539); 
U.S.P., 2,196,357, (Chem. Abstracts, 
1940,34, 5093). 

Aronow, U.S.P., 2,191,786, (Chem. Ab- 
stracts, 1940, 34, 4394). 

Machinskaya, Veseloskaya, /. Applied 
Chem. U.8.S.E., 1944, 17, 377, (Chem. 
Abstracts, 1945, 39, 3738). 

Korshak, Pakhomov, Chem. Abstracts, 

1942, 36, 3488. 

Henne, Hill, J. Am. Chem. Soc., 1943, 65, 

752. 
Ellis, Organic Syntheses, Collective Vol. I, 

2nd. Edition, 18. 

Adipic-dialdeliyde (Hexandial-l : 6) 
OHC-CH 2 -CH 2 -CH 2 -CH 2 CHO 
C 6 H 10 2 MW, 114 

B.p. 92-4 /9 mm. Sol. EtOH, Et 2 0, C 6 H 6 . 
Spar. sol. H 2 0. Polymerises on long standing. 
Dioxime : needles from H 2 0. M.p. 185-6. 
Di-semicarbazone : m.p. 206. 
Di-diethyl acetal : b.p. 155 /20 mm. 

Wohl, Schweitzer, Ber. } 1906, 39, 894. 
Henne, Perilstein, J. Am. Chem. Soc., 

1943, 65, 2183. 

Adipin Ketone. 

See Cyclopentanone. 

Adipoin. 

See 2-Cyclohexanolone-l. 

Adlumine 



CH0 




C 21 H 21 6 N MW, 383 

Alkaloid from Adlumiafungosa, Greene, M.p. 
180. 

Manskc, Can. J. Research, 1933, 8, 210, 
404. 



Adonitol (RiUtol) 

OH <j)H 
HOCH 2 C 0- 

H H H 



Adrenaline 



-CH 2 OH 



MW, 152 

Prisms from H 2 0. M.p. 102. Sol. H 2 O, hot 
EtOH. Insol. Et 2 0, ligroin. Does not reduce 
Fehling's. 

Di-triphenylmethyl ether : cryst. M.p. 141-5. 

2 : 4:-Methylene ether : m.p. 86. 

1:3:2: 4:-Dimethylene ether : m.p. 145. 

Lespieau, Compt. rend., 3198, 206, 1773 ; 

Advances in Carbohydrate Chemistry, 

1946, 2, 117. 

Fischer, Ber., 1893, 26, 633. 
Raphael, J. Chem. Soc., 1949, 544. 
Hann, Hudson, /. Am. Ghem. Soc., 1944, 

66, 1906. 

Adonose (Urythro-2-Jcetopentose, ribulose) 



HO-9- 
H-9-OH ^ 
H-9'OH | 

CH 2 -J 
C 6 H 10 5 MW, 150 

o-Nitrophenylhydrazone : orange needles from 
EtOH. M.p. 168-169-5. [a]^ + 48*3 3 
in MeOH. 

Syrup, [a]^ + 15-8. Py. > Z-arabinose. 
o-Nitrophenylhydrazone : orange needles from 
EtOH. M.p. 168-9 decomp. [a]}? - 47-5 in 
MeOH. 

p-Nitrophenylhydrazone : cryst. powder from 
AcOEt. M.p. 121-3, [V& 1 - 48-7. 

Glatthaar, Reichstein, fletv. Chim. Acta, 

1935, 18, 80. 
Reichstein, Helv. Chim. Ada, 1934, 17 y 

996. 

Levene, Tipson, J. JSiol Ghem,, 1036, 115, 
731. 

Adrenaline (l-[3 : k-Dihydroxyphenyl]* 2- 
methylaminoethanol) 



HO 



C 9 H 13 O a N MW, 

Z-. Epinephrine, Supmrenin, Ileminne. 

Active constituent of suprarenal gland* 
Cryst. M.p. 211-12 (215 rapid heat.), Sol, 
AcOH, min. acids, caustic alkalis, [a]j I53 r> 
in HCL FeClg > green col. Kcduoes Foh- 
ling's. Weakly alkaline to litmus* 

B,HCl : m.p. 157. 




Adrenalone 



35 



Aesculetin 



d-. 

Decomp. at 211-21. [a]*? + 50-5 in HC1. 

dl-. 

Decomp. at 230. Less physiologically active 
thanZ-base. 3 : 4:-Diacetyl : m.p. 168. B,HCl : 
m.p. 155-6. 

Ott, Ber., 1926, 59, 1068. 
Ciocca, Chem. Abstracts, 1934, 28, 4398. 
Bertrand, Bull. soc. chim., 1904, 31, 1188. 
Abderhalden, Bergell, Ber., 1904, 37, 
2024. 

Adrenalone (3 : 4:-Dihydroxy-p-methylamino- 
acetophenone) 

90-CH 2 -NHCH 3 




C 9 H n 3 N 



MW, 181 



Needles. M.p. 235-6 decomp. (darkens at 
200). Spar. sol. H 2 0, EtOH, Et 2 0. Red > 
adrenalin. FeCl 3 > emerald col. Similar 
physiological activity to adrenalin. 

B,HCl : plates +1 H 2 from EtOH. M.p. 
240 decomp. (243-4). 

Tribenzenesulphonyl : m.p. 106-7. 

Hochst, D.R.P., 152,814, (Chem. Zentr., 

1904, II, 270). 
Stolz, Ber., 1904, 37, 4152. 
JMedmann, Chem. Zentr., 1906, I, 1620. 

Adreno chrome 

0=/\ - 9HOH 



Suggested structure 

C H 9 3 N " MW, 179 

Brick red. M.p, 125-30. Very sol. H 2 0, 
EtOH. Unstable in solution (pH 4 at 
optimum conditions). Red, > leuco-adreno- 
chrome, [oftf 79-2. 

Oxime : orange needles +1H 2 0. M.p. 192 
decomp., +1|H 2 0, m.p. 278. 

p - N itrophenylhydrazone : brown needles 
+ 4H 2 from dioxan, m.p. 200 decomp. 

Groen, Richter, Biochem. J., 1937, 31, 

596. 

Voer, Rec. trav. chim., 1942, 61, 638. 
Bergol, Morrison, /. Chem. Soc., 1943, 48. 
MacCarthy, Chemie et Industrie, 1946, 55, 

435. 
Frankel, Allers, Biochem. Z., 1909, 18, 

401; ibid., 22, 131. 

Adrenocorticotropic Hormone. 
See A.C.T.H. 



Adrenodiamine 
C 12 H 12 2 N 2 MW, 216 

Phenolic base isolated from adrenal glands of 
cattle. Needles from EtOH. M.p. 219-21 
decomp. FeCl 3 > red col. Couples with 
diazotised ^-nitroaniline. Millon's reagent > 
green sol., turning brownish-red on warming. 
Gibbs' reagent > blue col. Absorption 
maxima in EtOH at 231, 271 and 300 m.(jL. 

B,2HCl : rosettes of needles from EtOH- 
AcOEt. M.p, 215-6 decomp. Loses HC1 in 
vacuo at 110. 

0-Monoacetyl: m.p. 176-7 decomp. No 
col. with FeCl 3 . 

Pfiffner, North, /. Biol. Chem., 1940, 132, 
461. 



Adrenosterone 

trione) 



(t^-Androstene-S : 11 : 17- 



C 19 H 24 3 




MW,300 



Constituent of the adrenal cortex. Leaflets 
from Et 2 or EtOH. M.p. 222 (corr.). Sub- 
limes in vacuo. [a]?, + 262 5 in EtOH. 
Absorption band at about 240 mpt. No cortical 
hormone activity, but has male sex hormone 
activity (J activity of androsterone). 

Disemicarbazone : cryst. from EtOH. Gradu- 
ally decomp. at about 270. 

Eeichstein, Helv. Chim. Acta, 1936, 19, 

61, 1125; 1937, 20, 979. 
Sarett, J. Am. Chem. Soc., 1946, 68, 2478. 

Adurol. 

See Bromohydroquinone. 
Aegelenine. 
See y-Fagarine. 
Aesculetin (Esculetin, 6 : 7-dihydroxycoumarin) 

CH 




C 9 H 6 4 MW, 178 

Needles + 1H 2 0. Prisms from AcOH. M.p. 
276. Sol. hot EtOH, dil. alkalis. Spar. sol. 
Insol. Et 2 0. Reduces Fehling's and 
IfeCl 3 - > green col. 
see Scopoletin. 

C 10 H 8 4 . MW, 192. Needles 
M.p. 184. Acetyl : needles from 
164-6. 
E 10 4 . * MW, 206. M.p. 143 



NH 3 .AgN0 3 . 
6 -If e ether : 
l~Me ether 

from MeOH. 

EtOH.Aq. M. 
7-Et ether 



Di-Me ether: CuILo 
fromH^O. M.p. 144: 



MW, 206. Needles 



Aesctilin 

Di-Et ether: C 13 H 14 4 . MW, 234. Plates 
from EtOH.Aq. M.p. 109. 
Diacetyl : prisms from EtOH. M.p. 133-4 . 
Dibenzoyl : cryst. M.p. 185-6. 
Di-p-nitrobenzoyl : cryst. M.p. 207-8. 

Merz, Arch. Pharm., 1932, 270, 476. 
Gattermann, Kobner, Ber., 1899, 32, 288. 
Bert, Cowpt. rend., 1942, 214, 230. 

Aesculin (Esculin, 6- $-glucosido-l-hydroxy- 
coumarin) 

CH 

C 6 H U 



gg Aetiocholanic Acid 

Ruzieka, Goldberg, Bosshard, Helv. CMm. 

Ada, 1937, 20, 547. 
Hildebrandt, U.S.P., 2,238,936, (Chem. 

Abstracts, 1941, 35, 4920). 




Joo 

C 15 H 16 9 MW, 340 

Occurs in bark of horse chestnut, Aesculus 
hippocastanum, Linn., and roots of wild jasmin, 
Gelsemium semgervirens, Ait. Prisms + 2H 2 0. 
M.p. 205 decomp. Sol. 670 parts H 2 at 10. 
Sol. 24 parts boiling EtOH. Sol. AeOH, 
AcOEt, alkalis. Spar. sol. Et 2 0. Aq. sol. 
fluor. blue. [oc]J> 8 _ - 14-6 in MeOH. Man. 
acids > aesculetin + glucose. 

Me ether: C 16 H 18 9 . MW, 354. Needles 
fromH 2 0. M.p. 225. 

Tetra-acetyl deriv. : m.p. 181-2. [a]? - 21 
in MeOH. 

Penta-acetyl deriv. : needles from EtOH. 
M.p. 130. 

Merz, Hagemann, Naturwiss., 1941, 29, 

650; Ghem. Zentr., 1942, II, 2038. 
Merz, Arch. Pharm., 1932, 270, 476. 
Seka, Kallir, Bar., 1931, 64, 622. 
Macbeth, J. Chetn. Soc., 1931, 1288. 
Bochleder, Schwarz, Ann., 1853, 87, 
186. 

Aetioallocholane . 

See Androstane. 
Aetioallocholanone . 

See Androstanone. 

Aetiocholane~3oc : 17|3-diol (Testane~3<x : 17(3- 
dial) 

on, 




HO-'" 

C 19 H 32 2 MW, 292 

Isolated from male urine. Needles from 
EtOKAq. M.p. 232, [oc] D + 26-5 in EtOH. 
No physiological activity. 

Diacetyl: leaflets from EtOH. M.p. 125 
corr. 

Butenandt, Ischermng, Danneaberg, 2* 
phytiol Chem,, 1937, 24?8, 205. 



Aetiocholane-3a-ol~17-one (S-Isoandro- 
sterone, testane-3u-ol-l7 -one) 




HO'*' 

MW, 290 

Needles from hexane. M.p. 153 corr., 139-5 
(low melting form). [a] p + 105. No physio- 
logical activity in 1000 y doses. 

Benzoyl : m.p. 165-6. 

JSemicarbazone of acetyl deriv. : cryst. from 
EtOH. M.p. 254r-5. 

Ruzicka, Goldberg, Meyer, Brunggcr, 
Eichenberger, Helv. Ohim. Acta* 1934, 
17, 1405. 

Aetiocholane-3p-ol-17-one 

17 -owe) 




C 19 H 30 2 MW, 290 

Needles from hexano. M.p. 151-2 corr., 
115-17 (low melting form). [a| -|- 89. No 
physiological activity in 1000 y doses. 

Acetyl : m.p. 157-8. 

Semicarbazone of acetyl : cryst. from EtOH. 
M.p. 244-5. 

Buzicka, Goldberg, Meyer, Briinggor, 
Eichenberger, II eh. Chim. Ada, 1934. 
17, 1406. 

Aetiocholanic Acid 




20 H 32 2 MW, 304 

Noodles from AcOH. M.p, 227*5-229. 
Me ester : needles from MoOK* M;p. 97- 
100. 

Boiohstein et al, I/elv. Ohm* Acta f J937, 
20, J040; 1938, 21,828. 



Aetiolithocliolic Acid 
Aetiolithocholic Acid 




37 Aetioporpliyrin III 

Aetioporpliyrin II (Isoaetioporphyrin, 
1:4:5: 8-tetrametkyl-2 : 3 : 6 : i-tetraethylporpbin) 



-, COOH 



HO 

^20 H 323 MW, 320 

Needles from MeOH or Me 2 CO. M.p. 273-5. 
Sol. MeOH, Me 2 00. Spar, sol Et 2 0. [aft 8 
+ 50 2 in dioxan. 

Me ester : needles from Et 2 0-pentane. M.p. 
141-2. 

Acetyl: cryst. from Bt 2 0-pentane. M.p. 
225-6. 

Reichstein et al. } Helv. Chim. Acta, 1937, 
20, 952. 

Aetiophyllin. 

See under Aetioporphyrin III. 



CH, 



CH 
V 



CJEL 



=CH- 




NH 



N 



CH 



=CH- 



C 32 H 38 N 4 



C 2 H 5 I=ICH 3 

MW, 478 
from Py. M.p. 



Synthetic. Black prisms 
360-6. Sublimes in vacuum. 

Cu salt: C 3 2H 36 N 4 Cu. Bed needles from 
CHCl 3 -AcOH. 

Fe salt : C 32 H 36 Isr 4 FeCl. Brown prisms from 
CHCl 3 -Et 2 0. 

Mg salt : C 32 H 36 N 4 Me. Leaflets from Et 2 0. 

P^crate : B,3C 6 H 3 7 N 3 . Red prisms from 
Et 2 0. M.p. 223. 

Picrolonate: B,2CH0N. Red needles 



oee unaer jfiemoporpnyrin ill. -* *wwitufi& . a^,xjw 10 xj. 8 v/5^ 4 . 

Aetioporphyrin I (1:3:5: 7-Tetramethyl- from CHCl 3 -Me 2 CO. M.p. 228. 



2:4:6: S-tetraethylporphin) 



/V~ 

CH 

NH 



N 



CH 



MW, 478 

Synthetic. Violet prisms from CHCL-MeOH. 
M.p. 400-5. Sol. AcOH, Ac 2 0, Py, C 6 H 6 . 
Sublimes unchanged. 

Ni salt : C 32 H 36 N 4 Ni. Needles + |Py from 
Py. M.p. 327 U . 

Co salt : C 32 H 36 N 4 Co. Needles from Py. 
M.p. 337. 

Zn salt : C 32 H 36 N 4 Zn. Needles from C 6 H 6 . 
M.p. 243. 

Mg salt : C 32 H 36 N 4 Mg. Violet prisms from 
MeOH. M.p. 347-9. 

Picrate: C 32 H 38 N 4 ,2C 6 H 3 7 N 3 . Violet prisms 
from Me 2 CO~-MeOH. M.p. 232. 

Picrolonate : B,2C 10 H 8 N 4 5 . Reddish-brown 
needles from CHCl 3 -MeOH. M.p. 262. 

Styphnate : B,2C 6 H 3 8 N 3 . Violet prisms 
from MeOH. M.p. 217-23. 

fflavianate : B,C 10 H 6 8 N2S. Purple needles 
from CH01 3 -Me 2 CO. M.p. 230. 

Fischer, Treibs, Ann., 1926, 450, 146. 
Fischer, Klarer, ibid., 190. 
Fischer, Stangler, Awn., 1927, 459, 91. 
Fischer, Orth, Chemie dea Pyrrols (Leip- 
zig, 1937), II, 191. 
Siodel, Winkler, Ann., 1943, 554, 162. 



StypJinate : B,3C 6 H 3 8 N 3 . Reddish- violet 
leaflets or prisms from MeOH. M.p. 217. 

Flavianate : B,3C 10 H 6 8 !N" 2 S. Red prisms 
from MeOH. M.p. 250. 

Fischer, Halbig, Walach, Ann., 1927, 
452, 284. 

Fischer, Halbig, Ann., 1926, 450, 
158. 

Fischer, Orth, Ohemie des Pyrrols (Leip- 
zig, 1937), II, 199. 



Aetioporpliyrin III (1 : 3 
2:4:6: 7 -tetraethylporphin) 



CH 3 



5 : S-Tetramethyl- 
|C 2 H 5 




C 32 H 38 N 4 

The above formula represents the nuclear 
complex of hsematin (blood) and of chlorophyll. 
Aetioporphyrin III is obtained from these sub- 
stances by degradation, from mesoporphyrinIX 

oil shale, petroleum, mineral wax, amber and 
various coals. It has been synthesised. Violet 
needles from Py or CHCl 3 ~pet. ether. M.p. 
360-3, Sol. Me 2 CO. Spar. sol. EtOH. 

Mg salt: C 32 H 36 N 4 Mg. Aetiophyllin (from 
chlorophyll). Bluish- violet cryst. 

Cu salt : C 32 H 36 N 4 Cu. Red needles from Py- 
AcOH. 



Aetioporphyrin IV 



38 



Agavogenin 



le salt: C 32 H 36 E" 4 FeCL Bark red needles 
from CHCl 3 ~Et 2 0. 

Fischer, Stangler, Ann., 1928, 462, 265 ; 

1928, 459, 76, 

Fischer, Orth, Chemie des Pyrrols (Leip- 
zig, 1937), II, 199. 

Aetioporphyrin IV (1 : 4 : 6 : 7-Tetramethyl- 
2:3:5: B-tetraethylporpMn) 

| ==|C t H 5 ^ C 2 H 5| | f,CH 3 

Y 



NH 




C 32 H 38 N, MW, 478 

Synthetic. Leaflets from CHCL-MeOH or 
Py. M.p. 355-7. 
Cu salt : C 32 H 36 N 4 Cu. Prisms. 

Fischer, Stangler, Ann., 1927, 459, 57, 
80. 

Fischer, Orth, Ghemie des Pyrrols (Leip- 
zig, 1937), II, 202. 

Aflinin (N-Isobutyldeca-1 : 5 : 1-trienoamide) 

CH 3 -CH:CH-CH:CH-CH 2 -CH 2 
(CH 3 ) 2 CH-CH 2 -NH-CO-CH:CH 
C 14 H 23 0]Sr MW, 221 

Powerful insecticide occurring in roots of 
fleliopsis longipes, (A. Gray) Blake. B.p. 100- 
162/0-3 mm, < 1-5128. H/Pt > N-iso- 
buty Icapramide . 

Jacobson, Acree, Haller, J. Org. Ghem., 

1947, 12, 731. 
Acree, Jacobson., Haller, /. Org. Ckem., 

1945, 10, 236, 449. 

Af zelin (Kcempferol- 3 -rkamnoside ) 
HO CO 

0-C 6 H n 4 




CWH 20 O 10 MW, 432 

A glycoside obtained from doussie', a timber 
derived from trees of the genus Afzelia, Yellow 
prisms + 1|H 2 0. M.p. 172-4. 

King, Acheson, J, Ghem. 8oc., 1950, 168. 
Agaric Acid (Agaricic acid) 
C 16 H 33 -CH(COOH)9(OH)-CH 2 -COOH 

COOH 
C 22 H 40 7 MW, 416 

Constituent of Polyporus officinalis> VilL 
Leaflets + 1|H 2 from EtOH.Aq. Anliyd, at 



100. M.p. 142 decomp. Spar. sol. EtOH, 
Et 2 0. [oft 9 - 8-84 in ISTaOH. Ale. KOH at 
160 > stearic acid. H 2 S0 4 > methyl 
heptadecyl ketone. 

Tri-Me ester: C 25 H 46 7 . MW, 458. M.p. 
634. 

Tri-Et ester :C 2S &MQ r MW,500. M.p. 36-7. 
Thorns, Vogelsang, Ann., 1907, 357, 

145. 
Roberts, Nature, 1945, 155, 697. 

Agarobiose 

C 12 H 20 10 MW, 324 

Degradation product of the agar-agar-like 
component ofGelidium amansii. [oc]i? 5-8. 

Hexa-Me: [a]f? -44 in H 2 0. Di-Me 
acetal : b.p. 155-6/0-052 mm. [oc]f? 11-0 in 
H 2 0. 

Araki, J. Chem. Soc. Japan, 1944, 65, 
533, 627. 

Agathic Acid (Agathic dicarboxylic acid) 
H 3 C COOH 




H-COOH 
CH 3 

CH 2 

C 20 H 30 4 MW, 334 

Present in manila and kauri copals. Oryet. 
from MeOH. M.p. 203-4. [oc] D +56-1 in 
EtOH, Dist. > noragathic acid + C0 2 . So 
dehydrogenation >- 1:2: 5-trimthylnaphth- 
alene. H-COOH ^ isoagathic acid by further 
ring- closure. 

Di-Me ester: C 22 H S4 4 . MW, 362. Di 7 
1-0777. n% 1-5163. [] n + S5-4 in EtOH. 

Buzicka, Jacobs, Mec, trav. Mm., 1938, 

57, 509. 
Hosking, Ghem. Abstracts, 1940, 34, 

6464. 
Buzicka, Hosking, Helv. GMm. Acta, 

1931, 14, 203 ; 1930, 13, 1402. 
Buzicka, Bernold, Tallichet, Helv. Ohim. 
Acta, 1941, 24, 223. 

Agavogenin (1 : 2-Dihydromanogenin) 
CH 3 



H-OIL 



HO 



MW, 448 




Agmatine 



39 



Ajmalinine 



A steroidal sapogenin isolated from Agave 
huachucensin. M.p. 242. CrO 3 > hecogenic 
acid. 

Triacetyl ; m.p. 228. 

Wagner et al, J. Am. Chem. Soc., 1943, 

65, 1199. 
Wagner, U.S.P., 2,408,835. 

Ag-matine (4:-Guanidinobutylamine) 



NH 
C 5 H 14 N 4 MW, 130 

Present in ergot, and pollen of Ambrosia 

artemisifolia. Ox. >- guanidine -f~ guanidino- 

butyric acid. 

BjHzSO* : needles from MeOH.Aq. M.p. 
229. 

B,2HAuCl : yellow needles from H 2 0. De- 
comp. at 220-3. 

Picrate : m.p. 235-6. 

Kossel, Z. physiol. Chem., 1910, 68, 170; 

1910, 66, 257. 
Heyl, J. Am. Chem. Soc., 1919, 41, 681. 

Agnosterol (Dehydrolanosterol) 




y CH-[CH 2 ycH:9 



< 
riTj 
UJtJU 
, , 
CH 3 

Suggested structure 

C 30 H 48 MW, 424 

Isolated from wool fat. Needles from EtOH. 
M.p. 162. [a] + 70-4 in CHC1 3 . Contains 3 
ethylenic linkages. 

Acetyl : needles from AcOESt. M.p. 173-4. 
ML 9 + 90-3 in CHCL. 

Bromoacetyl : leaflets from Me 2 CO. M.p. 
130-1. [oft + 78-3 in CHC1 3 . 

Benzoyl : clusters of needles from AcOEt. 
M.p. 203. [a]J> 7 + 103-3 in CHC1 3 . 

Marker, Whittle, J. Am. Chem. Soc., 1937, 

59, 2289. 

Marker, Whittle, Nixon, ibid., 1368. 
Windaus, Tschesche, Z. physiol. Chem., 

1930, 190, 51. 
Voser, Qiinthard, Jeger, Ktizicka, Helv. 

Chim. Ada, 1962, 35, 66. 
Voser, Jeger, Ruzicka, ibid., 503. 
Cavalla, McGhie, Pradian, /. Chem. Soc., 

1961, 3142. 
Barton, Fawcett, Thomas, ibid., 3147. 



Agropyrene 

C H 5 CH 2 -CH:CH-C:0*CH 3 



Occurs in roots of couch grass (Agropyron 
repens, Triticum repens). B.p. 140-3/10 mm. 
D 20 0-9744. < 1-5695. Sweet odour, remin- 
iscent of isochavibetol. Polymerizes at b.p. 
under atm. press. KOH >- brown resin. 
HN0 3 >- violet col. -> deep blue. KMn0 4 
> benzoic acid + oxalic acid. Na in EtOH 
-> 3-hexenylbenzene. 3 > phenylacetic 
acid + AcOBL Catalytic hydrogenation > 
hexylbenzene. 

Treibs, Ber., 1947, 80, 97. 
Aj acine (Acetylanthranoyllycocionine) 



MW, 156 



C 19 H 19 N- 

' 0-CO"C 6 H 4 -NH-COCH 3 
C 34 H 46 9 N 25 2H 2 O MW, 662 

Occurs in Delphinium ajacis. Cryst. from 
Et 2 0. M.p. 154. [a]f> 2 49-5 in EtOH, 30-8 
in HCL Alk. hyd. > lycoctonine + acetyl- 
anthranilic acid. HC1 > anthranoyllycocto- 
nine + AcOH. 

Keller, Volker, Arch. Parm., 1913, 251, 

209. 

Hunter, Pharm. J., 1943, 150, 82. 
Goodson, J. Chem. Soc., 1944, 108 ; 1945, 

245. 

Ajmaline 
C 20 H 26 2 N 2 MW, 326 

Alkaloid from Eauwolfia serpentina, Benth. 
Amber rectangular plates + 3|H 2 from moist 
AcOEt. Softens at 150. M.p. 158-60. Sol. 
EtOH, AcOEt, CHC1 3 . Spar. sol. Et 2 0, C 6 H e . 
[a]|? + 128 in CHC1 3 . Monacid base. 

B,HCl : amber prisms + 2H 2 0. M.p. 133-4. 
M.p. anhyd. 253-5. [oc] + 84-6 in H 2 0. 
B 2 ,H 2 PtCl Q : m.p. 217-18. 
Benzoyl deriv. : needles from C 6 H 6 . M.p. 
214-16. 

Picrate: plates from EtOH. M.p. 126-7. 
M.p. anhyd. 223. 

Siddiqui, Siddiqui, J. Indian Chem. Soc., 
1935, 12, 37; 1932, 9, 539; 1931, 8, 
667. 
Mukherji, Robinson, Schlittler, Experi- 

entia, 1949, 5, 215. 

Anet, Mukherji, Robinson, Schlittler, 
Chemistry and Industry, 1952, 20, 442. 

Ajmalinine 
C 20 H 26 3 N 2 MW, 342 

Alkaloid from Rauwolfia serpentina, Benth. 
Hexagonal prisms from moist AcOEt. M.p. 
180-1. Sol. EtOH, CHC1 3 . Spar. sol. Et 2 0, 
C 6 H 6 . Insol. pet. ether. Acts on the sym- 
pathetic nervous system, producing hypertension. 

B,HCl : semicryst. powder from EtOH-Et 2 0. 
M,p. 240-5 decomp. 



Akuammicine 



40 



Alanine 



Chloroplatinate : amorph. M.p. 254-8 de- 
comp. 

Methiodide : rods from EtOH. M.p. 233-4 
decomp. 

Picrate : yellow powder. M.p. 200-5. 

Siddiqui, Siddiqui, J. Indian Chem. Soc., 
1935, 12, 37; 1932, 9, 539; 1931, 8, 
667. 

Akuammicine 
C 19 H 20 4 N 2 MW, 340 

From Picralima Jclaineana Pierre. Leaflets 
from EtOH, M.p. anhyd. 177-5. [a]J? 
- 737-7 in CHC1 3 . 

B,HCl : prisms + 2H 2 from H 2 or EtOH. 
M.p. 144. M.p. anhyd. 171. [a]*? + 626-6 
in EtOH. 

Sulphate : cubes + H 2 from H 2 0. M.p. 
161. [a]J> 4 - 594 in H 2 0. 

Nitrate : needles. M.p. 182-5. 

Methiodide : yellow prisms from H 2 0. M.p. 
252. 

Picrate : yellow needles from CHCL-EtOH. 
M.p. 169. 

Clinquart, Edouard, J. Pharm. Belg., 

1927, 9, 187. 
Henry, Anderson, Sharp, J. Chem. Soc., 

1927 1950 
Henry, V. Chem. Soc., 1932, 2759. 

Akuammidine 
C 21 H 24 3 N 2 MW, 352 

From Picralima Jclaineana Pierre. Needles 
+ 1H 2 0. M.p. (air dried) 248-5. [a]Jf + 21 
in EtOH. Sol. EtOH, Et 2 0, CHCL. Insol. 
C 6 H 6 . 

B,H I : prisms + 3H 2 from EtOH.Aq. M.p. 
90. M.p. anhyd. 238. 

Perchlorate : prisms. M.p. anhyd. 110. 
Methiodide : prisms from MeOH.Aq. M.p. 
195. M.p. anhyd. 233. 

Acetyl deriv. : prisms from CHCL-EtOH. 
M.p. 272. 

Benzoyl deriv. : needles from EtOH. M.p. 
219. 

Picrate : yellow spheroids from EtOH. M.p. 
215. 

Clinquart, Edouard, J. Pharm. Belg. y 

1927, 9, 187. 
Henry, Anderson, Sharp, J". Chem. 3oc., 

1927, 1950. 

Henry, J. Chem. Soc., 1932, 2759. 
Hamet, Compt. rend., 1945, 221, 699. 

Akuammigine 
C 22 H 26 3 N 2 MW, 366 

From Picralima klaineana Pierre. Yellow 

tablets + 1H 2 from EtOH.Aq. M.p. 125. 
[ a ]jo _ 4440 in EtOH 

B,HCl : prisms from H 2 0, EtOH, or 

MeOHAq. M.p. 287. [oc]f? - 37-8 m MeOH, 



Nitrate : prisms from EtOH.Aq. M.p. 261. 
Picrate : garnet-red prisms. M.p. 240. 

Clinquart, Edouard, J. Pharm. Belg. y 

1927, 9, 187. 
Henry, Anderson, Sharp, J. Chem. Soc., 

1927 1950 

Henry, V. Chem. Soc., 1932, 2759. 
Hamet, Compt. rend., 1945, 221, 699. 

Akuammiline 

C 22 H 24 4 ^2 MW, 380 

From Picralima Jclaineana Pierre. Prisms 
from EtOH. M.p. 160. [a] 2 D +47-9 in 
EtOH. Sol. Et 2 0, CHC1 3 , warm C 6 H 6 . 

B,HCl : needles + 1H 2 O from H 2 or EtOH. 
M.p. 196. [a]g - 29-6 in H 2 0. 

B,HI : fine needles from EtOH.Aq. M.p. 
210. 

Nitrate : prisms from H 2 0. M.p. 204. 
Methiodide : rosettes of needles from H 2 0. 
M.p. 233. [o<& - 83-3 in EtOH. 

Clinquart, Edouard, J. , Pharm. Belg. 9 

1927, 9, 187. 
Henry, Anderson, Sharp, J. Chem. Soc., 

1927, 1950. 
Henry, J. Chem. Soc., 1932, 2759. 

Akuammine 
C 22 H 28 4 N 2 MW, 384 

Alkaloid from Picralima klaineana Pierre. 
Needles from EtOH. M.p. 255 (295). [og? 
-73-4 in CHC1 3 . Sol. CHC1 3 . Spar. sol. 
EtOH, Et 2 0. 

BJSOl : + H 2 0. M.p. 227. [a]?? - 26-6 
in H 2 0. 

B,HBr : prisms + H 2 from H 2 or EtOH. 
M.p. 228. [a] 2 D - 26 in H 2 0. 

B,HI : grey needles + H 2 0. M.p. 226. 

B,ZHNOz : needles from EtOH. M.p. 224. 

Sulphate: needles from H 2 0. M.p. 221. 
[a]Jf - 40-3 in H 2 0. 

Acetyl deriv. : prisms from EtOH. M.p. 
226. Hydrochloride : needles. M.p. 236. 

Methiodide : prisms from MeOH. M.p. 274. 

Picrate : yellow needles from EtOH. M.p. 
199. 

Picrolonate: yellow micro-needles. M.p. 194. 

Clinquart, Edouard, J. Pharm, Jtelg., 

1927, 9, 187. 
Henry, Anderson, Sharp, J. Chem. /S Y oc., 

1927, 1950. 
Henry, J. Chem. Soc., 1932, 2759. 

Alacreatine. 

See 1-Guanidinopropionio Acid. 

Alanine (l-Aminopropionic acid, cn-alanine) 

CH 3 'CH(NH 2 )-OOOH 
C 3 H 7 2 N MW, 89 

dl- (Hacemic alanine)* 

NTeedles or prisms from H0. Yellow cryst. 

from EtOH. M.p, 295-6. Sol 4-5 parts H a () 



Alanine 



41 



Alantolic Acid 



at 17, 500 parts 80 % EtOH in cold. Insol Et 2 0. 
Heat of form., 135-2 Cal. Heat of comb. CL 
389-2, C t 390-3 Cal. Jc (acid) = 9 x 10- 10 at 
25. k (base) = 5-1 x 10~ 12 at 25. Eeacts 
weakly acid to phenolphthalein and methyl 
orange. 

Me ester: C 4 H 9 2 N. MW, 103. B.p. 38- 
42 /15 mm. Sol. H 2 with alk. reaction. DJ 3 
1-0309. B,HCl: m.p. 158. N-m-Nitroben- 
zoyl: needles from MeOH.Aq. M.p. 110-11. 

Et ester : C 5 H n 2 N. MW, 117. B.p. 48 / 
II mm. D 12 0-9846. B,HCl : m.p. 64-8 
(129). N-Et: b.p. 53 /10 mm. NJMJB : 
b.p. 74-5 /13 mm. N-m-Nitrobenzoyl : needles 
from EtOH.Aq. M.p. 89. Picrate : m.p. 
171. F 

Amide: C 3 Hgp]Sr 2 . MW,88. M.p. 62. Sol. 
H 2 0, EtOH. B,HCl : m.p. 170. N-m-Nitro- 
benzoyl: needles from EtOH.Aq. M.p. 189-90. 
Picrate : m.p. 199-5. 

Nitrile: B,HCl: m.p. 115-17 (132-8 de- 
comp.). "N-Di-Et : b.p. 66 /15 mm. 

^-Di-Me : see Dimethyl-^-alanine. 

"8-Eti C 5 H n 2 N. MW, 117. Cryst. from 
EtOH. M.p. 211-15. 

Anhydride : see Dimethyldiketopiperazine. 

N-Acetyl : see Acetylalanine. 

N-Benzoyl : m.p. 165-6. 

T$-Q-Nitrobenzoyl : needles from H>0. M.p. 
165-6. 

~N-m~Nitrobenzoyl : needles from H 2 0. M.p. 
163-4, Picrolonate : m.p. 216 decomp. 

d- (d- Alanine). 

Hyd. product of many proteins. Rhombic 
cryst. M.p. 297 decomp. Sol. 4-5 parts H 2 0. 
Prac. insol EtOH. [a]g +2-7 in H 2 0, 
+ 9-55 in HC1. HN0 2 > cWactic acid. 

B,HGl : prisms. M.p. 204. [oc]i + 10-4 
in H 2 0. 

Me ester : N-i&-Nitrobenzoyl 



EtOH.Aq. M.p. 126. [a]? 



needles from 
12-7 in EtOH. 



Amide : prisms from CHC1 3 . M.p. 72. Sol. 
H 2 0, EtOH. Hygroscopic. "N-m-Nitrobenzoyl : 
leaflets from EtOH. M.p. 193-4. [<x]f m +24-2 
in EtOH. 

]$~Acetyl : cryst. from AcOEt-C 6 H 6 . M.p. 
116. [a]{f 45-6 in H 2 0. 

"N-Bromoacetyl : m.p. 96-7. 

'N-Benzoyl : m.p. 152-4. [a]g + 37-13 in 
alkali. 

y!~mNitrobenzoyl : needles from H 2 0. M.p. 
158. 

Picrolonate : m.p. 215 decomp. [0$ + 11-8 
in H 2 0. 

I- (I- Alanine). 

Prisms from EtOH.Aq. Decomp. at 297. 
Sol. hot H 2 0. [] - 9*68 in HCL 
>HCl : sol H 2 0. [oc]J> - 10*3 in H 2 0. 
Mt ester : 'NmNitrobenzoyl : needles from 



N-Benzoyl : m.p. 151. [o^ 37-3 in 
alkali. 

N-m-Nitrobenzoyl : needles from H 2 0. M.p. 
158. [a] D + 5-87 in EtOH. 

"N-Phenyl : see 1-Anilinopropionic Acid. 

Billmann, Parker, J. Am. Chem. Soc., 

1943, 65, 2455. 
Hamlin, Hartung, J. Biol. Chem., 1942, 

145, 349. 
Sisler, Cheronis, J. Org. Chem., 1941, 6, 

467. 
Kendall, Mackenzie, Organic /Syntheses, 

Collective Vol. I, 20. 
Skita, WulfT, Ann., 1927, 453, 199. 
Colles, Gibson, J. Chem. Soc. y 1931, 

279. 
Zelinsky, Stradmkoff, Ber., 1908, 41, 

2061. 
Fischer, Ber., 1907, 40, 491; 1906, 49, 

462. 

(3-Alanine . 

See 2-Aminopropionic Acid. 

Alanocy amine . 

See 1-Guanidinopropionic Acid. 

Alantic Acid. 

See Alantolic Acid. 

Alantolactone (Helenine) 



OH 8 




co 



MW, 232 



EtOH.Aq. 
EtOH. 



Mp. 104-5. [Jf +6-91 in 



C 15 H 20 2 

Lactone or anhydride of alantolic acid. Con- 
stituent of oil of elecampane. Needles. M.p. 
76. B.p. 275, 197 /10 mm. Spar. sol. H 2 O. 
Sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 , ligroin, alkalis. 
Volatile in steam. 

Hydrochloride : needles from EtOH.Aq. M.p. 
117. 

Hydrobromide : cryst. from EtOH. M.p. 
106. 

Dihydrochloride : needles or leaflets from 
EtOH. M.p. 134 decomp. 

Dihydrobromide : m.p. 117. 

Euzicka et al., Helv. Chim. Acta, 1933, 

16, 268. 
Bredt, Posth, Ann., 1895, 285, 358. 

Alantolic Acid (Alantic acid) 
C 15 H 22 3 J MW,250 

In oil of elecampane. Needles. M.p. 94. 

Me ester: C 16 H 24 3 . MW, 264. M.p. 83. 

Et ester : C 17 H 26 3 . MW, 278. M.p. 80. 

Amide: C 15 H 23 2 N. MW, 249. Cryst. from 
EtOH. M.p. 197 (210) decomp. T$-Acetyl: 
m.p, 179 decomp. 



42 



0-Aldehydobenzoic Acid 



Anhydride : see Alantolactone. 

Bredt, Posth, Ann., 1895, 285, 358. 

<I-Alanyl-<i-alanin6 

CH 3 -CH(3SrH 2 )-CO-NH-CH(CH 3 )-COOH 
C 6 H 12 3 N 2 MW, 160 

Prisms. M.p. 298 (rapid heat.). [a]g -21-6 
in H 2 0. 

Fischer, Raske, Ber., 1906, 39, 3981. 

Z-Alanyl-d!-alanine . 

Leaflets. M.p. 269-70 decomp. Sol. H 2 0. 
Spar. sol. EtOH. Insol. Et 2 0. [cc]| -68-5. 

Fischer, Raske, Ber., 1906, 39, 3981. 



d- Alanyi-I-alanine . 
M.p. 275-6 decomp. [< 
+ 65*96 in HCL 

Fischer, Raske, Ber., 1906, 39, 3981. 



<f-Alanyl-l-leucine. 

Leaflets from EtOH. M.p. 255-6 (rapid 
heat.). Sol. H 2 0. Spar. sol. EtOH. Insol. 
Et 2 0, Me 2 CO, CHC1 3 , C 6 H 6 . [off - 17-2 in 
H 2 0. 

Fischer, Ber., 1907, 40, 1766. 
Schonheimer, Z. physiol. Chem., 1926, 
154, 203. 

dZ-Alanyl-leucine . 

Two forms. M.p. 248. Sol. H 2 O. Spar. 
sol. EtOH. 

Fischer, Warburg, Ann., 1905, 340, 154. 

<J-Alanyl~<Z-valine 



MW, 188 



dl-Alanylalanine . 

Needles. M.p. 276 decomp. Sol. H 2 0. 
Insol. EtOH. 

Fischer, Raske, Ber., 1906, 39, 3981. 
Herbst, Shemin, /. Bid. Chem., 1943, 147, 
541. 

d-Alanylglycine 



+ 68-7 in H 2 0, C 8 H 16 3 N 2 

Needles or prisms from EtOH.Aq. M.p. 265 
(rapid heat.). Sol. H 2 0, MeOH. Spar. sol. 
EtOH. [a]? 5-9 in H 2 O, 1-9 in HCL 

Fischer, Scheibler, Ann., 1908, 363, 148. 



C 5 H 10 3 N 2 MW, 146 

Needles from EtOH.Aq. M.p. 235 decomp. 
M + 50-2 in H 2 0. 

Fischer, Ber., 1908, 41, 852. 

I- Alanylglycine . 

Cryst. from EtOH.Aq, M.p. 256 decomp. 
Sol. H 2 0. [oc]i - 48-6 in H 2 0. 

Fischer, Warburg, Ann., 1905, 340, 166. 

dl~ Alanylglycine . 

Needles. M.p. 235 decomp. Sol. H 2 0. 
Insol. EtOH, Et 2 0. 

Fischer, Axhausen, Ann., 1905, 340, 130. 
Schonheimer, Z. physiol. Chem., 1926, 
154, 203. 

Alanylhistidine . 

See Carnosine. 
<$-Alanyl-$-leucine 



Albsapogenin. 

See Gypsogenin. 
Alcapton 

See Homogentisic Acid. 
Aldehyde-ammonia . 
See 1-Aminoethyl Alcohol. 
Aldehydecollidine . 
See 6-Methyl-3-ethylpyridine. 
Aldehydoacetic Acid. 
See Formylacetic Acid. 
co-Aldehydoanisole . 
See Phenoxyacetaldehyde. 
4- Aldehy doantipyrine . 
See Antipyraldehyde. 

o-Aldehydobenzoic Acid (o-Phthalaldehydic 
acid, benzaidehyde-Q-carboxylic add) 

COOH 




C 8 H 6 3 MW, 150 

Leaflets from H 2 0. M.p. 98-9. Sol. .FLO, 
EtOH, Et 2 0. At 240-50 > anhydride. Eo- 
duces NH 3 .AgN0 3 . k = 3-6 X 10"* at 25. 

Me ester : C 9 H 8 3 . MW, 164. B.p. 220-2 , 



CHOCOEL 



C,H 18 3 N 2 

M.p. 
which ii 



M,W 202 
' 



, m.p. 46-7, 



Et ester : C 10 H |p 3 . MW, 178. B.p. 240-3, 
Anhydride : aiphthalide ether. C 10 H|00 S , 
221. Insol. H.O. Does not roctoco 



Smith, Brown, /. Am. Chem. $oc., 1941 
63, 2605. 



Anil : m.p. 174. 
Semicarbazone : m.p. 202, 



m-Aldehydobenzoic Acid 



43 



I-Aidehydoisobutyric Acid 



Phenylhydrazone : yellow needles from 
EtOH.Aq. M.p. 106. 

Shriner, Wolf, Organic Syntheses, 1943, 

XXIII, 74. 
Gardner, Naylor, Organic Syntheses, 1936, 

XVI, 68. 

Fuson, J. Am. Ghem. Soc. 9 1926, 48, 1093. 
Auwers, Heinze, Ber., 1919, 52, 596. 

m-Aldehydobenzoic Acid (Isophthalalde- 
hydic acid, benzaldehyde-m-carboxylic acid). 

Needles from H 2 0. M.p. 175. 

Me ester ; m.p. 53. Oxime : m.p. 104. 

Et ester: b.p. 278. D 18 1-093. 

Chloride : C 8 H 5 2 C1. MW, 158-5. B.p. 130 / 
20mm. 

Amide: C 8 H 7 2 N. MW, 149. Prisms. 
M.p. 190 decomp. 

Nitrite : C 8 H 5 ON. MW, 131. Needles from 
Et 2 O. M.p. 79-81. Volatile in steam. Oxime: 
powder from H 2 0. M.p. 99-101. 

Oxime : m.p. 188 decomp. > isophthalamic 
acid. 

Anil : m.p. 156. 

Semicarbazone : m.p. 265, 

Phenylhydrazone : m.p. 164. 

Simonis, Ber., 1912, 45, 1585. 
Davies, Perkin, J. Ohem. Soc., 1922, 121, 
2215. 

jp-Aldehydobenzoic Acid (TerephthalaUe- 
hydic add, benzaldehyde-p-carboxylic acid). 

Needles from H 2 0. M.p. 256. Spar. sol. 
H 2 0, Et 2 0, CHC1 3 . Sublimes. 

Me ester : needles from BUO or petrol. M.p. 
63. B.p. 265. Phenylhydrazone: m.p. 144- 
6. 

Chloride : m.p. 48. B.p. 258. 

Nitrile : needles from H 2 0. Prisms from 
Et 2 or EtOH.Aq. M.p. 92. B.p. 133/12 
mm. 

Oxime : m.p. 208-10. 

Phenylhydrazone : m.p. 226, 

Anil : m.p. 222. 

Simonis, Ber., 1912, 45, 1588. 

Davies, Perkin, J. Ghem. Soc., 1922, 121, 

2215. 

Aldehydobenzophenone . 

See Bonzoylbenzaldehydo. 

#-Aldehydobenzyl Alcohol. 

See jp-Hydroxymethyl-benzaldehydc. 

p-AMehydobutyrophenone . 

See 1 JJemoylbutyraldehyde. 

Aldehydocamphor . 

See 3-Hydro2cymethylnecamphor. 

Aldehydocaprylic Acid. 

See Azelaio Semi-aldehyde. 

Aldehy docarvacr ol . 

See Hydroxy-44sopropyl-m-toluic Aldehyde. 



4-Aldehydocinnamic Acid (p~Formykinn- 
amic acid) 



C 10 H 8 3 MW, 176 

Prisms or needles. M.p. 247. Sublimes. 
Sol. hot AcOH. Spar. sol. Et 2 0, CHCL, hot 
H 2 0. 

Me ester : C U H 10 3 . MW, 190. Cryst. from 
Et 2 O. M.p. 82-3. 

Low, Ann., 1885, 231, 375. 
Ephraim, Ber., 1901, 34, 2784. 

co-Aldehy doer esol . 

See Hydroxyphenylacetaldehyde. 
Aldehydo-vp-cumene . 
See Trimethylbenzaldehyde. 
2-Aldehydodiph.enyl (Diphenyl-2-aldehyde, 
o-phenylbenzaldehyde) 

9HO 



C 13 H 10 MW, 182 

B.p. 150/7 mm. 

Phenylhydrazone : yellow, m.p. 139. 

Zaheer, Faseeh, J. Indian Chem. Soc., 
1944, 21, 381. 

4-Aldehydodiphenyl (Diphenyl-4-aldehyde, 

p-phenylbenzaldehyde) . 

Pale yellow flakes from ligroin. M.p. 60. 
KMn0 4 > diphenyl-4-carboxylic acid. HI + 
p >. 4-methyldiphenyl. 

Oxime : m.p. 149-50. 

Semicarbazone : plates from EtOH. M.p. 
243 decomp. 

Phenylhydrazone : m.p. 188-9 decomp. 

2 : 4c-J}initrophenylhydrazone : scarlet plates 
from xylene. M.p. 239 decomp. 

Gattermann, Ann., 1906, 347, 381. 
Hey, J. Ohem. Soc., 1931, 2477. 

4-Aldehydodiphenyl Ether. 

See under ^-Hydroxybenzaldehyde. 
Aldehydoformic Acid. 
See Glyoxylic Acid. 
Aldehydohemimellitene . 
See Trimethylbenzaldehyde. 
Aldehydohydrindene . 
See Hydrindene-aldehyde. 
1- Aldehy doisobutyric Acid (a-Formyliso- 
butyric acid) 

H 3 0> x> ^p^xCO OH. 

H/*i ^ > ^ < ^ f^TT A 
y~> ^\JJUi\} 

C 6 H 8 3 MW, 116 

Et ester: C 7 H 12 3 . MW, 144. Liq. B.p. 
163-4 /746 mm., 65-6/20 mm. DJ 0-9834. 
Dil. H 2 S0 4 > isobutyraldehyde. Semicarb- 
azone : needles from EtOH. M.p. 161-2. 

Blaise, Hardily, Butt, soc* chim., 1904, 
31, 161. 



2-Aldehydoisobutyric Acid 



44 



o-Aldehydophenylglycine 



2-Aldehydoisobutyric Acid ($-Formyliso- 
butyric acid) 



CH 2 -CHO 
C 5 H 8 3 MW, 116 

Oil. B.p. 139-40 /12-5 mm. Miscible with 
H 2 0, EtOH, Et 2 0. Reduces NH 3 .AgN0 3 . 

Et ester: C 7 H 12 3 . MW, 144. Liq. B.p. 
82-4 /1 1 mm. Oxime : C 7 H ;3 3 N. MW, 159, 
B.p. 1 37-8 / 16 mm. Semicarbazone : m.p. 
110-5. p-Nitropkenylhydrazone : m.p. 89. 

Oxime : m.p. 77. 

Semicarbazone : m.p. 195. 

Phenylhydrazone : m.p. 71-2. 

p-Nitrophenylhydrazone : m.p. 198. 

Perkin, Sprankling, J. Chem. Soc., 1899, 

75, 19. 
Blaise, Compt. rend., 1911, 153, 71. 

2-Aldehydoisophth.alic Acid (Benzaldehyde- 
2 : 6-dicarboxylic acid) 

COOH 

ACHO 
IJCOOH 

C 9 H 6 5 MW, 194 

M.p. 175-8. Sol. EtOH, Et 2 0. 

Anhydride : C 9 H 4 4 . M.p. above 340. In- 
sol. H 2 0. Spar. sol. EtOH. 

Phenylhydrazone : cryst. from EtOH. M.p. 
86-90. 

Liebermann, Ber., 1897, 30, 697. 

Aldehydoisoquinoline . 

See Isoquinaldinic Aldehyde. 
Aldehydomalonic Acid (Formylmalonic 
acid, hydroxymethylenemalonic acid) 



or 

!OOH 
!OOH 

MW, 132 

The free acid has not been isolated. 

Di-M ester : C 8 H 12 6 . MW, 188. B.p. 217- 
19, 107-09/12 mm, DJ 4 1-127. < 1456. 
FeCl 3 on EtOH sol. > orange-red col. Hyd. 
by alkalis > formic + malonic acids. Di-Et 
acetal: b.p. 126-9/7 mm. n$ 1-4220. Ba 
deriv. : (0 8 H n 6 ) 2 Ba. M.p. 119 (138 anhyd.). 

Auwers, Ann., 1918, 415, 222. 
Fuson, Parham, Reed, J. Org. Chem., 
1946, 11, 194. 

Aldehydomesityleae . 
See Trimethylbenzaldohyde. 
Aldehydonaphthoic Acid. 

See Naphthaldehydic Acid. 



Aldehy donapMh.01 . 

See Hydroxynaphthaldehyde. 
Aldehydopelargonic Acid. 

See Aldehydononoic Acid. 
8-Aldehydonoaaoic Acid (S-Aldehydopelar- 
gonic acid) 

OHC-CH 2 -[CH 2 ] 6 -CH 2 -COOH 
C 10 H 18 3 MW, 186 

Me ester: C n H 20 3 . MW, 200. B.p. 
120-l/3 mm. Df 0-9663. < 1-4410. Semi- 
carbazone : m.p. 98-100. 

Noller, Adams, J. Am. Chem. /Soc., 1926, 
48, 1074. 

7-Aldehydo-octoic Acid. 

See Azelaic Semi-aldehyde. 
4-Aldeliydo-orsellinic Acid. 
See Hsematommic Acid. 
o-Aldehydophenoxyacetic Acid 

0-CHyCOOH 



C 9 H 8 4 MW, 180 

Yellow leaflets. M.p. 132. Sol. hot H 2 0, 
EtOH, Et 2 0. Spar. sol. C 6 H 6 , CHC1 3 . Sub- 
limes. Reduces Fehling's in warm. Forms 
bisulphite comp. 

Me ester: C 10 H 10 4 . MW, 194. Needles. 
M.p. 55. 

Et ester: C n H 12 4 . MW, 208. Needles. 
M.p. 47. B.p. 195-7 /23 mm. Semicarbazone : 
needles from EtOH. M.p. 178. 

Oxime : m.p. 138. 

Phenylhydrazone : m.p. 105 (softens at 60). 

Robertson, J. Chem. Soc., 1933, 492. 
Cajar, Ber., 1898, 31, 2809. 

tn-Aldehydophenoxyacetic Acid. 

Needles. M.p. 148. 

Et ester : cryst. mass. M.p. 120. 

Oxime : m.p. 145. 

Elkan, Ber., 1886, 19, 3042. 

l>~Aldehydophenoxy acetic Acid. 

Leaflets. M.p. 198. Sol. AcOH. Mod. sol. 
EtOH, Et 2 0. 

Et ester : m.p. 155 docomp. 
Oxime : m.p. 168. 

Elkan, Ber., 1886, 19, 3042. 



o-Aldehydoplienylglycine 

phenylaminoacetic acid) 

NH-OH 2 -COOH 

3HO 



Sol. 



(o~Aldehydo~ 




Plates. M.p. 176-7. 
Spar. sol. 6 H 6 CHC1 3 . 



MW, 179 
HgO, ItOH. 



Aldehydopiperidine 



45 



Aldelrydosuccinic Acid 



Oxime : m.p. 134 decomp. Sol. hot H 2 0. 
Gluud, J. Ckem. Soc., 1913, 103, 1251. 

Aldehydopiperidine . 

See Piperidine-aldehyde. 

2-Aldehydopropionic Acid (Succinic semi- 
aldehyde, $-formylpropionic acid, succinaldehydic 
acid) 

OHC-CH 2 -CH 2 -COOH 
C 4 H 6 3 MW, 102 

Oil with rancid odour which solidifies at low 
temps. B.p. 134-6 /14 mm. Sol. H 2 0, EtOH, 
Et 2 O, C 6 H 6 . Dg 1-2568. ug 1-4487. Volatile 
in steam. Reduces Fehling's and NH 3 .AgN0 3 . 
Dimerises on standing. 

Dimer : C 8 H 12 6 . MW, 204. Prisms. M.p. 
147. B.p. 234-6, 134-6 /14 mm. > mono- 
molecular acid. 

Et ester : C 6 H 10 3 . MW, 130. B.p. 84 /12 
mm. Oxime : b.p. 139/14 mm. Semicarb- 
azone : cryst. M.p. 161-2 decomp. Phenyl- 
hydrazone : needles from MeOH. M.p. 188-9. 
p-Nitrophenylhydrazone : brown cryst. from 
EtOH. M.p. 80-1. Anil : cryst. from EtOH. 
M.p. 118. 

Nitrite : C 4 H 6 ON. MW, 83. B.p. 77. D 15 
0-89. 

Oxime: cryst. from EtOH. M.p. 102-3 



B 

Semicarbazone : prisms or needles from H 2 0. 
M.p. 177-8 decomp. 

p-Nitrophenylhydrazone : reddish - violet 

needles. M.p. 185-7. 

2 : 4c-Dinitrophenylhydrazone : yellow cryst. 
M.p. 201. 

Perkin, Sprankling, J. Chem. Soc., 1899, 

75, 16. 
Wislicenus, Bdkler, Beuthe, Ann., 1908, 

363, 353. 
Carri&re, Ann. chim., 1921, 17, 38. 

Aldehydopyromucic Acid. 

See Furfural-5-carboxylic Acid. 

Aldehydoquinaldine . 

See Quinaldine-aldehyde. 

Aldehydoquinoline . 

See Quinoline-aldehyde. 

3-Aldelxydosalicylic Acid (m-Aldehydosali- 
cylic acid, 2-hydroxy^-aldehydobenzoic acid, o- 
hydroxybenzaldehyde-m.- carboxylic acid) 

COOH 

2 ,OH 
3 JCHO 



C 8 H 6 4 MW, 166 

Needles + 1H 2 from H 2 0, Anhyd. at 100. 
M.p. 179. Sol EtOH, hot H 2 O. EtOH sol. 
weak blue fluor, FeClg > red col. Sublimes. 



Heat with CaO > salicylaldehyde. KOH 
fusion > 2-hydroxyisophthalic acid. 

Me ester : C 9 H 8 4 . MW, 180. Needles from 
EtOH. M.p. 87. 

Et ester: C 10 H 10 4 . MW, 194. Needles 
from EtOH. M.p. 66-7. 

Oxime: yellow needles from H 2 0. M.p. 193. 

Phenylhydrazone : prisms from EtOH. M.p. 
188. 

Wayne, Cohen, J. Chem. Soc., 1922, 121, 

1022. 
Remfry, J. Chem. Soc., 1911, 99, 286. 

5-AldehydosaHcylic Acid (2-Hydroxy-5- 
aldehydobenzoic add, p-kydroxybenzaldehyde-m- 
carboxylic acid, 6-hydroxyisophthalaldehydicacid). 

Needles. M.p. 248-9. Sol. hot EtOH, Et 2 0. 
Spar. sol. hot H 2 0. Insol. CHC1 3 . PeCl 3 > 
red col. Heat with CaO > ^-hydroxybenz- 
aldehyde. KOH fusion > 4-hydroxyiso- 
phthalic acid. 

Me ester : needles from EtOH. M.p. 82-3. 
Acetate: needles from EtOH. M.p. 81-2. 
Benzoate : prisms from EtOH. M.p. 99-101. 
Oxime : needles from EtOH.Aq. M.p. 147-8. 
Semicarbazone : prisms from Py. M.p. 215-16. 
Phenylhydrazone : prisms from EtOH. M.p. 
120-1. p-Nitrophenylhydrazone : red prisms 
from Py. M.p. 265-7. 

Et ester: prisms from EtOH. M.p. 75. 
Phenylhydrazone : prisms from EtOH. M.p. 
135-6. 

Oxime : m.p. 179. 

Phenylhydrazone : needles from EtOH. M.p. 
219. 

Wayne, Cohen, J. Chem. Soc., 1922, 121, 

1022. 
Remfry, J. Chem. Soc., 1911, 99, 286. 

Aldehydosuccinic Acid (Formylsuccinic 
acid, hydroxymethylenesuccinic acid) 

OHC-9H-COOH 
CH 2 -COOH 

or 
HO-CHiq-COOH 

CH 2 -COOH 

MW, 146 

The free acid has not been isolated. 

Di-Me ester: C 7 H 10 O 5 . MW, 174. B.p. 
112-15 /12 mm. Cu salt: (C 7 H 9 5 ) 2 Cu,lH 2 0. 
Needles from MeOH. M.p. 133-5. 

Di-Et ester: C 9 H 14 5 . MW, 202. AUo- 
form : b.p. 134-40/19 mm. Enol-form : b.p. 
145 51 /1 9 mm. Equilibrium mixture : b.p. 
128-48 /15 mm. FeCl a on EtOH sol. > 
cherry-red col. Acids or alkalis > C 2 H 5 OH + 
formic + succinic acids. Semicarbazone : m.p. 
126. ip-Nitrophenylhydrazone : m.p. 100. Cu 
salt: (C 9 H 13 6 ) 2 Cu. Needles from EtOH. M.p. 



C 6 H 6 5 



Aldeliydothymol 



46 



Alginic Acid 



132-3. Nisalt: (C Q R^0 5 )^L Needles from 
EtOH. M.p. 219-20. 

Carriere, Ann. chim. 9 1922, 17, 41. 

Johnson, Peck, Ambler, J. Am. Chem. 
Soc. 9 1911, 33, 761. 

Aldehy dothymol . 
See Thymotinic Aldehyde. 
5-Aldehydovanillic Acid (4:-Hydroxy-3~ 
methoxy-5-aldehydobenzoic acid) 

COOH 




C 9 H 8 5 MW, 196 

Needles from H 2 0. M.p. 221-2. Spar. sol. 
cold H 2 O. Sol. EtOH, Et 2 0. Sol. NaOH to 
deep yellow sol. Fed 3 > violet col. 

Me ester: C 10 H 10 5 . MW, 210. Yellow 
needles. M.p. 134-5. 

Me ether : see Iso-opianic Acid. 

Tiemann, Mendelsohn, Ber., 1877, 10, 396. 

Aldehy do-xylenol . 

See Hydroxydimethylbenzaldehyde. 

Aldol (2-Hydroxybutyraldehyde, 2-butanolal-%, 
acetaldol) 

CH 3 -CH(OH)-CH 2 -CHO 
C 4 H 8 2 MW, 88 

Colourless syrupy liq. B.p. 83/20 mm., 77/ 
16 mm. At 85 decomp. to crotonaldehyde + 
H 2 0. Misc. with H 2 and EtOH. D 16 1-1094. 
Heat of comb, (liq.), 547 Gal. Reduces 
NH 3 .AgN0 3 . Polymerises to paraldol. 

Mono-acetyl : b.p. 87-9/18 mm. 

Tri-acetyl : b.p. 138-40 /12 mm. 

IH-Et acetal: b.p. 190-5, 75-81/12 mm. 
Sol. 5 parts H 2 0. 

y-Bromophenylhydrazone : leaflets. M.p. 127- 



8 



j)~Nitrophenylhydrazone : yellow, m.p. 115-6. 

Oxime: b.p. 110-20. 

Anil : glassy mass. M.p. 73-5. 

Kyriakides, J. Am. Chem. Soc., 1914, 36, 

532. 

Claisen, Ann., 1899, 306, 323. 
Grignard, Reif, Bull. soc. chim., 1907, 1, 
114. 

Alepric Acid 



C 14 H 24 2 MW, 224 

Occurs in Hydnocarpus wightiana oil. Needles 
from MeOH-pot. other. M.p. 48. B.p. 166- 
8/l mm. [] 77-1. Iodine no. 113-4. 

Et ester: b.p. 174/10 mm. n% 14562. 
Df e 0-915. [a]f? 66-5. Iodine no. 100-7. 

Cole, Cardoso, J. Am. Chem. Soc., 1939, 
61, 2349. 



Aleprolic Acid. 

See Cyclopentene-3-carboxylic Acid. 
Aleprylic Acid 



C 12 H 20 2 MW, 196. 

Occurs in Hydnocarpus wightiana oil. M.p. 
32. [a]J? 90-8. Iodine no. 129-7. 

Et ester: b.p. 148/10 mm. ri 1-4550. 
V 0-925. [a]| 5 79-1. Iodine no. 113-4. 

Cole, Cardoso, J. Am. Chem. Soc., 1939, 
61, 2349. 

Aleuritic Acid (8:9: 15-Trihydroxypalmitic 
acid) 

HOCH 2 -[CH 2 ] 5 -CH(OH)-CH(OH)-[CH 2 ] 7 -COOH 
C lfi Ho 5 5 MW, 307 



H 2 0. 



Leaflets from 
M.p. 102. 
azelaic acid + 



Constituent of shellac resin. 
EtOH.Aq., needles from 
HI > palmitic acid. Ox. 
HOCH 2 -[CH 2 ] 5 -COOH. 

Me ester: C 17 H 37 5 . MW,321. M.p. 63-4 
(73). Triacetyl : b.p. 232~4/0-15 mm. 

Hydrazide : m.p. 139-40. 

Azide : needles from EtOH. Decomp. at 50. 

" Nagel, Chem. Zentr., 1931, II, 557. 

Schae&r, Gardner, Ind. Eng. Chem., 
1938, 30, 333. 



Alginetin 




P.OH 

/C-CH, 



C 







Suggested structure 
10 H 8 4 MW, 192 

Obtained by heating alginic acid at 100 for 
3 hrs. Needles. M.p. 235. Sol. hot H 2 0, 
hot EtOH. Insol. ligroin. FeCl 3 > violet 
col. H 2 2 > 2 : 3-dihydroxyben2:oic acid* 

Diacetyl : m.p. 125. 

Dibenzoyl : m.p. 187. 

Me ether : m.p. 215. 

Acetyl-Me ether : m.p. 171. 

Kiyowhi, Aso, Chem. Abstracts, 1935, 29 ? 
1067. 



Alginic Acid 
COOH 



H 



N. 



OK 



-0 



H H 



COOH 



[C H 8 6 ] n 



Alginine 



d-AIkannin 



Occurs both free and as Ca salt in many sea- 
weeds (Laminaria, Fucus, etc.). Insol. org. 
solvents. Sol. aq. alkalis. Forms insol. Ca, Cu, 
Th salts. Forms a Me ester. Boiling MeOH- 
HC1 > degraded alginic acid + methyl d- 
mannuronoside. Hyd. > mannuronic acid. 
Na salt employed as stabilizer for ice cream and 
cheese. Alginates have applications in some 
branches of the textile and allied industries. 

Hirst, Jones, Jones, /. Chem. Soc., 1939, 
1882. 

Kelco, U.S.P., 2,036,922, (Chem. Ab- 
stracts, 1936, 30, 3442). 

Barry, Dillon, Sci. Proc. Roy. Dublin Soc., 
1936, 21, 285, 289. 

Lunde, Heen Oy, Kolloid. Zeit., 1938, 83, 
196. 

Tseng, Colloid Chemistry, 1946, 6, 629. 

Alginine 
C 23 H 39 3 N MW, 377 

Alkaloid isolated from Fritillaria sewerzowii. 
M.p. 271-2. [oc] D + 108-5 in EtOH. 
B,HCl : m.p. 3235. 
B,MeI : m.p. 310-11. 

Konovalova-, Or6khov, /. Gen. Chem. 
U.S.S.R., 1939, 9, 1911. 

Alizarin (1 : 2,-Dihydroxyanthraquinone) 
CO OH 




C 14 H 8 4 MW, 240 

Occurs naturally in madder root (Rubia 
tinctoria, Linn.) as glucoside, ruberythric acid. 
Orange or red needles or prisms from EtOH or by 
sublimation. M.p. 290. B.p. 430. Sol. H 2 
to 0-034% at 100. Sol. in H 2 by addn. of Na 
salt of naphthalenesulphonio acid. Mod. sol. 
EtOH, Et 2 0, AcOH, C 6 H 6 , Ph]ST0 2 , CS 2 . Sol. 
caustic alkalis, carbonates and NH 3 to violet 
sols. SoL cone. H 2 S0 4 to reddish- brown col. 
Sublimes. Heat of comb. CL and C v 1453-1 Cal. 
phthalic acid. H 2 S0 4 + MnO 2 > 
Zn dust > anthracene. Zn + 
3 : 4-dihydroxyanthrone. 

I'Me ether: C 15 H 10 4 . MW, 254. Orange 
needles. M.p. 179. Acetyl : yellow needles 
from EtOH. M.p. 209-10. 

2- Me ether : yellow needles from EtOH. M.p. 
232-3. SoL cone. H 2 S0 4 to violet-red sol. 
Acetyl : yellow needles from EtOH. M.p. 
204-6. 

Di~Me ether : 16 H 18 Q 




2-M ether: C 16 H 12 4 . MW, 268. Orange 
needles. M.p. 189. Acetyl : yellow needles 
from EtOH. M.p. 141. 

l-Et, 2-Me ether: C 17 H 14 4 . MW, 282. 
Cryst. from EtOH. M.p. 169-70. 

Di-Et ether : C 18 H 16 4 . MW, 296. Yellow 
needles. M.p. 162. 

2-Acetyl : orange leaflets from EtOH. M.p. 
198-201. 

Diacetyl : yellow cryst. from EtOH. M.p. 
184. 

2-Benzoyl : needles from EtOH. M.p. 214-6. 

Dibenzoyl : 2 forms. Unstable cryst. from 
PhN0 2 . M.p. 160. On standing ^stable 
form. Prisms from PhN0 2 . M.p. 187. 

2-Phenylacetyl : greenish-yellow needles from 
C 6 H 6 . M.p. 165. 

2-p-Bromobenzoyl : yellow needles from C 6 H 6 . 
M.p. 195. 

Vorozhtsov, Aleksandrov, Chem. Abstracts, 

1941, 35, 4375. 

Green, J. Chem. Soc., 1927, 2930. 
Badische, D.E.P., 287,270, (Chem. Zentr., 

1915, II, 935). 

Alkaloid L27. 

See Acrifoline. 
Alkannin 



HO O 




,CH(OH)-CH 2 -CH:C(CH 3 ) ; 



yellow needles. M.p. 215. 
and H 2 S0 4 + boric acid. 



MW, 268. Golden- 
Bed sols, in H 2 S0 4 



C 16 H 16 5 MW, 288 

Bed pigment of Alkanna tinctoria and Onosma 
echiodes. Bronze spears from Et 2 0-EtOH. 
M.p. 149. M d 157 (C 6 H 6 ). Optical anti- 
pode of shikonin. Sublimes at 140/0-001 mm. 
Dry dist. > 1-methylquinizarin. Zn dist. > 
2-methylanthracene. B/ed > alkannan. O 3 
>- acetone. 

Triacetyl: yellow. M.p. 132. [a] 2 c d -110 
in CeH 6 . 

Dibenzoyl : yellow. M.p. 174-5. 

Me ether : brownish red. M.p. 105. Identical 
with shikonin methyl ether. 

Et ether : brown red. M.p. 83. 

Propyl ether : red. M.p. 57-8. 

Brockmann, Both, Naturwiss., 1935, 23, 

246. 

Brockmann, Ann.> 1935, 521, 1. 
Baudnitz, Stein, Ber., 1934, 67, 1955; 

1935, 68, 1479. 

Carnelutti, Nasini, Ber., 1880, 13, 1514. 
Liebermann, Bomer, Ber., 1887, 20, 2428. 
Dieterle, Salomon, Nosseck, Ber., 1931, 

64, 2086. 

rJ- Alkannin. 

See Shikonin. 



Alkathene 



48 



AUitol 



Alkathene. 

See Ethylene. 

Allantoic Acid (Diureidoacetic acid) 



HN-CO-NH 

C 4 H 8 4 N 4 MW, 176 

Needles. Sinters at 168. M.p. 173 decomp. 

Spar. sol. cold H 2 O, org. sols, and dil. acids. 

Hot H 2 > glyoxylic acid + urea. 
M ester: C 6 H 12 4 N 4 . MW, 204. Needles. 

Decomp. about 200. Sol. EtOH, liot H 2 0. 
Behrend, Sckultz, Ann., 1909, 365, 21. 

Allantoin (Glyoxylic diureide) 
HN 



Allethrin (Allylrefhronyl chrysanthemate) 

9 H 3 

(CH 3 ) 2 C X y C=C 

1 H/CH-COO-CH I 
(CH 3 ) 2 C:CH-CH 







HN CO 



MW, 158 



C 19 H 2 A MW, 302 

Viscous oH. B.p. 127/0-002 mm., 100-102 / 
0-001 mm. rig 1-505. Synthetic analogue of 
pyrethrin. Insecticide. 

Schechter, Green, LaForge, J. Am. Chem. 

Soc., 1949, 71, 3165. 
Gersdorff, Journal of Economic Ento- 

mology, 1949, 42, 532. 
Harper et al, J. Chem. Soc., 1950, 3561. 

Allicin 

C 3 H 5 S(:0)SC 3 H 5 

or 

(C 3 H 5 S) 2 

C 6 H 10 OS 2 MW, 162 

Antibacterial principle of Allium satwum. 
D 20 1-112. wf> 1-561. Sol. 2-5 gm./lOO c.c. 



Occurs in allantoic fluid of cow. Monoclinic 
prisms from H 2 0. M.p. 238-40. Sol. EtOH, 
hot H 2 0. fc = MxlO- 9 at 25. Heat of 

form. 1704 Cal. Heat of comb. 0,, 413-9 Cal., ^ Oat 10 Alkalis > SO 
Q, 415-1 Cal. * 

1-Jfe : see 1-Meth.ylallantoin. 

3-Jfe : see 3-Meth.ylallantoin. 

3-Et : C 6 H 10 3 N 4 . MW, 186. Prisms from 
MeOH. M.p. 189-90 



Cavallito, Bailey, J. Am. Chem. Soc., 1944, 

66, 1950. 
Raghunandana Rao et al., J. Sci. Ind. 

Research, 1946, IB, 31. 



JJJ,V3V 
1 


JLJL. J.A.k/. J->*JU U\J 

Z-Di-Me : C 6 H 10 3 N 4 . MW, 186. 


from 


tEtOH. M.p. 214. 


1 


6-Di-Me : needles from AcOH. M 


7d 


ecomp. 


1 


S-Di-Me : prisms from H 2 0. M.p 


3 


8-Di-Me : prisms from H 2 0. M.p 


1 


3 : 6*Tri~Me : see Caffolino. 


1 


3 : S-Trt-Me : C 7 H ia 3 N 4 . MW 



Prisms 
M.p. 226- 



AHiin ($-Allylsulphenylalanine, S-attykysteina 
sulphoxide) 

CH 2 :CH-CH 2 -S-CH 2 -CH(NH 2 )-COOH 







200. 

Prisms from AcOEt. M.pT 152". 

1-Acetyl: leaflets from AcOH. M.p. 236 
decomp. 

1 : 3-Diacetyl : prisms from AcOH. M.p. 247 
decomp. 

Biltz, Giesler, Ber., 1913, 46, 3410. 
Biltz, Max, Ber., 1921, 54, 2451. 
Hartmann, Moffett, Dickey, Organic Syn- 
theses, XIII, 1. 

Allantoxanic Acid. 

See Oxonic Acid. 

Allene (Isoallylene, propadiene) 

CH a :c:cH 2 

C 3 H 4 MW, 40 

Gas. M.p. - 146. B.p. - 32. Dist. of 
H 2 80 4 sol. * Me 2 CO. Gives no Cu or Hg 
ppt. Bromine > tetrabromide. Readily iso- 
meriscs on heating -> CH 3 C =2 CH. 

Tetrabromide : see 1 : 2 : 2 : 3-Tetrabromopro- 
pane. 

Nitrosite : cryst. from Et 2 0. M.p. 89 de- 
comp. 

Vaubel, er,, 1891, 24, 1685. 



CH U 3 NS 



177 



Occurs in garlic oil (from Allium sativum, A. 
ursinum and A. triquetrum). Fine neodlcw from 
H 2 0-Me 2 CO, M.p. 163-5 decomp. M?> ! -I- 62-7 
in H 2 0. Alloxan > red col. Gives positive 
ninhydrin reaction. Heat with Na 2 Fo (CN) 6 NO 
^- red, col. Alliinase > allicin -|- pyruvi<5 
acid + NH 3 . 

TS-Acetyl : Irwine salt, m.p. 188-98 docomp. 
[ajf, 1 -29-0. 

N-Benzoyl: m.p. 152-3-5 dooomp. fa]^ 
-~6-0 in MoOH. 

T$-p-Nitrobenzoyl : m.p. 180-2 cleoomp, \a$? 
9-0 in MeOH. Me ester : m.p. 140-3. 

AniUnoformyl deriv. : m.p. 141-3 dooomp. 
[ a ] +76-0 in MeOH. 

Stoll, Seobock, Helv. OMm. Ada, 1949, 
32, 197; 1948, 31, 189. 

Allitol (Allodukitol) 

H H H II 

HOH 2 C-ri 6 6 (J.OH a OIf 

OH OH OH OH 
O fl H M O e MW, 182 

M.p. 150. 



Allobarfoitone 



49 



AHo-y-codeine 



Dibenzylidene deriv. : m.p. 249. 
2:4:3: 5-Dimethylene : m.p. 256. 

Steiger, Beichstein, Helv. Chim. Acta, 

1936, 19, 184. 
Lespieau, Wiemann, Butt, soc. chim., 

1933, 53, 1107. 
Wolfrom, Lew, Goepp, J. Am. Chem. Soc., 

1946, 68, 1443. 

Allobarbitone. 

See 5 : 5-Diallylbarbituric Acid. 
Allob er gapt ene 



CH 

HK 

CH 3 0!il x ^0 

o 

C 12 H 8 4 MW, 216 

Cryst. from MeOH. M.p. 207. H 2 2 > 
furan-2 : 3-dicarboxylic acid. Bed > tetra- 
hydro deriv. 

Spath, Wessety, Kubiczek, Ber., 1937, 

70, 243. 

Foster, Howell, Bobertson, J. Chem. Soc., 
1939, 930. 

Allobetulin. 

See Befrulin. 

Allobromocinnamic Acid. 
See Bromocinnamic Acid. 
Allocaffeine. 
See under Caffolide. 
Allocaffuric Acid. 
See under Caffuric Acid. 
Allochlorocinnamic Acid. 
See Chlorocinnamic Acid. 
Allocholanic Acid 



CH-[CH 2 ] 2 -COOH 





Allocholesterol (A^-Cholestenol) 

:iCH 2 ] 3 -CH(CH 3 ) 2 

C 27 H 46 MW, 386 

Needles from Et 2 0MeOH. M.p. 132 (115- 
8). Sol. most org. solvents, [og +43-7. 
Pptd by digitonin. HC1 in EtOH > A 2:4 - 
cholestadiene. 

Acetyl : needles from MeOH.Aq. M.p. 85. 

Chloride : M.p. 95. 

Schoenheimer, Evans, J. Biol. Chem., 
1936, 114, 567. 

epiAllocholester ol (A 4 - epiCholestenol ) 

r CH-[CH 2 yCH(CH 3 ) 2 



HO' 
C 27 H 46 



MW, 360 

"Bates from AcOH. M.p. 170. 

Me ester: C 25 H 42 2 . MW, 374. Needles. 
M.p. 91. 

at ester : C 26 H 44 2 . MW, 388. M.p. 84. 

Propyl ester: C 27 H 46 2 . MW, 402. M.p. 
103-4. 

Butyl ester: C 28 H 48 2 . MW, 416. M.p. 87. 

Windans, Bohne, Ann., 1923, 433, 284. 
Windaus, Neukirchen, Ber., 1919, 52, 

1918. 
Hofmann, Stoll, Helfenstein, Helv. Chim. 

Acta, 1935, 18, 644. 
Wieland, Dane, Martins, Z. physioL 

Chem., 1933, 215, 15. 

Blot, of Org. Gomp, I. 




MW, 386 



M.p. 84. Sol. most org. solvents. [og 4 
+ 120-8. Not pptd. by digitonin. HC1 in 
EtOH ^ A 2 4 -cholestadiene. 

Acetyl : needles. M.p. 82-5. 

Schoenheimer, Evans, J. Biol. Chem., 
1936, 114, 567. 

Allochrysoketone . 

See 3 : 4-Benzfluorenone. 
Allocinchomne . 
See Apocinchonine. 
Allocinnamic Acid. 
See Cinnamic Acid. 
AHo-y-codeine 




C 18 H 21 3 N . MW, 299 

Needles from AcOH. M.p. 116-17. [a]? 
235-4. 

B,HCl : m.p. 256-8 decomp. [a] 2 D 8 - 202. 
Salicyloyl deriv. : m.p. 202. [a] 145. 
Speyer, Krauss, Ann., 1923, 432, 233. 
Lutz, Small, J. Am. Chem. Soc., 1934, 56, 
2466. 

4 



Allocrotonic Acid 



50 



Allo-ocimene 



Allocrotonic Acid. 

See Isocrotonic Acid. 
a-Allocryptopine . 
See p-Homochelidonine. 
p-Allocryptopine . 
See y-Homochelidonine. 
Allodunnione 




H 3 C CH 3 

Tentative structure 

C 15 H 14 3 MW, 242 

Obtained by heating dunnione with alkali. 
Yellow needles. M.p. 161-2. [og? 10-2 in 
CHC1 3 . Cr0 3 >- acetone. 

2 : 4-Dinitrophenylhydrazone : yellowish orange. 
M.p. 315 decomp. 

Price, Robinson, J. Chem. Soc., 1939, 
1522; 1940, 1493. 

AUoemicymarin . 

See 17-Isoemicymarin. 
AUoglaucotoxigenin 

C 23 H 326 MW > 404 

Aglycone from Coronilla glauca. M.p. 235 
decomp. [a]| +27. No cardiac activity. 

Diacetyl deriv. : cryst. +5H 2 0. M.p. 192-3. 
[aft 8-8. Oxime: m.p. 265. [oc] 2 D -5-9 1. 

Stoll, Pereira, Lenz, Helv. Chim. Acta, 
1949, 32, 293. 

Alloimp eratorin 

CH 2 -CH:C(CH 3 ) 2 
I CH 
"V 




C 16 H 14 4 MW, 270 

Obtained by dist. of imperatorin. Yellow. 
M.p. 233 (235-6). Sublimes at 205-15 (bath 
temp.)/0-001 mm. Sol. in alkalis. 

'Me ether: m.p. 113-5. B.p. 185-195/0-01 
mm. 

Spath, Holzen, J3er., 1933, 66, 1137. 
Spath et al, er., 1937, 70, 1021. 



Alloinositol 



C 6 H 12 6 



HC-OH 

HO-9-H H-9-OH 
HO-C-H H-C-OH 

\ / 
HC-OH 



M.p. 270-5. 

Bangschat, Fischer, Naturwiss., 1939, 
27, 756. 



Alloisorubijervine 
C 27 H 43 2 N MW, 413 

Cryst. from EtOH-Et 2 O as rhombic platelets. 
M.p. 250-1. [a]? "" 



63 in CHCL. Trichloro- 



acetic acid > deep purple col. 

Jacobs, Craig, J". Bid. Chem., 1945, 159, 
617. 



Allolupeol 

C 30 H 50 MW, 426 

Obtained by heating lupeol with formic acid 
and saponifying. Three forms : 

Needles. M.p. 191. 
lormyl : m.p. 229. 
Acetyl : m.p. 199 (195-6). 
Benzoyl : m.p. 256. 

P- 

M.p. 151. 

Formyl : amorphous. M.p. 180-3. 

Acetyl : m.p. 196. 

Benzoyl : m.p. 228. 

y-. 

Leaflets. M.p. 176-7. 

Acetyl : leaflets. M.p. 268-9. 

Nojd, Arch. Pharm., 1927, 265, 381. 
Biedebach, Arch. Pharm., 1943, 281, 49. 

Allomucic Acid (Tetrahydroxyadipic acid) 

H 



H 
HOOC C 



H 



H 



9 9 COOH 
OH OH OH OH 

CflH 10 8 MW, 210 

Needles from H 2 0. M.p. 176 decomp. 
Heat of comb. C y 495-3 Cal. Sol. hot H 2 (), 
which distinguishes it from mucic acid. Spar. 
sol. EtOH. 

Di-ffl ester: C 10 H 18 8 . MW, 266. Crynt. 
from EtOH. M.p. 139-41. 

Amide : C 6 H U 7 N. MW, 209. Cryst. from 
H 2 0. M.p. 175-6. 

Diamide: C 6 H 12 C N 2 . MW, 208. Cryat, 
from H 2 0. M.p. 209 decomp. 

Phenylhydrazide : cryst. from EtOH. M.p. 
218 decomp. 

Butler, Crotchor, J. Am. Ghem. tioc. 9 1929, 

51, 2167. 
Fischer, JSer., 1891, 24, 2137. 



Allo-ocimene 

triene) 



MW,180 C 10 H ie 



(2 : Q-Dimethyl~2 : 5 : 7-octo- 



MW, 136 



Aiioperiplocymarin 

B.p. 188 /750 mm., 95/24 mm., 81/12 mm. 
D 15 0-8133. ^ 1-5447. 

Lozac'h, Bull. soc. chim., 1941, 8, 519. 
Nikitin, J. Applied Chem. U.8.S.S., 1946, 

19, 890, (Chem. Abstracts, 1947, 41, 

6550). 

Arbusow, Ber., 1934, 67, 563. 
Bnklaar, Eec. trav. chim., 1907, 26, 175. 

Aiioperiplocymarin. 

$ee 17-Isoperiplocymarin. 
AUoperiplogenin . 
See 17-Isoperiplogenin. 
Allop eucenin 

H 3 C\ /CH 3 




Suggested structure 



51 Allopregnane-3a : 11(3 : 17a : 21- 

tetrol-20-one 

Benzyl ester: C 9 H 10 3 N 2 . MW, 194. M.p. 
191*o . 

Amide : see Biuret. 
Methylamide : see under Biuret. 
Ethylamide : see under Biuret. 
Anilide : see co-Phenylbiuret. 
o-Toluidide : m.p. 180. 
m-Toluidide : m.p. 165. 
p-Toluidide : m.p. 215. 
Nitroanilide : see co-Nitrophenylbiuret. 

Bougault, Leboucq, Bull. soc. chim., 1930, 
47, 594. 

Gattermann, Ann., 1888, 244, 40. 

Behal, Compt. rend., 1919, 168, 945. 

Allophanylacetic Acid. 

See Malonuric Acid. 

Allophanylaniline . 

See co-Phenylbiuret. 

AUopregnane 3p : 11)3 : 17oc : 20(3 : 21-pentol 

(Beichstein's Substance A) 

HO, OH ' OH 



MW, 260 
heating with 



Obtained from peucenin by 
H 2 S0 4 . M.p. 303-4 decomp. 
Me ether : m.p. 170-1. 

Spath, Eiter, Ber., 1941, 74, 1851. 

Allophanamide. 

See Biuret. 

Allophanic Acid (Ureidoformic acid, N-car6- 
oxyurea, carbamylcarbamic acid) 

H 2 N-CO-NH-COOH 
C 2 H 4 3 N 2 MW, 104 

Not known in free state. Decomp. to C0 2 
and urea when liberated from its salts. Salts 
are unstable, being hyd. by H 2 to C0 2 , urea 
and carbonate. 

Me ester: C 3 H 6 3 N 2 . MW, 118. Needles 
from. H 2 0. M.p. 208 decomp. Sol. EtOH, hot 
H 2 0. 

M ester: C 4 H 8 3 N 2 . MW, 132. Needles 
from H 2 0. M.p. 195. Sol. EtOH, hot H 2 0. 
Spar, sol. EtOH. Dist. > cyanuric acid + 
EtOH. Acetyl deriv. : m.p. 107. 

Propyl ester : C 5 H 10 3 N 2 . MW, 146. Leaf- 
lets. M,.p. 150-60. Sol. EtOH, hot H 2 0. 

Isoamyl ester : C 7 H X 40 3 N 2 . MW, 174. M.p. 
162. Sol. EtOH, hot H 2 0. Volatile in steam. 

Octyl ester : C JO H 20 3 N 2 . MW, 216. Needles 
from EtOH. M.p. 155-6. 

Cetyl ester: G^H^O^. MW, 328. Leaf- 
lets from EtOH. M.p. 70. 

Mono-glycol ester: aH 8 4 N 2 . MW, 148. 
M.p. 160. Sol. H 2 0, EtOH. 

Mono-glyceryl ester : CgH 10 5 N 2 . MW, 178, 
M.p. 160. SoL hot EtOH, 

Phenyl ester: C 8 H 8 3 N 2 . MW, 180. M.p. 
194. 




C 21 H 36 5 MW, 368 

Isolated from adrenal cortical extracts. M.p. 
222. [a]i? +16 in EtOH. Physiologically 
inactive. 

Triacetyl : m.p. 220. [a] D + 74. 

Wintersteiner, Pfiffner, J. Biol. C"hem. 9 

1935, 111, 599. 

Keichstein, Helv. Chim. Acta, 1936, 19, 

29; 1937, 20,978. 
Mason, Myers, Kendall, J. Biol. Chem., 

1936, 114, 613. 

Shoppee, Helv. Chim. Acta, 1940, 23, 740. 
Reichstein, von Euw, Helv. Chim. Acta, 
1941, 24, 247E. 

AUopregnane~3(3 : 17a : 20(3 : 21-tetrol 

(Reichstein' s Substance K) 

C 21 H 36 4 MW, 352 

Isolated from adrenal cortical extracts. M.p. 
200. [a] D 1 in EtOH. Physiologically 
inactive. 

Triacetyl : m.p. 179. [a] D + 53. 

Steiger, Beichstein, Helv. Chim. Acta, 

1938, 21, 546. 

Serini, Logemann, Hildebrand, Ber., 

1939, 72, 391. 



Allopregnane-3oc : lip : 17cc : 21-tetrol-20- 

one (Heichstein's Substance C) 
C 21 H 34 5 MW, 366 

Isolated from adrenal cortical extracts. M.p. 



276. [<x] D 
inactive. 



+ 73 in EtOH. Physiologically 



Ailopregnane-3p : lip : 17ct : 21- 52 

tetrol-20-one 

Diacetyl : m.p. 205. [a] D + 74. 

Wintersteiner, Pfiffner, J. J?w?Z. Chem., 

1935, 111, 599. 
Reichstein, Helv. Chim. Ada, 1936, 19, 

29. 
Mason, Hoehn, Kendall, J. Biol. Chem., 

1938, 124, 459. 
Kuizenga, Cartland, Endrocrinology ; 1939, 

24, 526. 

Allopregnane-Sp : lip : 17<x : 21-tetrol-20- 

one (Eeichstein's Substance V) 

C 21 H 34 5 MW, 366 

Isolated from adrenal cortical extracts. M.p. 
225. [a] D + 51 in EtOH. Physiologically 
inactive. 

Diacetyl : m.p. 227. [a] D + 63. 

Von Euw, Eeiclistein, Helv. Chim. Acta, 
1942, 25, 988. 

Allopregnane-3(3 : 17a : 20a~triol (Seich- 
stein's Substance 0) 

C 21 H 36 3 MW, 336 

Isolated from adrenal cortical extracts. M.p. 
223. [op - 13 in EtOH. Physiologically 
inactive. 

Diacetyl : m.p. 250. [a] D 30. 

Steiger, Reichstein, Helv. Chim. Acta, 

1938, 21, 546. 
Reich, Sutter, Reichstein, Helv. Chim. 

Acta, 1940, 23, 170. 

Allopregnane-Sp : 17a : 20p-triol (Reich- 
stein's Substance J) 
C 21 H 36 3 MW, 336 

Isolated from adrenal cortical extracts. M.p. 
217. [a] D 8. Physiologically inactive. 
Diacetyl : m.p. 160. [a] D + 25. 

Reichstein, Helv. Chim. Acta, 1936, 19, 

1107. 
Reich, Sutter, Reichstein, Helv, Ghim. 

Acta, 1940, 23, 170. 

AUopregnane - 3p : 17oc : 21 - triol - 11 : 20 - 
dione (Reichstein' s Substance D) 

C 21 H 32 6 MW, 364 

Isolated from adrenal cortical extracts. M.p. 
242. [oc] D + 62 in EtOH. Physiologically 
inactive. 

Diacetyl : m.p. 224. [a] D + 72. 

Wintersteiner, Pfiffner, /. Biol. Chem., 

1935, 111, 599. 
Mason, Hoehn, Kendall, J. Biol. Chem., 

1938, 124, 459. 
Kuizenga, Cartland, Endocrinology, 1939, 

24, 526. 
von Euw, Reichstein, Helv. Chim. 

1942, 25, 988. 



Allosantenic Acid 



Allopregnane - 3(3 : 11(3 : 21 - triol - 20 - one 

(Reichstein' s Substance R) 

C 21 H 34 4 MW, 350 

Isolated from adrenal cortical extracts. M.p. 

204. Physiologically inactive. 
Diacetyl : m.p. 174. [a] D + 84. 

Reichstein, Helv. Chim. Acta, 1938, 21, 
1490. 

Allopregnane - 3p : 17oc : 21 - triol - 20 - one 

(Reichstein 3 s Substance P) 

CWHjjA MW, 350 

Isolated from adrenal cortical extracts. M.p. 
239. [OC]D +48 in EtOH. Physiologically 
inactive. 

Diacetyl : m.p. 209. [a] D + 38. 

Reichstein, Gatzi Helv. Chim. Acta, 
1938, 21, 1185. 

Allo quinidine 
CH 3 -CH:C 9H CH 2 




H-CH(OH)C 9 H 6 NOCH 3 
20 H 24 2 N 2 MW, 324 

Obtained by heating quinaldine with H 2 S0 4 . 
M.p. 249-50. [a]^ 230. AcOH > allo- 
quinotoxin. 

B,HI : m.p. 265-6 decomp. [aji? 185. 

,H 2 SO^ : m.p. 244-5 decomp. [a]g> 185. 

Methiodide : m.p. 252-3. [a]g 185. 

Di-Methiodide : m.p. 227. [a"| 2 D 179. 

Acetyl : m.p. 166-7. [a]g> 193. 

Benzoyl : m.p. 113-5. [a]f> 59. 

Lubwiczak, Sunko, Chem. Abstracls, 1937, 
31, 1816. 

Allosantenic Acid (1 : Z 

tane-l : 3-dicarboxylic acid) 

OOOHi 




9 H M 4 MW, 186 

Geometrical isomcr of Hantonic acid. 

M.p' 151-2. AoOH-HOl > tron form. 

Anhydride : needles. M.p. 92. 

Trans*. 
M.p. 166-7. 

Enkvist, Chem. Abstracts, 1033, 27, 715, 
Chakravarti, /, Indian Chem, floe., 1943, 
20, 243, 



Allose 



58 



Alloxanic Acid 



Allose 

9HO 

9HOH 

9HOH 

9HOH 

9HOH 

CH 2 OH 

C 6 H 12 6 MW, 180 

dl-. 

Osazone : m.p. 186-8 decomp, 
flk 

Cryst. from H 2 0. M.p. 128-128-5. jog? C 4 H 2 4 N 2 
4- 0*58. 

Osazone : m.p. 173-4 decomp. [a]f> 19-2 
4. 



Prisms from EtOH.Aq. M.p. 128-9. MD 
- 1-9. 

Phenylosazone : yellow cryst. from EtOH.Aq. 
M.p. 165. 

p-Bromophenylhydrazone : m.p. 141-5. [a]?? 
+ 6-4 in EtOH. 

Beich8tem> Steiger, Helv. Chim. Acta, 

1936, 19, 184. 
Phelps, Bates, /. Am. Chem. Soc., 1934, 

56, 1250. 
Austin, Humoller, J. Am. Chem. Soc., 

1934,56, 1153; 1933,55,2167. 



Allotephrosin . 

See Tephrosin. 

Allothxeonine. 

See under 2-Hydroxy-l-aminobutyric Acid. 

Allouzarigenin . 

See 17-Isouzarigenin. 

Alloxan (Mesoxalylmea) 




10 



MW, 142 

Bhombic prisms from H 2 0, having constitu- 
tion 



, 3H 2 




10 



Allositosterol 




9H(CH 3 ) 2 



CH 2 <CH 3 



HC 
C 29 H 50 MW, 414 

M.p. 158. 
Acetyl : m.p. 88. 

Marker, Oakwood, J. Am. Chem. Soc., 
1937, 59, 2708. 

Allostigmasterol 

UH. 9H 3 9H(CH 3 ) 2 

/\ , OH-CH:CK-CH 



Effloresces losing 3H 2 0. At 150 > C(OH) 2 >- 
> CO + H 2 0. Decomp. at 170. Sol. - H 2 O, 
EtOH. Aq. sol. reacts acid. Forms bisulphite 
comp. Heat of comb. C p 276-6 Cal. Jc = 
2-3 X 10~ 7 at 25. HN0 3 > parabanic acid. 
Bed. > alloxantin. Alk. hyd. ^ alloxanic 
acid >. mesoxalic acid + urea. Fe salts > 
deep blue col. 

5-Oxime : see Violuric Acid. 

5 : 6~Dioxime : yellow cryst. from EtOH. 
M.p. 242 decomp. 

5-Phenylhydrazone : m.p. 298 decomp. 6- 
Oxime : yellow cryst. from EtOH. M.p. 268. 

6-Phenylhydrazone : cryst. from EtOH. M.p. 
260. 

o-Nitrophenylhydrazone : m.p. 310. 

p-Nitrophenylhydrazone : m.p. 300. 

K-Naphthylhydrazone : red cryst. from AcOH. 
M.p. 264. 

Biltz, Heyn, Ann., 1917, 413, 60. 
Hartman, Sheppard, Organic Syntheses, 
1943, XXIII, 3. 

Alloxanic Acid 



/\1 



H 









J. J 



,-CHo 



MW, 412 



C 29 H 48 
M.p. 137. 
Acetyl : m.p. 132. 

Marker, Oakwood, J. Am. Ghem. Soc., 
1937, 59, 2708. 

Allostrophanthidin. 

See 17-Isostrophanthidin. 



C 4 H 4 5 N 2 MW, 160 

Prisms from Et 2 0. Decomp. at 162-3. Sol. 
H 2 0. Mod. sol. EtOH. Spar. sol. Et 2 0. 

Me ester: C 5 H 6 6 N 2 . MW, 174. Prisms 
from AcOEt. Needles from Me 2 CO-CHCl 3 . 
M.p. 171. 

Et ester : C 6 H 8 5 N 2 . MW, 188. Cryst. from 
Me 2 CO-CHCl 3 . M.p, 115. 

Amide : C 4 H 5 4 N 3 . MW, 159. Prisms from 
H 2 0. M.p. 191. 

Et amide: C 6 H 9 4 N 3 . MW, 187. Needles 
from EtOH. Decomp; at 136. 



Alloxanthoxyletin 



54 



Allyl Alcohol 



Phenyl amide : C 10 H 9 4 N 3 . MW,234. Cryst. 
from Et 2 0. M.p. 99. 

Biltz, Lachmann, J. praJct. Chem., 1926, 
113, 309, 333. 

Alloxanthoxyletin 




CH 3 CH 3 
C 15 H 14 4 MW, 258 

Isolated from bark of Xanthoxylum ameri- 
canum. Pale yellow elongated thick prisms 
from petrol. M.p. 115-5. Easily sol. C 6 H 6 , 
Et 2 0. Spar. sol. cold EtOH. Orange sol. in 
cone. H 2 S0 4 changing to orange-red in about 
1 min., to bright-red on warming to 100, finally 
becoming colourless. 

Dihydro deriv. : thick colourless prisms from 
petrol. M.p. 155 after sintering at 153. 

Eobertson, Subramaniam, J. Chem. Soc., 
1937, 1545. 



Alloxantin 

HN 90 

09 

HN CO 



NH 

90 

CO NH 



C 8 H 6 8 N 4 MW, 286 

Rhombic prisms + 2H 2 from H 2 0. Yellow 
at 225. Decomp. at 253-5. Spar. sol. cold 
H 2 0. Aq. sol. reacts acid. Reduces Ag salts. 
Ba(OH) 2 ^ blue ppt. Heat of comb. C. 
584-7 Cal. Ox. >- alloxan. Red. ^ dial- 
uric acid. 

Acetyl deriv. : leaflets + 1H 2 from H 2 0. 
M.p. 263-5 decomp. 

Benzoyl deriv. : leaflets from H 9 0. M.p. 
253-5. 

Hantzsch, Ber., 1921, 54, 1267. 
Deniges, Chem. Abstracts, 1929, 23, 4160. 
Nightingale, Organic Syntheses. 1943. 
XXIII, 6. 



Alloxazine 



N CO 




C 10 H 6 2 N 4 MW, 214 

Greyish-green powder. Decomp. above 300. 
Sol. alkalis or alkali carbonates, very spar. sol. 



EtOH. Insol. H 2 0, Et 2 0. Na salt, cryst. in 
yellow needles. Red. > red free radical. 

Kiihling, Ber., 1891, 24, 2364. 

Mohlau, Litter, J. prakt. Chem., 1906, 73, 

449. 

Kuhn, Bar, Ber., 1934, 67, 898. 
Tishler, Wellman, Ladenburg, J. Am. 

Chem. Soc., 1945, 67, 2165. 

Allulose. 

See Psicose. 

Allylacetaldehyde. 

See 4-Pentenal. 

Allyl acetate 

CH 2 :CH-CH 2 0-CO-CH 3 
C 5 H 8 2 MW, 100 

B.p. 103-4. D 0-938. < 1-40488. Readily 
polymerised in the presence of alkaline earths. 

Deulofeu, Chem. Abstracts, 1928, 22, 4104. 
Zinin, Ann., 1855, 96, 361. 

Allylacetic Acid ( 1 -ButyleneA-carboxylic 
acid, 3-pentenic acid, 2-vinylpropionic acid) 

CH 2 :CH-CH 2 -CH 2 -COOH 
C 5 H 8 2 MW, 100 

B.p. 188-9. Spar. sol. H 2 0. DJ 8 0-9843. 
nl 14341. A; = 2-lxlO- 5 at 25. Br > 
3 : 4-dibromo-n- valeric acid. KMn0 4 >- 3 : 4- 
dihydroxy- n- valeric -|- succinic acids. 

Et ester : C 7 H 12 2 . MW, 128. B.p. 144-6. 

Chloride : C 5 H 7 OC1. MW, 118-5. B.p. 128. 
D 16 1-0739. 

Amide: C 5 H 9 ON. MW, 99. M.p. 94. B.p. 
230. Sol. H 2 0. 

Nitrile: C 6 H 7 N. MW, 81. B.p. 140, 60- 
l/40mm. Insol. H 2 0. D}J 0-848, < 1-4213. 

Fittig, Messerschmidt, Ann., 1881, 208, 
92. 

Allylacetone (l-He%enone-&, methyl y-butenyl 
ketone) 

CH 2 :CH-CH 2 -CH 2 -Ct)-CH 3 
C 6 H 10 MW, 98 

B.p. 129-6. Dll 6 0-834. Cr0 3 > acetic 
and oxalic acids and C0 2 - KMn0 4 -> lovu- 
linic acid. 

Oxme : b.p. 190. Sol. EtOH, Et 2 0. hxsol. 
H 2 0. 

Semicarbazone : m.p. 100-2. 

2 : 4:-Dinitrophenylhydrazone : orange cryat. 
from EtOH. M.p. 104. 

Merling, Ann., 1891, 264, 323. 

Allylacetylacetone . 

See Diacetobutylene. 

Allyl Alcohol (Vinylcarbinol, 1-propenol"^) 

CH 2 :CH-CH 2 OH 

C 3 H 6 MW, 58 

Colourless liq. B.p. 96-7. Freezes at 50, 

Misc. with H 2 in aU proportions. 72-3% allyl 



Allylamine 



55 



Allyl chloride 



I constant-boiling mix- 
15 0-8573. < 141345. 
Cr0 3 >- acraldehyde + 
-> acraldehyde + glycerol 
oxalic + formic acids. 



alcohol + 27-7% H 2 

tore, b.p. 87-5. D 

Crit. temp. 271-9, 

H-C0 2 H. KMn0 4 

+ H-COOH. HM_ 

Ag catalyst > acrolern. Eed. 

alcohol. 

3 : S-Dinitrobenzoate : m.p. 48. 

Shokal, Evans, B.P., 577,992, (Chem. 

Abstracts, 1947, 41, 2067). 
Delaby, Dubois, Compt. rend., 1929, 188, 

710. 
Nef, Ann., 1904, 335, 228. 

Allylamine (3-Amino-l-propylene, 3-amino- 
propene-l) 

CH 2 :CH-CH 2 -NH 2 

C 3 H 7 N MW, 57 

Colourless liq. with ammoniacal odour. B.p. 
58. Misc. with H 2 in all proportions. Dl$ 
0-7436. nf 1-41943. Heat, of comb. G p 526-8 
Cal. Jc = 5-7 X 10- 5 at 25. HN0 2 > allyl 
alcohol. Mel > methylallylaniine. Br in 
acid sol. >- 2 : 3-dibromopropylamine. 
B,HCl : cryst. from H 2 0. M.p. 105-110. 
N-Jfe : see Methylallylamine. 
N-JW-Jfe: C 5 H n ]Sr. MW, 85. B.p. 64/ 
743 mm. Sol. H 2 0, EtOH, Et 2 0. 
N-Et : see Ethylallylamine. 
IS-Di-Et : see Diethylallylamine. 
see Propylallylamine. 
allylaniline. See under Aniline. 
see under Formamide. 
see under Acetamide. 
7- allyldiacetamide . 



B.p. 88- 



"N-Propyl : 
N-Phenyl : 
"S-Formyl 
"N-Acetyl : 
"N-Diacetyl : 
90 /14 mm. 

Picrate : m.p. 140-1. 

Gabriel, Eschenbach, 
1124. 

Brown, Jones, J. Chem. Soc., 1946, 781. 

5-Allylbarbituric Acid 

HN CO 

li e[ 



Ber., 1897, 30, 



4 

-co 

C 7 H 8 3 N 2 MW, 168 

Plates from EtOH. M.p. 167. Sol. hot 
H 2 0. Insol. C 6 H 6 . Cone. KOH at 140 
allylmalonic acid. 

Johnson, Hill, Am. Chem. J., 1911, 46, 

540. 

S.C.I., D.E.P., 268,158, (Chem. Zentr., 
1914, 1, 201). 

Allylbenzene (%-Phenylpropylene) 

C 6 H 5 -CH 2 -CH:CH 2 

C 9 H 10 MW, 118 

B.p. 156-7. D 18 0-9012. < 1-5110. 
Klages, Ber. 9 1906, 39, 2590. 
Kharasch, U.S.P., 2,404,235, (Chem. 
Abstracts, 1946, 40, 6503). 



Allylbenzylamine . 

See under Benzylamine. 

Allyl benzyl Ether. 

See under Benzyl Alcohol. 

Allyl bromide (3-Bromopropylene, 3-bromo- 
propene-1) 

CH 2 :CH-CH 2 Br 
C 3 H 5 Br MW, 121 

B.p. 70-1. DJ 1-398. < 1-46545. 

Kamm, Marvel, Organic Syntheses, Collec- 
tive Vol. I, 24. 

1-Allyl-l : 3-butadiene. 
See 1:3: 6-Heptatriene. 
3-AUyl-l-butylene . 

See 3-Methyl-l : 5-hexadiene. 
Allylcarbinol (l-Butenol-4) 

CH 2 :CH-CH 2 -CH 2 OH 
C 4 H 8 MW, 72 

B.p. 1 12-5-1 13*5(corr.) /755mm. Df 5 0-8379. 
< 5 1-4146. 
Phenylurethane : m.p. 23-5-24-5. 

Pariselle, Compt. rend., 1909, 148, 849. 
Grischkevitsch-TrochimovsM, J. Chem. 
Soc., 1917, 112, 154. 

3-Allylcatechol (2 : %-Dihydroxy-l-allylbenz- 
ene) 

OH 




C 9 H 10 2 MW, 150 

B.p. 141-55 /16mm. Df 1-1241. < 1-5656. 
Diacetyl : m.p. 65. 

Kawai, Sci. Papers Inst. Phys. Chem. 
Research, ToJcyo, 1925, 3, 263 (Chem. 
Abstracts, 1926, 20, 1798). 

4-Allylcatecliol (3 : 4c-Dihydroxy-l-allylbenz- 
ene). 

Constituent of betel-leaf oil. Needles from 
petrol or C 6 H 6 -petrol. M.p. 48-9. B.p. 139 / 
4 mm. Sol. H 2 0. FeCl 3 > green col. Ox. 
^ veratric acid. 

2 -Me ether : see Eugenol. 

l-Et : 2-Me ether : see under Eugenol. 

Di~Me ether : see under Eugenol. 

Di-Et ether: C 13 H 18 2 . MW, 206. B.p. 
125/13 mm. Df 0-9836. rig 1-5132. 

Dibenzoyl : m.p. 71-2. 

Schimmel, Chem. Zentr., 1907, II, 1741. 
Schopf et al, Ann., 1940, 544, 30. 

Allyl chloride ($-Chloropropylene, 3-chloro- 
propene-l) 

CH 2 :CHCH 2 C1 
C 3 H 5 C1 MW, 76-5 



Allylcyanamide 



56 



Allylethyl Alcohol 



B.p. 45. Bf 0-9379. < 1*41538. 

Bewael, Chem. Abstracts, 1930, 24, 2717. 
Coffey, Ward, J. Chem. Soc., 1921, 119, 

1301. 
I.G., B.P., 495,900, (Clem, Abstracts, 1939, 

33, 2912); B.P., 502,611, (Chem, 

Abstracts, 1939, 33, 7318). 

Allylcyanamide . 

See Triallyl tricyanamide. 
Allyl cyanide (Vinylacetonitrile) 

CH 2 :CH-CH 2 CN 
C 4 H 5 N MW, 67 

Constituent of some mustard oils. B.p. 119. 
B 16 0-8351. wg 1-40602. Ox. > AcOH. 
Cone. HC1 at 60 -> 2-chlorobutyric acid. 
Ale. KOBE >- crotonic acid. 

Supniewski, Salzberg, Organic Syntheses, 

Collective Vol. I, 38. 
Smith, Snyder, Organic Syntheses, 1944, 

XXIV, 96. 

Allylcyclohexane (3-Cyclohexylpropylene) 
CH 2 

H 2 <p 9H-CH 2 -CH: 
H 2 C CH 2 



ITT 

C 9 H 16 2 MW, 124 

B.p. 150-1. B 13 0-8196. < 3 1-4536. 

v. Braun, Beutsch, Schmalloch, Ber., 
1912, 45, 1255. 

1 - Ally Icy clohexanol 
CH 2 

(OH)-CH 2 -CH:CH 2 



, 140 



H 2 
C 9 H 16 

B.p. 188-92, 95-7/27-5 mm. B 22 0-9341. 
n% 1-4756. 

3 ; 5-Dinitrobenzoyl : needles from pet. ether. 
M.p. 101-3. 

Saizew, Chem. Zentr., 1913, I, 23 : 1909, 

1,1402. 
Mazurewitsch, Chem, Zentr.. 1911, II, 

1922. 

Aldersley, Burkhardt, Gillam, Hindley, 
,/. Chem. Soc., 1940, 14. 

2-Allylcyclohexanone 
CO 



. 
CH 



Liq. with odour of menthol. B.p. 94/I6 mm. 
n% 1*4666. 

Oxime : needles. M.p. 71. 

2 : 4:-Dinitrophenylhydrazone : m.p. 145-6. 

Cope et al, J. Am. Chem. Soc., 1941, 63, 

1842. 
Cornubert, Compt. rend., 1914, 158, 1901. 

5 -Allyl - 5 - A 2 - cyclohexenylthiobarbitnric 
Acid. 

See Kemithal. 
$-Allylcysteine (Deoxyalliin) 

CH 2 :CH-CH 2 -S-CH 2 -CH(NH 2 )-COOH 
C 6 H n 2 NS MW, 161 

Cryst. M.p. 218-19. [a]g -16-0 in H 2 0. 

TS-Acefyl: m.p. 120-2. [a] -34-0 in 
MeOH. 

S-Oxide: cryst. + |H 2 0. M.p. 146-8 de- 
comp. [a]i 12-0 in H 2 0. Synthetic ma- 
terial is not identical with natural alliin. 

Stoll, Seebeck, Helv. Chim. Acta, 1949, 
31, 189. 

Allyldiacetamide . 

See under Allylamine. 

a-Allyldiethyl Ketone. 

See 4-Methyl-l-heptenone-5. 

Allyl disulphide. 

See Biallyl disulphide. 

Allylene (Methylacetylene, propyne) 

CH 3 -C:CH 



C 3 H 4 



MW, 40 



Gas. Freezes at 110. M.p. 105. B.p, 
- 27-5 (- 24). Sol. EtOH, Et 2 0. Mod. soL 
H 2 0. Br 18 0-66. Heat of comb. G p 467-55 Cal. 
Gives many metallic comps., e.g., Ag, Cu, Na, 
Hg. Cone. HC1 > CH 3 -CC1 2 'CH 8 . HOBr 
> CH 3 -CO-CHBr 2 . Pptes Cu and Hg comps. 
from NH 3 solutions. IsomerisoB to CH 2 " C.~CH 2 . 
Red. (Na/liq. NH 3 ) > CH 3 OHOH 2 . 

Tetrabromide : see 1:1:2: 2-Tetrabromopro- 
pane. 

Bodroux, Compt. rend., 1939, 208, 1022. 
Lossen, Ann., 1905, 342, 171. 

Allylene-1 -aldehyde . 

See Tetrolaldehyde. 

Allylene-1 -carboxylic Acid, 

See Tetrolic Acid. 

Allylene dibromide. 

See 1 : 2-Bibromopropylene. 

Allylene-1 : 3-dicarboxylic Acid. 

See Glutinic Acid, 

Allylene dichloride. 

See 1 : 2-Bichloropropylone, 

Allylene di-iodide. 

See 1 : 2-Bi-iodopropylone, 

Allylethyl Alcohol (1 -PewtonoZ-S) 



H 2 



MW, 138 C 6 H 10 



MW,86 



Allylethylene 

B.p. 140-2. D 4 0-863. KMn0 4 >suo- 
cinic acid. 

Me ether : C 6 H 12 0. MW, 100. B.p. 96-8. 
Dg 0-787. * 

Acetyl : b.p. 150-1. Dg 0-907. 

Phenylurethane: b.p. 184-5/16 mm. D 15 
1-068. 

Allophanate : cryst. M.p. 148. 

Bouveault, Blanc, Bull. soc. chim.. 1904, 

31, 1215. 

Paul, Compt. rend., 1932, 195, 1289. 
Paul, Normant, Bull. soc. chim., 1943, 10, 

484. 
Kharasch, Fuchs, J. Org. Chem., 1944, 9, 

359. 

Allylethylene. 
See 1 : 4-Pentadiene. 
Allyl fluoride 

CH 2 :CH-CH 2 F 
C 3 H 5 F MW, 60 

Gas with garlic odour. Liq. at 3. Sol. 
to 2-8% in H 2 0, 60% in EtOH, 90% in 
Et 2 0. 

Meslans, Compt. rend., 1890, 111, 882. 

Allylguaiacol. 

See Eugenol, o-Eugenol and Chavibetol. 

Allylidene chloride. 

See 3 : 3-Dichloropropylene. 

Allyl iodide (3-Iodopropylene) 

CH 2 :CH-CH 2 I 
C 3 H 5 I MW, 168 

B.p. 101-2/734 mm. Dg 1-848. Heat of 
comb. 0, 476-9 Cal., CL 478-33 Cal. Na > 
diallyl. 

Norris, Watt, Thomas, J. Am. Chem. Soc. t 
1916, 38, 1076. 

Allyl isothiocyanate (Allyl Mustard Oil) 



57 Allyl phenyl Ether 



AUylmalonic Acid (l-Butylene-4: : &-dicarb- 
oxylic acid) 



C 4 H 5 NS 



CH 2 :CH-CH 2 -NCS 



MW, 99 



Chief constituent of natural mustard oil. 
Colourless oil. Freezes at 80. B.p. 151, 
85 /93 mm., 66/37 mm., 56/22 mm., 44/12 
mm., 31/5 mm. Sol. H 2 to 0-2%. Sol. 70% 
EtOH to 7-10%. Sol. Et 2 0, C 6 H 6 , pet. ether. 
DJ 5 1-0155. < 4 1-52212. Heat of comb. G v 
731-2 Cal. Heat of comb, of vapour CL 675-4 
Cal. Diss. P and S when hot. Ale. NH 3 > 
allylthiourea, Adds Br. Alkali hydrosul- 
phides > salts of i^-allyldithiocarbamic acid. 
Long standing with H^O > allyl cyanide + S. 
Hyorazine ^ allylthiosemicarbazide. Ba(OH) 2 
> iV2y'-diallylurea. Ac 2 at 180 > di- 
acetylallylamine. Phthalic anhydride > N- 
allylphthalimide. 

Tollens, Ann., 1870, 156, 158. 



C 6 H 8 4 MW, 144 

Cryst. from Et 2 0. M.p. 105. Sol. H 2 O, 
Et 2 0, EtOH, hot C 6 H 6 . Heat of comb. C^'and 
C, 638-4 Cal. k = 1-54 x 10- 3 at 25. Heat. 
at 180 > allylacetic acid. Cone. HBr > 
3-bromopropylmalonic acid. 

Ag salt : m.p. 60 decomp. Insol. H 2 0. 

Di-Et ester: C 10 H 16 4 . MW, 200. B.p. 
222-3, 193-4 /330 mm., 93/6 mm. ~D\I 1-014. 

p-Nitrobenzyl ester: cryst. from EtOH. 
M.p. 46. 

Nitrile : Et ester : b.p. 223. Amide : m.p. 
98. B.p. 289. 

Di-nitrOe: f.p. -12. B.p. 217-18. D 19 
1-0231. 

Conrad, Bischoff, Ann., 1880, 204, 168. 

Allyl Mercaptan (Allyl thioalcohol) 

CH"CH-CH 2 SH 
C 3 H 6 S MW, 74 

B.p. 67-8. DJ 8 0-925. 

Braun, Murjahn, Hahn, Ber., 1926, 59, 
1202. 

Allyl Mustard Oil. 

See Allyl isothiocyanate. 
1-AUylnaphthalene (S- 

CH 2 -CH:CH 2 




C 13 H 12 " ' MW, 168 

B.p. 265-7, 129-30/10 mm. DJ 1-0228. 
TI| 1-6140. Isomerised by heated A1 2 O 3 to 
1 -propenylnaphthalene. 
Picrate : m.p. 69. 

Levina et al., Chem. Abstracts, 1941, 35, 

2479. 
Tiffeneau, Daudel, Compt. rend., 1908, 

147, 678. 
jp-Allylphenol. 
See Chavicol. 

Allylphenylcarbinol (k-HydroxyA-p"henyl- 
butylene- 1 , k-phenyl- l-butenol-4c) 

C 6 H 6 -CH(OH)-CH 2 -CH:CH 2 
C 10 H 12 MW, 148 

B.p. 228-9, 100-l/4 mm. D 18 1-004. 
Acetyl: b.p. 239-40. D 18 1-015. 

Fournier, Bull. soc. Mm., 1893, 9, 600. 

Allyl phenyl Ether 

C 6 H 5 0-CH 2 -CH:CH 2 

C 9 H 10 MW, 134 

B.p. 192-5. Insol. H 2 0. D} 8 8 0-9856. Vola- 
tile in steam. 

Perkin, J. Chem. /Soc,, 1896, 69, 1225. 



2-Allylpropionic Acid 



58 



Alstoniline 



2-Allylpropionic Acid (l-Amylene-5-carb- 
oxylic acid, l-pentene-5-carboxylic acid, 4c-hexenic 
acid) 

CH 2 :CH-CH 2 -CH 2 -CH 2 -COOH 

C 6 H 10 2 MW, 114 

B.p.203. D 19 0-9639. < 1*4375. Jc = 1-91 
X 10- 5 at 25. 

Wallach, Ann., 1905, 343, 48. 

JV- Allylpyrrole . 
See under Pyrrole. 

Allylsuccinic Acid (l-AmyleneA : 5-dicarb- 
oxylic acid) 

CH 2 :CH-CH 2 -9H-COOH 
CH 2 -COOH 
C 7 H 10 4 MW, 158 

Leaflets from EtOH. M.p. 93-4. k = 1-09 
X 10- 4 at 25. 

Hjelt, Ber., 1883, 16, 334. 

Ally! sulphide. 

See Diallyl sulphide. 

Allylthiourea (AUylthiocarbamide, Thiosin- 
amine) 



C 4 H 8 N 2 S MW, 116 

Monoclinic or rhombic prisms. M.p. 78. 
Sol H 2 0, EtOH. Spar. sol. Et 2 0. Insol. 
C 6 H 6 . D2S 1-219. n 1-59362. wff 1-63454. 
Heat of comb. 0, 790-4, C p 781-8 Cal. PbO or 
HgO > allylcyanamide. 

Gadamer, J. Chem. Soc., 1896, 70, 414. 
Kofler, Arch. Pharm., 1943, 281, 8, 
(Chem. Zentr., 1943, 1, 1796). 

2V-AUyltoluidme. 

See under Toluidme. 
Allyl tolyl Ether. 
See under Cresol. 
Allylurea (Allylcarbamide) 

CH 2 :CH-CH 2 -NH-CO-NH 2 
C 4 H 8 ON 2 MW, 100 

Needles from EtOH. M.p. 85. Sol. H 2 0, 
EtOH. Spar. sol. Et 2 0, CHC1 3 . Insol. pet. 
ether, toluene, CS 2 . 

Andreasch, Monatsh., 1884, 5, 37. 

4-AHylveratr ol . 

See under Eugenol. 

Aloe-emodin ($-Hydroxymethylchrysazin, 
4 : &-dihydroxyanthraquinonylcarbinol-2, 4 : 5-di~ 
hydroxy-2-hydroxymethylanthraquinone) 

HO CO OH 




>OH 



From most varieties of aloes and from senna 
leaves (Cassia acutifolia, Delile ; C. augustifolia, 
Vahl). Orange-yellow needles from hot EtOH. 
M.p. 223. Sol. Et 2 0, C 6 H 6 , hot EtOH. Sol. 
dil. KH 3 and cone. H 2 S0 4 to cherry-red sols. 
Sublimes in C0 2 . Ox. > rhein. Red. > 
chrysophanic acid. Zn dust > 2-methyl- 
anthracene. Purgative. 

Diacetyl deriv. : cryst. from AcOH. M.p. 
177-8. 

Tribenzoyl : greenish -yellow needles from 
AcOEt. M.p. 235. 

Tri-Me ether: C 18 H 16 5 . MW, 312. Red 
needles from Me 2 CO. M.p. 163. Sol. Me 2 CO, 
AcOH, CHC1 3J C 6 H 6 , Py. 

Cahn, Simonsen, J. Chem. Soc., 1932, 2573. 
Mitter, Banerjee, J. Indian Chem. Soc., 
1932, 9, 375. 

Aloetic Acid (2:4:5: l-Tetranitro-aloe- 
emodin) 

HO CO OH 




2 N CO NO, 
C 16 H 6 13 N 4 - MW, 450 

Golden-yellow cryst. + 1H 2 0. Softens at 285. 
Decomp. explosively on heating. Mod. sol. hot 
H 2 > violet-red sol. Sol. EtOH, NH 3 Aq. 
> violet sol. 

Leger, Ann. chim., 1916, 6, 353, 361, 364. 

Alpinone (3 : &-Dihydroxy-l-m,ethoxy-2-methyl- 
fiavanone) 

HO CO 

'V'XnH-OH 



l7^l<fis 






MW, 300 

Isolated from the Japanese drug u IsoiHyuka- 
sya," prepared from tho seeds ofAlpina japonica. 
M.p. 178. [all? 79-11 in 5 H 5 N. ' (Jorio. HNO S 
> indigo blue col. Mg -[- HOI > yellow 
col. Heating with HC1 - -> noralpinouo, 
Ci A H M p 6 , m.p. 136-7. Warm with 10 20% 
KOH in H 2 > apoalpinono, C 16 H 14 0J light 
yellow, m.p. 148. 

Diacetyl : m.p. 118. 

Dibenzoyl : m.p. 208-9. 

Di-Me ether : m.p. 115. 

Oxime : m.p, 203-4. ^ 

Semicarbazone anhydride : CioHj^NLCX, m.p. 
200-1. 

Kimura, Hoshi, Proc. Imp, Acad. Tokyo, 
1936, 12, 285, (Chem. Abstract, 1037, 
81, 1807). 



(JO 



Alstoniline 



MW, 270 



MW, 358 



Alstonine 



59 



Alumiaium isopropoxide 



Alkaloid from bark of Alstonia constricta. 
Cryst. from MeOH, decomp. sharply at 372. 

B,HCl, H^O : fine red needles. Decomp. over 
wide range without melting. 

B 2 ,H 2 SO^ : m.p. 260-4, decomp. 

B,H 2 : m.p. 356 (sharp decomp.). 

B,H 2 picrate : red needles, m.p. 294 
decomp. 

Hawkins, Elderfield, J. Org. Chem., 1942, 
7, 573. 

Alstonine 




Suggested structure. 
C 21 H 20 3 N 2 MW, 348 

Alkaloid from Alstonia constricta. M.p. 205- 
10 decomp. 

B^SO^Hcf) : m.p. 195-6, foams at 208. 
[a] 2 ? 127. 

^O : m.p. 203-4. [a] 2 ? 120. 
: m.p. 243-4 decomp. [a] 2 ? 120. 

^O : m.p. 220-1 decomp. 
B,HCl : m.p. 278-9 decomp. [a] 2 ? 141. 
B,HNO Q : m.p. 252-4 decomp. 
B,HI : m.p. 270 decomp. 
B.HGIO. : m.p. 239-40. [a] 2 D + 154 4 in 
Me 2 CO. 

Leonard, Elderfield, J. Org. Chem., 1942, 

7, 556. 
Raymond-Hamet, Gompt. rend., 1948, 

227, 344. 
Elderfield, Gray, J. Org. Chem., 1951, 16, 

506. 

Schlitter, Schwarz, Bader, Helv. Chim. 
Acta, 1952, 35, 271. 

Alstyrine 

C 18 H 20 N 2 (C 19 H 22 N 2 ) MW, 264(278) 

Prepared from alstonine by heating with Se at 

300 for 10 min. Pale yellow. M.p. 113. 

Unchanged on heating with cone. HC1 at 130 

for 15 hrs. or on boiling with 50% NH 4 OH/KOH 

for 2 hrs. 

Picrate : m.p. 215-16. 

Sharp, J. Chem. Soc., 1938, 1353. 
Altrose 




d-. 



Prisms from MeOH-EtOH. M.p. 103-5. 
[a]? + 32-6 in H 2 0. 

2:3: 4=-Triacetyl : m.p. 100-1. [a] 2 ? 172 
in CHC1 3 . 

p-2 : 3 : 4 : 6-Tetra-acetyl : m.p. 85-90 [a]^ 
-6inCHCl 3 . 

a-Penta-acetyl : m.p. 118-9. [a]| +63 in 
CHC1 3 . 

Oxime : m.p. 143-4. [a] 2 D 5 -9-8 in H 2 0. 

Z-. 

Prisms from EtOH or AcOH. M.p. 107- 
109-5. [a]^ 32-3 in H 2 0. Hydrogenation 
> Z-talitol. 

Phenylosazone : m.p. 165. 

Benzylphenylhydrazone : m.p. 147-8. 

Richtmyer, Hudson, J. Am. Chem. Soc., 

1935, 57, 1720; 1941, 63, 1727. 
Hockett, Chandler, J. Am. Chem,. Soc., 

1944, 66, 627. 
Austin, Humoller, J". Am. Chem. Soc., 

1934, 56, 1153. 
Richtmyer, Advances in Carbohydrate 

Chemistry, Vol. I, 37. 



Aluminium tert.-butoxide 

A1[OC(CH 3 ) 3 ] 3 
C 12 H 27 3 A1 



MW, 246 



C H 12 6 



CHO 



MW, 180 



White powder. Sublimes in high vac. 
Readily sol. C 6 H 6 . Used as condensing agent 
and also in the oxidation of alcohols to carbonyl 
compounds. (For mechanism, see Adkins et al, 
J. Am. Chem. Soc., 1938, 60, 1158; 1939, 61, 
3364; 1940, 62,3305). 

Oppenauer, Eec. trav. chim., 1937, 56, 137. 
Wayne, Adkins, Organic Syntheses, 1941, 
XXI, 39. 

Aluminium ethoxide 

A1(OC 2 H 6 ) 3 
C 6 H 15 3 A1 MW, 162 

Colourless liq. B.p. 200 /6-8 mm., 175-80/3 
mm. Slowly solidifies to white solid, m.p. 140. 
Employed for reduction of carbonyl compounds 
to alcohols. Catalyst for preparation of esters 
from aldehydes and alcoholysis of diketones. 

Adkins, J. Am. Chem. Soc., 1922, 44, 2178. 
Meerwein, Schmidt, Ann., 1925, 444, 232. 
Sumiya, Yamaba, Tajima, Chem. Ab- 
stracts, 1932, 26, 3481. 

Aluminium isopropoxide 

A1[OCH(CH 3 ) 2 ] 3 
C 9 H 21 3 A1 MW, 204 

Colourless liq. B.p. 145-50/5 mm. Slowly 
solidifies to white solid, m.p. 118. Condensing 
agent and also used in reduction of carbonyl com- 
pounds to alcohols. Can be employed, like 



Aluminium magnesium ethoxide 60 

tert.-l)utoxide, for oxidation of 



aluminium 
alcohols. 

Adkins, J. Am. Chem. Soc., 1922, 44, 2178. 
Lund, Ber., 1937, 70, 1521. 
Young, Hartung, Crossley, J. Am. Chem, 
Soc., 1936, 58, 101. 

Aluminium magnesium ethoxide 

Mg[Al(OC 2 H 5 ) 4 ] 2 
C 16 H 40 8 Al 2 Mg MW, 438 

Ice blue cryst., m.p. 129. Distils in vacuo 
without decomp. B.p. 220-8/4 mm. (chiefly at 
225). Easily sol. benzene, chlorobenzene, 
petrol. InsoL CHC1 3 , Et 2 0. Used as catalyst 
for trans-esterification of alkyl silicates. 

Meerwein, Bersin, Ann., 1929, 476, 113. 
Peppard, Brown, Johnson, J. Am. Chem. 
Soc., 1946, 68, 77. 



Amarin 

is weak. 



C 6 H 15 A1 



Aluminium triethyl 

A1(C 2 H 5 ) 3 

MW, 114 

M.p. -52-5. B.p. 194. w 1480. Takes 
fire in air. Explodes with H 2 0. 

Cahours, Ann., I860, 114, 242. 
Laubengayer et al., J. Am. Chem. Soc., 
1941, 63, 559. 

Aluminium trimethyl 

A1(CH 3 ) 3 ' 
C 3 H 9 A1 MW, 72 

M.p. 15. B.p. 130. DJ 0-752. < 1-432. 
Inflames in air. Exists as a dimer at 70. 

Buckton, Odling, Ann., 1866, SuppL, 4, 

112. 
Laubengayer et al., J. Am. Chem. /Soc., 

1941, 63, 559. 
Levi, Newitt, J. Ghem. Soc., 1946, 468. 

Amalic Acid (Tetramethyl-alloxantin) 
Jo 6(OH)- 



CH 3 -N~~CO 



Cryst. from H 2 0. 



CO N-CH 



MW, 342 



Billmann, Berg, Ber., 1930, 63, 2188. 
Cope et al., J. Am. Chem. Soc., 1943. 63, 
356. 

a-Amantine (<x-Amanitine). 

Isolated, together with p-amantine and 
phalloidme, from Amanita phalloides. Very 
poisonous (fatal dose, 2-5 y per mouse). Induces 
hypogluoemia. Colourless needles. M.p. 254- 
5 decomp. [a]?? + 191 in H 2 0. Gives posi- 
tive Hopkins-Cole, Xanthoprotein, and Millon- 



Pauly reactions. Buiret reaction 
Probably contains peptide bonds. 

Wieland, Hallermeyer, Zilg, Ann., 1941, 
548, 1. 

Wieland et al, Ann., 1949, 564, 152. 

(3-Amantine ($-Amanitine). 

Isolated from Amanita phalloides. Very 
poisonous (fatal dose 8-10 y per mouse). Needles 
from MeOH. Decomp. above 300. Easily sol. 
MeOH, EtOH, H 2 0. Gives positive Folin and 
Hopkins-Cole reactions. 

Wieland et al., Ann., 1949, 564, 152. 

Amarbeline 

C 18 H 16 0/H 2 MW, 362 

Colouring matter from seeds of Cuscuta 
refiexa. Lemon yellow needles, m.p. 234. 
Diacetyl : m.p. 152. 
Dibenzoyl : m.p. 166 decomp. 

Agarival, J. Indian Chem. Soc., 1936, 13, 
531. 

Amaric Acid (4-Hydroxy-Z : 3 : 4~triphenyl 
n-valeric acid) 

C 6 H 5 -CH(OH)-CH CH-CH 2 -COOH 

\ MW, 346 



Needles + H 2 from EtOH.Aq. M.p. 140-5. 
Heat > lactone : m.p. 141. 



Needles from 50% EtOH. M.p. 156. Heat 
> lactone : m.p. 168. 

y-$orm. 

M.p. 173. Heat > lactone : m.p. 171-2. 

Meerwein, J. prakt. Chem., 1918, 97, 225. 

Amarin (2:4: fr-Triphenyldihydroglyomlim., 
triphenyliminazoline ) 

C 6 H 6 -9H-NH X 

C 6 H B -CH " 

C 21 H 18 N 2 MW, 298 

Prisms + PI 2 from EtOH.Aq. M.p. 106". 
Prisms from dry Et 2 0. M.p. 136. Sol. KtOH, 
Et 2 0. InsoL H 2 0. 

B,HCl: cryst. from EtOH. M.p. 302. 

B,HBr: cryst. from EtOH. M.p. 288. 

B,HNO : prisms from EtOH. M.p. 1(15". 

N-Jfe: C a ,H 20 N 2 . MW, 312. Crynt. from 
Et 2 0. M.p. 184=. Very aol. EtOH, Et 2 0, 
CHCL, C 6 H 6 . 

N-l' : CosHozNo. MW, 320. Loallots from 
Et 2 0. M.p. 163. Sol. EtOH, OH01 8 , 9 H 9 . 
Spar. sol. Et 2 0. 

N-Benzyl: C 28 H M N 2 . MW, 388. Noodles 
from EtOH. M.p. 123-4. Sol. EtOH, Et a O, 
OHC1 8 . 



Amaron 



61 



3-Aminoacenaplitiiene 



'N-Benzoyl : prisms from Et 2 0. M.p. 180. 
Japp, Moir, J. Chem. Soc., 1900, 77, 611. 
Delepine, Compt. rend., 1898, 127, 623. 
Glaus, Scherbel, Ber., 1885, 18, 3079. 

Amaron (Tetraphenylpyrazine) 



C 28 H 20 lsr 2 MW, 384 

Needles from AcOH. M.p. 246. Sol. CHC1 3 , 
hot C 6 H 6 . Spar. sol. Et 2 0, hot EtOH. Sub- 



limes. 



Sol. cone. H 2 S0 4 



blood-red sol. 



Japp, Wilson, J. Chem. Soc., 1886, 49, 

826. 
Japp, Davidson, J. Chem. Soc., 1895, 67, 

35. 

Amasatin. 

See under Isamic Acid. 
Ambrein 

CH, 




C 30 H 62 MW, 428 

Isolated from EtOH soluble portion of 
ambergris. M.p. 82-3. [a] 14-1 (c, 1-0 in 
C 6 H 6 ). Gives strong yellow col. with tetra- 
nitromethane. 

Ruzicka, Lardon, Helv. Chim. Acta, 1946, 

29, 912. 
Ruzicka, Gutmann, Jeger, Lederer, Helv. 

Chim. Acta, 1948, 31, 1746. 
Durst, Jeger, E/uzicka, Helv. Ghim. Acta, 

1949, 32, 46. 

Ambrettolic Acid (16- Hydroxy - 6 - hexa - 
decenoic acid) 

HOCH 2 -[CH 2 ] 7 -CH:CH-[CH 2 ] 5 -COOH 
C 16 H 30 3 MW, 270 

Obtained from musk seed oil. 
vi-Isomer : m.p. 53-5. 
$-Isomer : m.p. 26-7. 
Lactone : see Ambrettolide. 

Baudart, Compt. rend., 1945, 221, 205. 
Stoll, Gardner, Helv. Chim. Acta 9 1934, 
17, 1609. 



Ambrettolide 



Lactone of ambrettolic acid. Strong musk- 
like odour. B.p. 154~6/1 mm. Df 0-9580. 
< 1-4815. 

Baudart, Compt. rend., 1945, 221, 205. 
Stoll, Gardner, Helv. Chim. Acta, 1934, 
17, 1609. 

Ameliaroside . 

See Piceoside. 
Amethocaine . 
See Decicaine. 
Amido-G Acid. 

See 2-Naphthylamine-6 : 8-disulphonic Acid. 
Amidodicyanic Acid. 
See Cyanourea. 
Amido-R Acid. 

See 2-Naphthylamine-3 : 6-disulphonic Acid. 
Amidol. 

See under 2 : 4-Diaminophenol. 
Amidone (G-Dimethylamino-^ : 4c-diphenyl- 
heptanone-3) 



CH 3 *CH-CH 2 -C(C 6 H 5 ) 2 -CO-CH 2 -CH 3 
C 21 H 27 ON MW, 309 

Powerful analgesic equalling morphine in 
potency. 

B,HCl: white cryst. M.p. 236-6-5. Sol. 
H 2 0, EtOH. Insol. Et 2 0. 

Scott, Chen, J. Pharmacol., 1946, 87, 63. 

Kleiderer, Eice, Conquest, Williams, Re- 
port No. 981, Office of Publication 
Board, Dept. of Commerce, Washing- 
ton, U.S.A. 

2-Aminoacenaphthene 




MW, 252 



MW, 169 

M.p. 135. 

B,HCl : decomp. at 270. 
Picrate : yellow prisms from Et 2 0. M.p. 260 
decomp. 

Morgan, Stanley, J. Soc. Chem. Ind. } 
1925, 44, 493T. 

3-Aminoacenaphthene . 

Buff plates from EtOH, needles from pet. 
ether. M.p. 81-5. Sol. usual org. solvents. 
Turns pink in air. Ale. PeCl 3 > bluish- 
violet col. 

N-Formyl : needles from EtOH. M.p. 151-2. 
Sol. EtOH, Me 2 CO, AcOH. Less sol. C 6 H 6 , pet. 
ether. 

TS-Acetyl : needles from EtOH. M.p. 192-3. 

TX-Benzoyl : needles from EtOH. M.p. 209- 
10. 



4-Aminoacenaphthene 



62 



Aminoacethydrazide 



Picrate : yellow needles from Me 2 CO. De- 
comp. at 221. 

Morgan, Harrison, J. Soc. Chem. Ind., 
1930, 49, 415T. 



Aminoacetamide (Glycine amide] 



C 2 H 6 ON 2 



H 2 N-CH 2 -CONH 2 



Decomp. at 190-200. 

Morgan, Stanley, J. Soc, Chem. Ind., 1924, 
43, 345T. 

5-Aminoacenaph.tliene . 

Needles from pet. ether. M.p. 108. 



MW, 74 

Needles. M.p. 65-7. Sol. H 2 0, EtOH, 
MeOH. Mod. sol. Me 2 C0 3 CHC1 3 , AcOEt. 

)S 

glycine + NH 3 . 



'N-Octanoyl : see Penilloaldehyde-K. 
N-Phenylacetyl : see Penilloaldehyde-G. 
N-Benzoyl : see Hippuric Aldehyde. 

Fischer, Ber., 1908, 41, 1021. 

, . . , ^ Curtius, J. prakt. Chem., 1917, 95, 212. 

4-AmmoacenapMliene . 

Needles from hot H 2 0. M.p. 87. Very sol. 
volatile org. solvents. 

'N-Acetyl : prisms from EtOH.Aq. or AcOH. 
M.p. 175-6. Sol. Me 2 CO, CHC1 3 . Insol. H 2 0. 

N-Benzoyl : prismatic needles from 90% 

AcOH. M.p. 196. IVJ-CVXl. 1YJLUU. SUJL. 1YJLC 2 0\^, V-MJLVJg, .tt-UV^JLLiU. 

Picrate : yeUow needles from EtOH or Me 2 CO. Spar. sol. Et 2 0, C 6 H 6 . Reacts strongly alkajine. 

Absorbs C0 2 . Hot H 2 
B,HCl : m.p. 186-9. 
B,HAuCl : needles. M.p. 197-8. 

Kdnigs, Mylo, Ber., 1908, 41, 4429. 
Bergell, v. Wulfing, Z. physiol. Chem.> 
1910, 64, 354. 

-vr ,-, 7 ,, r TVL/VTT A -MT Yang, Rising, J. Am. Chem. Soc., 1931, 
N-Formyl: needles from EtOH.Aq. M.p. ~- 8 ' &J ' 

172. 

N-Acetyl : plates from EtOH. M.p. 238. 

^-Dmcetyl : plates from EtOH. M.p. 122. 

N-Benzoyl : needles from EtOH. M.p. 210 
(199). 

Picrate : yellow needles from EtOH. De- 
comp. at 190-200. 

Morgan, Stanley, J. Soc. Chem. Ind., 1924, 



in steam. FeCl 3 > blue col. 



Volatile 
needles from EtOH.Aq. M.p. 



53, 3183. 

Cook, Heilbron, Levy, J. Chem. Soc., 
1948, 201. 



43, 345T. 

Aminoacetal (Aminoacetaldehyde diethyl 
acetal, 2 : 2-diethoxyethylamine) 

H 2 N-CH 2 -CH(OC 2 H 5 ) 2 

C 6 H 15 2 N MW, 133 

B.p. 163. D 25 0-9159. < 1-4123. Sol. 
H 2 0, EtOH, Et 2 0, CH01 3 . Volatile in steam. 
Beacts alkaline. Cone. HC1 > amino- 
acetaldehyde. 

TS-Me : see under Methylaminoacetaldehyde. 
Picrate": m.p. 143. 

Allen, Clark, Organic Syntheses, 1944, 

XXIV, 3. 
Woodward, Doering, J. Am. Chem. Soc., 

1945, 67, 860. 
Richmond, Wright, Can. J. Research, 

1945, 23s, 158. 

Buck, Wrenn, J. Am. Chem. Soc., 1929, 
51, 3612. 

Aminoacetaldeliyde (Glycine aldehyde) 

H 2 N>CH 2 "CHO 
C 2 H 5 ON MW, 59 

Stable in cone, acid solutions. Readily poly- 
merises. Reduces Fehling's. Br > glycine. 
HBr > dihydroxypiperazine. 

B%,H 2 PtCl Q : prisms or plates from H 2 0. M.p. 
125. 

"N~0aproyl : me Amylpemlloaldehyde. 

"^^Hexenoyl : see Penilloaldehydo-F. 

T$-p-Hydro%yphenylacetyl ; see PenUloalde- 
hyde-X. 



<o-Aminoacetanilide . 

See under Glycine. 

o-Aminoacetanilide (Acetyl-o-phenylenedi- 
amine) 

NH-CO-CH 3 



MW, 150 
Sol. H 2 0, 



C 8 H 10 ON 2 

Plates from C 6 H 6 . M.p. 132 
EtOH, hot C 6 H 6 . Less sol. Et 2 0. 

Bell, Kenyon, J. Chem. Soc., 1926, 954. 
Levitz, Bogort, /. Org. Chem., 1945, 10, 
341. 

n- Arainoacetanilide ( A ceiyl-m-pltenylene 
diamine). 

Needles or platos from C 6 H 6 . M.p. 87-9. 
Very aol. cold H 2 0, EtOH, Me 2 00. Spar, wol 
C 6 H 6 . 

B,HCl : plates from 95% EtOH. Rintora at 
248-51, entirely liquid at 280. Sol. H a (). 

"N-p-Toluenesulphonyl: noodles from KtOH. 
M.p. 241. 

Wallaoh, Sohuko, Ber., 1882, 15, 3020. 
Jacobs, Hoidolborgor, J. Am, Chem. $oc* f 
1917, 39, 1448. 



j>-Aminoacetanilide 

amine). 

Needles from H0. DarkoriB in air. M.p. 
162-3 (159-60), Sol. EtOH, JBt a O. Spar. noL 
cold H 2 0. Hyd, by cone. HOI. 

B,H%SO^ : m.p. 285 clocomp. 

Sachs, Goldmann, J5er, 1902, 35, 3341. 

Aminoacethydrazide , 

See under Glycine. 



Arainoacetic Acid 63 



Aminoacetic Acid. 

See Glycine. 
1-Aminoacetoacetic Ester. 

See Ethyl 1-aminoacetoacetate. 
Aminoacetone 

CH 3 -CO-CH 2 -NH 2 
C 3 H 7 ON MW, 73 

Not isolated in free state. Reduces Eehling's. 
Ox. - > 2 : 5-dimethylpyrazine. 

B,HCl : plates from EtOH-Et 2 0. M.p. 75. 
Very hygroscopic. 

B 2 ,H^PtCl Q : orange-yellow needles from 
EtOH. M.p. 188-9. Very sol. H 2 0. 

Gabriel, Colman, Ber., 1902, 35, 3805. 
Neber, Huh, ,47m., 1935, 515, 293. 



p-Aminoacetophenone 
plates from EtOH. M.p. 



Aminoacetonitrile 

methylamine) 



(Glycine nitrile, cyano- 



C 2 H 4 N 2 MW, 56 

B.p. 58/15 mm., part decomp. HC1 > 
glycine hydro chloride. 

B,HCl : m.p. 165 decomp. Spar. sol. EtOH, 
Et 2 0. Hygroscopic. 

J5,H 2 /S0 4 : m.p. 101. Sol. H 2 0. Insol. Et 2 0. 

B,H%SO : m.p. 165 decomp. 

Pier ate : m.p. 165 decomp. 

Klages, Ber., 1903, 36, 1511. 
Gesellschaft fur Kohlentechnik, m.b.H., 

B.P., 436,692, (Chem. Abstracts, 1936, 

30, 2201). 
Anslow, King, Organic Syntheses, Collec- 

tive Vol. I, 298. 
Cook, Heilbron, Levy, J. Chem. Soc., 

1948, 201. 

o-Aminoacetophenone 
CO-CH 3 

/\NH 2 

C 8 H 9 ON MW, 135 

Cryst. M.p. 20. B.p. 250-2 slight decomp., 
130'5714 mm., 124/10 mm. Volatile in steam. 

B,HCl : prisms. Decomp. at 168. Sol. 
EtOH. 

B,HI : m.p. 150 decomp. 

J$-Formyl : needles, M.p. 79. 

N-Acetyl : needles from ligroin. M.p. 76-7. 
Sol. EtOH, Et 2 0. Spar. sol. cold H 2 0. Oxime : 
needles from H 2 0. M.p. 149-50. 

T$-Propionyl : plates from Et 2 0. M.p. 69. 

*$-Butyryl : prisms from ligroin. M.p. 52. 

"N-Isobutyryl : prisms from Et 2 0. M.p. 50. 

"N-Benzoyl : needles from Et 2 0. M.p. 98. 

N-p-Toluenesulphonyl : plates from EtOH. 
M.p. 148. 

Oxime: needles from H 2 0. M.p. 109. 
Sublimes. 



Semicarbazone : 
290 decomp. 

Phenylhydrazone : needles from EtOH. M.p. 
108. 

Skita, Meyer, Ber., 1912, 45, 3587. 
Elson, Gibson, Johnson, J. Chem. Soc., 

1930, 1131. 
Simpson et aL, J. Chem. Soc., 1945, 

646. 
Leonard, Boyd, J. Org. Chem., 1946, 11, 

405. 

m-Aminoacetoplienone . 

Pale yellow plates from EtOH. M.p. 98-9 
(92-3). Part, volatile in steam. Weak base. 

"N-Acetyl : needles from EtOH.Aq. M.p. 
128-9. Oxime: needles from EtOH.Aq. M.p. 
192-4. 

N-Chloroacetyl : prisms from EtOH. M.p. 
114. 

N-p-Toluenesulphonyl : needles from EtOH. 
M.p. 130. 

Semicarbazone : prisms from H 2 0. M.p. 196 
decomp. 

Hydrazone : cryst. from EtOH or C 6 H 6 . M.p. 
98. 

Cobb, Chem. Abstracts, 1946, 40, 7180. 
Simpson et al., J. Chem. Soc., 1945, 646. 
Marvel et al., J. Am. Chem. Soc., 1946, 68, 

1088. 
Leonard, Boyd, J. Org. Chem., 1946, 11, 

405. 
Elson, Gibson, Johnson, J. Chem. Soc., 

1930, 1130. 

Camps, Arch. Pharm., 1902, 240, 15. 
Rupe, Braun, v. Zembruzski, Ber., 1901, 

34, 3522. 

p-Aminoacetoplienone . 

Cryst. from H 2 0. M.p. 106. B.p. 293-5. 
Sol. boiling H 2 0, EtOH, Et 2 0. Spar. sol. 
C 6 H 6 , pet. ether. 

N~Acetyl : needles from H 2 0. M.p. 166-7. 

N-Propionyl : prisms from EtOH. M.p. 136. 

N-Benzoyl: plates from EtOH or CHCL. 
M.p. 205. 

Oxime: needles from EtOH. M.p. 147-8. 

Semicarbazone : yellowish cryst. from EtOH. 
M.p. 250. 

2 : 4-Dinitrophenylhydrazone : dark red. M.p. 
263. 

Kunckell, Ber., 1900, 33, 2641 ; D.E.P., 
105,199, (Chem. Zentr., 1900, I, 240). 

Klingel, Ber., 1885, 18, 2691. 

Chattaway, J. Chem. Soc., 1904, 85, 
388. 

Florence, Chem. Abstracts, 1933, 27, 422g. 

Kursanov, Chem. Abstracts, 1944, 38, 959. 

Leonard, Boyd, J. Org. Chem., 1946, 11, 
405. 



co-Aminoacetophenone 



64 



2-Aminoacridone 



co-Aminoacetophenone . 

See Phenacylamine. 

1-Aminoacridan (l-Amino-5 : 10-dihydro- 
acridine) 

CH 2 




C 13 H 12 N 2 MW, 196 

Needles from pet. ether. M.p. 114. Sol. 
EtOH, Et 2 0, Me 2 CO, AcOH, dil. HCL Cone. 
H 2 S0 4 > deep yellow sol. 

N-Acetyl deriv. : plates from MeOH. M.p. 
177. 

Clemo, Perkhi, Bobinson, J. Chem. Soc., 
1924, 1785. 

2-Aminoacridan (2-Amino-5 : IQ-dihydro- 
acridine) . 

Leaflets from EtOH.Aq. M.p. 193 6, 206- 
7 (sealed tube). Spar. sol. Me 2 CO, xylene. 
Insol. Et 2 0. Bed sols, in cone. HC1 and H 2 SO 4 . 
Oxidises in air, particularly in presence of 
alkalis. 

Scherlin, Bras, Jakubowitsch, Worob- 
jowa, Ssergejew, Ann., 1935, 516, 223. 



(3-Amino~5 : IQ-dihydro- 



3-Aminoacridan 

ocridine) . 

Yellow needles from MeOH. M.p. 191-2. 
Insol. H 2 0. Dark red sol. in dil. HCL Oxidises 
in air. 

Scherlin, Bras, Jakubowitsch, Worob- 
jowa, Ssergejew, Ann., 1935, 516, 226. 

l-Aminoacridme 




MW,194 

Beddish-brown needles from pet. ether. M.p- 
108. Very sol. EtOH to yellow sol. Sol. 
Et 2 0,C 6 H 6 . Spar. sol. ligroin. Yellow in H 2 S0 4 
with greenish-blue fluor. Brownish-red in dil. 
HCL Spar. sol. 50% H 2 S0 4 . K 2 Cr 2 7 to H 2 S0 4 
sol. > violet col. 

B,HGl : yellow needles from EtOH.Aq. M.p. 
234 decomp. 

"N-Acetyl : yellow needles from pet. ether. 
M.p. 117. 

Jtf-p-Tolwenesulphonyl : plates from EtOH. 
M.p. 169-70. 

Monopicrate : purplish-black plates. M.p. 
220 (206). 

N-Jfe: C M H 12 N 2 . MW,208. Orange prisms 
from pot. ether. M.p. 75. 

N-AY: C 15 H 14 N 2 . MW, 222. Orange-red 



plates from pet. ether. M.p. 65. Acetyl : 
plates from pet. ether. M.p. 95. 

Clemo, Perkin, Bobinson, J. Chem. floe., 

1924, 125, 1786. 

Ullrnann, Maag, Ber., 1907, 40, 2522. 
Albert. Bitchie, J. Soc. Chem. Ind. } 1941, 
60, 122T. 

2-Aminoacridine . 

Yellowish-orange needles from EtOH.Aq. 
M.p. 224 corr., after drying. Sol. EtOH, C 6 H 6 . 
Mod. sol. Me 2 CO, xylene. Ale. and aq. sols, 
show yellow fluor. 

Scherlin, Bras, Jakubowitsch, Worob- 
jowa, Ssergejew, Ann., 1935, 516, 224. 

Albert, Linnell, J. Chem. Soc., 1936, 1616. 

Albert, Bitchie, J. Soc. Chem. Ind., 1941, 
60, 122T. 

3-Aminoacridine . 

Yellow needles + C 2 H 5 OH from EtOH. M.p. 
213-4. Sols, fluor. yellowish-green. 

Albert, Bitchie, J. Soc Chem. Ind., 1941, 

60, 122T. 
Albert, Australian P. 115,480, (Chem. 

Abstracts, 1946, 40, 3479). 

4-Aminoacridine . 

Yellow needles + H 2 from 50% EtOH. M.p. 
183 corr. after drying. 

Albert, Bitchie, J. Soc. Chem. Ind., 1941, 
60, 122T. 

5-Aminoacridine . 

Yellow needles from EtOH or M 2 CO. M.p. 
236-7 (241 corr., after drying). 
Carbethoxyl : m.p. 188-94. 
"N-Acetyl : cryst. from EtOH. M.p. 268-9. 
N-Diaoetyl : cryst. from EtOH. M.p. 148-9. 

M. L. B., Chem. Abstracts, 1924, 18, 1131. 
.Drozdov, Cherntzov, Chem. Abstracts, 

1936, 30, 3433. 
Albert, Bitchie, J. Soc. Chem. Ind., 1941, 

60, 123T. 

1 -Aminoacridone 




C 13 H 10 ON 2 " MW, 210 

"Dark yellow noodles from KtOH. M.p. 

340-2. Sol. hot AoOH, PKN0 2 , aniline. Spar. 

sol. EtOH, Et a O, C 6 H r Prao. innoi. ligroin. 

H 2 S0 4 > greonish-yollow sol. with blue lluor. 
TJllmann, Ann., 1907, 355, 329. 

Lehmstedt, Ber,, 1937, 70, 1535. 

2-Aminoacridone . 

Palo yellow needles from EtOH.Aq, JMLp. 



3-Aminoacridone 



65 



1-Aminoanthracjuiaone 



301-3 corr, Sol. in EtOH exhibits violet fluor. 
> yellowish-green with trace of acid. Sol. in 
AcOH > green fhior. 

Albert, linnefl, J. Chem. 8oc., 1936, 1618. 

3-Aminoacridone . 

Yellow needles from EtOH. M.p. 298. Sol. 
boiling EtOH, Me 2 CO. Spar. sol. C 6 H e . Insol. 
H 2 3 ligroin. Cone. H 2 S0 4 > bluish-green 
fiuor. 

Ullmann, Ann., 1907, 355, 329. 

4- Aminoacridone . 

Yellow needles from EtOH. M.p. 285. Sol. 
EtOH, AcOH, Spar. sol. Et a O, C 6 H 6 . Insol. 
ligroin. Cone. H 2 S0 4 > bluish -green fluor. 

Ullmann, Ann, 1907, 355, 329, 
Lehmstedt, Ber., 1937, 70, 1535. 

1-Aminoadipic Acid 

CH 2 -CH(NH 2 )-COOH 
CH 2 -CH 2 -COOH 

C 6 H 1X 4 N MW, 161 

Cryst. M.p. anhyd. 206. Sol. 450 parts 
H 2 at 40. Spar. sol. EtOH, Et 2 0. PeCl 3 ^ 
reddish -brown col. Heat > a-piperidone-oc'- 
carboxylic acid. 

Dieckmann, Ber., 1905, 38, 1656. 
Waalkes, Fones, White, J. Am. Chem. 
Soc. 9 1950, 72, 5760. 

3-Aminoalizarin (1 : Z-Dihydroxy-S-amino- 
antJiraguinone, $-aminoalizarin) 

CO OH 

!OH 



MW, 255 
M.p. above 




Dark red prisms from AcOH. 
300. Sol. KOH.Aq, with blue col. 
or NH 3 .Aq, > brown sols. 

Aceiyl deriv. : yellowish-brown cryst. 
238-40. Sol. C 6 H 6 . Sublimes. 



NaOH.Aq. 



M.p. 



Diacetyl deriv. : reddish-brown cryst. M.p. 
268-71. Sol. EtOH. 

B&moyl deriv. : dark yellow needles. M.p. 
275. Sol. EtOH, Spar. sol. Et 2 0, CHC1 3 , 
C 6 H r 

Dibenzoyl deriv. : yellow leaflets. M.p. 252. 

Boemer, er. } 1885, 18, 1666. 



4-Aminoalizarin (1 : ^ 
anthraquinone , a.-aminoalizariri) . 

Greenish-black cryst. from EtOH. Sol. EtOH. 
Sol. alkalis to carmine-red sols. Sol. Ac 2 O with 
reddish-violet coL Forms two diacetyl comps. : 

(a) With excess Ac a O. Beddish-brown leaf- 
lets. M.p. 245. Sol. AcOH, Ac 2 0, toluene. 

Diet, of Org. Oomp. I. 



Cone. H 2 SO 4 > red sol. Boiling EtOH >- 
isomeric diacetyl (below). 

(b) With Ac 2 + AcONa. M.p. 205. Hot 
Ac 2 O > isomeric comp. (above). 

Di-Me ether : C 16 H 13 4 N. MW, 283. Dark 
red cryst. from Py.Aq. M.p. 182-3. Spar. sol. 
EtOH, Et 2 0, ligroin. Cone. H 2 SO 4 >- blood- 
red sol. 

Benzoyl deriv. : reddish-brown needles. M.p. 
above 310. 

Dibenzoyl deriv. : light brown needles. M.p. 
255. 

Schultz, Erber, Ber., 1902, 35, 906. 
Seer, Karl, Monatsh., 1913, 84, 640. 
Turski, B.P., 564,610, (Chem. Abstracts, 
1946, 40, 4080). 

Aminoallylerie . 
See Propargylamine, 
Amino-amyl Alcohol. 
See Aminopentanol. 
co-Arnino-n-amylbenzene . 
See 5-Phenyl-?i~amylamine. 
3- Amino- A 16 -andr ostene 

C 19 H 2D 01Sr MW, 287 

Cryst. from MeOH. M.p. 163-5 corr. 

Prelog, Ruzicka, Meister, Wieland, Helv. 
Chim. Ada, 1945, 28, 618. 

Aminoanilinobenzoic Acid. 

See Aminodiphenylamine-carboxylic Acid. 

Aminoanilinoforrnic Ester. 

See Aminophenylur ethane. 

Aminoanisic Acid. 

See under Hydroxyaminobenzoic Acid and 
Hydroxyanthranilic Acid. 

Aminoanisole . 

See Anisidine. 

Aminoantliracene , 

See Anthramine. 

1-Aminoanth.raquinone (x-Aminoanthra- 
quinone) 

CO 1STH 2 




C M H 9 2 N MW, 223 

Orange to brick-red cryst. M.p. 252 (243). 
Sol. hot PhN0 25 toluene, xylene, Et 2 O, AcOH, 
CHC1 3 , C 6 H e . Spar, sol cold EtOH. Insol. 
H 2 0. Cone. H 2 S0 4 > pale yellow sol. HS0 3 -C1 
> 2-sulphonic acid. Weak base. Salts with 
HC1 and H 2 S0 4 easily hydrolysed. 

JX-Acetyl : yellow or orange-red needles. M.p. 
218. 

N-Benzoyl : olive-green cryst. M.p. 255. 
Insol. EtOH. Cone. H 2 S0 4 > orange sol. 

"N-ip-Toluenesulphonyl : m.p. 228-9, 

5 



2-Aminoanthraquinone 



66 



Aminoanthrol 



N-Oxalyl : anthraquinone-1-oxamic acid, 
(-NH-CO-COOH). M.p. 226. 

Beverdin, Helv. CUm. Ada, 1918, 1, 209. 
I.G., D.R.P., 575,580, (Ohem. Abstracts, 
1933, 27, 4819). 

2-Aminoantliraquinoiie ($-Aminoanthra- 
quinone). 

Bed needles from EtOEL M.p. 303-6. 
Spar. sol. EtOH. Insol. H 2 0. Weak base. 
Salts hyd. by H 2 0. Cone. H 2 S0 4 >- pale 
yellow sol. 

TS-Acetyl : yellow cryst. M.p. 262. 
TS-Diacetyl : yellow cryst. from AcOH. M.p. 
258. 

'E-Benzoyl : yellow cryst. from AcOH. M.p. 
227-8. 

Groggins, Stirton, Newton, Ind. Eng. 

Chem., 1931, 23, 893. 
Groggins, Stirton, Ind. Eng. Chem., 1933, 

25, 42. 

Newport Chem. Corporation, B.P., 
370,724, (CUm. Abstracts, 1933, 27, 
2967). 

2 - Aminoanthraquinone - 1 - carboxylic 
Acid 

CO COOH 

s\ 

NIL 




C 15 H 9 4 N MW, 267 

Salmon-pink needles. M.p. 250-2. 
Amide: C 15 H 10 3 N 2 . MW, 266. Orange 
cryst. from PhN0 2 . M.p. about 300. 



5 - Aminoanthraquinone - 1 - carboxylic 
Acid. 

Red leaflets from AcOH. M.p. 277 decomp. 
(265). Sol. Me 2 CO, Py. Spar. sol. EtOH, 
toluene. Insol. Et 2 0, ligroin. 

Nitrile : red leaflets from EtOH. 

Gattermann, Ann., 1912, 393, 176. 
Ullmann, v. der Schalk, Ann., 1912, 388, 
210. 



9 



6-AminoantliraqTiinone-l -carboxylic Acid. 

Brown noodles from dil. AcOH. M.p. 247- 

Pritchard, Simonscn, /. Chem. Sac., 1938, 

2047. 



1 - AminoantkraquiJioixe - 2 - carboxylic 
Acid 

CO NH 2 

COOH 




C 15 H 9 4 N MW, 267 

Reddish-brown needles from PhN0 2 . M.p. 
295-6 (286). Sol. PhN0 2 , aniline. Spar. sol. 
EtOH, Et 2 0, C 6 H 6 . Insol. H 2 0, ligroin. Cone. 
H 2 S0 4 > yellowish-brown sol. 

Jfee^r:C ie E u 4 N. MW, 281. M.p. 228. 
M ester : C 17 H 13 4 N. MW, 295. M.p. 198. 
Phenyl ester : C 21 H 13 4 N. MW, 343. M.p. 
198. 

Benzyl ester : C 22 H 15 4 N. MW, 357. M.p. 
182 

Amide : C 15 H 10 3 N. MW,266. Red needles 
from PhN0 2 . M.p. 279-81. 

Nitrile: C 15 H 8 2 N 2 . MW, 248. Orange- 
brown cryst. from chlorobenzene. 

~N-Acetyl : brown leaflets from AcOH. M.p. 
214-15. 

Terres, Ber. } 1913, 46, 1634. 

General Aniline Works, U.S. P., 1,929,863, 

(Chem. Abstracts, 1934, 28, 338). 
I.G., B.P., 314,020, (Chem. Abstracts, 

1930, 24, 1123). 

M. L. B., D.R.P., 275,517, (Chem. Zentr., 
1914, II, 279). 



ryau. .uum JT.U.JL.'NVJ^. ivju.p. tiuuuu ouv . 

Nitrile : C 15 H 8 2 N 2 . MW, 248. Brownish- 362-3 
yellow needles from PhN0 2 . 

Perkin, Spencer, J. Chem. Soc., 1922, 121, 

481. 
Schaarschmidt, Ann., 1914, 405, 116. 

4 - Aminoauthraquinone - 1 - carboxylic 
Acid. 

Dark brown needles from AcOH. M.p. 246- 
8 decomp. 

Gattermann, Ann., 1912, 393, 176. 



3 - Aminoanthraquinone - 2 - carboxylic 
Acid. 

Orange-yellow needles from PhN0 2 . M.p. 
" ~~ Sol. hot Py, PhN0 2 . Spar. sol. AcOH. 



O\JjCj~O . k3UJL. I1UO JL y, X, IliNWo;. k 

Insol. H 2 0, Et 2 0, CHC1 3 , C 6 H 6 . 

TS-Acetyl : yellow needles from EtOH. M.p* 
248. 

TS-Chloroacetyl : orange-red cryst. from I?hNO.>. 
M.p. 350. 

'N-rt'Toluenesul'phonyl : yellow noodles from 
AcOH. 

I.G., D.R.P., 479,355, (Chem. Zentr., 

1930, 1, 588). 

Ullmann, Dasgupta, Ber., 1914, 47, 562, 
Willgerodt, Maffozzoli, J, pra/d. Chem.* 

1910, 82, 213. 



5 - Aminoanthraqriinone - 2 * carboxylic 
Acid, 

Brownish-red needles from AcOH.Aq. M.p. 
338. Sol. Me 2 CO, AcOH. 

Eckert, Monatsh., 1914, 35, 295, 

4-Aminoanth.rarufin . 

du Pont, U.S.P., 1,957,936, (Chem. Zentr,, 
1934, II, 3184). 

Aminoanthrol . 

See Hydroxyaathramino. 



4-Aminoantipyrine 



67 



o-Aminoazoxybenzene 



4-Aminoantipyrine 
I -phenylpyrazolone-5) 



U H U ON 8 



: 3-diTnethyl- 



00 N-CH 3 
N-CH, 



MW,203 



Pale yellow cryst. from C 6 H 6 . M.p. 109. 
Sol. H 2 0, EtOH, C 6 H 6 . Spar. sol. Et 2 0. 

B,HCl : m.p. about 231 decomp. 

B,H 2 SOt: m.p. about 215. Sol. H 2 0. 

TS-Acetyl: m.p. 199. Sol. H 2 0, EtOH. 
Mod. sol. hot AcOEt, CHC1 3 . Spar. sol. C 6 H 6 . 
Insol. ligroin. FeCl 3 > faint reddish col. 

Picrate : m.p. 144. 

Waser, Helv. Ohim. Ada, 1925, 8 } 121. 
Freedman, Sherndal, U.S.P., 1,877,166, 

(Chem. Abstracts, 1933, 27, 103). 
Turpeinen, Kallro, Chem. Abstracts, 1942, 

36, 426. 

o-Aminoazobenzene (2-Aminoazobenzene) 
H 2 N 



C 12 H H N 3 



MW.197 
59. Very 



Red prisms from EtOH. M.p. 
sol. usual org. solvents. SnCl 2 + HC1 
aniline + o-phenylenediamine. 

J3-Acetyl : reddish-yellow needles from AcOH. 
M.p. 126. 

N-Benzoyl : reddish-yellow needles from 
AcOHorMeOH. M.p. 122. 

Witt, Ber., 1912, 45, 2383. 

m-Aminoazobenzene (3-Aminoazobenzene) . 

Obtained in 2 cryst. forms by regeneration 
from the sulphate (m.p. 190-2). (1) Orange 
yellow needles, m.p. 69-70. (2) Brownish red 
spears, m.p. 90-1. Sol. EtOH, Et 2 0, Me 2 CO, 
CHC1 3 , C 6 H 6 . 

"N-Acetyl : both cryst. forms give same deriv. 
Golden yellow needles from AcOH. M.p. 130- 
1. Sol. EtOH, Et 2 0, CHC1 3 , C 6 H . Insol. pet. 
ether. Fe + dil. AcOH > m-aminoacetanilide 
+ aniline. 

Benzylidene deriv. : yellowish orange. M.p. 
73-4. 

Mills, J. Chem. Soc., 1895, 67, 928. 
Ruggli, Wiist, Helv. Chim. Acta, 1945, 28, 
781. 

jrj-Arainoazobenzene (4c~Aininoazobenzene) . 

Orange needles with blue cast from EtOH. 
M.p. 126. Boils undecomp. above 360. Sol. 
Et 2 0, hot EtOH. Spar. sol. H 2 0. Reduces ale. 
NH 3 .AgN0 3 . k = 9-5 X 10~ 12 at 25. Red. 
or boil with cone. HC1 > aniline + p- 
phenylenediaminc. Ox. > benzoquinone. 

B,HGl : reddish-blue needles. 



B,HBr: dark violet needles. M.p. 206-7. 
Spar. sol. EtOH, Et 2 0, C 6 H 6 . 

B,HgCL : orange cryst. M.p. 170. Sol. 
Me 2 CO. 

TS-Acetyl : golden needles from EtOH. M.p. 
144-6. 

"N-Propionyl : orange-red plates from EtOH. 
M.p. 170. 

1$-Benzoyl : orange cryst. from EtOH. M.p. 
211 (205). Sol. AcOH. 

Stadel, Bauer, Ber., 1886, 19, 1954. 
2-Amino-l : I'-azonaphthalene 




C 20 H 15 N 3 MW, 297 

Red needles with green lustre. M.p. 154. 
Sol. EtOH, CHC1 3 . Spar. sol. pet. ether, ligroin. 
Cone. H 2 S0 4 > red col. 
Ni comp. : (C 20 H 14 N 3 ) 2 Ni. M.p. 271. 
Co comp. : (C 10 H 14 N 8 ) a Co. M.p. 250. 

Elter, Gazz. cMm. ital, 1915, 45, II, 315. 
Crippa, Gazz. cMm. ital., 1927, 57, 20. 

4-Amino-l : l'-azonaphthalene. 

Reddish-brown needles with green lustre. 
M.p. 175 (183 corr.). Spar. sol. EtOH, Et 2 0, 
C 6 H 6 . Sn + HC1 > 1-naphthylamine + 1:4- 
naphthylenediamine . 

Michaelis, Erdmann, Ber., 1895, 28, 2198. 
2-Amino-l : 2 r -azonapthalene 




C 20 H 15 N 3 MW, 297 

Red needles from aniline or xylene. M.p. 
156. Sol. cone. H 2 S0 4 to violet sol. 

Metzki, Goll, Ber., 1886, 19, 1281. 

4-Amino-l : 2'-azonaphthalene. 

Brownish-yellow needles from EtOH. M.p. 
152. Sol. cone. H 2 S0 4 to violet sol. 

Metzki, Gottig, Ber., 1887, 20, 612. 

Aminoazotoluene . 

See Aminodimethylazobenzene. 
o-Aminoazoxybenzene (2 -Aminoazoxybenz- 
ene) 

H 2 N 



C 12 H U ON 3 



MW, 



p-Aminoazoxybenzene 



68 



w~Aminobenzamide 



Prisms from EtOH.Aq. M.p. about 98. 
"N-Acetyl : yellow needles from AcOH. M.p. 
156. 

Cusmano, Delia Nave, Gazz. cMm. Hal., 
1921, 51, i, 69. 



p- Aminoazoxyb enzene 

benzene). 
Exists in two isomeric forms. 



(4c-Aminoazoxy- 



<x.-Form. 

Orange prismatic leaflets. M.p. 138. Cone. 



H 2 S0 4 



brown sol. 



~N-Acetyl : yellow needles from MeOH.Aq. 
M.p. 151. 



Pale yellow cryst. M.p. 136. Cone. H 2 S0 4 
>- brown sol. 

i^-Acetyl : yellow prisms from MeOH.Aq. or 
EtOH. M.p. 172. 

Vorlander, Schuster, J. prakt. Chem., 

1934, 140, 193. 
Bigiavi, Albanese, Gazz. Mm. ital., 1934, 

64, 897. 

Aminoazo-xylene . 

See Aminotetramethylazobenzene. 
o-Aminobenzaldehyde (Anthranilaldehyde) 

CHO 



C 7 H 7 ON MW, 121 

Silvery leaflets. M.p. 39-40. Sol. EtOH, 
Et 2 0, CHC1 3 , CsH 6 . Spar. sol. cold H 2 0. Insol. 
ligroin. Volatile in steam. Gives bisulphite 
comp. Porms add. comp. with HgCl 2 . Min. 
acids > H 2 N-C 6 H 4 -CH:N-C 6 H 4 "CHO (so-called 
anhydride). Tris-anhydro comp., C 21 H 17 ON 3 , 
cryst. from EtOH. M.p. 234. Bed. (H 2 /JRaney 
M) > o-aminobenzyl alcohol. Heat > 
polymer. Ac 2 + AcONa > carbostyril. 

Oxime : o-aminobenzaldoxime. Needles from 
C 6 H 6 . M.p. 134-5. Sol. EtOH, Et 2 0, AcOH, 
CS 2? acids and alkalis. Spar. sol. cold H 2 0, 
C 6 H 6 , ligroin. Sublimes. 1$-Acetyl : m.p. 194. 
Sol. hot EtOH. 

Hydrazone : yellowish leaflets from ligroin. 
M.p. 62. Dipicrate : m.p. 188. 

p-Nitrophenylhydrazone : m.p. 218-20. 

tSemicarbazone : yellow. M.p. 247. 

J3-Acetyl : o-aldehydo,acetanilide. Needles 
from H 2 6. M.p. 70-1. Oxime : see above. 

TX-Benzoyl : o-aldehydobonzanilide. Needles 
from ligroin. M.p. 7*3-4. Sol. EtOH, Et 2 0, 
C H 

6 JD*-"jre acetal: b.p. 137-8/25 mm. Very 
unstable. 

Ruggli, Schmid, Helv. CMm. Acta> 1938, 

18, 1235. 
Bambergor, Ber., 1927, 60, 319. 



wi-Aminobenzaldeliy de . 

Yellow amorphous powder. Sol. Et 2 0, min. 
acids. 

Oxime : m-aminobenzaldoxime. M.p. 195. 

'N-Acetyl : colourless cryst. M.p. 122. 

Semicarbazone : yellow needles. Decomp. 
above 280. 

p-Nitrophenylkydrazone : m.p. 225-6. 

Woodward, Organic Syntheses, 1945, 

XXV, 55. 
Bupe, Vogler, Helv. Chim. Acta, 1925, 8, 

832. 
Bissell, U.S.P., 1,499,761, (Chem. 

Abstracts, 1924, 18, 2716). 

p-Ammobenzaldehyde . 

Leaflets. M.p. 70-2. Sol. H 2 0, EtOH, 
Et 2 0, min. acids. Undergoes change to red 
insol. isomer. 

Oxime : ^-aminobenzaldoxime. Yellow cryst. 
M.p. 124. Sol. EtOH, Et 2 0, cone, alkalis, min. 
acids. N-Acetyl : m.p. 205-6. 

Semicarbazone : yellow platelets + |H 2 
fromH 2 0. M.p. 173. 

Phenylhydrazone : leaflets from EtOH. M.p. 
156 (175). Turns yellow in air. 

"N-Dibenzyl : pale yellow needles from EtOH. 
M.p. 88-90. 

"N-Acetyl : needles from hot H 2 O. M.p. 153. 
Phenylhydrazone : m.p. 209. Thiosemi- 
carbazone : Thiacetazone. Yellow hexagonal 
plates from cone. AcOH. M.p. 228 (234) 
decomp. Oxime : see above. 

Beard et al, J. Chem. Soc., 1944, 4, 
Vilsmeier, Haack, Ber., 1927, 60, 121. 
Janse, Rec. trav. chim., 1921, 40, 286. 

o-Aminofoenzamide (Anthranilic acid amide) 

CONH 2 
/\NH 2 

C 7 H 8 ON 2 MW, 136 

Leaflets. M.p. 109-1 11 -5. Sol. EtOH, hot 
H 2 0. Spar. sol. Et 2 0, C 6 H 6 . Hyd. by HOI. 

N-Benzoyl: decomp. at 2 14-1 5. 

JB 2 + oxalic Et ester : m.p. 87-9. Sol H s (), 
EtOH, Et 2 0. 

"N-Acetyl : see under Aootylanthraziilio Acid. 

Jacobs, Hoidolborgor, /. Am. Chem, Soc,, 
1917, 39, 1437. 

Hoilbron et al, J. Chem, Moc., 1945, 861. 

rn-Aminobenzamide . 

Yellow noodles + 1H 2 from H a O. M.p. 
113-14 oorr. Sol. Et 2 0, Spar. sol. cold 
CHC1 3 , cold C 6 H 6 . 

Hydrate ; m.p. 79-80* 

Jacobs, Hoidelborgor, J* Am. Chem. Soc* 9 
1917, 39, 1437. 



p -Aminobenzamide 



69 



p-Aminobenzoic Acid 



p-Aminobenzamide . 

Yellow cryst. + pI 2 0. M.p. 183. Spar. 
sol. H 2 0. 

"N-Acetyl : prisms from EtOH.Aq. M.p. 
274-5. 

N-Chloroacetyl : needles from EtOH. M.p. 
241-3. 

Beilstein, Keichenbach, Ann., 1864, 132, 
144. 

Aminobenzanilide . 

See under Anthranilic Acid and ra-Amino- 
benzoic Acid. 

Aminobenzdioxole . 

See Methylenedioxyaniline. 

Aminobenzenesulphonamide . 

See Sulphanilamide and under o- and m~ 
Aniline-sulphonic Acids. 

Aminobenzenesulphonic Acid. 

See Aniline-sulphonic Acid. 

o-Aminobenzhydrol (o-Aminodiphenylcarb- 
inol) 

CH(OH)-C 6 H 5 




C 13 H 13 ON ^ MW, 199 

Prisms from EtOH. M.p. 120. Sol. most 
org. solvents. 
N-Acetyl : needles from EtOH. M.p. 118. 

Gabriel, Stelzner, Ber., 1896, 29, 1304. 

m-Aminobenzhydrol (m-Aminodiphenyl- 
carbinol). 

Needles from EtOH.Aq. M.p. 78. A second 
form (probably a hydrate) softens at 64, m.p. 
76-7. Sol. EtOH, Et 2 0, Me 2 CO, AcOH, CHC1 3 , 
C 6 H 6 . Insol. cold H 2 0. 

Esselen, Clarke, J. Am. Chem. Soc., 1914, 
36, 308. 

l>-Aminobenzhydrol (p-Aminodiphenyl- 
cardinal). 

Needles from C 6 H 6 , or hot H 2 0. M.p. 121. 
Sol. EtOH, MeOH, AcOEt. Spar. sol. Et 2 0, 
ligroin. 

B,HCl : m.p. 270-3 decomp. 

Benzoyl : needles from EtOH. M.p. 145. 

Eappenberg, Ber. 9 1897, 30, 1136. 

2-Aminobenzidine . 

See 2:4: 4 / -Triaminodiphenyl. 
o-Aminobenzoic Acid. 
See Anthranilic Acid. 
* m-Aminobenzoic Acid 

COOH 



C 7 H 7 2 N 




Jc = 8-5 X 10- 5 
M.p. 225, (an- 



M.p. 174. Very sol. hot H 2 O. Spar. soL 
cold H 2 0. Sol. EtOH, Et 2 0. Aq. sols, turn 
brown in air. D 4 1-5105. Sublimes with some 
decomp. Forms sol. salts with min. acids. 
NaHg, or HI at 180 > benzoic acid + NH 3 . 
Br > tribromo deriv. HC1 + KC10 3 > 
chloranil. &(acid) = 1-63 X 10~ 5 at25. &(base) 
= 1-2 X 10- 11 at 25. 

'N-Acetyl : m-acetylaminobenzoic acid. Small 
needles. M.p. 248 decomp. SoL hot EtOH. 
Spar. sol. hot H 2 0. Sublimes, 
at 25. 

2 ,# 2 4 : needles + H 2 0. 
hyd.) 230. SoL hot H 2 0. 

Me ester: C 8 H 9 2 N. MW, 151. Cryst. M.p. 
36-8. B.p. 152~3/11 mm. Very sol. EtOH, 
Et 2 0, CHC1 3 , C 6 H 6 . Spar. sol. pet. ether. 
B,HCl : m.p. 201-2. Acetyl : m.p. 136-7. 

Et ester : C 9 H n 2 N. MW, 165. Oil. B.p. 
294. Mod. sol. H 2 O. B,HCl : m.p. 185 

n-Butyl ester : C n H 15 2 N. MW, 193. 
below 0. B.p. 245. B,HCl: plates. 
128. 

d-Amyl ester : C 12 H 17 2 N. 

184-7/35 mm. 

+ 646. 

l-Menthyl ester : 

Benzyl ester : pale yellow liq. 

p-Nitrobenzyl ester : m.p. 201. 

Amide : see m-Aminobenzamide. 
see m-Aminobenzonitrile. 

m-aminobenzanilide. 
Needles from H 2 0. M.p. 140 



D 18 1-051. 



MW, 207. 
%> 1-5351. 



M.p. 
M.p. 

B.p. 



b.p. 168/l-8 mm. 
B.p. 308 



C 13 H I2 ON 2 . 



Nitrile : 

Anilide : 
MW, 212. 
H 2 0. 

p-Iodophenylurea deriv. : m.p. 220-1. 

Brill, /. Am. Chem. Soc., 1921, 43, 1320. 
Popov, CTiem. Abstracts, 1934, 28, 1671. 
Holleman, Voerman, Eec. trav. ckim., 
1902, 21, 58. 

jp-Aminobenzoic Acid. 

Yellowish-red cryst. M.p. 186-7. SoL H 2 0, 
EtOH, Et 2 0. &(acid) = 1-21 x 10- 5 at 25. 
7c(base) = 2-3 X 10~ 12 at 25. Br ^ dibromo 
deriv. HC1 + KC10 3 > chloranil. HC1 at 
180 > aniline + C0 2 . Alkylaminoalkyl 

esters used extensively as local anaesthetics. 

Me ester: C 8 H 9 2 N. MW, 151. Leaflets 
from MeOH.Aq. M.p. 112. 

Et ester : see Benzocaine. 

Propyl ester : see Propaesin. 

Isopropyl ester : cryst. from EtOH. M.p. 
79. B,HCl : needles. M.p. 184. 

n-Butyl ester : see Butesin. 

Isobutyl ester : see Cycloform. 



Allyl ester : C 10 H 1:1 02N. MW, 177. Cryst. 
from EtOH. M.p. 52. B,HCl : plates. M.p. 
180. 

n-Amyl ester: C^H 17 2 N. MW, 207. 
Needles from ligroin. M.p. 56-8. 

d-Amyl ester: m.p. 27-30. B.p. 215 /35 



MW, 137 mm. D 76 1-050. < 1-5369. [] + 5-47 



o-Ammobenzonitrile 



70 



Aminobenzophenone-carboxylic Acid 



Menthyl ester : m.p. 89. B.p. 175 /0-2 mm. 
slight decomp. B,HCl : m.p. about 200. 

Benzyl ester : needles. M.p. 90. B,HCl : 
m.p. 184. 

$-Nitrobenzyl ester : m.p. above 248. 

$-NapWiyl ester : needles from EtOH. M.p. 
171. Sol. Me 2 CO, C 6 H 6 . Mod. sol. CHC1 3 , 
EtjjO, CS 2 . 

$-Diethylaminoethyl ester : see Novocaine. 

2 : 2-Dimethyl-3-diethylaminopropyl ester hydro- 
chloride : see Larocaine. 

Amide : see ^-Aminobenzamide. 

Nitrile : see ^-Aminobenzonitrile. 

N-Formyl : needles from EtOH. M.p. 268 
decomp. 

N-Acetyl : jj-acetylaminobenzoic acid. 
Needles. M.p. 250 decomp. Spar. sol. H 2 0, 
Et 2 0. Hyd. by hot HC1. k = 5-2 x 1(H at 
25. 

TS-Benzoyl : needles from EtOH. M.p. 278. 
Sol. EtOH, Et 2 0, AcOH. Spar sol. H 2 0. 

p-Iodophenylurea deriv. : m.p. 231-2. 

Popov, Ghem. Abstracts, 1934, 28, 1671. 
Brill, J. Am. Ghem. Soc., 1921, 43, 1320, 



o-Aminobenzpnitrile 

nitrile } o-cyanoaniline) 

ON 



C 7 H 6 N 2 



(Anthranilic acid 




MW, 118 



Yellow prisms from CS 2 , needles from pet. 
ether. M.p. 51. B.p. 267-8/777 mm. Sol. 
EtOH, MeOH, Me 2 CO, Et 2 0, CHC1 3 , Py, CS 2 . 
Spar. sol. H 2 0, 

Kalle, B.B.P., 212,207, (Ghem. Zentr., 

1909, II, 486), 
Eeissert, Grube, Ber., 1909, 42, 3712. 

m-Aminobenzonitrile (m-Cyanoaniline) . 

Needles from EtOH.Aq. M.p. 53-4. B.p. 
288-90. Sol. EtOH, Et 2 0, CHC1 3 , AcOEt. 
Spar. sol. H 2 0. Fe + AcOH > benzonitrile 



Fricke, Ber., 1874, 7, 1321. 
I.G., D.R.P., 523,273, (Ghem. Abstracts, 
1931, 25, 3359). 

p-Aminobenzonitiile (p- Gyanoaniline) . 

Prisms. M.p. 86. Very sol. EtOH, Et0, 
Me 2 CO, AcOH, CHC1 3 , C 6 H 6 , boiling H 2 0. 
Spar, sol CS 2 , ligroin, Alk. H 2 2 >- p- 
aminobenzamide. 

Picrate : golden yellow needles from EtOH.Aq . 
M.p. 150. 

N-Formyl : cryst. from H 2 0. M.p. 188-9. 

NAcetyl : needles from H 2 0, M.p. 205*5. 

yt-Propionyt : cryst. from H 2 0. M.p. 169. 



TS-Benzoyl : cryst. from EtOH.Aq. M.p. 170. 

Bogert, Wise, J. Am. Ghem. Soc., 1912, 

34, 693. 
I.G., D.R.P., 523,273, (Ghem. Abstracts, 

1931, 25, 3359). 
Ashley et al, J. Ghem. Soc., 1942, 103. 

o-Aminobenzophenone (o-Aminodiphenyl 
Jcetone) 



C 13 H n ON 




MW, 197 

Pale yellow cryst. from EtOH. M.p. 105-6. 
PbO at 320 > acridone. NaHg > o- 



ZnCL 



aniline + ben- 



156. Acid- 



aminobenzhydrol. 
zoic acid. 

B,HCl : m.p. 179-80 decomp. 

Oximes : alkali-stable, m.p. 
stable, m.p. 127. 

N-Acetyl : needles from EtOH.Aq. M.p. 72 
(89) . Oxime : leaflets from EtOH. M.p. 180. 

N-Propionyl : needles from EtOH.Aq. M.p. 
78-5. 

^Butyryl : cryst. from EtOH. M.p. 56. 

'N-Benzoyl : needles from EtOH.Aq. M.p. 
80-5. Sol. hot EtOH, C 6 H 6 . 

Gabriel, Stelzner, Ber., 1896, 29, 1303. 
Hayashi, Namikawa, Morikawa, J. Ghem. 

Soc. Japan, 1935, 56, 1106. 
Simpson et al., J. Chem. Soc,, 1945, 646. 

m-Aminobenzophenone . 

Yellow needles from hot H 2 0. M.p. 87. Sol. 
EtOH, Et 2 0. Spar. sol. H 2 0. NaHg > 
m-aminobenzhydrol. 

B,HCl : needles from dil HOI. M.p, 187. 

Geigy, Konigs, Ber., 1885, 18, 240L 

p-Aminobenjzophenone . 

Leaflets from EtOH.Aq. M.p. 124. 
EtOH, Et 2 0, AcOH. Mod. sol. hot H 2 0. 

Oxime : exists in two forms, (i) Prisms from 
EtOH. M.p. 168. (ii) Needles from EtOH.Aq. 
M.p. 126. 

Hydrazone : yellow needlea from EtOH. M.p. 
139-40. 

N-Acetyt : needles from EtOH.Aq. M.p. 
153. Sol. EtOH, C 6 H g , AcOH. Insol H 2 0, 

N~Benzoyl : leaflets from EtOH. M.p, 152, 
Sol. C 6 H 6 , AcOH, hot AcOH. Insol BLO, 

N-Propionyl : plates from EtOH. M.p. 139. 

Ddbner, Ann., 1881, 210, 268. 

Clarke, Esselen, J. Am, Chem* Soc* 9 1911, 

33, 1138, 
Montagne, JBec. trav. chim,, 1923, 42, 

506, 

Aminobenzophenone-carboxylic Acid* 

See Aminobenzoylbenssoic Acid. 



Sol. 



Amino-p-benzoquinone 



71 



o-Aminobenzyl Alcohol 



Amino-p-foenzoquinone (Aminoquinone) 
O 



2-Aminobenzth.iazole (p-Aminobenzthiazole) 




MW, 123 

N-Acetyl : reddish-yellow needles or prisms 
from C 6 H 6 . M.p. 142. Sol. most ord. org. 
solvents. 

Diana : C 6 H 5 N:C 6 H 3 (NH 2 ):NC 6 H 5 .C 18 H 15 N 3 . 
Bed prisms. M.p. 167. Sol. Et 2 O, Me 2 CO, 
CHC1 3 , C 6 H 6 , CS 2 . Spar. sol. EtOH. 

Orlov, Chem. Abstracts, 1929, 23, 1125. 

p-o-Aminobenzoylalanine . 

See Kynurenine. 

o-Aminobenzoylanthranilic Acid. 
See Anthranoylanthranilic Acid. 
4-Amino-o-benzoylbenzoic Acid (5- 

Aminobenzophenone-2-carboxylic acid) 

900H 




C 14 H n 3 N MW, 241 

Colourless needles from H 2 0. Yellow prisms 
+ lEtOH from EtOH. M.p. 195 decomp. 

Kliegl, Ber., 1905, 38, 296. 

5-Amino-o-benzoylbenzoic Acid (4- 

Aininobenzophenone-2-carboxylic acid) . 

Yellow cryst. from H 2 0. M.p. 193-4 de- 
comp. Sol. warm MeOH. Insol. Et 2 0, AcOEt, 
CHC1 3 , ligroin. 

Rainer, Monatsh., 1908, 29, 437. 

S'-Amino-o-benzoylbenzoic Acid (3'- 

Aminobenzophenone-2-carboxylic acid) . 
Yellow cryst. M.p. 174-5. 

Earner, Monatsh., 1908, 29, 180; 1905, 
26, 974. 

S'-Amino-jp-benzoylbenzoic Acid (3'- 
Aminobenzophenone-4:-carboxylic acid) . 

Cryst. + IHoO from EtOH.Aq. M.p. 145. 
Sol. EtOH, hot H 2 0. Insol. Et 2 0. 

B,HCl : needles. M.p. above 250. 

Limprieht, Lenz, Ann., 1895, 286, 318. 

4 / -Amino-|>-benzoylbenzoic Acid (4'- 

Aminobenzophenone-4:-carboxyUc acid) . 

Pale yellow needles from H 2 0. M.p. 211, 
Sol. EtOH. 

Limprieht, Samietz, Ann., 1895, 286, 331. 

p-Aminobenzoylcarbinol . 

See ^-Aminophenaoyl Alcohol. 
o-Aminobenzoylformic Acid. 

See Isatic Acid. 




C 7 H 6 N 2 S MW, 150 

Leaflets. M.p. 132 (129). Sol. cone. HCL 
Very stable and distils undecomp. 

B,HCl: m.p. 236-7. 

"N-Phenyl: 2-aniHnobenzthiazole. C 13 H 10 N 2 S. 
MW, 226. Needles. M.p. 159. Picrate ; m.p. 
222. yt-Acetyl : m.p. 158. 

N-Acetyl : prisms from EtOH. M.p. 186. 

N-Benzoyl : prisms from EtOH. M.p. 186. 

Picrate : m.p. 256. 

Note. Alternative numbering : 



1ST 

Hunter, J, Chem. Soc., 1925, 127, 2023 ; 

1926, 1385. 
I.G., D.R.P., 615,526, (Chem. Abstracts, 

1935, 29, 8003) ; B.P., 345,735, (Chem. 

Abstracts, 1932, 26, 1944). 

4- Aminobenzthiazole . 

Leaflets from C 6 H 6 -pet. ether. M.p. 94. 

Erlenmeyer, Ueberwasser, Helv. Chim. 
Acta, 1940, 23, 328. 

0-Amin.obenzyl Alcoliol (o-Aminophenyl- 
carbinol) 

CH 2 OH 



C 7 H 9 ON MW, 123 

Needles from C 6 H 6 . M.p. 82. B.p. 270-80 
part, decomp., 160/5-10 mm. Sol. EtOH, 
AcOH, CHC1 3 , C 6 H 6 . Mod. sol. H 2 0, Et 2 0. 
Spar, volatile in steam. 

' Me ether : methyl o-aminobenzyl ether. 
C 8 H n ON. MW, 137. Colourless oil. B.p. 
227 with part, resinification, 124 /30 mm. DJ 7 
1-05. Darkens in air. Resinified by acids. 
Oxalate : m.p. 124. 

M ether : ethyl o-aminobenzyl ether. 
C 9 H 13 ON. MW, 151. Yellow oil. B.p. 123- 
9/25 mm. Kesinified by acids and when dist. 
at ord. press. B,HCl : m.p. 81-2. Oxalate : 
m.p. 136. 

Phenyl ether : phenyl o-aminobenzyl ether. 
C 13 H 13 ON. MW, 199. Cryst. from EtOH. 
M.p. 81-2. Sol. hot EtOH. 

0-Acetyl: oil. B,HCl: needles. M.p. 
116. 

N-Acetyl : needles from C 6 H 6 . M.p. 114. 

0-Benzoyl: cryst. from EtOH-Et 2 O. M.p. 
198-9. 



m-Aminobenzyl Alcohol 



72 



cc-Aminofoenzyl cyanide 



B,HCl : m.p. 108. 

B 2 ,H 2 SO : m.p. 114. 

Oxalate : m.p. 130. Sol. H 2 0, hot EtOH. 

Picrate : m.p. 110. 

Gabriel, Posner, Ber., 1894, 27, 3512. 

Eeissert, Cramer, Ber., 1928, 61, 2555. 

Coleman, Johnson, Organic Syntheses, 
1941, XXI, 10. 

m-Aminobenzyl Alcohol (m-Aminophenyl- 
carbinol). 

Plates from C 6 H 6 . M.p. 97. Sol. EtOH, 
Et 2 0, CHC1 3 , hot H 2 0. Mod. sol. C 6 H 6 . 

N-Acetyl : needles from CJBL. M.p. 106-7. 
Sol. EtOH. 

N-Benzoyl : needles from EtOH.Aq. M.p. 
115. Sol. EtOH, Et 2 0, AcOH. 

0-Benzoyl : cryst. from CHCL-pet. ether. 
M.p. 144-5. 

QN-Dibenzoyl : needles from EtOH. M.p. 
113-14. 

Shima, Chem. Abstracts, 1928, 22, 3884. 
Lutter, Ber., 1897, 30, 1065. 

j>-Aminobenzyl Alcohol (p-Aminophenyl- 
carbinol) . 

Plates and leaflets from C 6 H 6 . M.p. 65. 
Very sol. H 2 0. Sol. EtOH, Et 2 0, C 6 H 6 . 

QN-Diacetyl : needles from EtOH.Aq. M.p. 
188. Sol. EtOH, AcOH. 

N-Benzoyl : cryst. from H 2 0. M.p. 150-1. 
Thiele, Dimroth, Ann., 1899, 305, 119. 

o-Aminobenzylamine ( <x-Amino-o-toluidine, 

oc : 2-diaminotoluene) 

CH 2 NH 2 



C 7 H 10 N 2 MW, 122 

Sol. H 2 0. Mod. volatile in steam. Decomp. 
on dist. with evolution of NH 3 . Absorbs C0 2 . 

Benzoate: C 7 H 10 N 2J C 7 H 6 2 . Leaflets. M.p. 
167. Sol. H 2 0, EtOH. 

cJ$-Acetyl : " needles from hot H 9 0. M.p. 

113. * 

ccN-Phenyl : o-aminobenzylaniline. C 13 H 14 N 2 . 

MW, 198. Needles from EtOH. M.pt 86-7. 

Sol. most org. solvents except ligroin. 

oflS-Di-Me : o-aminobenzyldimethylamine. 
H M N a . MW, 150. M.p. 36-7. B.p. 107 / 
14 mm. B,2HOl : prisms from EtOH. M.p. 
205. ^ F 

a-N-Di-Et : 0~aminobemyldiethylamme. 

CnHigNg. MW, 178. B.p. 153~-5/42 mm. 
Monopicraie : orange yellow. M.p. 143-4. 
Dipicrate : yellow cryst. M.p. 135 g . 

Gabriel, Colman, Ber., 1904, 37, 3644. 
Busch, J. prakt. Chem., 1895, 51, 261. 
Noelting, Kregcssy, Bull soc, chim,, 1916, 

19, 339. 
Stedman, J. Ohem. Soc., 1927, 130, 1904. 



m-Aminobenzylamine ( a- A mino-m-tolu- 
idine, a : 3-diaminotoluene). 

<xN-Di-Me : m-aminobenzyldimethylamine. 
C 9 H 14 N 2 . MW, 150. M.p. 46. B.p. 129 /13 
mm. B,2HOl: prisms from EtOH. M.p. 225. 
aN-Di-Et : m-aminobenzyldiethylamine. 

C n H 18 N 2 . MW, 178. B.p. 167-8 /42 mm. 
Picrate : orange red. M.p. 142. Dipicrate : 
yeUow. M.p. 148. 

oN-Phenyl : m-aminobenzylaniline. C 13 H 14 N 2 . 

MW,198. Needles. M.p. 60. 9 2HCl:m.p.l61. 

Purgotti, Monti, Gazz. chim. ital., 1900, 

30, ii, 258. 

Stedman, J. Chem. Soc., 1927, 1906. 
Noelting, Kregczy, Butt. soc. chim., 1916, 
19, 339. 

p-Aminobenzylamine (a-Amino-p-tolu- 
idine, a : 4.-diaminotoluene) . 

B.p. 268-70. Sol. EtOH. Mod. sol. H 2 0. 
Insol. Et 2 0. D 20 1-08. Absorbs C0 2 . 

oiN-Di-Me : ^-aminobenzyldimethylamme. 
CoH 14 N 2 . MW, 150. B.p. 133 /16 mm. 
B,2HCl: needles from EtOH. M.p. 216. 

<xN-Di-Et : ^p-aminobenzyldiethylamine. 

C^HjgNg. MW, 178. B.p. 165-6/42 mm. 
Monopicrate : red. M.p. 109-10. Dipicrate : 
yeUow. M.p. 130. 

oN-Phenyl : ^-aminobenzylaniline. C 13 H 14 N2. 
MW, 198. M.p. 49-50. Sol. EtOH, Et 2 0, 
C 6 H 6 . IM1. HC1 > 4 : 4 / -diaminodiphenyl- 
methane. 

Salkowski, Ber., 1889, 22, 2142. 
Paal, Sprenger, Ber., 1897, 30, 70. 
Stedman, J. Chem. Soc., 1927, 1906. 
Noelting, Kregczy, Bull, soc, (Mm., 1916, 
19, 339. 

Aminobenzylaniline . 
See under Aminobenzylamine. 
o-Aminobenzyl chloride 
CH 2 C1 




C 7 H 8 NC1 MW, 141-5 

N-^tce^Z : cryst. from C 6 H 6 . M.p, 114. 
"N-Benzoyl : needleB. M.p. 124-5 U . 

Gabriel, Posnor, Ber,, 1894, 27, 3513. 

m-Aminobenzyl chloride, 

"N-Acetyl : needles from G 6 H 6 -pet, ether* 
M.p. 89. 

Kuhn, Ber., 1900, 33, 2903. 

jp-Aminobenzyl chloride. 

H$-Acetyl : needles from 6 H e . M.p. 155* 
Kiihn, Ber., 1900, 33, 2903. 

a-Aminobenzyl cyanide (ot-Gyanobenzyl* 
amine, a-aminophenylacetonitrile) 
C 6 H 6 -CH(NH 2 )-CN 
C 8 H 8 N 2 MW, 132 



o-Aminobenzyl cyanide 



73 



1 - Amino-sec . -w-butyl Alcoliol 



. 

Tartrate: [<x] D + 41-1. 

N-Acetyl: needles from AcOEt-pet ether. 
M.p. 130-8. 

N-Benzoyl : m.p. 151. 

(fik 

Leaflets from ligroin. M.p. 55. 

B,HCl : needles. M.p. 173 decomp. 

Picrate : yellow needles. M.p. 160-1 de- 
comp. 

N-Benzoyl: needles from H 2 0. M.p. 159-60. 

Dubsky, Wensink, Granacher, Ber., 1919, 

52, 232. 
Ruggeri, Rigoli, Gazz. chim. ital, 1924, 

54, 554. 
Reihlen, Weinbrenner, v. Hessling, Ann.,' 

1932, 494, 156. 

o-Aminobenzyl cyanide (o-Aminophenyl- 
acetonitrile) 

COLON 




C 8 H 8 N 2 MW, 132 

Leaflets from EtOH.Aq. M.p. 72. Sol. 
EtOH, C 6 H 6 . Insol. H 2 0. Na + EtOH > 
2-aminoindole. 

TX-Acetyl : m.p. 120. 

Pschorr, Hoppe, Ber., 1910, 43, 2543. 

m-Aminobenzyl cyanide (m-AminopTienyl- 
acetonitrile) . 

B.p. 183-7/13 mm. 
N-Acetyl : m.p. 100-2. 
Picrate : m.p. 200 decomp. 

Koelsch, J. Am. Chem. Soc., 1943, 65, 437. 
Salkowski, Ber., 1910, 43, 2543. 

jp-Aminobenzyl cyanide (p-Aminophenyl- 
acetonitrile). 

Leaflets from H 2 0. M.p. 46. B.p. 312, 
177/11 mm. Spar. sol. CS 2 , hot H 2 0. Sol. 
most other org. solvents. Spar, volatile in 
steam. 

B,HCl : m.p. 217-20. 

Picrate : m.p. 185. 

"N-Formyl : cryst. from H 2 0. M.p. 135. 

T$-Benzoyl : m.p. 176-7. 

N~Acetyl: needles fromH 2 0. M.p. 97. Sol. 
EtOH, Et 2 0, CHC1 3 , AcOH. Spar. sol. C 6 H 6 , 
CS 2 . Distils undecomp. 

TS-Diacetyl; needles. M.p. 152-3. Sol. 
CHC1 3 , hot H 2 0. Mod. sol. Et 2 0, C 6 H 6 , AcOH, 
CS 2 . 

v. Braun, Blessing, Ber., 1923, 56, 2156. 
I.G., D.E.P., 523,273, (Chem. Abstracts, 
1931, 25, 3359). 

Aminobutane. 
See Butylamine. 



2-Amino-w-biityl Alcohol (2-Amino- 
butanol'l) 

CH 3 -CH -CH(NH 2 )-CH 2 OH 
C 4 H U ON ~ MW, 89 

B.p. 172-4. 

B 2 ,(COOH) 2 : m.p. 176. 

B 2 ,H z PtCl B : yellow leaflets. M.p. 189-90. 

dk 

B.p. 80/11 mm. D 20 0-947. [a]|> + 9-8 in 

*0xalate : m.p. 190-2. [a] + 11-3 in H 2 0. 

Z-. 

Oxalate : [a]g> 11-3 in H 2 0. 

Stienon, Chem. Zentr., 1902, 1, 717. 
Blaise, Picard, Ann. chim. phys., 1912, 

26, 273. 
Stoll, Hofmann, Hdv. Chim. Acta, 1943, 

26, 922. 

Johnson, Degering, J. Org. Chem., 1943, 
8,7. 

3-Amino-n-butyl Alcohol (3-Amino- 
butanol-l) 

CH 3 -CH(NH 2 )'CH 2 -CH 2 OH 
C 4 H U ON MW, 89 

B.p. 82-5/19 mm. Sol. H 2 0. 

Bayer, D.E.P., 247,144, (Chem. Zentr., 

1912, II, 159). 

Schnider, Jubilee Vol. Emil Barrett, 1946, 
85, (Chem. Abstracts, 1947, 41, 6199). 

4-Ammo-w-butyl Alcohol (^-Aminobutanol- 
1, 4c-hydroxy-iL-butylamine, butanolamine) 

H 2 N-CH 2 -CH 2 -CH 2 -CH 2 OH 
C 4 H n O]Sr MW, 89 

B.p. 206/776 mm., 148/148 mm., 125/34 
mm. Sol. EtOH. Insol. Et 2 0. D 12 0-967. 
Forms a hydrate in H 2 0. Absorbs C0 2 and 
H 2 0. 

Me ether : C 5 H 13 01Sr. MW, 103. B.p. 142- 
5. Sol. H 2 0, EtOH, Et 2 0. 

Et ether : C 6 H 15 0]5L MW, 117. B.p. 153- 
4 /746mm. Sol. H 2 0. D 20 0*864. 

'N-Chloroacetyl : m.p. 30. B.p. 165-7/0-7 
mm. 

Henry, Ber., 1900, 33, 3170. - 

l-Amino-sec.-n-butyl Alcohol (1-Amino- 
butanol-2, 2-hydroxy-n-butylamine) 

CH 3 -CH 2 -CH(OH)-CH 2 NH 2 
4 H U ON MW, 89 

B.p. 168-70, 75~7/12 mm. 
Et ether : C 6 H 15 ON. MW, 117. B.p. 139- 
41. Picrate : needles. M.p. 156. 
B 2 ,(COOH) 2 : m.p. 193. 
Picrolonate : yellow needles from EtOH. 
M.p. 154. 

Bookman, Ber., 1895, 28, 3117. 
Montmollin, Ackermann, Helv. Chim. 
Acto, 1929, 12, 874. 



3-AmIno-see.-n~butyl Alcohol 



74 



o-Amino-n-btitylbenzene 



3-Amino-sec.-n-biityl Alcoliol (3-Amino- 
butanol-2) 

CH 3 'CH(NH 2 )'CH(OH)-CH 3 
4 H n ON MW, 89 

B.p. 159-60 /745 mm., 78-80 /20 mm. Sol. 
H 9 O, EtOH, Et 2 0. D|g 0-9416. nf? 1-4445. 

~B 2 ,(COOH) 2 : leaflets from EtOH. M.p. 208 
decomp. (211-12). 

B,(COOH) : cryst. from EtOH. M.p. 164- 
5. 

N-Chloroacetyl : cryst. M.p. 38-9. B.p. 
119/0-3 mm. Sol. H 2 0, EtOH, CHC1 3 . 

Batalin, Ugryumov, Chem. Abstracts, 

1936, 30, 6701. 
Wieland, Bossert, Ann., 1934, 509, 12. 

4-Amino-sec.-n-butyl Alcohol (k-Amino* 
butanol-2 , 3 -hydroxy-n-butylamine) 

H 2 N-CH 2 -CH 2 -CH(OH)-CH 3 
C 4 H n OJST MW, 89 

B.p. 172/755 mm, 

B 2 ,H 2 PtCl$ : orange-yellow plates from MeOH. 
M.p. 206 decomp. 

Picrate : yellow prisms EtOH. M.p. 122. 

Et ether : C 6 H 15 ON. MW, 117. B.p. 148. 
D 19 0-8468. 2 ,Hj>tClt : m.p. 19. B 2 ,(COOH) 2 : 
m.p. 198-200. 

Robinson, Suginome, J. Chem. Soc., 1932, 
307. 

Amino-tert.-butyl Alcohol (2-Hydroxyiso- 
butylamine,aminotrimethylcarbinol) 

(CH 3 ) 2 C(OH)-CH 2 NH 2 

C 4 H n ON MW, 89 

B.p. 151. DJ 0-95. 

NJX-Jfe : C 6 H 15 ON. MW, 117. B.p. 60/ 
48 mm. 

Krassusky, Compt. rend., 1908, 146, 238, 



amne) 

C 6 H 5 -CH(NH 2 )-CH 2 -CH 2 -CH 3 

C 10 H 15 N MW, 149 

B.p. 220/748 mm., 107-~9/16 mm. D? 
0-9367. Very sol. EtOH. Spar. sol. Et 2 0. 

B,HGl: needles from H 2 0. M.p. 288; 

B Z) H 2 PtOl e : golden-yellow cryst. M.p. 184. 

y^-Phenyl : a-amlinobutylbenzene. B.p. 200 / 
20 mm. B,HCl: needles from EtOH-Et 2 0- 
M.p. 205. B,HNO : cryst. from dil. HN0 3 . 
M.p. 168. 

N-Benzoyl : needles. M.p. 128. 

Busch, Leefhelm, J. <prakt. Chem., 1908, 

77, 11. 

Konowalow, Ber., 1895, 28, 1857. 
Busch, Rinck, Ber., 1905, 37, 1765. 



y-Amino-w-butylbenzene ( 

butylamine) 

C 6 H 5 -CH 2 -CH 2 -CH(NH 2 )-CH 3 
C 10 H 15 N MW, 149 

Oil with weak ammoniacal aromatic odour. 
B.p. 221-2/750 mm., 101-2/14 mm. DJ 5 
0-9289. < 1-51520. Spar. sol. H 2 0. Absorbs 
C0 2 . 

B,HCl: needles from EtOH-Et 2 0. M.p. 
144. 

Neutral sulphate : m.p. 255 decomp. 

B,H Z P0 4 : m.p. 172. 

B^HcftGlQ : yellow leaflets from H 2 0. De- 
comp. at 220. 

N-Benzoyl : needles from EtOH or ligroin. 
M.p. 108. 

NJfe : 13L H l? lSr. MW, 163. B.p. 112-14 / 
14 mm. Volatile in steam. B,HCl : needles from 
EtOH-Et 2 0. M.p. 94-6. B 2 ,ff 2 PCZ 6 : orange- 
red needles. M.p. 169. 

N-Di-Me: C, 2 H 19 N. MW, 177. B.p. 124- 
5/20 mm. Volatile in steam. B,HCl : m.p. 
127-9. B 2 ,H 2 PtCl Q : m.p. 173. Picrate: 
needles. M.p. 113-14. 

v. Braun, Neumann, Ber., 1917, 50, 53. 
Harries, de Osa, Ber., 1903, 36, 2999. 
Schlenk, J. prakt. Chem., 1908, 78, 58. 



amine) 

C 6 H 5 -CH 2 -CH 2 -CH 2 "CH 2 ]SrH 2 

C 10 H 15 N MW, 149 

B.p. 123-4/17 mm. Insol. H 2 0. 

B%,H 2 PtCl Q : cryst. from H 2 0. Docomp. 
at 205. 

Picrate : yellow leaflets from Et 2 0. M.p. 125. 

"E-Benzoyl : needles from EtOH. M.p. 83-5. 

"N-p-Toluenesulphonyl : m.p. 53 '5-53*9. 

N-Jfe: C H H 17 N. MW, 163. B.p. 5-0- 
95-4 /5mm. Dg 0-9126. < 1-50350. B,EOl: 
m.p. 126-2-6'8. N-'p-Toluenesulphonyl : m.p. 
60-5-61-1. B.p. 241-5 /2 mm. 

v. Braun, Ber., 1910, 43, 2844. 
Cope, McElvain, J. Am, Chem. Hoc., 1931, 
53, 1587. 

o-Amino-w-butylbenzene (o-n-Butylaniline) 




C 10 H 15 N MW, 149 

Yellow oil B.p. 122-5 /12 mm. I)J 0*953. 
B,HCl : scales from C H 6 . M.p. 137, 
TS-Acetyl : needles from MoOH.Aq. M,p. 
100. 

Bead, Mullin, J. Am. Chem, 8oc, 9 1928, 

50, 1764. 

Eeilly, Hickinbottom, J. Ghem. *9oo, 
1920, 117, 116, 



m-Amino-n-butylbenzene 



75 



1-Amino-w-butyric Acid 



m ~ Amino - n - butylbenzene (m - n - Butyl - 

aniline). 

Pale yellow oil. 

TS'Benzoyl : needles from EtOH. M.p. 68. 

Reilly, Hickinbottom, J. Ghem. Soc., 
1920, 117, 119. 

p-Amuao-n-butylbenzene (p-n-Butylanil- 
ine). 

B.p. 258~60/750 mm., 133-4/14 mm. Df 
0-945. 

B 2 ,H 2 PtCl Q : needles from MeOBL Decomp. 
at 200-2. 

N-Acetyl : plates from EtOH. M.p. 105. 
"N-Benzoyl : needles from EtOH. M.p 126. 
Reilly, Hickinbottom, J. Chem. Soc. 9 

1920, 117, 119. 

Bead, Mullin, J. Am. Chem. Soc., 1928, 
50, 1764. 



o- Amino-sec .-n-butylbenzene 

Butylaniline) 

9H 3 
CH-CH 2 -CH 3 



(o-sec.-n- 



MW, 149 
B.p. 120-2 /16 mm. DJ 0-957. 

Read, Hewitt, Pike, J. Am. Chem. Soc., 
1932, 54, 1194. 

m-Amino-sec. -n-butylbenzene (m-sec.-n- 
Butylaniline). 
B.p. 120 /18 mm. 

Bead, Hewitt, Pike, J. Am. Chem. Soc., 
1932, 54, 1194. 

p- Ammo-sec, -n-butylbenzene (p-sec.-ii- 
Butylaniline). 

d-. 

B.p. 114/12 mm. DJ 0-945. [a]*J 61 + 39-8 
in CHC1 3 . 

B.p. 238, 130-3/26 mm., 118/15 mm. DJ 6 
0-949. 

N-Acetyl : plates from EtOH. M.p. 125-6 
(123). Sol. Et 2 0, Me 2 CO, AcOEt. Spar. sol. 
H 2 0. 
N-Benzoyl : m.p. 130. 

Harrison, Kenyon, Shepherd, J. Chem. 

Soc., 1926, 660. 

Eeilly, Hickinbottom, J. Chem. Soc., 
1920, 117, 119. 

o- Amino-ter t . -butylbenzene (o-tert. -Butyl- 
aniline) 

C(OH 8 ) 3 



10 H 15 N 




MW, 149 



B.p. 233-5. D 15 0-977. Turns red in air. 
N-Acetyl : needles from C 6 H 6 . M.p. 159-61. 

Craig, J. Am. Chem. Soc., 1935, 57, 195. 

m-Amino-tert.-butylbenzene (m-tert.- 
Butylaniline). 

B.p. 229 /708 mm. Sol. EtOH, Et 2 0, C 6 H 6 . 

'E-Acetyl: leaflets from H 2 0. M.p. 101. 
Sol. EtOH, Et 2 O, C 6 H 6 . 

Gelzer, Ber., 1888, 21, 2947. 

p-Amino-*er*.-butylbenzene (p-tert.- 

Butylaniline) 

Cryst. from pet. ether. M.p. 17. B.p. 
228-30/762 mm., 238-40/766 mm. Misc. with 
EtOH, Et 2 0. Spar. sol. H 2 0. Volatile in 
steam. 

HS-Formyl : leaflets from pet. ether. M.p. 
59. B.p. 314-6. Sol. EtOH, Et 2 0. 

N- Acetyl : leaflets from EtOH. M.p. 169-70. 

TX-Benzoyl : leaflets from EtOH. M.p. 134-6. 

~N-p-Toluenesulphonyl : plates from EtOH. 
M.p. 179-80. 

Willgerodt, Rampacher, Ber., 1901, 34, 

3667. 

Craig, J. Am. Chem. Soc., 1935, 57, 196. 
Hickinbottom, Preston, /. Chem. Soc., 

1930, 1568. 
Malherbe, Ber., 1919, 52, 322. 

Aminobutylene . 

See Crotylamine. 
4-co- Aminobutylgly oxaline . 
See 4- [4-Iminazolyl]-n-butylamine. 
1-Amino-n-butyric Acid 

CH 3 -CH 2 -CH(NH 2 )-COOH 
C 4 H 9 2 N" MW, 103 

d-. 

Found in sperm whale tendon. Leaflets from 
EtOH.Aq. M.p. about 292 decomp. (303 in 
sealed tube). fag, + 8. 

B,HCl : needles. Sol. H 2 0. [ag? + 14-51. 

TS-Formyl: cryst. from EtOH. M.p. 126. 
[aE> 27-74inH 2 0. 

N-Chloroacetyl : needles from AcOEt-pet. 
ether. M.p. 119. [a - 61-94 in H 2 0. 

Leaflets from EtOH.Aq. M.p. about 292 
decomp. [og? 7-86 in H 2 0. 

TX-Formyl: cryst. from EtOH. M.p. 126. 
[a]* + 27-98 in H 2 0. 

"N-Chloroacetyl : needles from AcOEt-pet. 
ether. M.p. 119. [a + 19 in H 2 0. 

M.p. 304 (307 in sealed tube). Sol. H 2 0. 
Spar. sol. EtOH. Insol. Et 2 0. Sublimes above 
300. 

Me ester: C 6 H U 2 N. MW, 117. B,HCl: 
m.p. 139. Sol. H 2 0, EtOH. Insol. Et 2 O. 

Et ester : C 6 H 13 2 N. MW, 131. Oil. B.p. 



2-Amino-n-butyric Acid 



76 



4-Aminocamphor 



61~2/H mm. (58/16 mm.). Sol. H 2 0, most 
org. solvents. B,HCl : m.p. 130-1. Picrate : 
m.p. 127. 

Amide: C 4 H 10 OE" 2 . MW 5 102. Prisms. 
M.p. 74-5. Sol. H 2 0, EtOH. Et 2 0, C 6 H 6 , 
ligroin. 

N-Formyl : needles from EtOH. M.p. 153. 

N-Chloroacetyl : leaflets from AcOEt-pet. 
ether. M.p. 130. 

N-Benzoyl : m.p. 145-6. 

Cocker, Lapworth, /. Ohem. Soc., 1931, 

1399. 
Knoop, Oesterlin, Z. physiol. Chem., 1925, 

148, 294. 

Oikawa, Clem. Abstracts, 1926, 20, 1672. 
Abderhalden, Chang, Wurms, Z. physiol. 

Chem., 1911, 72, 28. 
Fischer, Mouneyrat, Ber., 1900, 33, 2388. 

2-Amino-n-butyric Acid 

CH 3 -CH(NH 2 )-CH 2 -COOH 
C 4 H 9 2 N MW, 103 

(Z-. 

Prisms from MeOH. Decomp. at 220. [og? 
+ 35-3 in H 2 0. 

Me ester: C 5 H 1]L 2 ]Sr. MW 5 117. B.p. 54- 
5/13 mm. [a + 8-91. 

Z-. 

Prisms from MeOH. Decomp. at 220. [ag, 
35-2 in H 2 0. 

Me ester: CJi^O^. MW, 117. B.p. 54- 
5/Hmm. D 19 0-991. [oc]i? - 6-97. 

dl-. 

Cryst. M.p. 193-4. Sol. 1 part H 2 0. InsoL 
EtOH, Et 2 0. Tasteless. 

B,HCH : very hygroscopic. M.p. 109-5-10-5. 

Me ester : C 5 H n 2 N". MW, 117. B.p. 54- 
5/13 mm. D 2 * 0-993. Sol. H 2 0, EtOH, Et 2 0, 
ligroin. 

m ester : C 6 H 13 2 N. MW, 131. B.p. 60-1 / 
14 mm. Misc. with H 2 0, EtOH, Et 2 0, ligroin. 
B Z ,(COOH) 2 : m.p. 88-90. Picrate : m.p. 147- 
8. TS-Acetyl : b.p. 158/12 mm. 

"N-Benzoyl: m.p. 154 C . 

Fischer, Scheibler, Ann., 1911, 383, 339. 
Skita, Wulif, Ann., 1927, 453, 206. 

3-Amino-ra-butyric Acid (Piperidinic acid) 

H 2 N-CH 2 -CH,/CH 2 -COOH 
C 4 H 9 2 K" " " MW, 103 

Widely distributed in higher plants. Prisms 
from EtOH. M.p. 203 decomp. (193). Sol. 
H 2 0. Insol. EtOH, Et 2 0, C 6 H.. fc(aoid) = 
3-7 X KH 1 . A(base) = 1-7 X 10-^. Heat ^ 
pyrrolidone. 

B,HCl : m.p. 135-6. 

tit ester: 6 H I3 2 K MW, 131. B.p. 75- 
7/12mm. ,HOl: m.p. 65-72. Hygroscopic. 



Lactam : see Pyrrolidone. 

Tafel, Stern, Ber., 1900, 33, 2230. 
Curtius, Hechtenberg, J. prakt. Chem., 

1923, 105, 319. 
Hulme, Arthington, Nature, 1950, 165, 

716. 

Westall, ibid., 717. 
Synge, Biochem. J., 1951, 48, 429. 

3-Aminobutyrolactam . 

See Pyrrolidone. 
4-Aminobutyrophenone 

H 2 N/~\CO-CH 2 'CH 2 -CH 3 

C 10 H 13 ON MW, 163 

Cryst. from H 2 0. M.p. 84. Sol. EtOH. 
B,HCl : needles. M.p. 178. 
B 23 H 2 SO^: m.p. 216. 
N-Acetyl : needles from H 2 0. M.p. 142. 

Kunckell, Ber., 1900, 33, 2643. 

Ammocamphane . 

See Bornylamine. 
3-Aminocamphor (a-Aminocamphor) 



CH 2 




C 10 H 17 ON 



MW, 167 



M.p. about 110-115 decomp. Changes on 
standing or by heating at 100 to anhydro- 
6^aminocamphor, C 20 H 30 Kr 2 . Na + EtOH > 
2-aminobomeol. 

"N-Formyl : cryst. from H 2 0. M.p. 87. 

N-Acetyl : m.p. 121. 

N-Benzoyl: m.p. 141. 

Oxime : aminocamphoroxime. Cryst. from 
C 6 H 6 . M.p. 145. Mod. sol. EtOH, C 6 H 6 , 
CHC1 3 . InsoL cold H 2 0, ligroin. L]x> 8 + 65-5 
in EtOH, + 36-7 in dil. HC1. SubHmoH if care- 
fully heated. 

Hydrazone : needles from pot. other. M.p. 
105. 

B,HI : needles. M.p. 252-3 dooomp. 

B,(COOH)* : leaflets. M.p. 11)4. 

Picrate : docomp. at 191. 

Eupo, Buxtorf, Helv. Chim. A eta, J930, 

13, 447. 
Duden, Pritzkow, Ber., 1899, 32, 1539, 

4- Ammocamphor . 

Cryst. from pet. ether. M.p. 230-2. Sol 

H 2 Et 2 0, CHCL, C 6 H 6 , toluene. Mod. sol 
pet. other. Aq. sol. reacts alkaline to litmus. 
N-Acetyl : cryst, from toluene. M,p. 122-3, 

Sol. H 2 0, Et 2 0, CHC1 3 . Spar, sol pet- ether, 

Houbon, Pfankuoh, Ann., 1931, 489, 217, 



1-Aminocapric Acid 



77 



7-Amino-n-caprylic Acid 



1-Aminocapric Acid (1-Aminodecanoic acid) 

CH 3 -[CH 2 ] 7 -CH(NH )-COOH 
C 10 H 21 2 N " MW, 187 

M.p. 264. Spar. sol. H 2 0. 
N-Benzoyl : m.p. 130. 

Albertson, J. Am. Chem. Soc., 1946, 68, 
450. 

2-Aminocapric Acid (2-Aminodecanoic acid) 

CH 3 -[CH 2 ] 6 -CH(NH 2 )-CH 2 -COOH 
C 10 H 21 2 N MW, 187 

M.p. 205-6. 

Lang, Adickes, Z. physiol. Chem., 1941, 
269, 236. 

9-Aminocapric Acid (a-Aminocapric acid, 
IQ-aminodecanoic acid) 

NH 2 -CH 2 -[CH 2 ] 7 -CH 2 -COOH 
C 10 H 21 2 N MW, 187 

M.p. 187-8. Sol. hot H 2 0. 



Lactam : 2-ketohexamethyleneimine. B.p. 
140/12 mm. N-Benzoyl: m.p. 45-7. B.p. 
150-5 in vacuo. 

Amide : hygroscopic. M.p. 50-1. 

N-Benzoyl: m.p. 75-8. 

Kuzicka, Helv. Ohim. Acta, 1921, 4, 477. 
Y. Braun, J3er., 1907, 40, 1839. 

1-Amino-n-caprylic Acid 

CH 3 -[CH 2 ] 5 -CE(NH 2 )-COOH 
C 8 H 17 2 N MW, 159 

Leaflets from H 2 0. M.p. 270 (263-4). 
Spar. sol. cold H 2 0, EtOH, Et 2 0. Sublimes. 

Me ester: C 9 H 19 2 N. MW, 173. ,HCl: 
m.p. 76-7. 

Et ester : C 10 H 21 2 N. MW, 187. B.p. 110/ 
10 mm. wg 1-436. B,HCl : m.p. 53-^. 

Amide : C 8 H 18 0]SF 2 . MW, 158. Reacts 
strongly alkaline. Absorbs C0 2 . Hyd. by dil. 
HCL 



Nitrile : C 8 H 16 N 2 . MW, 140. Oil. Freezes 
Blaise, HoniUon, Compt. rend., 1906, 143, a t 5. Sol. EtOH, Et 2 0. Insol. H 2 0. 



362. 

1-Amino-n-caproic Acid. 
See Norleucine. 
2-Amino-n-caproic Acid 

CH 3 -CH 2 -CH 2 -CH(NH 2 )-CH 2 -COOH 
C 6 H 13 2 N MW, 131 

Et ester : C 8 H 17 2 N. MW, 159. B.p. 102- 
4/25 mm. Oxalate : m.p. 130 decomp. 

D6combe, Ann. chim., 1932, 18, 137. 
3-Amino-n-caproic Acid 

CH 3 -CH 2 -CH(NH 2 )-CH 2 -CH 2 -COOH 
C 6 H 13 2 N MW, 131 

Cryst, from Et 2 0. M.p. 205-7 decomp. 
(180-1). Heat > lactam. 
B,HCl : m.p. 120-1. 

B 2 ,H 2 PtClQ : reddish-brown cryst. M.p. 
190-1 decomp. 

~N-Benzoyl : cryst. from H 2 0. M.p. 150-2. 
Lactam : 5-ethyl-2-pyrrolidone. M.p. 22. 
B.p. 256-7, 130 /8 mm. DJ 87 1-026. < 7 
1-4800. Bz,H z PtCl$ : reddish-brown cryst. M.p. 
125-7. 

Spath, Kuf ner, Ensfellner, Ber., 1933, 66, 

598. 
Miiller, Eeld, Monatsh., 1931, 58, 22. 

5-Amino-n-caproic Acid 

H 2 N-CH 2 "CH 2 -CH 3 -CH 2 -CH 2 -COOH 
C 6 H 13 2 N MW, 131 

Leaflets. M.p. 202-3. Sol. H 2 0. Insol. 
EtOH. 

B,HBr : m.p. 105. 

M ester : C 8 H, 7 2 N. MW, 159. B.p. 80- 
2/l mm., 60-2 /0-05 mm. TS-Benzoyl : m.p. 
35. B.p. 184-6 /O-l mm. 



N-Iormyl : cryst. from EtOH. M.p. 118. 
~N-Chloroacetyl : cryst. from EtOH. M.p. 
82-3. 
N-Benzoyl : m.p. 128. 

Abderhalden, Goto, Chem. Abstracts, 1924, 

18, 3041. 
Marvel, Noyes, /. Am. GTiem. Soc.> 1920, 

42, 2275. 

Erlenmeyer, Sigel, Ann., 1875, 177, 125. 
Albertson, J. Am. Chem. Soc., 1946, 68, 

450. 

2-Amino-w-caprylic Acid 

CH 3 -[CH 2 ] 4 -CH(NH 2 )-CH 2 -COOH 
C 8 H 17 2 N MW, 159 

Cryst. from EtOH. M.p. 204-6 decomp. 
Et ester : C 10 H 2 ,0 2 N. MW, 187. B.p. 132- 
3/25 mm. Phenylurethane : m.p. 114. 

D6combe, Ann. chim., 1932, 18, 138. 
Lang, Adickes, Z. physiol. Chem., 1941, 
269, 236. 

4-Amino-n-caprylic Acid 

CH 3 -[CH 2 ] 2 -CH(NH 2 )-[CH 2 ] 2 -CH 2 -COOH 
C 8 H 17 2 N MW, 159 

Needles. M.p. 158 > anhydride. Sol. 
H 2 0, EtOH. Insol. Et 2 0. 

Baum, Ber., 1886, 19, 502. 



7-Amino-n-caprylic Acid 

H 2 N-CH 2 -[CH 2 ] 6 -COOH 
C 8 H 17 2 N 

M.p. 172. Sol. EtOH, hot H 2 0. 
Behrend, Ber. 9 1896, 29, 808. 



MW, 159 



1-Aminocarfoazole 
1 -Aminocarb azole 



C 12 H 10 N 2 MW, 182 

Needles from C 6 H 6 . M.p. 193. Sol. EtOH, 
AcOH. 

N-Diacetyl : cryst. from C 6 H 6 or AcOH.Aq. 
M.p. 186. 

N-Bromoacetyl : m.p. 188. 

N-Benzoyl : m.p. 242. 



Lindemann, Werther, Ber., 1924, 57, 1316. 
I.G., D.R.P., 507,797, (OAem. Abstracts, 

1931, 25, 716). 

Gen. Aniline Works, U.S.P., 1,878,168, 
(Chem. Abstracts, 1933, 27, 313). 

2-Aminocarbazole . 

Needles from H 2 0. M.p. 238. 

Blank, Bar., 1891, 24, 306. 

I.G., D.R.P., 542,422, (Cftem. Abstracts, 

1932, 26, 2469). 

3- Aminocarb azole . 

M.p. 254 decomp. after darkening and 
sintering at 240-3. Sol. AcOH. Mod. sol. 
EtOH. Spar. sol. Et 2 0, C 6 H 6 , ligroin. 

3-1$-Acetyl : needles or leaflets from EtOH. 
M.p. 217. Insol H 2 0. 

Diacetyl deriv. : needles from EtOH. M.p. 
199-5. 

Triacetyl : needles from EtOH. M.p. 174-5. 

'N-Chlomcetyl : m.p. 203. 

S-'N-Benzoyl : plates from AcOH. M.p. 
250-1. 

N-p-Aminobenzenesulphonyl : m.p. 251 de- 
comp. 

Kehrmann, Zweifel, Helv. Ghim. Acta, 

1928, 11, 1215. 
Whitner, J. Am. Chem. Soc. 9 1924, 46, 

2326. 

Aminocarb ostyril . 

See 2-Hydroxy-5-aminoquinoline, 2-Hydroxy- 
6-aminoquinoline, 2-Hydroxy-7-aminoquinolme. 

Anainocatechol . 

Methyl ether : see Aminoguaiacol. 

Methylene ether : see Methylenedioxyaniline. 

3-Aminoch.alkone (to-[3~Aminobenzylidene]* 
acetophenone) 



78 o-Aminocinnamic Acid 

'N-Acetyl : yellow needles from AcOH. M.p. 
104. 

Eupe, Porai-Koschitz, Chem. Zentr., 1906, 
II, 1761. 

4-Aminochalkone (a-[4~Aminobenzylidene]- 
acetophenone). 

Golden plates from EtOH. M.p. 151, Sol. 
EtOH, Me 2 CO. Spar. sol. H 2 0, Et 2 O, C 6 H 6 . 
Sol. AcOH > red col. 

Oxime : cryst. M.p. 139. 

N-Acetyl : green plates. M.p. 179. 

Koipe, Porai-Koschitz, Chem. Zentr., 1906 ? 
II, 1761. 

2 / -ArQinoch.alkone (2-Amino-u>-benzylidene- 
acetophenone). 

Yellow prisms. M.p. 147. EtOH sol. of 
hydrochloride ox. by air >- indigo. 

N-Acetyl : m.p. 165. 

Engler, Dorant, Ber., 1895, 28, 2500, 

p-Ammochalkone (o>-Amino-<*-benzyUdene- 
acetophenone) , 
Needles from EtOH.Aq. M.p. 97. 

Ruhemann, Watson, J. Chem. Soc., 1904,, 
85, 1181, 1323. 



C 15 H 13 ON 



JO-CHICH 



MW, 223 



Yellowish-green plates from EtOH or C 6 H 6 . 
M,p. 159, Sol. MegCO. Mod. sol. EtOH. 
Spar. sol. H 2 0, Et 2 0, C 6 H e , Hgroin, 



3-Ammochrysazin. 

aminoanthraquinone) 

HO CO OH 



(1 : S-Dihydroxy-3- 




GSHBL 



C 14 H 9 4 N MW, 255 

Vermilion needles from AcOH. M.p. 258".. 
Sol. dil. HC1. Dil. alkalis > red col 

Di-Me ether : red prisms with green metallic 
reflex. M.p. 243. Sinters at 240* 

Robinson, Simonsen, J. Chem. Soc n 1009, 

95, 1095. 
Oesterle, Chem. Zentr., 1912, I, 142. 

4-Aminochrysazin (1 ; ^Dihydroxy^- 

aminoanthraquinone} . 

Bayer, D.R.P., 216,668, (Chem, Zentr. r 
1910, I, 216.) 

0-Aminocinnamic Acid 

OBCOH-OOOH 




C 9 H 9 2 N MW, 

Yellow needles. M,p. 158-9 deoomp. Mod. 

sol. EtOH, EtjO, hot H 2 0. Sols, show intense 
greenish-blue fluor. Hoat with HC1 > carbo- 
styril 

Me ester: 10 H u OJNr. MW, 177, YoUow 
needles. M.p. 66, NAcetyl : noodles from, 



m-Aminocinnamic Acid 



79 



3-Amino-o-cresoI 



C 6 H -ligroin. M.p. 137. Spar. sol. H 2 0, 
ligroin. Sol. most other org. solvents. N- 
Benzoyl : m.p. 176-7. 

Et ester : G 1: fL lB QJ$. MW, 191. Pale yellow 
needles from EtOH.Aq. M.p. 77-8. Sol. most 
org. solvents "with, greenish-yellow fluor. Distils 
undecomp. HC1 at 120 or SOC1 2 in C 6 H 6 > 
carbostyril. Hyd. by ale. KOH. Picrate : m.p. 
145. 

Menthyl ester : m.p. 85. 

Nitrite: C 9 H 8 N 2 . MW, 144. Cryst. from 
H 2 0. M.p. 134-5. Sol. Et 2 0, CHC1 3 , C 6 H 6 , 
hot EtOH. Sublimes. N-Acetyl : m.p. 172-4. 
Sol. EtOH, Et 2 0, hot H 2 0. Sublimes. Picrate : 
m.p. 192-3. 

N-Acetyl ; needles from EtOH. M.p. 250-1. 
Sol. Me 2 CO, AcOEt, hot H 2 0. Mod. sol. EtOH, 
AcOH. 

TS-Diacetyl : prisms from ligroin. M.p. 158. 
Anhydride : leaflets from EtOH. M.p. 156-8. 

"N-Benzoyl : needles from EtOH. M.p. 191- 
3. Sol. EtOH, Et 2 0, CHC1 3 , AcOH. An- 
hydride : needles from AcOEt. M.p. 194-5. 

N-PJithalimido : pale yellow. M.p. 233. 

Heller, Ber., 1913, 46, 3982. 
Gabriel, Ber., 1882, 15, 2294. 
Pschorr, Ber., 1898, 31, 1296. 

m-Aminocinnamic Acid. 

Cis-. 

Yellow cryst. M.p. 193. Spar. sol. most 
solvents. 

Trans-. 

Pale yellow needles from EtOH. M.p. 181. 
Sol. EtOH, Et 2 0. Mod. sol. hot H 2 0. 

Me ester : m.p. 84. N-Chloroacetyl : needles 
from EtOH.Aq. M.p. 122. N-Benzoyl : m.p. 
144-6. 

Et ester : prisms. M.p. 64. Sol. EtOH, 
Et 2 0, CHC1 3 , Insol. H 2 0, ligroin. 

Menthyl ester : b.p. 230 /2 mm. 

T$-Acetyl: cryst. from EtOH. M.p. 237 
(235). 

N-Benzoyl : needles from AcOEt. M.p. 229. 
Sol. hot EtOH, Me 2 CO, AcOH. Spar. sol. C 6 H 6 . 
Anhydride : cryst. from Me 2 CO. M.p. 148. 

Amide : N-p-Aminobenzenesulphonyl, m.p. 
246. 

Wollring, Ber., 1914, 47, 113. 
Gabriel, Ber., 1883, 16, 2038. 
Salkowski, Ber., 1895, 28, 1921. 
De, /. Indian Chem. Soc., 1928, 5, 30. 

j>-Aminocinnamic Acid. 

Cis-. 

Yellow needles, Decomp. at 103-4. 

Trans-. 

Pale yellow needles. M.p. 175-6 decomp. 
Sol. EtOH, Et 2 0, hot H 2 0. 

Me ester : yellowish -brown needles from C 6 H 6 . 
M.p. 128-9. 'N-Chloroacetyl : needles or leaflets 



from EtOH. M.p. 155-6. N-Benzoyl : m.p. 
187-5-8. 

Et ester : yellow cryst. from EtOH. M.p. 
68-9. Sol. EtOH, Et 2 O, C 6 H 6 . 

Menthyl ester : m.p. 122. 

N-Acetyl : m.p. 259-60. Sol. hot EtOH, hot 
AcOH. Spar. sol. H 2 0. Insol. Et 2 0, C 6 H 6 , 
ligroin. 

N-Benzoyl : leaflets from AcOH, needles from 
Me 2 CO. M.p. 274. SoL hot AcOH. Spar, 
sol most other solvents. 

N-Phthalimido : pale yellow. M.p. 320. 

WoHring, Ber. y 1914, 47, 114. 
Miller, Kinkelin, Ber., 1885, 18, 3234. 
Einhorn, Oppenheimer, Ann., 1900, 311^ 
158. 

3-Ammocoumarin 

CH 




C 9 H 7 O 2 N MW 3 161 

Yellowish needles from H 2 0. M.p. 130. SoL 
ord. org. solvents. Boiling NaOH.Aq. >- 3- 
hydroxycoumarin. 

N-Acetyl : needles from EtOH.Aq. M.p. 
201-2. Sol. ord. org. solvents. 

TS-Benzoyl : m.p. 173. 

Linch, J. Chem. Soc., 1912, 101, 1762. 



(Often in literature as 
Sol. EtOH, 



6-Aminocoumarin 

5-aminocoumarin) . 

Yellow needles. M.p. 168-70. 
hot H 2 0. 

N-Formyl : cryst. from H 2 0. M.p. 175-6. 

yS-Acetyl: m.p. 216-17. 

* N-Propionyl : needles from H 2 0, M.p. 186- 
8. 

N-Benzoyl : m.p. 173. 

N-Benzenesulphonyl : cryst. from H 2 0. M.p. 
159. 

'N-p-Aminobenzenesulphonyl : m.p. 191. 
W-Acetyl: m.p. 230. 

Morgan, Micklethwait, J. Chem. /Soc., 

1904, 85, 1230. 
Kondo, Ui, J. Chem. Soc., 1924, 126, i, 87. 

8- Aminocoumarin . 

Pale yellow prisms from EtOH. M.p. 145-6. 

Clayton, J". Chem. Soc., 1910, 97, 1350. 

co- Aminocres ol . 

See Hydroxybenzylamine and Salicylamine. 
3-Amino-o-cresol (2~Hydroxy-m-tolmdine) 

CH 



C,H 9 ON 



MW, 123 



4-Amino-o-cresol 



80 



6-Amino-w-cresol 



Plates from H 2 0. M.p. 89. Sol. MeOH, 
EtOH, Et 2 0, Me 2 CO, CHC1 33 C 6 H 6 , CC1 4 , hot 

HoO. Insol. pet. ether. FeCl 3 > red col. 

Me ether: CgH^ON. MW, 137. B.p. 223. 
B,HGl : cryst. M.p. 168. N-Acetyl : needles 
fromH 2 0. M.p. 100-1. 

N-Acetyl : 2-hydroxyacet-m-toluidide. Prisms 
from CCL. M.p. 78-9. Sol. MeOH, EtOH, 
Et 2 0, Me 2 CO, CHC1 3 , C 6 H 6 , hot H 2 O, CC1 4- 

Insol. pet. ether. FeCl 3 >- blue col. 

Proskouriakoff, Titherington, J. Am. 

Chem. Soc., 1930, 52, 3982. 
Hofmann, Miller, Ber., 1881, 14, 570. 

4-Amino-o-cresol (Z-Hydroxy-p-toluidine] . 

Plates from H 2 0. M.p. 161. Sol. EtOH, 
Et 2 0. Mod. sol. hot H 2 0. Spar. sol. cold H 2 0. 
Sublimes when carefully heated. 

Me ether: cryst. M.p. 58. B.p. 250-2. 
Sol. EtOH, C 6 H 6 . N-Acetyl: leaflets from 
C 6 H 6 . M.p. 132. 

m ether: C 9 H 13 ON. MW, 161. B.p. 249- 
50. Sol. EtOH, Et 2 0. Volatile in steam. 
B,HCl: needles. M.p. 245. 

Q-p-Toluenesulphonyl : cryst. from EtOH.Aq. 
M.p. 111-12. Sol. EtOH, Et 2 0, C 6 H 6 . 

N-Acetyl : 2-hydroxyacet-j9-toluidide. Prisms 
from EtOH.Aq. M.p. 225. Sol. EtOH, 
NaOH.Aq. Sublimes. 

N-Diacetyl : prisms from Et 2 0-EtOH. M.p. 
132-3. 

IS-Chloroacetyl : plates from AcOH. M.p. 
154-5. Sol. EtOH, Me 2 CO. Spar. sol. hot 
H 2 0, CHC1 3 . 

Proskouriakoff, Titherington, J. Am. 

Chem. Soc., 1930, 52, 3981. 
Ullmann, Fitzenkam, Ber.,, 1905, 38, 3791. 



Needles from C 6 H fi 
Et 2 0. ~ ' ~ 



5-Amino-o-cresol (&-Hydroxy--m-toluidine) . 
~ "" M.p. 175. Sol. EtOH, 
Spar. sol/H 2 0, C 6 H 6 . Sublimes. Ox. 
toluquinone. 
Me ether: cryst. from 50% EtOH. M.p. 
599-5 (92-3). Sol. EtOH, Me 2 CO, Et 2 0, 
C 6 H 6 . Spar. sol. cold H 2 0. TS-Acetyl : cryst, 
from EtOH.Aq. M.p. 103-103-5 (158). Sol. 
EtOH, Me 2 CO, Et 2 0, CHC1 3 . Spar. sol. H 2 0. 
C 6 H 6 . "N-Chloroacetyl : needles from C 6 H 6 - 
ligroin. M.p. 90-2. 

M ether : oil. Volatile in steam. B,HCl : 
m.p. 210. TS-Acetyl : plates from H 2 0. M.p. 
108. 

Q-p-Toluenesulphonyl : needles from C a H 6 - 
ligroin. M.p. 109-10. Sol. EtOH, C 6 H 6 . 
Mod. sol. Et 2 0. 

T$~Acetyl : 6-hydroxyacet-m-toluidide. Needles 
fromH 2 0. M.p. 179. 

QN-Dibenzoyl : needles from AcOH. M.p. 
194. 

Heidelbergcr, Jacobs, J. Am. Chem. $oc., 
1919, 41, 1453. 



6-Amino-o-cresol (6-Hydroxy-o-toluidine). 
Needles from H 2 O. M.p. 129. Spar. sol. 
Et 2 0, cold H 2 0. Turns brown in air. 

Q-p-Toluenesulphonyl : m.p. 108. 

Ullmann, Ber., 1884, 17, 1962. 

2- Ammo- w-cr e s ol ( 3 -Hydroxy- o - toluidine ) 
CH 3 



C 7 H 9 ON MW, 123 

Plates. M.p. 150. 

N-Benzoyl: m.p. 189. Spar. sol. C 6 H 6 . 

Hodgson, Beard, J. Chem. Soc., 1925, 127, 
498. 

4-Amino-m-cresol (3-Hydroxy-p-toluidine) . 

Prismatic needles from 50% EtOH. M.p. 
162 decomp. Sol. hot H 2 0, MeOH, EtOH, 
Et 2 0, Me 2 CO, C 6 H 6 . Insol. pet. ether. FeCl 3 
-- >- red col. 

Me ether: C 8 H 1X ON. MW,137. B.p. 237-9. 

N-Acetyl : 3-hydroxyacet-p-toluidide. Plates 
from 50% EtOH. M.p. 171. Sol. MeOH, 
EtOH, Me 2 CO. Mod. sol. hot H 2 O. Spar. sol. 
H 2 0, pet. ether. Insol. CC1 4 . No col. with FeCl 3 . 

^-Benzoyl: needles from Me 2 CO-pet. ether. 
M.p. 169. 

Q~N-Dibenzoyl : needles from MeOH. M.p. 
162-3. 

Proskouriakoff, Titherington, J. Am. 

Chem. Soc., 1930, 52, 3982. 
Auwers, Borsche, Weller, Ber., 1921, 54, 

1314. 

6-Amino-m-cresol (5-Hydroxy~>Q4oluidine). 

Prisms from 50% EtOH. M.p. 179. Ox. 
^ toluquinone. 

Me ether : cryst. from ligroin. M.p. 29-30 
(13-14). B.p. 146-7/23 mm. TS-Actiyl : 
needles from H 2 0. M.p. 134. Sol. EtOH. 
Spar. sol. EtoO, ligroin. ^-CUoroacetyl : needles 
from toluene. M.p. 135. Sol. Mo 2 Cb 2 , (JHC1 3 . 
Spar. sol. cold EtOH. 

Et ether: C 9 H 13 ON. MW, 151. Oil. N- 
Acetyl: needles from H 2 0. M.p. 114. 

Q-Benzoyl : needles from pot. other. M.p. 
92. B.p. 220/12 mm. Sol. ord. Holvontn. 
Insol. cold pet. other. 

"N-Acetyl : 5-hydroxyacot-o-toluidklo. Noodlon 
from HjjO. M.p. 130. 

B,HGl : needles from cone. HCL M.p. 215, 

Heidelbergcr, Jacobs, J. Am. Chem, Hoc., 

1919, 41, 1464. 
Proskouriakoff, Titborington, J. Am. 

Chem. Sac., 1930, 52, 3983. 
Gibson, J. Chem. Soc., 1923, 123, 1276. 
A.G.P.A., D.K.P., 295,841, (Ohm. 

1917, 1, 295), 



2-Amino-iJ-cresol 



81 



3-Aminocuminic Acid 



2-Am.ino-p-cresol (^-Hydroxy-o-toluidine) 
GEL 



MW, 123 



H 



C 7 H 9 ON 

M.p. 144. 

Me ether: C 8 H n ON. MW, 137. Needles 
from H 2 0. M.p. 47. B.p. 253. Sol. Et 2 0. 
Mod. sol. hot H 2 0. Volatile in steam. 

N-Acetyl : 4-hydroxyacet-o-toluidide. Cryst. 
from EtOELAq. M.p. 178. 

ON-Diacetyl : cryst. M.p. 128-9. 

N-Benzenesulphonyl : m.p. 183. 
Knecht, Ann., 1882, 215, 91. 

3-Amino-p-cresol (4:-Hydroxy-m-toluidine) . 

Cryst. from H 2 O. M.p. 135. Sol. EtOH, 
Et 2 0, CHC1 3 . Spar. sol. C 6 H 6 . Insol. cold 

H 2 0. Ac 2 + AcONa > 2 : 6-dimethylbenz- 

oxazole. 

Me ether : cresidine. Needles from pet. 
ether. M.p. 93-4 (51-2). B.p. 235. Sol. 
EtOH, Et 2 O, C 6 H 6 . Spar. sol. hot H 2 0. 
Intermediate for azo dyestuffs. N-Formyl : 
prisms from EtOH.Aq. M.p. 86. N-Acetyl : 
leaflets. M.p. 110. 

Et ether: C 9 H 13 ON. MW, 151. Needles 
from H 2 0. M.p. 41. B.p. 240. N-Acetyl: 
plates from H 2 0. M.p. 106-5. 

'N-Acetyl : 4-hydroxyacet-m-toluidide. Needles 
from H 2 0. M.p. 160. 0-Propionyl : needles 
from C 6 H 6 -ligroin. M.p. 104-5. O-Benzoyl : 
needles from MeOH. M.p. 146. 

QJS-Diacetyl : plates. M.p. 145. 

"N-Propionyl : needles from C 6 H 6 ligroin. 
M.p. 95-6. 

Q~N-Dipropionyl : leaflets from C 6 H 6 -ligroin. 
M.p. 91-2. 

~N-Benzoyl : leaflets from EtOH. M.p. 191. 
0-Acetyl : leaflets from C 6 H 6 -ligroin. M.p. 
134. 

ON-Dibenzoyl : leaflets from EtOH. M.p. 
190-1. 

"Robinson, J. Chem. Soc., 1916, 109, 1088. 
Bradt, Hart, Chem. Abstracts, 1931, 25, 

4802. 
Ashkinazi, Rabinovich, Chem. Abstracts, 

1935, 29, 2521. 
Auwers, Eisenlohr, Ann., 1909, 369, 223. 

2-Aminocrotonic Acid (2-Iminobutyric acid) 

CH 3 -C(NH 2 ):CH-COOH 

or 

CH 3 -C(:NH)-CH 2 -COOH 

C 4 H 7 2 N MW, 101 

Me ester: C 5 H 9 2 N. MW, 115. Prisms. 
M.p. 85. Sublimes. 

Et ester : CeH n 2 N. MW, 129. Exists in 
two forms : labile and stable. Labile : prisms, 

Diet, of Org. Oomp. I. 



m.p. 20; N-acetyl, m.p. 109-10, sol. EtOH, 
insol. H 2 O. Stable : prisms, m.p. 33, b.p. 
210-15 decomp., 153-5/90-100 mm., 105/15 
mm., sol. EtOH, Et 9 O, CS 2 , C 6 H 6 , insol. H 2 O, 
D1 5 5 1-0273, < 149882. TS-Acetyl: m.p. 63, 
b.p. 231-3, sol. EtOH, insol. H 2 0. 
Nitrile : see Diacetonitrile. 

MichaeHs, Ann., 1909, 366, 337. 
Momm, Gottschaldt, Ber., 1922, 55, 2068. 

Aminocumene . 

See Cumidine, 2-Phenylpropylamine and 
Phenylisopropylamine . 



See 2 : 4-Dimethylbenzylamine. 
3-Amino-^-cumene (3-Amino-l : 2 : 4-tri- 
methylbenzene) 




C 9 H 13 N MW, 135 

B.p. 235. 
TX-Acetyl : m.p. 186. 

Huender, Eec. trav. chim., 1915, 34, 10. 

5-Amino-vp-cninene . 

See ^-Cumidine. 

6-Amino-vf-cumene (6-Amino-l : 2 : 4-tri- 
methylbenzene) . 

M.p. 36. B.p. 233. Sol. H 2 0. Easily 
volatile in steam. 

Huender, Rec. trav. chim., 1915, 34, 11. 

3-Ammocuminic Acid (S-Amino-k-isopro- 
pylbenzoic acid) 

COOH 




J3(CH 3 ) 2 
Ci H 13 2 N MW, 179 

M.p. 129. Sol. EtOH, Et 2 0, hot H 2 0. Long 
heating with H 2 at 100 > labile form, m.p. 
104. 

Me ester: C n H 15 O 2 N. MW, 193. Prisms 
or plates from C 6 H 6 -ligroin. M.p. 51-2. Sol. 
EtOH, Et 2 0, C 6 H 6 . Spar. sol. ligroin. N- 
Chloroacetyl : needles from EtOH.Aq. M.p. 
101-2. Sol. EtOH, Et 2 0, C 6 H 6 . Spar. sol. 
H 2 0, ligroin. 

Nitrile: C 10 H 12 N 2 . MW, 160. Needles from 
H 2 0. M.p. 45. B.p. 305. Sol. EtOH, Et 2 0. 
Spar. sol. H 2 0. 

^S-Acetyl : needles from EtOH. M.p. 248- 
50. Sublimes. 

Meti, Gazz, chim. ital, 1880, 10, 12. 
Abenius, J.prakt. chem., 1889, 40, 439. 

6 



Aminocyclobutazie 



82 



4-Aminodibenzyl 



Aminocyclobutane . 

See Cyclobutylamine. 
Aminocyclolieptane . 
See Cycloheptylamine. 
Aminocyclohexane . 
See Cyclohexylamine. 
Aminocyclohexane-carboxylic Acid. 
See Aminohexahydrobenzoic Acid. 
2-Aminocyclohexanol (Hexahydro-o-amino- 
phenol) 

CH-OH 



C 6 H 13 ON 



H 2 C CH 2 

CH 2 

MW, 115 

Hygroscopic cryst. with odour of piperidine. 
M.p. 66. B.p. 219. Sol. H 2 and most org. 
solvents. 

B,HCl : needles. M.p. 175. 

B,HN0 3 : m.p. 144. 

N-Jtfe : C 7 H 15 ON. MW, 129. B.p. 229. 

TS-Et: C 8 H 17 ON. MW, 143. M.p. 44. 
B.p. 222. 

TX-Di-Et: C 10 H 21 ON. MW, 171. B.p. 230. 
Picrate : yellow. M.p. 94-5. 

N-Phenyl: C 12 H 17 ON. MW, 191. M.p. 
150-1. 

Brunei, Compt. rend., 1903, 137, 199; 
Ann. chim., 1905, 6, 253. 

l-Amino-2-cycloliexylpropiomc Acid. 

See Hexahydrophenyl-a-alanine. 
Amiuocyclopentane . 
See Cyclopentylamine. 
Aminocyclopropane . 
See Cyclopropylamine. 
Aminocymene . 
See Cymidine and Thymylamine. 
9-AminodecahydronapMhalene ($-Decal- 
ylamine) 

H 2 C 




CJEln OJB.C 



MW, 153 



C 10 H 19 N 

Cis-. 

M.p. - 13-5. B.JD. 227-6/757 mm., 111/18 
mm., 82 /7 mm. Df 2 0-9508. ng, 1-49820. 

W-Formyl : cryst, from AcOEt. M.p. 165-6. 
decomp. 

TS-Acetyl : cryst. from Me 2 CO. M,p. 127. 

W-Benzoyl : cryst. from Me 2 CO. M.p. 147. 

Trans-. 

M.p. -25. B.p. 222-6 /757 mm., 90/13 
mm, DJ* 0-9391, < e fl 149211. 



N-Formyl: cryst. from AcOEt. M.p. 172 
decomp. 

TS-Acetyl : m.p. 183. 

N-Benzoyl : cryst. from Me 2 CO. M.p. 148-9. 
Htickel, Blohm, Ann., 1933, 502, 114. 

Aminodecaliy dronaphthalene . 

See also Decahydronaphthylamine. 
a-Aminodeoxybenzoin (ms-Aminodeoxy- 
benzoin, desylamine) 

NH 2 



/WT>\ I /2~3\ 

& iV-OO-CH 4 9 



C 14 H 13 ON 



MW, 211 
corr. Sol. 



Needles from Et 2 0. M.p. 109 
EtOH, Et 2 0, C 6 H 6 , CHC1 3 . 

B,HCl: needles from EtOH-Et 2 0. M.p. 
243. 

B z ,H 2 PtCl 6 : m.p. 192-3 decomp. 
Phenylhydrazone : yellow needles from AcOH. 
M.p. 226-7 corr. 

Pschorr, Briiggemann, Ber., 1902, 35, 

2740. 

Braun, Ber., 1889, 22, 557. 
Neumann, Ber., 1890, 23, 996. 

4-Aminodeoxybenzoin . 

M.p. 95-6. Sol. hot EtOH. Spar. sol. hot 
H 2 0. 

Galubew, Ber., 1878, 11, 1939. 

Aminodibenzi nran . 

See Aminodiphenylene oxide. 
a-Aminodibenzyl . 
See I : 2-Diphenylethylamine. 
2-Aminodibenzyl (%-Amino-&ym.-diphenyl~ 
ethane) 

H 2 N 



C 14 H 15 N MW, 197 

M.p. 33. B.p. 173-83/ll mm. 

B,HGl: needles from EtOH. M.p. 198. 

B 2 ,H 2 SO^ : cryst. from EtOH. M.p. 202. 

y$-Acetyl : cryst. from EtOH. M.p. 117. 

TS-Benzoyl : cryst. from EtOH. M.p. 166. 

Picrate : yellow needles from EtOH. M.p. 
167-8. 

Ruggli, Staub, Schmid, Ilelv. CMm* A eta, 
1937, 20, 50. 

3- Aminodibenzyl 

Plates from 60-80 pot. other. M.p. 5 1 . B.p. 
180/6 mm. 
N-Acetyl : plates. M.p. 128-9. 

Bergmann, Schapiro, J. Org. Chem n 1947,, 
12, 67. 

4-AmmodibenzyL 

Plates from Et 2 0-pet. other, M.p, 48, 
B,HGl: plates from dil HCL M.p. 210, 



Axiiiiiodibenzylaniline 



83 



m-Aminodimetliylaniline 



B 2 ,H 2 PtCl Q : m.p. 286-9. Insol. H 2 O. 
'N-Benzoyl : m.p. 170-1. Spar. sol. EtOH, 
Et 2 0. 

v. Braun, Deutsch, Koscielski, Ber., 1913, 
46, 1514. 



See ims^m.-Dibenzylphenylenediamine. 
1-Amiaodiethylacetic Acid 



C 6 H 13 2 N MW, 131 

Prisms from H 2 . Sublimes without melting, 

but melts in sealed tube at 309. Sol. H 2 O. 

Spar. sol. EtOH. Insol. Et 2 0. 

Et ester : C 8 H 17 2 N. MW, 159. Oil. B.p. 

76/15 mm. Sol. H 2 0. 



Rosenmund, Ber., 1909, 42, 4472. 

o-Aminodietkylaniline (unsym. Diethyl- 
o-phenylenediamine) 



C 10 H 1G N 2 MW, 164 

Viscous oil. B.p. 312-13/744 mm., 127/25 
mm. 

Chlorostannate : silky needles. M.p. 145. 
"N-p-Toluenesulphonyl : m.p. 64-5. 
Monopicrate : orange. M.p. 162. 
Dipicrate ( ?) : m.p. 236. 

Weissenberger, Monatsh., 1912, 33, 821. 
Hall, Turner, J. Chem. Soc., 1945, 694. 

m-Aminodiethylaniline (imsym.-Diethyl- 

m-phenylenediamine) . 
B.p. 276-8, 117/4mm. 
Picrate : m.p, 152. 

Moore, J. Am. Chem. Soc., 1910, 32, 382. 

p~Aminodiethylaniline (imsym..-Diethyl-p- 
phenylenediamine) . 

Pale yellow oil. B.p. 260-2, 139-40/10 
mm. Darkens in air. Easily oxidised by 
Fe01 3 , etc. 

N-Chloroacetyl : pink needles. M.p. 83-4. 

Lippmann, Fleissner, Monatsh., 1883, 4, 

297. 
2-Aminodiethyl Ether (2-Mhoxyethylamine) 

CH 3 *CH 2 '0-CH 2 -CH 2 NH 2 
C 4 H U ON 3 MW,89 

Liq. with strong ammoniacal odour. B.p. 
108/758 mm. Df 0-8512. rig 1-4101. Misc. 
with H 2 0, BtOH, Et 2 0. Reacts strongly 
alkaline. 
Picrate : yellow cryst. M.p. 122. 



Picrolonate : yellow cryst. M.p. 204 decomp. 
Knorr, Meyer, Ber., 1905, 38, 3130. 

Aminodi-isobutyl . 
See 2-Amino-2 : 5-dimethyl-w-hexane. 
2-Amino-l : 4-dimethoxybenzene. 
See under Aminohydroquinone. 
5-Amino-l : 2-dimetliylacridine 

NIL 




MW, 222 

J.V j.-x a 

M.p. 167. 

Albert, Gledhill, J. Soc. Chem. Ind., 1945, 



Albert, GledhiU, /. Soc. Chem. Ind., 1945, 
64, 169. 

2-Amino-3 : 7-dimethylacridine. 

Brownish-yellow cryst. from toluene. M.p. 
244-5. Sol. EtOH, Et 2 0, dil. AcOH, with 
green fluor. Spar. sol. C 6 H 6 . 

N-Acetyl: m.p. 258. Spar. sol. EtOH. 

Fox, Hewitt, J. Chem. Soc., 1904, 85, 531. 



o-Aminodimethylaniline 

methyl-o -phenylenediamine) 

N(CH 3 ) 2 



(unsym. -Di- 




C 8 H 12 N 2 MW, 136 

Oil. B.p. 218/751 mm., 99-101/20-25 mm. 
B,2HCl : prisms. Turns red and melts at 
184r-6 decomp. 

N-Acetyl : needles from pet. ether. M.p. 
72-3. 

N-Benzoyl: needles from MeOH.Aq. M.p. 51. 
Picrate : m.p. 138-40 decomp. 
Pinnow, Ber., 1899, 32, 1668. 
Bamberger, Tschirner, Ber., 1899, 32, 
1905. 

m-Aminodimethylaniliaie (unsym. -Di- 

methyl~m-phenylenediamine) . 

B.p. 268-70/740 mm. (258), 138/10 mm. 
D 25 0-995. 

B,mCl: prisms. M.p. 218. 

TS-Acetyl : needles from EtOH.Aq. M.p. 87. 

N-Diacetyl : cryst. from EtOH. M.p. 69. 

N-Chloroacetyl : cryst. from 95% EtOH. 
M.p. 101-5-2-5 . Sol. Me 2 CO. Spar. sol. EtOH, 
Et0. 

^-Benzoyl : prisms from EtOH. M.p. 163-4. 

, Jaubert, Bull soc. chim., 1899, 21, 20. 
Groll, Ber., 1886, 19, 200. 



p-Aminodimetlaylaiiiline 



84 



4-Amino~3 : 5-dimethyIazobenzene 



$?-AmInodimetliy!anIliiie (unsym.~Di- 
methyl-p-phenylenediamine). 

M.p. 53 (41, 36). B.p. 262, 146-8/24 
mm., 95-100 /! mm. DJ 1-036, D 90 1-0168. 
Sol. EtOH, Et 2 0, cold H^O. Spar, volatile in 
steam. Ox. >- benzoquinone. 

N-Formyl: leaflets from H 2 0. M.p. 108. 
Sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . Insol. Hgroin. 
Picrate : m.p. 188. 

T3-Acetyl ; needles from H 2 0. M.p. 132-3. 
B.p. 355 slight decomp. Very sol. EtOH, 
CHC1 3 . Sol. AcOH, Et a O, C 6 H 6 . Spar. sol. 
cold H 2 0. InsoL ligroin. 

N-Diacetyl : needles from pet. ether. M.p. 
68-9. 

"N-Chloroacetyl : needles from EtOH. M.p. 
146-7. Spar. sol. EtOH, Et 2 0. Insol. H 2 0. 

N-Benzoyl : needles from C 6 H 6 . M.p. 228. 
Spar. sol. EtOH. 

TS-p-Nitrobenzoyl : bronze needles from EtOH. 
M.p. 258. 

Picrate : m.p. 186 (139). 

Winans, AdMns, J. Am. Chem. See., 1932, 

54, 311. 
Fischer, Ber., 1883, 16, 2235. 

4-Amino~2 : 2 / -dimetliylazobenzene (o- 

Tolueneazo-m-toluidine) 

CH 3 




C 14 H 15 N 3 MW, 225 

Yellow needles from ligroin. M.p . 1 1 6-1 7 . 
Mehner, J. prakt. Chem., 1902, 65, 448. 

4r-Amino-2 3 / -diinetliyla.zob6iizn,0 (m- 

Tolueneazo-m-toluidine, m-aminoazotoluene) . 

Golden-yellow needles from EtOH, yellowish- 
brown needles from ligroin. M.p, 80. Sn + 
HC1 >- 2 : 5-tolylenediamine. 

l$-Di-Me: C 16 H 19 N 3 . MW, 253. Red cryst. 
from EtOH, M.p. 73-4. 

Mehner, J. prakt. Chem., 1902, 65, 448. 

4-Arnino-2 : 4'-dimethylazobe:azene (p- 

Tolueneazo-m-toluidine) . 

Yellow plates from EtOH, golden-yellow 
needles from ligroin. M.p. 127. Sn + HC1 
> 2 : 5-tolylenediamine. 

'N-Di-Me : light red needles from BtOK. 
M.p. 121. Sol. EtOH, Et 2 0, ligroin. S 9 HOl : 
cryst. from EtOH. M.p. 121. 

Mehner, J. prakt. Chem., 1902, 65, 448, 

4-Amino-3 : 2'-dimethylazobenzene (o- 

Tolueneazo~o4oluidine, o-aminoazotoluene) . 

Yellow leaflets from EtOH. M.p. 100. Heat 
of comb G p 1894-3 Cal. Sn + SnCl 2 > o-tolu- 
idinc + 2 : 5-tolylenediamino. 

TX-Acetyl : red needles from EtOH. M,p. 185. 

" exists in two forms* (1 ) Reddish- 



yellow needles from ligroin. M.p. 65. (2) Red 
cryst. M.p. 75. Very sol. most solvents. 

IS-CUoroacetyl : needles from EtOH. M.p. 
171-2. 

Willgerodt, Lewino, /. prakt. Chem,., 
1904, 69, 321. 

4-Amino-3 : S^dimethylazobenzeaae (m- 

Tolueneazo-o-toluidine) . 

Yellowish-brown leaflets or needles from 
ligroin. M.p. 124. 

Mehner, J. prakt. Chem., 1902, 65, 445. 

4-Amino-3 : 4 / -dimethylazobenzeiie (p- 

Tohieneazo-o-toluidine) . 

Orange-yellow needles from ligroin. M.p. 
128. Spar. sol. ligroin. Sn + HC1 ^ p-tolu- 
idine + 2 : 5-tolylenediamine. 

Mehner, J. prakt. Chem., 1902, 65, 437. 

Nietzki, Ber., 1877, 10, 662. 

6-Amino-3 : 4'-dimethylazobenzeiie (p- 

Tolueneazo-p-toluidine, p-aminoazotoluene) . 

Orange-red prisms from AcOEt. M.p. 118*5. 
Very sol. C 6 H 6 . Sol. hot EtOH, AcOEt. 
Red. ^ 3 : 4-tolylenediamine + jp-toluidine. 
Phthalic anhydride >-phthaloyl derir., m.p. 
220. 

B,HCl : yellow needles from ale. HCL M.p, 
174. Easily hyd. 

N-Acetyl : yellow needles from EtOH-AcOH . 
M.p. 157. 

N-JBenzoyl : orange-yellow needles from EtOH. 
M.p. 135. 

"N-Carboethoxyl : orange -yellow needles from 
EtOH. M.p. 94. Verysoi.C 6 H 6 . Sol. EtOH, 
Et 2 0. 

Halting, Witt, Ber., 1884, 17, 78. 

v. Walthor, Gricshammer, J. prakt. Chem., 

1915, 92, 228. 
Morgan, Walls, J. Chem. See., 1930, 1506. 

4-Amino~2 : 3-dimethylazobenzene. 
Reddish-yellow cryst. from C 6 H 6 -ligrom. M .p. 



98 



Menton, Ann., 1891, 263, 333. 



4-Amino-2 : 5-dim,etliylazobiiz0ii,6. 
Orange cryst. from O fl BC 6 -ligroin, golden 

leaflets from EtOH.Aq. M.p. 104-5. 

Troeger, Westorkamp, Arch. Pharm., 
1909, 247, 684. 

4-Amino2 : 6-dimetb.ylazobeEzene. 

Red needles from pet. other, M.p. 67, Sol. 
most org. solvents. 

Auwers, Borscho, Ber., 1915, 48, 1720. 

4-Amino-3 : S-diraethylazobeiwseBe- 
BrowniBh needles from pet, other, M.p, 99- 
101. Sol- moat org. solvents. 

Auwers, Borsche, JBer., 1915, 48, 1720. 



2-Amino-3 : 5-dimetfcylbenzaldeliyde 

2-Amino-3 : 5-dimethylbeiizaldeliyde (4- 

Aminomesitylenic aldehyde) 

CHO 



85 



2-Amino-4 : 4 / -dimethyldip]ienyl 




C 9 H U ON MW, 149 

Yellow needles from pet. ether. M.p. 48-9. 

Sol. EtOH. Spar. sol. H 2 0. 
Oxime : needles. M.p. 170-1. 

Meisenheimer, Senn, Zimmermann, Ber., 

1927,60,174. PIT N 

Bamberger, Demuth, Ber., 1901, 34, 1317. ^^^ 

2-Amino-3 : 5-dimethylbenzoic Acid (4- 

Aminomesitylenic acid) 

COOH 



3-Amino-2 : 2-dimethyl-M-bntane 

CH 3 -CH(NH 2 )-C(CH 3 ) 2 -CH 3 
C 6 H 15 N MW, 101 

Liq. Freezes at 20. B.p. 103. Very 
sol. cold H 2 0, less sol. hot. 
B,HAuCl : m.p. 186-7 (178). 

Markownikow, Ber., 1899, 32, 1448. 



2-Amin.o2 : 3-dimeth.yl-w-butane 
NH 2 

CH 3 -CH(CH 3 )-C(CH 3 )-CH 3 



B.p. 104-5. DJ 0-7683. 
sorbs C0. 



MW, 101 
14096. Ab- 




Konowalow, Chem. Zentr., 1906, 1, 737. 

4-Amino3 : 5-dimethyldiphenyl 

CH 3 



C 9 H U 2 N MW, 165 

Needles from EtOH. M.p. 191. EtOH sol. 
shows bluish- violet fluor. in sunlight. 

Me ester: C 10 H 13 2 N. MW, 179. Cryst. 
fromMe 2 CO. M.p. 39. 

Nitrile : N-acetyl, 2 : 4-dimethyl-6-cyanoacet- 
aniKde. Needles. M.p. 196-7. Sol. EtOH. 
Boiled with acid or alkali ^ 2:6: 8-trimethyl- 
quinazoline. 

Wheeler, Hoffmann, Am. Cliem. J., 1910, 
44, 119. 

4~Amino-3 : 5-dimethylbenzoic Acid (2- 

Aminomesitylenic acid). 

Needles from EtOH. M.p. 242 (235). Spar. 
sol. H 2 0. 

Me ester : cryst. from MeOH.Aq. M.p. 93. 

Et ester: C U H 15 2 N. MW, 193. Plates 




C 14 H 15 N " MW, 197 

N-Acefyl : m.p. 203-4. 

I.G., F.P., 739,052, (Chem. Zentr., 1933, 
II, 1255). 

6-Amino-2 : 2'-dimetliyldiphenyL 
Light yeUow. M.p. 105. B.p. 169-70/20 
mm. 

N-p-Nitrobenzoyl : pale yellow plates. M.p. 
122. 

Mascarelli, Angeletti, Gazz. chim. itaL, 

1938, 68, 29. 
Eitchie, Chem. Abstracts, 1946, 40, 879. 



MJU OOC/0/ . Vy-^^JUL jgV/JjJL'X . J.TJL V V , X7O. J- JUfcUOO *-X:k,lIllIlO"O . TC 

from pet. ether. M.p. 67. Spar. sol. hot H 2 0. Amino-mp' '-ditolyl) 



4-Amino-3 : 4 / -dimethyldiph.enyl 



(P- 



Wheeler, Hoffmann, Am. Chem. J., 1910, 
44, 119. 

1-Amino-l : 3-dimethyl-n~butane (1:3- 
Dimethyl-n-butylamine) 



(CH 3 ) 2 CH-CH 9 -CHNHo 
C 6 H 15 N * " MW, 101 

B.p. 100-3. 
B 2i (OOOH) 2 : m.p. 219. 

Gulewitsch, Wasmus, Ber., 1906, 39, 1192. 

l-Amino-2 : 2-dimethyl-n-butane (2 : 2- 

Dimethyl-n-butylamine) 



MW, 101 



CHo 



C 6 H 16 N 

B.p. 113-14. Absorbs C0 2 . 
BJBCl: m.p. 225-8. 

Eschert, Freund, Ber., 1893, 26, 2492. 



M.p. 42. B.p. 205-7/4 mm. 

N-Acetyl : needles. M.p. 206 (199-200). 

Kliegl, Huber, Ber., 1920, 53, 1646. 
I.G., F.P., 739,052, (Chem. Zentr., 
1933, II, 1255). 

6-Amino-3 : 4'-dimethyldiphe:ayl (6- 

Amino-mp' -ditolyl) . 

B.p. 165-7/4 mm. 

B,HCl : needles from EtOH-HCL Decomp- 
at 216-26. 

"N-Acetyl : needles from pet. ether. M.p. 
104. Sol. EtOH, CHC1 3J C 6 H 6 . 

Morgan, Walls, J. Chem. Soc., 1930, 1507. 

2-Amino-4 : 4'-dimethyldiplienyl (o- 

Amino-~pp'- ditolyl) . 
Prisms from EtOH.Aq. M.p. 62-3. 
TS-Acetyl : needles. M.p. 118-19. 
N-Benzoyl : needles. M.p. 95-6. 

Marler, Turner, J. Chem. Soc., 1932, 2393. 



3-Amino-4 : 4'-dimetliyldiplienyi 



86 



2-Amino-2 : 4-dimethyi-n-pentane 



3-Amino-4 : 4'-dimethyldiplienyl (m- 

Amino-pp'-ditolyl) . 

Needles from EtOH. Aq. M.p. 104-5. 
B,HCl : needles. M.p. about 230 decomp. 
N-Acetyl : needles. M.p. 156-7. 
"N-Benzoyl : m.p. 160-1. 

Marler, Turner, J. Chem. Soc., 1932, 2393. 

4-Amino-2 : 5-dimethyldiphenylamine 
H 3 C 



2-Amino-l : 4-dimethylnaphtiialene (1:4- 
Dimethyl-2-naphthylamine) 




C 14 H 16 N 2 MW, 212 

M.p. 86-7. 

I.G., F.P., 752,207, (Chem. Zentr., 1934, 1, 
295). 

4-Amino-3 : 2! - dimethyldiphenylamine 

(p-Amino-o'm-ditolylamine, 5-N-o-tolyl-2 : 5-tolyl- 
enediamine). 
Prisms. M.p. 63-4. 

Bamberger, Biisdorf, Sand, Her., 1898, 31, 
1518. 

4 - Ammo -3:4'- dimethyldiphenylamine 

(p-Amino-mp'-ditolylamine) . 
M.p. 73-4. 

Gen. Aniline Works, U.S.P., 1,900,426, 
(Chem. Abstracts, 1933, 27, 2963). 

6 - Amino -3:4'- dimethyldiphenylamine 

(o-Amino-mp' -ditolylamine, 3-N-p-fofo/-3 : 4- 
tolylenediamine) . 

Leaflets from EtOH. M.p. 107. Sol. EtOH, 
Et 2 0, C 6 H 6 . Spar. sol. ligroin. 

Biehringer, Busch, Ber., 1903, 36, 341. 

2 - Amino-4 : 4'-dimethyldiphenylamme 

(Q-Amino-pp' -ditolylamine, 4-N-p-toZ^-3 : 4~ 
tolylenediamine) . 

Cryst. from hot ligroin. M.p. 109. Cone. 
H 2 S0 4 > blue sol. 

Fischer, Sieder, Ber., 1890, 23, 3798. 

3-Amino-4 : 4 / -dimethyldiphenylamine 

(m-Amino-pp'-ditolylamine, 4:-T$-p-tolyl-2 : 4- 
totylenediamine). 

Prisms from ligroin. M.p. 71. Sol. EtOH, 
Et 2 0, C 6 H 6 . Insol. H 2 0, 

Jaubert, Ber., 1895, 28, 1649. 

2-Amino-2 : 5-dimethyl-n-hexane (Amino-* 
di-isobutyl) 



C 8 H 19 MW, 129 

B.p. 144/750 mm. DJ 0*7803. 
B,HCl: needles. M.p. 157-60. Sol. H 2 0, 
EtOH, Et 2 5 C 6 H 6 . 
B&iJSOi : m.p. 235. 

Konowalow, Ber., 1895, 28, 1854; Chem. 
Zentr., 1906, IT, 312. 



C 12 H 13 N 




MW, 171 

Prisms from Et 2 0. M.p. 75. B.p. 333. 
Sol. EtOH, Et 2 0. 

TS-Acefyl : needles from EtOH. M.p. 219- 
20. 

Cannizzaro, Andreocci, Gazz. chim. itaL, 
1896, 26, i, 15. 

l-Amino-2 : 3-dimethylnaplitlialene (2 : 3- 

Dimethyl- 1 -naphthylamine ) . 
M.p. 42. B.p. 177/14 mm. 

Willstaedt, Chem. Zentr., 1943, 1, 750. 

l-Amino-2 : 6-dimethylnaphthalene (2 : 6- 

Dimethyl'I-naphthylamine). 

Needles from EtOH. M.p. 91. Volatile in 
steam. 

N-Acetyl : needles from AcOH. M.p. 211. 

N-Benzoyl : brown leaflets from xylene. 
M.p. 219-20. 

Mayer, Alken, Ber., 1922, 55, 2280. 

3-Amino-2 : G-dimethylnaphthalene (3 : 7- 

Dimethyl-2-naphthylamine) . 

Needles from pet. ether. M.p. 129 (134-5). 
B,HCl : plates. M.p. 275 decomp. 

TS-Acetyl: needles from EtOH. M.p. 231 
(233-4). 

Coulson, J. Chem. Soc., 1934, 1410. 
Vesely, Stursa, Chem. Zentr., 1932, I, 
2464. 

4-Amino-2 : 6-dimethylnapMh.alene (3 : 7- 
Dimethyl-l -naphthylamine), 
Needles from pot. other. M.p. 93-4. 

N~Acetyl : noodlos from AcOH. M.p. 207-8. 
Vesely, Stursa, Chem. Zentr., 1932, T, 
2464. 

3-Amino-2 : 7-dimethylnaplithalen0 (3 : 6- 

Dimethyl-2-naphthylamine) . 

Plates from pot. other, M.p. 139. SoL 
EtOH, C 6 H 6 . 

B,HCl : m.p. 283 docomp. 

"N-Acetyl: noodles from AcOH or EtOH. 
M.p. 207. 

Coulson, J. Chem. tioc., 1935, 79. 

2-Amino-2 : 4-dimethyl-ti-pentane 



C 7 H 17 N 



CH3-CH(CH 3 )-OH a -0(CH 8 )-CH 3 

MW, 115 
B.p. 122. D? 0-7720. < 14009. 
B,HCl : needles. M.p. 208-9. HygroHeopio. 
Chonin, Chem. Zentr., 1909, II, 687. 



3-Amino-2 : 4-dimethyl-n-pentane 

3-Amino-2 : 4-dimetliyl-ra-pentane 

CH 3 -CH(CH 3 )-CH(NH 2 )-CH(CH 3 ) 2 
C 7 H 17 N - MW, 115 

B.p. 125. 

Mailhe, Bull soc. chim., 1914, 15, 328. 

4-Amino-2 : 6-dimethylpiperidine 
CH-NH 2 



87 



2-Amino-4 : 6-dimethylpyrimidine 



HoC-HC CH-CH, 



NH 

C 7 H 16 N 2 MW, 128 

B.p. 195-6. Misc. with H 2 0. 

Platinichloride : orange-red cryst. Decomp. 
above 250. 

Picrate : decomp. above 220. 

Marckwald, Ber., 1894, 27, 1329. 

l-Amino-2 : 2-dimethylpropane (2 : 2-Di- 
methyl-n -propylamine) 

(CH 3 ) 3 C-CH 2 NH 2 
C 5 H 13 N MW, 87 

B.p. 82-3. HN0 2 > dimethylethylcarb- 
inol. 

Preund, Lenze, Ber., 1891, 24, 2156. 

4-Amino -2:6- dimethylpyridine (y- 

Amino- aa' -lutidine ) 

NH 2 




C 7 H 10 N 2 MW, 122 

Needles from H 2 or C 6 H 6 . M.p. 186. B.p. 
246. Sol. EtOH, Me 2 CO. Mod. sol. H 2 0. 
Spar. sol. Et 2 0, C 6 H 6 . 

B 2 ,H 2 PtCl Q : reddish-yellow prisms. Decomp. 
at 250. 

Picrate: yellow needles. M.p. 194-5. Spar. 
sol. H 2 0, EtOH. 

N-Acetyl : m.p. 113. 

Marckwald, Ber., 1894, 27, 1325. 
Tschitschibabin, Ghem. Zentr., 1916, I, 
1032. 

4-Amino-2 : G-dimethylpyrimidme (2 : 6- 

Dimethyl-4:-pyrimidone imide, 
methylpyrimidine, Cyanmethine) 

N C-CH 3 



C 6 H N 3 MW, 123 

Needles from EtOH. M.p. 183. Sol. to 
0-64% in H 2 at 18. Sol. to 5*25% in EtOH 



at 18. Sublimes. [Forms add. comp. with 
AgN0 3 . 

B,HCl : sublimes without melting. 

N-p-Nitrobenzeriesulphonyl : m.p. 188-90 
decomp. 

T$-ip~Aminobenzenesulphonyl : m.p. 236. N 4 - 
Acetyl : m.p. 310. 

N-Phenyl : 4-anilino-2 : 6-dimethylpyrimid- 
ine, 2 : 6-dimethyl-4-pyrimidone anil. M.p. 104. 

Picrate : yellow needles. M.p. 214. 

Morgan, Beilly, J. Chem. Soc. 3 1913, 103, 
808. 

2-Amino-4 : 5-dimetliylpyrinndine (2- 

Amino-5 : 6-dimethylpyrimidine, 4 : 5-dimethyl-2- 
pyrimidone imide). 

Needles from H 2 0. M.p. 214-15. Sol. EtOH, 
Me 2 CO, CHC1 3 , C 6 H 6 . Spar. sol. Et 2 0, ligroin. 
Sublimes undecomp. 

B,HAuClt : yeUow needles. M.p. 112. 

B 2 ,H 2 PtCl 6 : reddish-yellow needles. M.p. 
227 decomp. 

"S-^AminobenzenesulpJionyl : m.p. 222. 

Picrate : m.p. 250. 

Schlenker, Ber., 1901, 34, 2819. 

6-Amiiio-4 : 5-dimetkylpyrimidine (5 : 6- 

Dimethyl-4:~pyrimidone imide, 4c-amino-5 : $-di- 
methylpyrimidine) . 

Cryst. from H 2 0. M.p. 230. Sol. warm 
EtOH, Me 2 CO, CHC1 3 , C 6 H 6 . Spar. sol. Et 2 0. 
Insol. ligroin. Aq. sol. turns litmus blue. 

TS-Plienyl : 6-anilino-4 : S-dimethylpyrimid- 
ine, 5 : 6-dimethyl-4-pyrimidone anil. Plates 
fromH 2 0. M.p. 152. Sol. EtOH, Et 2 0, Me 2 CO, 
C 6 H 6 . Spar. sol. ligroin. 

Schlenker, Ber., 1901, 34, 2823. 

2-Amino~4 : 6-dimethylpyrimidine (4 : 6- 

Dimeihyl-2 -pyrimidone imide, acetylacetonylguan- 
idine). 

Cryst. H 2 from H 2 0, m.p. 197. Yellow 
needles from Me 2 CO, m.p. 200 (153). Sol. 
CHC1 3 . Mod. sol. H 2 0, EtOH, Me 2 CO, C 6 H 6 , 
AcOEt. Insol. Et 2 0, ligroin. Distils undecomp. 

N-Jfe : prisms from pet. ether. M.p. 98. 

"N-Phenyl : 4 : 6-dimethyl-2 -pyrimidone anil. 
Plates from toluene. M.p. 88-9. Sol. EtOH, 
C 6 H 6 . Picrate : yellow leaflets. M.p. 186. 

B$HCl : needles. M.p. 181. Sol. H 2 0, EtOH. 

B,H 2 PtCl B : yellow prisms. M.p. 225. 

"N-ip-Nitrobenzenesulphonyl : pale yellow plates 
M.p. 220-1. 

N-p- Aminobenzenesulpkonyl : m.p. 177 (198- 
9). 

Picrate : yellow leaflets. M.p. 230. 

Angerstein, Ber., 1901, 34, 3962. 
Combes, Combes, Bull. soc. chim., 1892, 

7, 788. 
Hale, Vibrans, J. Am. Chem. Soc., 1918, 

40, 1061. 



4-Amino-2 : 3-dimetliyl<puiioline 88 

4~Amino-2 : 3-dimethylqtunoline 

NH 2 



o-Amiaodiphenyl 




C U H 12 N 2 MW, 172 

Needles from Me 2 CO.Aq. M.p. 188-5-9-5. 
N-Acetyl: m.p. 216-17. 
Methiodide : needles. M.p. above 310. 

Petrow, J. Chem. Soc., 1945, 18. 

7(or 5)-Amino-2 : 4-dimethylquinoline. 

Needles from ligroin. M.p. 94100. B.p. 
above 300 decoiup. Hygroscopic. Liquefies 
in air and solidifies in yellow needles + 2H 2 0. 

'E-Acetyl : needles from EtOH.Aq. M.p. 212. 

Picrate : yellow needles. M.p. 215-17. 

Marckwald, Ann., 1893, 274, 369. 

5-Aniino-2 : G-diiiiethylqiiinoliiie. 

Needles from EtOH.Aq. M.p. 189-9-5. 
TX-Acetyl: needles. M.p. 211-12. 

Price, Velzen, Guthrie, J. Org. Chem., 
1947, 12, 203. 

7-Amino-2 : 8-dimethylquinoline. 

Cryst. from H 2 0. M.p. 104. Sol. most org. 
solvents. 

Marckwald, Ann., 1893, 274, 363. 

8-Amino-5 : 6-dimethylquinoline. 

M.p. 78-9. 
Picrate : m.p. 213. 

Manske, Marion, Leger, Can. /. Research, 
1942, 20, 133. 

6-Amino-5 : 7-dimethylquinoline. 

Yellow needles from EtOH. M.p. 175. B,p. 
above 300. Sol. Et 2 0, Me 2 C0 5 C 6 H 6 , CHC1 3 . 
Spar. sol. EtOH. Prac. insol. hot H 2 0, ligroin. 
Sublimes. Spar. vol. in steam. 

^-Acetyl : needles. M.p. 212. 

Picrate : orange-red. Sinters at 182. 
Marckwald, Ber., 1890, 23, 102L 

5-Amino-6 : 8-dimetliylquinolin.. 
Yellow needles from EtOH.Aq. M.p. 91. 
Spar. sol. boiling H 2 0. Sol. most org. solvents. 
N-Acetyl : needles from H 2 0. M.p. 201. 

Noelting, Trautmann, Ber,, 1890, 23, 
3683. 

l-Amino-4 : 5-dimethyl-l : 2 : 3-triazole 



MW, 112 




Plates from C 6 B 6 -EtOH. M.p. 95. Distils 
on careful heat. Explodes on rapid heat. Sol. 
H 2 0, EtOH. Mod. sol. C 6 H 6 , Et 2 0, CHC1 3 . 
Insol. ligroin. Eeduces NH 3 .AgN0 3 and Fehl- 
ing's. 

B : HCl : needles. M.p. 131. 

B^AgNOz : prisms. M.p. 188. 

B.HgGl^ : needles from H 2 0. M.p. 145. 

Chloroplatinate : decomp. at 215. 

Picrate: yellow prisms from H 2 0. M.p. 
124-5. 

Stoll6, B&r., 1926, 59, 1742. 
v. Pechmann, Bauer, Ber., 1909, 42, 665 ; 
1900, 33, 645. 

l-Amino-2 : 5-dimethyl-l : 3 : 4-triazole 



N- 



CH 



4 H 8 N 4 MW, 112 

Prisms from AcOEt. M.p. 199. Sol. hot 
H 2 0, EtOH. Prac. insol. Et 2 0, C 6 H 6 , CHC1 3 , 
ligroin. Jc = 1-4 X 10- 10 . 

B,HCl : needles from EtOH. M.p. 232. 

B 2 ,H 2 SO^ : from H 2 0. M.p. 230. 

B 2i H 2 PtCl e ,2H z O : m.p. anhyd. 260. 

Pellizzari, Atti accad. Lincei, 1899, 8, 330 ; 

Gazz. chim. itaL, 1909, 39, 535. 
Dedichen, Ber., 1906, 39, 1855. 
Silberrad, J. Chem. Soc., 1900, 77, 1185. 



o-Aminodiphenyl 



H 2 N 



C 12 H U N " MW, 169 

Cryst. from EtOH.Aq. M.p. 49-50. B.p. 
299, 170/15 mm., 1458/5 mm. Volatile in 
steam. Heat with lime > carbazolo. 

yf-Formyl: ncedlcR from EtOH.Aq. M.p. 
75. Very sol. EtOH, Et 2 0, OH01 3 , 6 "Ht r 
Heat with ZnCl 2 - > phenanthridine. 

"N-Acetyl : needles from EtOH.Aq. or pet. 
""" B.p. 355. Sol EtOH, 



ether. 
Et0. 



M.p. 121 



: oolourloss needles. M.p. 84, 
; needles from EtOH.Aq. M.p. 
65. 

TS-Benzoyl : leaflets from EtOH.Aq. M.p. 
102 (88). Sol. EtOH, Bt,0, CHOI* 6 H . 
N-Jfcfe : b.p. HS-16/2 mm. < 1-6052. 
N-JW-Jfe : m.p. 98-9. 

Chaix, Eocheboti^t, Bull. soc. chim^ 1936. 

2, 277. 
Morgan, Walk, /, Soc. Chem. Ind, 3 1930, 

49, 15T. 
Scarborough, Waters, J. Ofam. 80$*, 

1927, 91. 



m-Aminodlphenyl 



89 



2~Aminodiphenyiene oxide 



m-AminodiphenyL 

Needles. M.p. 30. B.p. 254/135 mm., 176- 
8/18 mm. Sol. most org. solvents. Turns dark 
in air. Volatile in steam. 

N-Acetyl : needles from EtOH. M.p. 148. 

Fichter, Sulzberger, Ber., 1904, 37, 882. 

jp-Aminodiphenyl (Xenylamine). 

Leaflets from EtOH.Aq. M.p. 50-2. B.p. 
302, 191/15 mm., 166/5 mm. Sol. EtOH, 
Et 2 0, CHC1 3 . Spar. sol. cold H 2 0. Volatile in 
steam. 

N-Formyl : needles from EtOH.Aq. M.p. 
172. Sol. Et 2 0. Spar. sol. EtOH. 

'N-Acetyl : cryst. from MeOH.Aq. M.p. 171 
(167). Very sol. MeOE, Me 2 CO. Sol. EtOH. 

N-Diacetyl : needles from ligroin. M.p. 120. 
Sol. ligroin. 

"N-Bewzoyl: cryst. from EtOH. M.p. 229- 
30. Spar. sol. AcOH. Insol. CHC1 3 , C 6 H 6 , 
pet. ether. 

N-p-Toluenesulphonyl : m.p. 254-5 (160). 

I.G., B.P., 395,152, (Chem. Abstracts, 

1934, 28, 340). 
Morgan, Walls, J. Soc. Chem. Ind., 1930, 

49, 15T. 

o-Aminodiphenylamine (Phenyl-o-phenyl- 
enediamine) 

H 2 N_ 

-NH- 



4 - Aminodiphenylamine - 2 - carboxylic 
Acid (5-Amino-2-anilinobenzoic acid] 

900H 



MW, 184 

Needles from H 2 0. M.p. 79-80. Sol.Me 2 CO, 
CHC1 3 , C 6 H 6 . Spar. sol. ligroin. Dist. with 
PbO > phenazine. 

o-N-Acetyl: m.p. 121. HC1 or ale. NaOH 
>- 2-methyl-l -phenylbenziminazole. 

o-'N-Benzoyl : m.p. 136. HC1 > 1 : 2-di- 

phenylbenziminazole . 

Kehrmann, Havas, Ber. } 1913, 46, 341. 

m-Aminodiphenylamine (Phenyl-m- 

phenylenediamine) . 

Leaflets from hot H 2 0. M.p. 76-7. Sol. 
most org, solvents. 

Wieland, Eheinheimer, Ann., 1921, 423, 
28. 

p- Aminodiphenylamine (Phenyl-p -phenyl- 
enediamine, Diphenyl Black Base P). 

Needles from EtOH. M.p. 66. Cryst, from 
ligroin. M.p. 75. B.p. 354 in H, 155/0-026 
mm. Sol. EtOH, Et 2 0. Spar. sol. H 2 0. Heat 
with S > aminothiodiphenylamine. Used in 
calico printing and in the dyeing of fur. 
T$~Acetyl : leaflets or needles. M.p. 158. 
I.C.I., F.P., 783,088, (Chem. Abstracts, 

1935, 29, 6904). 
Meyer, Ber. 9 1920, 53, 1265. 




C 13 H 12 2 N 2 MW,228 

M.p. 233-4 decomp. 

B,HCl : needles. Spar. sol. cold H 2 0. 

Graebe, Lagodzinski, Ann., 1893, 276, 41. 

2 7 - Aminodiphenylamine - 2 - carboxylic 
Acid. 

Plates from EtOH. M.p. 204 decomp. 
(210). Prac. insol. boiling C 6 H 6 . Readily 
oxidised in moist air. 

B,HCl: prisms from EtOH. M.p. 260. 

McCombie, Scarborough, Waters, J. 

Chem. Soc., 1928, 358. 
Clemo, Perkin, Robinson, J. Chem. Soc., 
1924, 1779. 

3 X - Aminodiphenylamine - 2 - carboxylic 
Acid. 

Needles from toluene. M.p. 166 decomp. 
Sol. EtOH, AcOH. Spar. sol. C 6 H 6 . Insol. 
Et 2 0, ligroin. 

UUmann, Ann., 1907, 355, 331. 

4 r - Aminodiphenylamine - 2 - carboxylic 
Acid. 

Needles from xylene. M.p. 205 decomp. 
Sol. hot EtOH, hot AcOH. Insol. C 6 H 6 , ligroin. 
Ullmann, Ann., 1907, 355, 334. 

2 - Aminodiphenylamine - 4 - carboxylic 

Acid (3-Amino-4:-amlinobenzoic acid). 

Needles from hot H 2 0. M.p. 153. Sol. 
EtOH, Me 2 CO, CHC1 3 . Mod. sol. C 6 H 6 . Insol. 
ligroin. 

m ester: C 15 H 16 2 N 2 . MW 3 256. Plates 
from EtOH.Aq. M.p. 76-7. 

Schopff, Ber., 1889, 22, 3286. 

Aminodiphenylcarbinol . 

See Aminobenzhydrol. 

1 - Aminodiphenylene oxide ( 1 -Aminodi- 
benzfuran) 



MW,183 




NH 2 



C 12 H 9 ON 

M.p. 84-5-85-5. 
JS-Acetyl : m.p. 172-5. 

Earkpatrick, Parker, J. Am. Chem. Soc., 

1935, 57, 1126. 

Gilman, van Ess, J. Am. Chem. Soc., 
1939, 81, 1365. 

2- Aminodiphenylene oxide. 

Cryst. from EtOH.Aq, M.p. 94. 
B,HCl : plates. Decomp. about 220. 



3-Aminodiplienyleiie oxide 



90 



a-Aminodiphenylmethaiie 



TS-Acetyl : m.p. 178. 

N-DiocefyZ: needles from EtOH.Aq. M.p. 
83. 

13-Benzoyl : m.p. 201. 
N-p-Aminobenzenesulphonyl : m.p. 24=2-3. 
N-Jfe: C ia H u ON. MW, 197. M.p. 48-9. 
B.p. 190/4 mm. B,HCl : m.p. 245-7 decomp. 
N-Di-JJfe: C^HjoON. MW, 211. M.p. 96. 
B.p. 211~12/4 mm. B,HCl : m.p. 230-2 de- 
comp. 

N-DWSfe: C ie E 17 ON. MW, 239. B.p.205 / 
2 mm. JSjlKTZ : m.p. 203-5 decomp. 

Kirkpatrick, Parker, /. Am, Chem. Soc., 

1935 3 57, 1123. 

Cullinane, J. Chem. /Sac., 1930, 2267. 
Borsche, Schake, Ber,, 1923, 56, 2498. 

3-Aminodiplienylene oxide. 

Plates from EtOHAq. M.p. 128 (125-6). 

Cullinane, J. Chem. Soc., 1932, 2365. 
Oilman et al. 7 J. Am. Chem. Soc. } 1934, 
56, 2473 

4-Aminodiplienylene oxide. 

Needles from MeOH.Aq. M.p. 74. 
N-Acetyl: m.p. 205. 

Oilman, van Ess, J. Am. OJiem. Soc., 
1939, 61, 1365. 



.-diphenylethane . 

See Aminodibenzyl and I : 2-Diphenylethyl- 
amine. 

oc-Amino-Mnstf7n.-diplienyleth.ane . 
See 1 : 1-Diphenylethylamine. 
p-Amino-wnst^n.-diplienylethane . 
See 2 : 2-Diphenylethylamine. 
4-Amino-tftnst^n .-diphenylethane 




C 14 H a6 N MW, 197 

J? 2 ,F 2 $0 4 : needles from EtOH. M.p. 206-7. 
Mod. sol. EtOH. Spar. sol. H 2 0. 
TS-Benzoyl : plates from EtOH. M.p. 128. 

Busch, Rinck, Ber., 1905, 38, 1763. 

o-Aminodiphenyl Ether (o-Aminophenol 
phenyl ether) 



MW 5 185 

Oryst. from ligroia. M.p. 42-3. B.p. 307-8 / 
728 mm. Very sol. usual solvents. 

B,HCl: needles. M.p. 154. Very sol. H.O, 
EtOH. 

yi'f'Aminobenzenesulphonyl : m.p. 149. N* 
Acetyl : m.p. 162. 

Ullmann, Ber,, 1896, 29, 1881. 
Jones, Cook, */. Am, Chem. 8oc,, 1916, 
38, 1540. 



m-Aminodiplienyl Etlier (m-Aminophenol 
phenyl ether). 

Prisms from ligroin. M.p. 37. B.p. 315, 
190-F/14 mm. 

B,HCl : leaflets. M.p. 139. Sol. H 2 0. 

TS-Aceto/l : prisms from ligroin. M.p. 83. 
"Ullmann, Sponagel, Ann., 1906, 350, 104. 

p-Aminodiphenyl Ether (p-Aminophenol 
phenyl ether). 

Needles from H 2 0. M.p. 84 (95). Sol. 
EtOH, Et 2 0. 

B>HCl : plates. M.p. 225-7 decomp. (122). 
*N-Acetyl : m.p. 127. 

'N-p-Aminobenzenesulphonyl : m.p. 177-8. 
W-Acetyl : m.p. 183. 

Ullmann, Sponagel, Ann., 1906, 350, 105 
Jones, Cook, J. Am. Chem. Soc., 1916, 
38, 1545. 

a-Aminodiphenylmethane (BenzhydryL 

amine) 



C 13 H 13 N 

B.p. 304-l/763 



MW, 183 

mm. (288), 175-~6/23 

mm. Df fl 1-0635. n%* 1-59631. Reacts strongly 
alkaline. Absorbs C0 2 > product m.p. 91. 
Ox. > benzopbenone oxime. 

B,HCl: needles. M.p. 293 (270). Spar, 
sol. cold H 2 0. 
B.CH^COOH: m.p. 141. 
B*(COOH)* : m.p. 135-6. 
: m.p. 152-4. 

needles from H 2 0. M.p. 132, 
needles from EtOH.Aq. M.p. 



N-Formyl 

T$~Acetyl : 
146-7. 

N-Benzoyl 
(166-7). 

Picrate : yellow 
205-6 decomp. 



needles from EtOH. M.p. 172 
needles from H 2 0. M.p, 



C M H 15 N 4 MW, 197, Cryst. from 
pet. ether. M.p. 40. B.p. 168/20mm. IlJtCl: 
needles. M.p. 238. B 9 HNO : platen from 
EtOH. M.p. 146. 

N-jB<: C 15 H 17 N. MW,21L Brownish oil. B.p. 
175/20 mm. B,HCl : noodles from EtOH. M.p. 
248. J5,f^O s :loaliotsfromBtOH. M.p. 142. 

lS-I*opropyl: 10 H ld K MW, 225, Oryst. 
M.p. 11-5. B.p.l81'5-82 G /25mm.,173 Q /iymm. 
DJ 3 1-001. < 1-5602. BJICl: cryst. + H 8 
from H 2 0. M.p. 213-5-4. Picrate: yellow 
noedlos from C a H 6 . M.p. 189-90, 

N - Phenyl : oc - anilinodi]>honylmothano. 
Gt 9 H 17 ]Sr. MW, 259. Noedlow from KtOH. 
M.p. 58. B.p. 232-4/20 mm., 224-5/12 mm, 
B,HCl : needles from EtOH. M.p, 199, 

Busoh, Leefhelm, J. prakt. Ch&m. t 1008, 

77, 14. 
BUtz, Seydel, Ber. y 1911, 44, 411. 

Semper, Lichtenstadt, B*r. 9 1918, 51, 934. 



2-Aminodiph.enylmethane 



91 



Ainino-etliylaziiiHie 



2-Aminodiplienylmetiiaiie 




C 13 H 13 N MW, 183 

Pale yellow prisms from Et 2 0. M.p. 52. 
B.p. 190/22 mm. 5 172/12 mm. PbO > 
acridine. HN0 2 > fluorene. 

'N-Acetyl : needles from EtOH.Aq. M.p. 135. 
N-Benzoyl : prisms from EtOH.Aq. M.p. 116. 
B,HCl : m.p. 137 decomp. (175). 

Carre, Bull soc. chim., 1909, 5, 120. See 

also Compt. rend., 1909, 148, 101. 
Fischer, Schiitte, Ber., 1893, 26, 3086. 

3-Aminodiphenylmethane . 

Cryst. from ligroin. M.p. 46. 
N-Acetyl : leaflets from C fi H fi -pet. ether. 
M.p. 91. 

Becker, Ber., 1882, 15, 2092. 

4-Aiiiinodiphenyliiieth.ane . 

Cryst. from ligroin. M.p. 34-5. 
'N-'p-Nitrophenylacetyl : m.p. 86. 

Easier, Ber., 1883, 16, 2718. 

Aminodiphenylpropane . 

See Diphenylpropylamine. 
6-Amino-2 : 3-diphenylquinoxalme 

N 




C 20 H 15 N 3 MW, 297 

Yellow cryst. from EtOH. M.p. 177. Mod. 
sol. EtOH, Et 2 with greenish-yellow fluor. 
Cone. H 2 S0 4 gives deep red sol. > green on 
dilution. 

N-Acetyl: cryst. from CHC1 3 . M.p. 252. 
Cone. H 2 S0 4 > yellow sol. 

Bertels, Ber., 1904, 37, 2277. 

o-Aminodiphenyl sulphide (o-Aminothio- 
phenol phenyl ether) 



C 12 H U NS MW, 201 

Plates from EtOH. M.p. 35-6. B.p. 258 / 
100 mm., 212/25 mm. 

Bourgeois, Huber, Rec. trav. chim., 1912, 
31, 30. 

p-Aminodiphenyl sulphide (p-Aminothio- 
phenol phenyl ether). 

Cryst. from ligroin. M.p. 93 (96). B.p. 
282/100 mm., 243/29 mm. 
T$-Acetyl : needles from EtOH. M.p. 146. 
Bourgeois, Huber, Rec. trav. chim., 1912, 
31, 30. 



Aminodithioforinic Acid. 

See Dithiocarbamic Acid. 

AminoditolyL 

See AminodimethyldiphenyL 

Aminoditolylamine . 

See Aminodimethyldiphenylamine. 

1-Aminododecane . 

See Dodecylamine. 

oo-Aminododecylcyclopentene . 

See Homohydnocarpylamine. 

Arolnodurene . 

See Duridine. 

Aminoethanesnlpkonic Acid. 

See Taurine. 

Aminoethoxybenzoic Acid. 

See under Hydroxyaminobenzoic Acid and 
Hydroxyanthranilic Acid. 

1-Aminoethyl Alcohol (Aldehyde-ammonia, 
1 -hydroxyethylamine) 



C 2 H 7 ON MW, 61 

Rhombic cryst. M.p. 97 (70-80). B.p. 
110 part decomp. Sol. H 2 0. Spar. sol. Et 2 0. 
Heat of comb. C p 347 Cal. Dil. acids > 
acetaldehy de . 

Aschan, Ber., 1915, 48, 874. 

Matheson, U.S.P., 1,456,702, (Chem. Ab- 

stracts, 1923, 17, 2428). 
Skirrow, Morrison, U.S.P., 1,551,176, 
(Chem. Abstracts, 1926, 20, 210). 

2-Aminoethyl Alcohol (2-Hydroxyethyl- 
amine, ethanolamine, colamine) 

H 2 N-CH 2 -CH 2 OH 
C 2 H 7 ON MW, 61 

Colourless oil. B.p. 171. Misc. all propor- 
tions with H 2 0, EtOH. Sol. CHC1 3 . Spar. sol. 
Et 2 0, C 6 H 6 , ligroin. DJ 1-022. < 1-4539. 
Strong base. Volatile in steam. Absorbs C0 2 
and H 2 0. 

B,HCl : m.p. 100. 
B,HNC>3 : m.p. 52-5. Hygroscopic. 
B,2HNO^: cryst. 

0-Acetyl : 2-aminoethyl acetate. B.p. 160- 
l/4 mm. < 1-4716. B,HCl : m.p. 130. 
Picrate : m.p. 158. 
Et ether : see 2-Aminodiethyl Ether. 

Kawai, J. Chem. Soc. Japan, 1923, 44. 303. 
Putokhin, Chem. Abstracts, 1929, 23, 2938. 
I.G., P.P., 650,574, (Chem. Abstracts, 

1929, 23, 3232). 

Carbide and Carbon Chemical Corp., 
U.S.P., 1,904,013, (Chem. Abstracts, 
1933, 27, 3222). 

Nobel, D.R.P., 517,832, (Chem. Abstracts, 
1931, 25, 2740). 

2-[(3-Aminoethylamino]-ethyl Alcohol. 

See N- [p-Hydroxyethyl]-ethylenediamine. 
Amino -ethyl aniline . 
See Ethylphenylenediamine. 



a-Aminoethylbenzene 92 

a-Aminoetliylbenzene (1 -Phenylethylamine) 



p-p-Aminoethylbenzoic Acid 

0-Aminoethylbenzene (o-Ethylaniline) 
CH 2 'CH 3 



C 8 H U N 



MW, 121 
10-8 in MeOH. 



B.p. 187/760 mm. [aft 

B,HCl : m.p. 159-60. 

l-Mandelate : plates from EtOH. M.p. 177. 
[aft 5 - 60-4 in H 2 0. 

d-<x.-Bromocamphorsulphonate : m.p. 183-6. 
[aft 5 + 63-3. 

dl-a-Bromocamphorsulphonate : prisms from 
EtOH. M.p. 170. [aft 5 + 1'20. 

B.p. 54/l mm. [a]g - 38 in MeOH. 

B,HCl : m.p. 171. [a] D - 8-27 in H 2 0. 

d-Mandelate : [aft 5 + 58-9 in H 2 0. 

d-K-Bromocamphorsulphonate : prisms from 
H 2 0. M.p. 206-7. WiSfi + 77-6 in H 2 0. 

N-Acetyl : m.p. 103-4. 

N-Benzoyl: m.p. 163-3-5. 

dl-. 

B.p. 187-5, 87/24 mm. D 15 0-9395. Sol. 24 
parts H 2 at 20. Absorbs C0 2 . 

B 2 ,(COOH)z : m.p. 238. 

B,HCl : m.p. 158. 

d-Mandelate : plates from H 2 0. M.p. 176. 

dl-Mandelate : plates from H 2 0. M.p. 138. 

dL~<z-Bromocamphorsulphonate : needles from 
H 2 0. M.p. 155. 



8 H U N 



MW, 121 
D 22 0-983. 



B.p. 215~16/769 mm. (210-1 r 
n% 1-5584. 

B,HCl : m.p. 191 (172-3). 

N-Acetyl : o-ethylacetanilide. Cryst. M.p. 
111-12. B.p. 304-5. Sol. hot H 2 6. 

N-Benzoyl : o-ethylbenzanilide. C 15 H 15 ON. 
MW, 225. Leaflets. M.p. 147. 

Picrate : m.p. 194-5. 

Paucksch, Ber., 1884, 17, 2801. 

m-Aminoethylbenzene (m-Ethylaniline) . 
B.p. 214-15. Sol. hot H 2 0. D 0-990. 
TS-Me : b.p. 81-5/l mm. Picrate : m.p. 
133-4. 

N-Acetyl : m-ethylacetanilide. M.p. 24-5. 
B.p. 312-13. 

B6hal, Choay, Bull. soc. chim., 1894, 11, 
211. 

j-Aminoeth.ylbenzene (p-Ethylaniline) . 
M.p. -5. B.p. 213-14. D 22 0-975. < 
1-5529. 
N-Acetyl : ^-ethylacetanilide. Needles from 



TS-Acetyl: m.p. 57. B.p. 292-3. Sol. EtOH. H 2 0. M.p.' 94. B.p. 315-17. Spar. sol. H 2 0. 

rt . _i i. . i TT r\ _ ._*._ .,.,.*- ^^ ^fi^f 



N-Benzoyl : jp-ethylbenzamlide. C 15 H 15 ON. 
MW, 225. Needles. M.p. 151. 

Willgerodt, 'Bergdol^Ann., 1903, 327,286. 

o-p-Aminoethylbenzoic Acid (o~Carboxy-%~ 
phenylethylamine ) 

OOOH 



Spar. sol. hot H 2 0. 
N-Benzoyl : needles. M.p. 120. 

Ramberg, Hannerz, Chem. Abstracts, 

1925, 19, 13. 
Andr6, Vernier, Compt. rend., 1931, 193, 

1192. 

Ingold, Wilson, J. Chem. Soc., 1933, 1502. 
Kindler, Peschke, Brandt, Ber., 1935, 68, 

2241. 
Robinson, Snyder, Organic Syntheses, 

1943, XXIII, 68. CflHiAN - MW)1C5 

p-Aminoetliylbenzene (2-Phenylethylainine). -vr ^i i\/r I/-A po Q 14, i IT t\ tf^n^ 
?-P-l 97 r 8 ::..^-..^9H,^t 2 0. Mod. sol. J^ShJd^bSUl ' 

B,HOl : plates. M.p. 199-200. 




H 2 0. Df 0-9580. Absorbs C0 2 . 
B,HCl : cryst. from EtOH. M.p. 217. 
B,(COOH) 2 : needles. M.p. 181. 
B 2 ,(COOH)z : plates. M.p. 218. 
Picrate : prisms from EtOH. M.p. 167. 
N-J? 7 orm?/2:b.p,210-14 /35mm. J 180-l /14mm. 
TS-Acetyl : needles. M.p. 51 (42-4). B.p. 
305-6. 

JS-Bemoyl : leaflets from EtOH. M.p. 116, 
Kriokson, Ber., 1926, 59, 2667. 
Ing, Manske, J. Ohem. Soc,, 1926, 2350. 
Mignonao, F.P., 638,550, (Chem. Abstracts, 

1929, 23, 154). 

Kindler, D.R.P,, 562,714, (Chem. Ab- 
stracts, 1933, 27, 995). 
Robinson, Snyder, Organic Syntheses, 
1943, XXHi, 71. 



N-Benzoyl : cryst. from H or AcOEt. 
172. 

Bamberger, Dieckmann, Ber. 9 1893, 26, 
1217. 



jp-p-Aminoethtylbenzoic Acid ( 

2- phenylethylamine ) . 

Me ester : yellow noodles. M.p. 178. It ,1101: 
m.p. 208-11*. 

Et ester: bright yellow needles. M.p. 112, 
BJICl: m.p. ]78. 

yS-Acetyl : m.p. 173-5. 

Slotta, Kothur, Ber., 1938, 71, 59. 
Blicko, Lilionfold, J. Am. Ohem, $oc, 9 
1943,65,2281. 



4-Amino-2-ethylbenzoic Acid 



93 



9-Aminofluoreiie 



4-Amino-2-eth.ylben.zoic Acid 

COOH 



C 9 H U 2 N " 

Needles from H 2 0. M.p. 179-80. 
Gieke, Ber., 1896, 29, 2537. 



MW, 165 



5-Amino-2-ethylbenzoic Acid. 

Needles from H 2 0. M.p. 179-80. Mod. sol. 
EtOH, Et 2 0. Spar. sol. CHC1 3 , C 6 H 6 , Hgroin. 
Gieke, Ber., 1896, 29, 2537. 

Aminoethylbromide . 

See Bromoethylamine. 

l-Amino-2-ethyL-n-foutane (2-flthyl-n- 
butylamine, ^-hexylamine) 

CH 3 -CH 2 -CH(C 2 H 5 )-CH 2 im 2 
C 6 H 15 N MW, 101 

B.p. 125. 

B,HCl : needles from EtOH. M.p. 187 de- 
comp. 

Freund, Herrmann, Ber., 1890, 23, 192. 

4- [p-Aminoethyl]-cyclohexanol . 

See Hexahydrotyramine. 
Aminoethylene . 
See under Ethyleneimine. 
2-(3-Aminoethylfuran. 
See 2-[a-Furyl]-ethylamine. 
4- [co-Aminoethyl]-glyoxaline . 
See Histamine. 

2- [oo-Aminoethyl]-indole (2- [2-Indolyl]- 
ethylamine] 



MW, 160 
Fused with 



NH 

C 10 H 12 N 2 

Prisms from C 6 H 6 . M.p. 120 
KOH > indole-2-carboxylic acid. 
B,HCl : leaflets. M.p. 246. 
N-Benzoyl : m.p. 173-4. 
Benzylidene deriv. : C 17 H 16 lSr 2 . Leaflets. M.p. 
122. 

Asahina, Mayeda, Chem. Abstracts, 1917, 
11, 332. 

3- [co-Aminoethyl]-indole . 
See Tryptamine. 
Aminoethyl iodide. 
See 2-Iodoethylamine. 
Aminoethylmalonic Acid 



C 5 H 9 4 N MW, 147 

Cryst. + 1H 2 0. M.p. 122 decomp. Sol. 
H 2 0. Mod. sol. EtOH. Insol. Et 2 0. Heat at 
125 > 1-aminobutyrio acid. 



Di-Et ester : N-acetyl, m.p. 83. 
Lutz, Ber., 1902, 35, 2553. 

Aminoetliyl Mercaptan. 

See Mercaptoethylamine. 
Aminoethylnaphthalene . 

See Naphthylethylamine. 



See Tyramine. 
j>-Amino-a-et3iylpIienylacetic Acid. 
See 1-p-Aminophenylbutyric Acid. 
1- Aminoethyl plienyl Ketone. 
See p-Aminopropiophenone. 
2-AminoethyI phenyl Ketone . 
See y-Aminopropiophenone. 
5-p-Atninoetliylpyrogallol trimetlrvl 
Ether. 

See Mescaline. 

Aminoethylsnlphonic Acid. 
See Taurine. 
4-Amino-l-ethyl-w-valeric Acid 

H 2 N-CH 2 -[CH 2 ] 2 -CH(C 2 H 5 )-COOH 
C 7 H 15 2 N MW, 145 

Cryst. from boiling H 2 0. M.p. 200 with 
effervescence. Sol. H 2 0. Insol. EtOH, Et 2 0. 
Aschan, Ber., 1890, 23, 3693. 

4- [(3- Aminoethylj-veratrol . 
See Homoveratrylamine. 
Aminof enchane . 
See Fenchylamine. 
jp-Aminoflavoline . 
See Flavaniline. 
2-Aminofluorene 



C 13 H n N MW, 181 

Needles from 50% EtOH. M.p, 129. 
"S-Acetyl: needles from 50% EtOH. M.p. 
191. 

"N-Chloroacetyl : m.p. 189. 
TS-Vakryl : fine needles. M.p. 166. 
'N-Isovaleryl : m.p. 142. 
N-p-Aminobenzenesulphonyl : m.p. 239. 
N "Benzylidene : m.p. 152. 
N-Phthalimido : m.p. 276. 
Urefhane : prisms. M.p. 121-2. 

Kuhn, Organic Syntheses, 1933, XIII, 74. 
Of. Bennett, Noyes, J. Am. Chem. Soc., 

1930, 52, 3438. 

Buu-Hoi, Royer, Bull. soc. chim,, 1946, 
379. 

9- Aminofluorene . 

a-. 

Cryst. from pet. ether. M.p. 64. Sol. EtOH, 
Et 2 0, Me 2 CO, CHC1 3 , C 6 H 6 . Spar. sol. H 2 0. 
B,HCl : cryst. from boiling H 2 0. M.p. 255. 
TS-Acetyl : m.p. 262. 



l-Aminofhiorenone 



94 



5-Aminohemimellitene 



'N-Benzoyl: needles from EtOH. M.p. 260-1. 

M.p. 46-7. Unstable. 
B,HCl : m.p. 216. 
'N-Acetyl : m.p. 245-6. 

Kuhn, Jacob, Ber., 1925, 58, 1432, 2232. 

Ingold, Wilson, J. Chem. Soc., 1933, 1499. 

1-Aminofluorenone 




C 13 H 9 ON " MW, 195 

YeUow needles from EtOH.Aq. M.p. 118- 

18-5 (110). Very sol. org. solvents. Mod. sol. 

boiling H 2 0. 

'N-Acetyl : yellow. M.p. 138. 
'N-Benzoyl : yellow. M.p. 149-50. 

Goldschmiedt, Monatsh., 1902, 23, 886. 

2-Aminofluorenone . 

Violet-red prisms from EtOH. M.p. 163. 
Mod. sol. EtOH, Et 2 0, AcOH. Spar. sol. pet. 
ether. Insol. H 2 0. 

TS-Acetyl : red cryst. M.p. 227-8. Hydraz- 
one : yellow leaflets. M.p. 212-14. 

N-Diacetyl : m.p. 143-4. 

'N-Carbethoxyl : reddish-yellow needles from 
chlorobenzene. M.p. 167-8. 

Hydrazone : orange needles. M.p. 209. 
Dids, Ber., 1901, 34, 1764. 

3-AminofLuorenone . 
Cryst. M.p. 158-9. 

N-Acetyl : pale yellow cryst. from AcOH.Aq. 
M.p. 215. 

Eckert, Langecker, J. prakt. Chem., 1928, 
118, 267. 

4- Ammofluorenone . 

Bed needles from EtOH. M.p. 138. Very 
sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . 

Courtot, Ann. chim., 1930, 14, 77. 
Graebe, Schestakow, Ann., 1895, 284, 
311. 

Aminoform. 

See Hexamethylenetetramine. 

Aminoformic Acid. 

See Carbamic Acid. 

Aminogentisic Acid. 

See 2 : S-Dihydroxy-3-aminobenzoic Acid. 

Aminoglutaric Acid. 

See Glutamic Acid. 

Aminogranatanine . 

See Granatylamine. 

3-Aminoguaiacol 

QCH* 



OH 

INH 2 



Leaflets from pet. ether. M.p. 83-5. FeCl 3 
^ wine-red col. 

Triacetyl : needles from pet. ether. M.p. 
122-4. 

Oxford, J. Chem. Soc., 1926, 2007. 

4- Aminoguaiacol . 
M.p. 125-7. 
N-Acetyl : m.p. 116-19. 
(JN-Dibenzoyl : m.p. 162-4. 

Jona, Pozzi, Gazz. chim. ital., 1911, 41, i y 

722. 

5-Arainoguaiacol . 

Prisms from H 2 0. M.p. 176-7 decomp. 
(184). 

~N-$-Aminopropyl : creamy white prisms. 
M.p. 156-7. B,HCl: plates. M.p. 251 
decomp. Pier ate : bright red prisms. M.p. 
162. 

N-Acetyl: m.p. 111-13. 

Eupe, Ber., 1897, 30, 2447. 

6- Aminoguaiacol . 

Needles from pet. ether. M.p. 95-6. FeCl a 
> brown col. 

Oxford, J. Chem. Soc., 1926, 2007. 

Aminoguanazole . 

See Guanazine. 

Aminoguanidine ( Guanylhydrazine ) 



CH 6 N 4 MW, 74 

Cryst. Sol. H 2 0, EtOH. Tnsol. Et 2 0. Turns 
red in air. Strong base. Jc =1-1 x 10" 3 . 

B,HCl : prisms from EtOH.Aq. M.p. 163. 
Sol. H 2 0, EtOH. Insol. Et 2 0, 

B 2 ,H^O^ : needles + H 2 0. M.p. 207-8. 

J5,r 2 /%> 4 : plates. M.p. 161. 

B,HNOz : plates from H 2 0, noodles from 
EtOH. M.p. 146. 

B,H 2 PtCl Q : m.p. 145-6 decomp. 

'N-'p-Aminobenzenesulphonyl : ^-acelyl, m.p. 
117-118 decomp. 

Trojan Powder Co. ? U.S.P., 1,990,511, 
(Chem, Abstracts, 1935, 29, 183G). 

Smith, Anzelmi, J. Am. Chem. Soc., 1935 y 
57, 2730. 

du Pont, U.S.P., 2,033,203, (Chem. Ab- 
stracts, 1936, 30, 2992). 

l-Amino^4-guanidiaovaleric Acid, 

See Arginine. 

5~Ammohemimellitene (8-Aminol : 2 ; 3 
trimethylbenzene) 

CH 3 



HJNfl 



MW, 139 C 9 H 13 N 




MW, 13ft 



l-Aminobeptadecane 95 

Needles. M.p. 75. B.p. 240. Insol. cold 
H 2 0. 

N-Formyl : m.p. 98-5. 
"N-Acetyl : m.p. 163-4. 

Limpach, Ber. 3 1888, 21, 643. 

1-Aminoh.eptadecane . 

See Heptadecylamine. 
1-Amino-n-beptane (n-Heptylamine) 

CH 3 -[CH 2 ] 5 -CH 2 NH 2 
C 7 H 17 N MW, 115 

F.p. -23-0. B.p. 155-25/760 mm. D 20 
0*777. < 65 141954. Heat of comb. C p 1183, 
C, 1181-3 Gal. 

Picrate : yellow needles. M.p. 120-2. 

Hoogewerff, van Dorp, Bee. trav. chim., 
1887, 6, 386. 

2-Amino-n-beptane 

CH 3 -[CH 2 ] 4 -CH(NH 2 )-CH 3 
C 7 H 17 N MW, 115 

B.p. 142. Sol. EtOH, Et 2 O. Spar. sol. 
H 9 0. K 9 0-7665. < 141997. 

B,HCl: needles. M.p. 81-3 (133). 

B,HBr : needles. M.p. 65-7 (163). 

J3 2 ,H 2 ,S0 4 : m.p. 230-40. 

B,HAuCli: m.p. 82-4 (63-4). Spar. sol. 
cold H 2 0. 

B 2 ,(COOH) 2 : plates. M.p. 226-8 (204). 

B 2 ,H z PtCl Q : m.p. 225 decomp. 

Benzoate : m.p. 95-7. 

Malate : m.p. 121-3. 

Maleate : m.p. 81-3. 

Gluconate : m.p. 141-3. 

Succinate : m.p. 106-8. 

Clarke, /. Am. Chem. Soc. 9 1899, 21, 1027. 
Rohrmann, Shonle, J. Am. Chem. Soc., 

1944, 66, 1516. 
Robinson, Snyder, Organic Syntheses, 

1943, XXIII, 68. 

4-Ammo-tt-h.eptane 

CH 3 -[CH 2 ] 2 -CH(NH 2 )-[CH 2 ] 2 -CH 3 
C 7 H 17 N MW, 115 

B.p. 139-40. DJ 0-767. Strong ammonia- 
cal odour. 

B 9 ffCl: needles from H 2 0. M.p. 246-7. 
Very sol. EtOH. Sol. cold H 2 0. 

B^,H 2 PtCl Q : plates from H 2 O. Decomp. 
about 235. 

Noyes, Am. Chem. J., 1893, 15, 542. 
Pyman, J. Chem. Soc., 1913, 103, 859. 

1-Aminob.exadecane . 

See Cetylamine. 



p-Aamnohexabydrobenzoic Acid 



1-Aminobexabydrobenzoic Acid (1- 

A minocyclohexane-l -carboxylic acid) 



H - 

H 2 C CH 2 

CH 2 

C 7 H 13 2 N MW, 143 

Plates from H 2 O. M.p. 350 (320) in sealed 
tube. Sol. H 2 0. Spar. sol. Hot AcOH. Insol. 
other org. solvents. Sweet taste. 




14^*^. ^ 4 -- 

Nitrite: *CrHN 2 . MW, 124. Cryst. from 
Et 2 0. M.p. 26-7. Sol. H 2 O, EtOH, Et 2 0. 
Beacts alkaline. B,HCl ; plates from EtOH. 
M.p. 233 decomp. 

Picrate : yellow needles. M.p. 209-10 de- 
comp. 

Zelinsky, Annenkow, Kulikow, Z. physioL 

Chem., 1911,73,466. 
Cocker, Lapworth, Peters, J. Chem. Soc., 

1931, 1390. 

Bucherer, Brandt, J. praJct. Chem., 1934, 
140, 142. 

o-Aminobexahydrobenzoic Acid. 

See Hexahydroanthranilic Acid. 

m-Aminohexabydrobenzoic Acid (Amino- 
cyclohexane-3-carboxylic acid, cyclohexylamine-3- 
carboxylic acid) 

CH-COOH 



H, 

H 2 Q 



C 7 H 13 2 lsr MW, 143 

Cryst. from EtOH.Aq. M.p. 268-9. Sol. 
H 2 0. Insol. EtOH, Bt a O, Me 2 CO, C 6 H 6 . 

B,HCl: leaflets from EtOH-Et 2 0. M.p. 
156. 

ffl ester : C 9 H 17 2 K MW, 171. B.p. 123 / 
11 mm. Sol. H 2 0, EtOH, Et 2 O, CHC1 3 , Me 2 CO. 
Turns yellow in air. ~N-Chloroacetyl : needles 
from EtOH. M.p. 115. N-Benzoyl: cryst. 
fromligroin. M.p. 111. 

B^HJPtCl^ : orange-yellow prisms from H 2 0. 
M.p. 239. 

Bauer, Einhorn, Ann., 1901, 319, 329. 

jp-Aminohexahydrobenzoic Acid (Amino- 
cyclohexane-4-carboxylic acid, cyclohexylamine-k- 
carboxylic acid). 

Cis-. 

Leaflets from EtOH. M.p. 303-4. SoL 
H 2 0, AcOH. Spar. sol. MeOH, EtOH. Prac. 



co-Aminohexahydrotoluene 



96 



a-Aminohydratropic Acid 



insol. Et 2 0, ligroin. Sublimes above 330. 
Heat > lactam, m.p. 196. Bitter taste. 

B,HCl : m.p. 217. 

N-Acetyl : m.p. 145-6. 

N-Benzoyl : m.p. 200. 

Et ester, HBr : m.p. 152-5. 

Trans-. 

B,HCl: m.p. 273. 

TS-Acetyl: m.p. 234. 

T$-Benzoyl : m.p. 272. 

Houben, Pfau, Ber., 1916, 49, 2296. 
Ferber, Bruckner, Ber., 1943, 76, 1019. 

oo- AminohexaJiy dr otoluene . 

See Hexahydrobenzylarnine. 

1 - Amino-t a-liexane (\\-Hexylamine} 

CH 3 -[CH 2 ] 4 -CH 2 NH 2 

C 6 H 15 N MW, 101 

F.p.-19. B.p. 129-30/742 mm. DJ 0-7855, 
DJ 5 0-763. Heat of comb. G p 1026-1 Cal. 
B,HCl : leaflets. M.p. 219. 
B 2 ,H 2 PtCl Q : yellow leaflets. M.p. 236-8 
decomp. 

Frentzel, Ber., 1883, 16, 744. 

v. Braun, Sobecki, Ber., 1910, 43, 3599. 

2- Amino~w-]iexa;ne ( 1 -Methyl-n-amylamine) 

CH 3 "CH 2 -CH 2 "CH 2 -CH-NH 2 
C 6 H 15 N MW, 101 

B.p. 70/155 mm. Df 0-755. [a]|> 7 + 4-30. 
[M]g + 4-3. 

B,HOl: m.p. 102-3. [a] 2 D fi -5-68. [M]l? 
7-82 in EtOH. 

Benzoyl : m.p. 86-8. [a]ff + 14-3. [Mjg 5 
+ 29-7 in EtOH. 

B.p. 117-18. D? 0-7534. 
B 2) H 2 SO^,H 2 : cryst. Sol. H 2 0. Spar. sol. 
EtOH. Shows adrenaline-type activity. 

Konowalov, Compt. rend., 1892, 114, 27. 

Kishner, Chem. Zentr., 1900, 1, 957. 



5-Amiuo-l-liexene 

CH 3 -CH(NH 2 )-[CH 2 ] 2 -CH:CH 2 
G 6 H 13 N MW, 99 

B.p. 117-18. Misc. with H 2 0. D 16 0-779. 
Merling, Ann., 1891, 264, 324. 

4-Araino-2-liexene 

CH 3 -CH 2 -CH(NH 2 )-CH:CH-CH 3 
C 6 H 13 N MW, 99 

B.p. 135. 

I.G., D.R.P., 487,787, (Chem. Abstracts, 
1930, 24, 2140). 

o-Aminohippuric Acid (o-Aminobenzoyl- 
aminoacetic acid, v-aminobenzoylglycine) 

CO-NH-CH 2 -COOH 



Levene, Mardashow, / Biol Chem.', 1937, methylphenylacetic acid) 



C 9 H 10 3 N 2 MW, 194 

Me ester : C 10 H 12 3 N 2 . MW, 208. Cryst. 
from Et 2 0-pet. ether. M.p. 87-9. 

Spath, Kufifner, Ber., 1934, 67, 1495. 

m-AminoMppuric Acid (m-Aminobenzoyl- 
aminoacetic acid, m-aminobenzoylglycine). 

Leaflets or needles from H 2 or EtOH. M.p. 
194. Sol. hot H 2 0, hot EtOH, Et 2 0. 

Schwanert, Ann., 1859, 112, 70. 

jp-AminoMppuric Acid (p-Aminobenzoyl- 
aminoacetic acid, p-aminobenzoylglycine). 
M.p. 198-9. 

Landsteiner, v. der Scheer, Chem. Ab- 
stracts, 1932, 26, 3293. 

Anainohydr aery lie Acid. 

See Serine. 

a-Aminohydratropic Acid (^Phenylalan- 
ine, l-amino-l-phenylpropionic acid, amino- 



117, 707. 
Levene, Bothen, Kuna, J. Biol. Chem., 

1937, 120, 759. 
Levene, Kuna, /. Biol. Chem., 1938, 122, Q jj Q jj 



/C 6 H 5 
'C6 COOH 

\NH 2 



291. 

Olin, Schwoegler,U.S.P. 2,373,705, (Chem. 

Abstracts, 1945, 39, 3541). 
Lilly, B.P. 575,677, (Chem. Abstracts, 

1947, 41, 6673). 

S-Amino-n-liexane 

CH 3 -[CH 2 ] 2 -CH(NH 2 )-CH 2 -CH 3 
6 H 15 N MW, 101 

B.p. 130. 

B,HOl : m.p. 227-9. 
BfrHzPtClt : m.p. 190-200. 

Bewad, J. praU. Chem., 1901, 63, 230. 



MW, 166 



Prisms from H 9 0, Sublimes at 295, []J> 8 
+ 70*0 in H 2 0, "Spar. sol. H 2 0, insol. org, 
solvents. Gives deep blue coL with aq. CuS0 4 . 
HNOo > atrolactinic acid. 

N~JVmt/Z ; needles from JLO. M.p, 194-5 
decomp. [a]i 8 + 91-9 in EtOH. 

I-. 

Prisms from BLO. Sublimes at 296, (ali 
- 69-5 in H 2 0. 

JS~Pormyl : noodles from BLCX M.p. 1945 
deoomp, [afe 7 - 91-0 in EtOH. 



a'-Aminoliydratropic Acid 



97 



a-Aminohydrocinnamic Acid 



dl-. 

Needles from H 2 0. Sublimes at 260. Very 
sol. H 2 0. Insol. EtOH, Et 2 O. HND 2 > 
atrolactinic acid. 

Et ester: C n H 15 2 N. MW, 193. B.p. 135-6 / 
15 mm. < 1-5135. B,HCl : m.p. 121-3. 

-4mt& : B,HCl : prisms. M.p. above 250. 
'N-Carbethoxyl : needles from EtOH.Aq. M.p. 
191. 

Nitrile : yellow oil. B.p. 101-4/12-5 mm. 
B,HCl : yellowish needles from Et 2 0. M.p. 
967 . 

McKenzie, Myles, Ber., 1932, 65, 212. 
McKenzie, Clough, J. Chem. Soc. 9 1912, 
101, 390. 

a'-Aminohydratropic Acid (2-Amino-I- 
phenylpropionic acid, 1 -aminomeihyl-l -phenyl- 
acetic acid) 



C 6 H K 



I O O 

H 2 N-CH 2 -CH-COOH 



MW, 165 



dl-. 

M.p. 222-4 



(233). Spar. sol. H 2 O, Et 2 0, 



Me 2 CO, CHC1 3 , C 6 H 6 , CS 2) pet. ether. 

McKenzie, Strathern, J. Chem. Soc., 1925, 
127, 85. 



p-Aminoliydratropic 

phenyl]-propionic acid) 



Acid (l-[p~Amino- 



/ \CH-COOH 

C 9 H n 2 N MW, 165 

M.p. 128. Sol. 



Yellow leaflets from H 2 0. 



H 2 O, EtOH, Et 2 O, CS 2 . 

Trinius, Ann., 1885, 227, 267. 

o-Aminohydrazobenzene 



C 12 H 13 N 3 



MW, 199 



Colourless prisms. M.p. 94-5. 
2-TS-Acetyl : m.p. 167-8. 

Ruggli, Holzle, Helv. Chim. Acta, 1943, 
26, 1190. 

m-Aminohydrazobenzene . 

Yellow needles. M.p. 107. 

Ruggli, Holzle, Helv. Chim. Acta, 1943, 
26, 1190. 

jp-Aminohy drazobenzene . 

Cryst. Unstable. Turns yellow at 50, m.p. 

AO 



81-4' 



EtOH, EtfcO. Insol. H 2 0. SnCl ? + HC1 > 
4-acetylamino-4 / -aminodiphenylamine. 

Schultz, Ber.> 1884, 17, 463. 

Jacobson, Kunz, Ann., 1898, 303, 362. 

Ruggli, Holzle, Helv. Chim. Acta, 1943, 
26, 1190. 

Aminohydrindene . 

See Hydrindamine. 

3- Aminohy dr ocarbostyril (3-Aminodi- 
hydrocarbostyril, a : 2-diaminohydrocinnamic acid 
lactam) 

CH 9 



C 9 H 10 ON 2 

Cryst. from Et 2 0. 



i/LlO 

NH 

MW, 162 

M.p. 149-50. Sol. H 2 0, 

EtOH, CHC1 3 . Mod. sol. Et 2 O, C 6 H 6 . Diazo- 
tisation > carbostyril. 

B,HCl : cryst. M.p. about 310 decomp. 
Picrate : yellow leaflets + 2H 2 from H 2 0. 
M.p. 214 decomp. 

" C 1s H 1A ON ft . MW, 238. Cryst. 



: C M H 15 ON 3 . MW,241. Pale yellow 



- 15142 . , . . 

M.p. 178. Sol. AcOH, hot EtOH. Spar. sol. 
H 2 0. 

^Benzoyl : cryst. from EtOH. M.p. 205. 

Ueda, Ber., 1928, 61, 148. 

7-Aminohydrocarbostyril (7-Aminodi- 
hydrocarbostyril, 2 : 4c-diaminohydrocinnamic acid 
lactam). 

Needles or prisms. M.p. 211. Sol. EtOH, 
hot H 2 0. Spar. sol. Et 2 0. Insol. CS 2 . 

Gabriel, Zimmermann, Ber., 1879, 12, 
602. 

a-Aminohydrocinnamic Acid (I-Amino-2- 
phenylpropionic acid, $-phenylalanine) 

C 6 H 5 -CH 2 -CH(NH 2 )-COOH 
C 9 H n 2 N MW, 165 

a-. 

Leaflets from H 2 0. M.p. 283-4 decomp. 
(rapid heat). Sol. 35-5 parts H 2 at 16. [a]?, 1 
+ 35 in H 2 0. Insol. most org. solvents. 

TS-Formyl: plates from H 2 O. M.p. 167. 
Sol. 145 parts H 2 O at 27. 

T3-Benzoyl : needles from hot H 2 0. M.p. 
146-8. [a]*> - 17-1 in KOH.Aq. 

N-Tp-Toluenesulphonyl : needles from 50% 
EtOH. M.p. 164-5. [a]g + 24 in Me 2 CO. 

I-. 

Widely distributed in plant proteins. Needles 
from H 2 0. M.p. 283 decomp. (rapid heat). 
[a]! 2 35-03 in H 2 0. &(acid) = 2-5 X 10" 9 
at 25. fc(base) = 1-3 X 10" 12 at 25. Sol. 33 
parts H 2 at 25. 

Et ester: B,HCl: needles from EtOH- 



Vl^AJLl CV/X>Q. XTX TV , JU"XJL 4- CtAC? J CfJLiWY JJJV t/ot/t// . jL^,xjtvyi/ . jun->v 

EtOH.Aq. M.p. 146 decomp. Sol. Et 2 0. [a]J? - 7-6 in H 2 0. 

Dtot. of Org. Oomp. L 



(3-Aminoliydrocinnamic Acid 



98 



Aminohydroqriinone 



TS-Formyli plates from H 2 0. M.p. 167. 
[ofe + 75-2 in EtOH. 

^CUoroacetyl : cryst. &om H 2 0. M.p. 126. 
Ml? + 51-80 in HaO. 

^-Glycyl : needles from H 2 0. M.p. 267 de- 
comp. [a]f> + 42-0. Bitter taste. 

Picrolonate : m.p. 208 decomp. [og? + 30-1 
in EtOH. 

Sk 

Prisms from H 2 0. M.p. 271-3. Spar. sol. 
cold H 2 5 EtOH. Insol Bt 2 0. Sublimes part 
decomp. Sweet taste. Dry dist. >- {3-amino- 
ethylbenzene. 

Me ester : C 10 H 1S 2 N. MW, 179. B.p. 141 / 
12 mm. D? 1 096. < 1-5203. B t HCl : needles. 
M.p. 158 decomp. ^-Bmzoyl : cryst. from 
ligroin. M.p. 87. 

Et ester : O n H l5 O s 3Sr. MW, 193. B.p. 143 / 
10 mm. D 1B 1-065. B,HCl : m.p. 127. Picrate : 
prisms. M.p. 156-5. "N-Benzoyl : needles from 
ligroin. M.p. 95. 

Amide: C 9 H 12 ON 2 . MW, 164. Prisms from 
CHC1 3 . M.p. 138-40. Sol. EtOH, hot CHC1 3 , 



C 6 H 6 r Spar. sol. cold H 2 0. Alk. Cu sol. 
violet col. "N-Benzoyl : needles from CHC1 3 . 
M.p. 198. 

N-Formyl: cryst. from H 2 0. M.p. 168-9. 
Sol. EtOH, MeOH. Mod. sol Me 2 CO, AcOEt. 
Spar. sol. Et 2 0, C 6 H 6 . 

^-CUoroacetyl . plates from H 2 0. M.p. 130-1. 
Sol. EtOH, Me a CO, CHC1 3 . Spar. sol. Et 2 0, 
r* TT 

*yt*fflycyl : cryst. from hot EtOH.Aq. M.p. 

about 270. Sol. H 2 O. Spar, sol, org. solvents. 

: leaflets. M.p. 187-8, 



Pischer, Schoeller, Ann., 1907, 357, 4. 
Curtlus, Sieber, Ber., 1922, 55, 1543. 
Bergmann, Stern, Witte, Ann., 1926, 

449, 289. 
Locquin, Cerchez, Bull. $oc. chim. t 1930, 

47, 1386. 
Hoffmann-La Eoche, B.R.P., 484,838, 

(Chem. Abstracts, 1930, 2-1, 1123). 

p-Aminohydrociixnamic Acid (2-Amino- 
2-pJienylpropionic acid) 

C 6 H 5 'CH(NH 2 )-CH 2 -COOH 
C 9 H U 2 N MW, 165 

dk 

Plates from H 2 0. M.p. about 234-6. [agf 
-f 7 in H 2 0, Mod. sol. cold H 2 0. Spar, sol 
warm RtOH. 

m ester : C^H^OgN. MW, 193. B.p. 155V 
13mm. DJ 4 1-063. [agM- 13-7. 

TS-Formyl : needles from H 2 0. M.p. 142-3. 
[oc]i + 1104 in EtOH. 

L. 

Cryst. from H 2 0. M.p. 234-5. [a]?? - 7-5 
in BUG, Mod. sol. H 2 0, warm EtOH. 
Et ester : b.p- 165/13 mm. I)f 1-063. 



: needles from H 2 0. M.p. 142-3. 
[oc]g> - 114-4 in EtOH. 

di~. 

Cryst. from H 2 0. M.p. 231. Sol. hot H 2 0. 
Spar. sol. EtOH. Insol. Et 2 0. Tasteless. 

B,HCl : prisms from EtOH. M.p. 218. SoL 
H 2 0. Less sol. EtOH. 

TS'Iarmyl : prisms from H 2 0. M.p. 128-9. 
SoL warm EtOH, Me 2 CO, AcOEt. Mod. sol. 
H 2 0. Spar. sol. Et 2 3 C 6 H 6 . Insol. pet. 
ether. 

yi-Acetyl : eryst. from EtOH. M.p. 161-2, 
yt-enzoyl : cryst. from MeOH. M.p. 194-6. 
Fischer, Scheihler, Groh, Ber., 1910, 43, 

2024. 
Kodionow, Malewinskaja, Ber., 1926, 59, 

2956. 

Kodionow, D.R.P., 479,228 5 (Chem. Ab- 
stracts, 1929, 23 } 4777). 
Johnson, Livak, J. Am. Ch&m. Soc., 1936, 
58, 301. 

o-Aminohydrocmnaraic Acid. 

See Hydrocarbostyril. 
m-Aminohydrocinnamic Acid (m-Amino- 

2-phenylpropionic acid) 

CH 2 -CH,-COOH 




C 9 H n 2 N " MW, 165 

Cryst. from H 2 0. M.p. 84-5. Sol. EtOH, 
Et 2 0, AcOH. 

BJELCl : needles. M.p. 191. 
TS-Acetyl : cryst. from AcOH.Aq. M.p. 162. 

De, J. Indian Chem. Soc., 1928, 5, 31. 

Slotta, Szyszka, Ber., 1935, 68, 188. 



jp-Anxinoliydrocmiiainic Acid ( 

phenylpropionic acid). 

Leaflets or prisms from H 2 0. M.p. 132. 

Et ester : CiJEL.OJSr. MW, 193. Cryst. from 
EtOH, M.p,34, 

"NAcetyl : cryst, + H^Ofrom AoOILAq. M.p. 
124, anbyd. 143. Sol. EtOH, Et,/), AcOH. 
Spar. sol. GgH 6 . 

'N-Benzoyl : leaflets from 50% AcsOH. M.p, 
194-5. Sol, AcOH, Spar. sol. other Bolvents. 
Shoppee, J. Chem. Soc., 1930, 985. 
Stdhr, Ann., 1884, 225, 59, 

Aminohydroquinone (2 : &*Dihydroxya>nU- 



C 6 H 7 2 N 

yt- 
from 




MW, 125- 

; 2 ; B-dihydroxyaootanilide. Crynt, 

M.p. 100^. Sol H a O, org. solved, 



Amino-co-hydroxyacetoplienone 



99 



3-Aminoindole 



N-Benzoyl : 4-Jf e ether : needles from 
EtOILAq. M.p. 160. Sol. hot EtOH 3 C 6 H 6 . 
Spar. sol. Et 2 0, ligroia. 

Di-Me ether : 2-amino-l : 4-dimethoxybenz- 
ene, 2 : 5-dimethoxyaniline C 8 H n 2 N. MW, 
153. M.p. 81. B.p. 270 part decomp. Sol. 
H 2 0, EtOH, hot ligroin. ~N-Acetyl : 2 : 5-di- 
methoxyacetanilide. Cryst. from H 2 0. M.p. 
91. Sol. H 2 0, EtOH, CHC1 3 , C 6 H 6 , ligroin. 

Di-Et ether : 2-amino-l : 4-diethoxybenzene, 
2 : 5-diethoxyaniline. C 10 H 15 2 ]Sr. MW, 181. 
White cryst. M.p. 86-7 uncorr. B.p. 138 / 
1-2 mm. 

k-Benzoyl : plates from EtOH.Aq. M.p. 161-4. 

Eoberts, de Worms, Clark, J. Ghem. Soc., 

1935, 198. 

Bassler, Ber., 1884, 17, 2119. 
Kehrmann, Bahatrian, Ber., 1898, 31, 

2400. 

Ammo-co-hy droxy acetophenone . 

See Aminophenacyl Alcohol. 

l-Amino-2- [4-hydroxycycloliexyl] - pro- 
pionic Acid. 

See Hexahydrotyrosine. 

2- Aminohypoxanthine . 

See Guanine. 

1-Aminohystazarin (2 : 3-Dihydroxy-I- 
aminoanthraquinone) 

CO NEL 




C 14 H 9 4 N MW, 255 

Orange-red. Does not melt below 316. 
Di-Me ether : C, 6 H 13 4 N. MW, 283. M.p. 
171-5. 

Waldmann, Wider, J. praJct. Chem., 1938, 
150, 107. 

1- Ammo-2-iminazolylpropionic Acid . 

See Histidine. 

Aminoindanol . 

See Hydroxyhydrindamine. 

3-Aminoindazole (&-Aminobenzpyrazole) 



MW, 133 



NH 



C 7 H 7 N 3 

Prisms from Et 2 0-C 6 H 6 . M.p. 154. 

B,H^SO^ : needles. M.p. 223-4. 

Diacetyl deriv. : needles. M.p. 177-8. 

Dibenzoyl deriv. : needles from xylene. M.p. 
182. 

S-N-p-Aminobenzenesulphonyl : m.p. 225-6. 
W-Acetyl: m.p. 253. 

Bamberger, Ber., 1922, 55, 3371. 



4-Aminoindazole (^Aminobenzpyrazole). 

Leaflets. M.p. 151. Sol. Me 2 C0 3 EtOH, hot 
H 2 0. Spar. sol. Et 2 0, C 6 H 6 . 

4-N-J.ceiyZ : prisms. M.p. 145-8. 

N-Diacetyl deriv. : two forms. Stable, m.p. 
202; labile, m.p. 155-60. IDil. HC1 >4-acetyl- 
aminoindazole hydrochloride, m.p. 223-5. 

Auwers, Schwegler, Ber., 1920, 53, 1211. 

5- Aminoindazole (5-Aminobenzpyrazole) . 
Needles. M.p. 181. 

5-TS-Acetyl : cryst. from H 2 0. M.p. 165. 
5-N-p-Aminobenzenesulphonyl : m.p. 248. 
N*-Acetyl : m.p. 250-2. 

Fries, Tampke, Ann., 1927, 454, 306. 

G-Aminoindazole (6-Aminobenzpyrazole) . 

Needles from H 2 0. M.p. 210. Sol. boiling 
H 2 0. Mod. sol. EtOH. Sublimes. Strong base. 

B&HCI : needles. Decomp. at 230. 

6-N-^.cefa/Z : needles from EtOH.Aq. M.p. 
248. Sol. EtOH. Distils undecomp. 

Diacetyl deriv. : needles from EtOH.Aq. M.p. 
184-5. 

6-N-ip-Aminobenzenesulphonyl : m.p. 195-6. 
W-Acetyl : m.p. 245-6. 

Witt, Nolting, Grandmougin, Ber., 1890, 
23, 3640. 

7- Aminoindazole (7 ' -Aminobenzpyrazole) . 

Leaflets from EtOH.Aq. M.p. 155-6. Sol. 
EtOH, C 6 H 6 . Spar. sol. H 2 0, ligroin. Turns 
red in air. FeCl 3 + HC1 > red col. > violet. 

~N-Diacetyl deriv. : needles or prisms from 
EtOH. M.p. 161. 

l-N-p-Aminobenzenesulphonyl : m.p. 254-6. 
TX*-Acetyl : m.p. 258-60. 

Nolting, Ber., 1904, 37, 2577. 

2-Aminoindole (a.-Aminoindole, a.-indolyl- 
amine, 2-indolylamine) 




C 8 H 8 ISr 2 MW, 132 

Prisms from EtOH. Sol. EtOH. Mod. sol. 
hot H 2 0. Spar. sol. Et 2 O, C 6 H 6 . Aq. sol. 
reacts alkaline. Turns violet in air. Na + 
EtOH > indole. 

2-"N-Acetyl : 2-acetylaminoindole. M.p. 167. 

Diacetyl deriv. : greenish needles from MeOH. 
M.p. 142. Warm K 2 C0 3 > mono-acetyl 
(above). 

Pschorr, Hoppe, Ber., 1910, 43, 2543. 

3-Aminoindole ($-Aminoindole, $-indolyl- 
amine, %-indolylamine). 

Leaflets from H 2 0. M.p. 117 decomp. 

S-N-Acetyl : plates from EtOH. M.p. 162-3 
decomp. 

Madelung, Ann., 1914, 405, 92. 



6-Aminoindoie 



100 



3-Aminoisonicotinic Acid 



6-Axninoindole (6-Indotylamine). 
Amorph. ppt. Very unstable. 
JB,HCl : pale yellow needles. 

Majima, Kotake, Ber., 1930, 63, 2241. 

l-Amino-2~[3-indolyl]-propionic Acid. 

See Tryptopban. 
2-Aminoisoarayl Alcohol. 

See Valinol. 

1-Aminoisoanthraflavic Acid (2 : 1-Di- 
hydroxy- 1 'aminoanthraquinone) 
CO JSTH 2 




C U H 9 4 N MW, 255 

Greenish black cryst. from EtOH. Sol. alkalis 
with purple col. 

Perkin, J. Chem. Soc., 1878, 33, 216. 

1- Aminoisobutane . 

See Isobutylamine, 
1-Aminoisobutylacetic Acid. 

See Leucine. 

a-Aminoisobutylbenzene (\-Phenylisobutyl- 
amine) 

C 6 H 5 -CH(NH 2 )-CH(CH 3 ) 2 
C 10 H 15 N MW, 149 

B.p. 214. D? 0-920. < 1-51226. 
B,HCl : m.p. 275-7 decomp. 
Bto(COOH)i : m.p. 120-2 decomp. 
Picrate : yellow needles. M.p. 166-8. 

Konowalow, Ber., 1895, 28, 1859. 

p-Aminoisobutylbenzene (-p-Isobutylam- 
line) 

CH 2 -CH(CH 3 ) 2 




NH 2 
C 10 H 15 N MW, 149 

Pale yellow liq. B.p. 235-6/762 mm. Misc. 
with usual org. solvents. Almost insol. H 2 0. 

N-Acetyl : plates from EltOH. M.p. 127-8. 

'N-p-Toluenesulphonyl : prisms from EtOH. 
M.p. 136-7. Sol. MeOH, Et 2 0, C 6 H 6 , AcOEt. 
Spar. sol. CC1 4 , pet. ether. 

Hickinbottom, Preston, J. Chem. Soc., 
1930, 1569. 

1-Aminoisobutyric Acid 



MW, 103 

Prisms from H 2 0, Sublimes at 280 without 
molting. Sol. H 2 0. Spar. sol. EtOH. Insol. 
Et 3 0. HN0 2 > 1-hydroxyisobutyric acid. 

Sweet taste. 



Me ester : C 5 H 13L 2 N. MW, 117. B.p. 136 / 
749 mm., 45/20 mm. DJ 2 0-9787. BJSCl: 
m.p. 183. Sol. HoO, EtOH. 

Et ester: C 6 H 13 6 2 N. MW, 131. B.p. 38-5- 
41/llmm. Di 7 1-0974. n 17 1-4169. ^-Acetyl : 
prisms from Et 2 0. M.p. 88. 

Nitrile : C 4 H 8 N 2 . MW, 84. Oil. B.p. 51-2 / 
15 mm., 49-50/12 mm. Df 9 0-8899. Sol. H 2 O, 
EtOH, Et 2 0, C 6 H 6 . Aq. sol. reacts alkaline" to 
litmus. B,HCl: needles from EtOH-Et 2 O. 
M.p. 144-6. ~N-Acetyl : plates or needles from 
Et 2 0. M.p. 106. 

Amide : C 4 H 10 ON 2 . MW, 102. Cryst. from 
CHCl 3 -pet. ether. M.p. 127. Sol. H 2 0, EtOH. 
Spar. sol. pet. ether. B,HBr : cryst. from 
EtOH.Aq. M.p. 200-10 decomp. 

N-Benzoyl : m.p. 202 decomp. 

Dubsky, Wensink, Ber. } 1916, 49, 1139. 
Zelinsky, Stadnikow, J5er., 1906, 39, 1726. 
Jacobson, J. Am. Chem. Soc., 1946, 68, 
2628. 

2-Aminoisobutyric Acid (u-Methyl-$-alan- 
ine) 



C 4 H 9 2 N MW, 103 

White cryst. from H 2 0. M.p. 177 (182). 
Found in urine. 

Et ester : b.p. 71/13 mm., 356/l mm. 
Picrate : m.p. 108-9. 

Clemo, Melrose, /. Chem. Soc , 1942, 424. 
Pollack, J. Am. Chem. Soc., 1943, 65, 

1335. 
Grumpier et al, Nature, 1951, 167, 307. 

1-Aminoisocaproic Acid. 

See Leucine. 
Aminoisohexane - 

See 2-Methyl-^-amylamine, 4-Amino-iJ- 
mothyl-^-pentane and Isohexylamino. 
2-Aminoisohexyl Alcohol. 

See 2-Amino-4-mothyl-n-amyl Alcohol. 
3-Aminoison.icptiixic Acid (3-Aminopyrid- 
ine-^carboxylic acid) 

OOOH 




6 H e O^T a MW, 138 

Prisms from H 2 0. M,p, 306-10 (292) 
decomp. Sol. boiling H 2 0, EtOH. Sol. acids, 
bases. Sublimes. Distil with lime ->3- 
aminopyridine. 

B,HCl : prisms. M.p. 244-5 dooomp. 

BtHNO^ : yellowish needles. M.p. 196-7. 

Me ester: C 7 H 8 O a N a . MW 9 152. Yellow 
needles from pet, other. M.p. 86-7* Aq, HO!. 
deposits a hydrate, m.p. 50 (rapid boat*). 

Gabriel, Colman, JBer., 1902, 35, 2832. 



Aminoisopentane 

Amin oisopentane . 

See Amino-2-methyl-w-butane. 

2-Aminoisophthalic Acid 

COOH 



101 



1 - AminoisoqTiinoline 




J-XJ-J-Q 

COOH 
C 8 H 7 4 N MW, 181 

Yellow plates from EtOH. M.p. above 260. 
Sol. EtOH, Et 2 0. Mod. sol. H 2 0. 

"N-Acetyl : needles from EtOH.Aq. Decomp. 
at 205-6. 

Noelting, Gachot, Ber., 1906, 39, 74. 

4-Aminoisophthalic Acid. 
Needles from H 2 0. M.p. 336-7. Sol. EtOH, 
hot AcOH. Mod. sol. Et 2 0, Me 2 CO. Spar. sol. 



H 2 0. 



l-Me ester: C 9 H 9 4 N. MW, 195. Cryst. 
from EtOH. M.p. 224-5 decomp. Jc = 4-4 x 
10- 5 at 25. N-Acetyl : m.p. 218-19. k = 6-9 x 
10- 4 at 25. 

3-lfe ester : cryst. from MeOH. M.p. 228- 
30 decomp. Jc = 2-67 x 10~ 5 at 25. 

Di-Me ester: C 10 H U 4 K MW, 209. Needles 
from EtOH. M.p. 131-5. N-Acetyl : cryst. 
from MeOH. M.p. 126. ^-Benzoyl : needles 
from C 6 H 6 . M.p. 132. 

l-Et ester: C 10 H U 4 N. MW, 209. Cryst. 
from EtOH. M.p. 216-18. k = 4-0 X 10~ 5 at 
25. TX-Acetyl: cryst. from EtOH. M.p. 193-4. 

Di-Et ester : C 12 H 15 4 N. MW, 237. Cryst. 
from EtOH. M.p. 79-80. J$-Acetyl : needles 
from EtOH. M.p. 109-10. 

N-Acetyl: cryst. from H 2 0. M.p. 295-6 
decomp. 

N-Jfe: C 9 H 9 4 N. MW, 195. Cryst. from 
EtOH. M.p. 298 decomp. Sol. EtOH. Spar, 
sol. H 2 0, Et 2 0, xylene. Insol. CHC1 3 , C 6 H 6 , 
ligroin. l-Me ester: C 10 H n 4 N. MW, 209. 
Cryst. from MeOH. M.p. 244-5 decomp. 
Di-Me ester: C n H 13 4 N. MW, 233. Cryst. 
from MeOH. M.p. 115. Volatile in steam. 
N-Acetyl: needles from H 2 0. M.p. 223 de- 
comp. Jc (first) = 7-2 x 10 4 , Jc (second) = 
5-6 x 10 5 at 25. 

"8-Di-Me: C 10 H n 4 N. MW, 209. Cryst. 
from EtOH. M.p. 285 decomp. Jc = 2-65 x 
10~* at 25. l-Me ester: C n H 13 4 N. MW, 
223. Prisms from C 6 H 6 . M.p. 180. Jc = 
5-6 X 10~ 7 at 25. 3-Jfe ester : plates from 
C 6 H 6 . M.p. 190. Di-Me ester: C 12 H 15 4 N. 
MW, 237. Plates from EtOH. M.p. 71. 

UUmann, Uzbachian, Ber., 1903, 36, 1804. 
Wegscheider, Monatsh., 1916, 37, 219. 
Wegscheider, Malle, Ehrlich, Skutezky, 
Monatsh., 1918, 39, 375, 

5-Aminoisophthalic Acid. 

Prisms from EtOH. M.p. above 300. Sol. 
962 parts H 2 at 15, 108 parts at 99. EeCl 3 
>- reddish -brown col. 



N-Acetyl : red needles from H 2 0. Decomp. 
at 314-15. 

N-Benzoyl : prisms from AcOH. Decomp. 
above 360. 

Di-Me ester : plates from MeOH. M.p. 176. 
Sol. Et 2 with violet-red fluor. Spar. sol. H 2 0. 

Di-Et ester : plates from EtOH. M.p. 118. 
Sol. Et 2 with violet-red fluor. Spar. sol. H 2 . 

Meyer, Wesche, Ber., 1917, 50, 450. 

1-Aminoisopropyl Alcohol (l-Amino- 
propanol-2, isopropanolamine, 2-Jiydroxy-n- 
propylamine) 

CH 3 -CH(OH)-CH NH 2 
C 3 H 9 ON - MW, 75 

Z-. 

[a] D about 25-5. 

B 2 ,H 2 PtCl 6 : yellow needles"^from EtOH. 
M.p. 198 decomp. [a - 12-2. 

dl-. 

B.p. 160-1 /750 mm. D 18 0-973. Sol. H 2 0. 
B,HCl : cryst. from EtOH-AcOEt. M.p. 
72-5-74. 

'B^H^PtClQ : yeUow leaflets. M.p. 195. 
'N-CJiloroacetyl : cryst. M.p. 33-4. B.p. 
131-2/0*6 mm. 
Picrate : yellow cryst. M.p. 142. 

Levene, Kuna, J. Biol. OJiem., 1936, 113, 

153. 
Levene, Scheidegger, J. Biol. Chem., 

1924, 60, 179. 
Levene, Walti, J. Biol. Chem., 1927, 71, 

461. 
Brachfeld, Smola, Austrian P., 135,351, 

(Chem. Abstracts, 1934, 28, 1355). 
Karrer, Klarer, Helv. CJiim. Acta* 1925, 8, 
394. 

Aminoisopropylbenzene . 

See Cumidine. 

a- Aminoisopropylbenzene . 

See 1-Phenylisopropylamine. 

p- Aminoisopropylbenzene . 

See Phenylpropylamine. 

3-Amino-4-isopropylbenzoic Acid. 

See 3-Aminocuminic Acid. 

Aminoisopropyl Mercaptan. 

See 2-Mercaptopropylamine. 

1 -Aminoisoquinoline 




C 9 H 8 N 2 " MW, 144 

Plates from H 2 0. M.p. 122-3. Sol. EtOH. 
Spar. sol. Et 2 0. HN0 3 > isocarbostyril. 

B,HCl: m.p. 233. Sol. H 2 0, EtOH. Insol. 
Et 2 0. 

Bz,H 2 PtCl 6 ,2H 2 : orange needles. M.p. 
above 300. Spar. sol. H 2 0, EtOH, Me 2 CO. 

TS-Acetyl : m.p. 148-8-5. 



4-AminoisoquinoIine 



102 



Aminomalonic Acid 



N-Dibenzoyl : m.p. 223*5-4-5. 

N~ip~Aminobenzenesulphonyl : m.p. 264-7. 
W-Acetyl : m.p. 246-7. 

Picrate : yellow cryst. M.p. 290-1. Spar, 
sol. H 2 0, EtOH, Me 2 CO. 

Bergstrom, Ann., 1934, 515, 34. 
Tschitschibabin, Oparina, Chem. Zentr., 

1923, III, 1023. 
Craig, Cass, J. Am. Chem. Soc. 9 1942, 64, 

783. 

4- Aminoisoquinoline . 

M.p. 108. 

N-Acetyl : m.p. 167-8. 
N-Benzoyl : m p. 188-9. 
N-p-Aminobenzenesulphonyl : m.p. 21 1 5- 
212-5. W~Acetyl : m.p. 304-6 decomp. 

Bergstrom, Rodda, J. Am. Chem. Soc., 

1940, 62, 3030. 
Craig, Cass, J. Am. Chem. Soc., 1942, 64, 

783. 

S-Aminoisoquinoline . 

Needles from pet. ether. M.p. 128. 

~N-Acetyl : m.p. 166. 

N-Benzoyl : m.p. 158-9. 

"N-p-Aminobenzenesulphonyl ; m.p, 223-4 
decomp. W-Acetyl : m.p. 284-8 decomp. 

B,HCl : needles. M.p. 220 decomp. 

Picrate : yellow cryst. Decomp. above 200. 

Methochloride : yellow needles from ELO. 
M.p. 288 decomp. 

Methiodide : yellow needles from EtOH. 
M.p. 228. 

Ethiodide : yellow needles. M.p. 216. 

Claus, Gutzeit, J. prakt. Chem,, 1895, 52, 
18. 

Tyson, J. Am. Chem. Soc., 1939, 61, 183. 
Craig, Cass, J. Am. Chem. Soc., 1942, 64, 

783. 

8-Aminoisoquinoline . 

M.p. 174. 

Robinson, J. Am. Chem. Soc., 1947, 69, 
1944. 

l-Amiaoisovaleric Acid. 
See Valine. 
2-Aminoisovaleric Acid 

(CH 3 ) 2 C(NH 2 )-CH 2 -COOH 
C 5 H U 2 N MW, 117 

Cryst. + H 2 from EtOH.Aq., needles (an- 
hyd.) from Et 2 0~EtOH. M.p. 217. Very sol. 
H 2 0. Spar. sol. EtOH. Insol. Et 2 0. Sweet 
taste. 

,HCl: needles + H 2 0. M.p. 120. Sol. 
BL>0,EtOH. Insol. Et 2 0. 

M ester : CJH 15 2 N. MW, 145. B.p. 1707 
760 mm. s 76 b /22 mm. Df 0-8165. ,HCl: 
m.p. 75. Very hygroscopic. 

Slimmer, Ber., 1902, 35, 408. 




2-Aminolactic Acid. 

See Isosenne. 

2-Aminolepidine (2-Amino-4:-methylquinol- 

ine) 



IKBL 



C 10 H 10 N 2 MW, 158 

Cryst. from C 6 H 6 . M.p. 133. B.p. 320. 
Sol. EtOH, Et 2 0, AcOH, CHC1 3 , hot C 6 H 6 . 
Spar. sol. H 2 0. Not volatile in steam. 

Sulphate : needles from dil. HoS0 4 . M.p. 
155. 

B 2 ,H z PtCl Q : orange needles. M.p. 230. 

Picrate : yellow needles. M.p. about 250. 

N-Phenyl : plates from EtOH. M.p. 129-30. 

Ephraim, Ber. y 1892, 25, 2707. 

5-Aminolepidme (5~Amino-4c-methylquino- 
line). 

Pale yellow. M.p. 82-5-3-5. 
BJELCl : yellow. M.p. 285-9 decomp. 

Krahler, Burger, J. Am. Chem. Soc., 1941, 
63, 2367. 

6-Aminolepidine (Q-Amino-4:-methylquino- 
line). 

Needles from H 2 0. M.p. 169-70. Sol. 
EtOH, CHC1 3 . Mod. sol. Et 2 0, hot H 2 0. 

Chloroplatinate : cryst. M^.p. above 300. 

Busch, Koenigs, Ber., 1890, 23, 2685. 

8-Aminolepidine (ti~AminoA~methylquino- 
line). 

M.p. 84. 

Johnson, Hamilton, /. Am. Ohem. Soc., 
1941, 63, 2864. 

Aminolutidine . 

See 4-Amino-2 ; 6-dimethylpyridino. 

Araiuomalonic Acid 



C 3 H 5 4 N MW, 119 

Prisms + H 2 0. M.p. 109 with oflbrvoHOonoe 
* glycine + C0 2 - Loses water of cryst, in 
desiccator. Spar. sol. EtOH. Boiling H 2 -> 
glycine. k = 7-74 X 10* 4 at 26, Iodine ~-> 
mesoxalic acid. 

Di~Me ester ; C 6 H.0 4 N. MW, 147. B,HCl : 
leaflets from MoOH-Et ft (). M.p. 159. N- 
Pormyl : cryst. from MoOH. M.p, 85. Spar. 
sol. KtftO. 

Di+Et ester; C 7 H p 4 N. MW, 175. B.p. 
116-18 G /12 mm. Sol H/3 org. Bolvontn, 
Absorbs C0 2 . BJELCl : needles from Mo-OO. 
M.p. 162 decomp. JS,(COOH) a : needles. M.p. 
138. Sol H 2 0, EtOH. Insol. Et,0, ligroin. 



Aminomentliane 



TS-Farmyl: m.p. 48. TS-Acetyl : m.p. 95-6. 
~N-Benzoyl : cryst. from pet. ether. M.p. 61. 
N-Carbethoxyl : needles from EtOH.Aq. M.p. 
163. 

Diamide : aminomalonamide. C 3 H 7 O 2 NQ. 
MW, 117. Needles from EtOH. M.p. 167 
(192). TS-Formyl: prisms from EtOH.Aq. 
M.p. 214 decomp. N-Carbethoxyl : leaflets 
from EtOH. M.p. 178. 

Locquin, Cerchez, Compt. rend., 1928, 186, 

1360. 
Levene, Schormiiller, J. Biol. Chem., 1934, 

106, 600. 
Johnson, Nicolet, J. Am. Chem. Soc., 

1914, 86, 361. 

Aminomentliane . 

See Menthylamine. 

a-Amino-p-mercaptoisovaleric Acid. 

See Penicillamine. 

Aminomercaptopropionic Acid. 

See Cysteine and Isocysteine. 

Aminomesitylene . 

See Mesidine and 3 : 5-Dimethylbenzylamine. 

Aminomesitylenic Acid. 

See Amino-3 : 5-dimethylbenzoic Acid. 

Aminomethoxybenzoic Acid. 

See under 4-Hydroxy-m-aminobenzoic Acid, 
3-, 4-, 5-, and 6-Hydroxyanthranilic Acids, and 
3- and 5-Aminosalicylic Acids. 

Amino-iV-metlxylacetanilide . 

See under JV-Methylphenylenediamine. 

Amino-methylamino-valeric Acid. 

See under Ornithine. 

2-Amino-4-methyl-n-amyl Alcohol (1- 
Hydroxy-2 -amino-k-methyl-n-pentane, 2-amino- 
isohexyl alcohol, leucinol) 

(CH 3 ) 2 CH-CH 2 'CH(NH 2 )-CH 2 OH 
C 6 H 15 ON " MW, 117 

B.p. 198-200/768 mm. Sol. H 2 0, EtOH. 
Spar. sol. Et 2 0. D 13 0-9173. 

Picrolonate : yellow cryst. Decomp. at 245- 

7. 

d-. 

B.p. 98-9/H nun. 

Oxalate : m.p. 216. [aft 7-0. 

Z-. 

B.p. 98-9/ll Him. 

Oxalate : m.p. 216. [>]> + 7-0. 

Picrate : m.p. 120-1. [a]| 6 + 5-9 in MeOH. 

Mousset, Chem. Zentr., 1902, 1, 400. 
Karrer, Karrer, Thomann, Horlacher, 

Mader, Helv. Chim. Acta, 1921, 4, 90. 
Enz, Leuenberger, Helv. Chim. Acta, 1946, 

29, 1048. 
Adkins, Pavlic, J. Am. Chem. Soc., 1947, 

69, 3039. 

Amino-me thylaniliixe . 

See Methylphenylenediamine. 



103 4-Amino-3-inetliyIbenzoplienone 

l-Ajnino-2-inethylantliraqtiinone 

CO 




CisHnOgN MW, 237 

Eed needles from EtOH or PKN0 2 . M.p. 
205. Sol. EtOH, CHC1 3 . C 6 H 6 , AcOH. Spar, 
sol. Et 2 0. Insol. H 2 0. 

18-Phenyl : l-aniIino-2-methylanthraquinone. 
C 21 H 15 2 N. MW, 313. Violet needles from 
AcOH. M.p. 229-5. Sol. C 6 H 6 , toluene. 

'N-Acetyl : light red needles from AcOH. 
M.p. 176-7. 

N-Diacetyl : m.p. 203-6. 

"N-p-Toluenesulphonyl : yellow prisms from 
AcOH. M.p. 218. Sol. AcOH, C 6 H 6 . Insol. 
EtOH, Et 2 0. 

Ullmann, Bincer, Ber., 1916, 49, 742. 

3- Amino-2-methylanthr aquinone . 
Orange-red needles from PhN0 2 . M.p. 258-9. 

A.G.F.A., D.R.P., 281,010 (Chem. Zentr., 
1915, 1, 32). 

5-Amino-2-methylbenzophenone (Phenyl 
5-amino-o-tolyl Icetone) 

H 3 C 




C 14 H 13 ON MW, 211 

B,HCl : m.p. 120-50. 

Bt,H 2 SO: needles + |H 2 0. M.p. anhyd. 
147-9. 
yS-Benzoyl: needles from EtOH. M.p. 136-8. 

Hanschke, Ber., 1899, 32, 2029. 

2 / -Amino-2-methylbenzophenone (2- 

Aminophenyl o-tolyl Jcetone). 
Bright yellow needles. M.p. 84. 
TS-Acefyl : m.p. 104. 

Inagak, Chem. Abstracts, 1939, 33, 3791. 
Lothrop, Goodwin, J. Am. Chem. Soc., 
1943, 65, 363. 

4-Amino-3-meth.ylbenzoplienone (Phenyl 
4:-amino-m-totyl ketone). 

Pale yellow prisms from H 2 0. M.p. 112. 
Sol. EtOH. Spar. sol. H 2 0. 

B,HCl : plates. M.p. 215-20 decomp. 

2 ,# 2 4 : plates. Decomp. at 105-10. 

TS-Acetyl : plates from EtOH. M.p. 175. 

J$-Propionyl : needles from EtOH. M.p. 128. 

N-Benzoyl : prisms from EtOH. M.p. 158. 
Chattaway; Lewis, J. Chem. Soc., 1904, 
85, 590. 



6-Amino~3-raetliyIbenzoplienone 



G-Ammo-S-metliylbenzophenone 

6-amino-m-tolyl ketone). 

Yellow needles or hexagonal plates. M.p. 
66. Sol. EtOH, Et 2 0, Me 2 CO, AcOH, CHC1 3 , 
pet. ether. 

B,HCl : m.p. 195-7 (179-80). 
N-Acetyl : plates from EtOH. M.p. 159. 
N-Propionyl : plates from EtOH. M.p. 99. 
N-Benzoyl : needles from EtOH. M.p. 118. 
Picrate : yellow prisms from EtOH. M.p. 
145. 

Hanschke, Ber., 1899, 32, 2023. 
Chattaway, Lewis, J. Chem. Soc.. 1904, 
85, 594. 

2 / -Amino-3-metliylbenzophenone (2- 

Aminophenyl m-tolyl ketone). 
Yellow needles from MeOH.Aq. M.p. 57. 
Lothrop, Goodwin, J. Am. Chem. Soc., 
1943, 65, 363. 

2-Amino-4- methylbenzophenone (Phenyl 
2-amino-p-tolyl ketone ) . 
Yellow needles from pet. ether. M.p. 66. 
Ritchie, Chem. Abstracts, 1947, 41, 3094. 

3-Amino-4-methylbenzophenone (Phenyl 
3-amino-j)-tolyl ketone). 

Yellow needles from MeOH. M.p. 109. Sol. 
Et 2 0, C 6 H 6 , CHC1 3 . 

B,HBr : needles from dil. HBr. M.p. 130. 

N-Acetyl : needles from MeOH. M.p. 108. 
Weis, Monatsh., 1928, 50, 109. 

2'-Amino-4-methylbenzophenone (o- 

Aminophenyl p-tolyl ketone). 

Yellow prisms or plates from EtOH. M.p. 
96. Sol. EtOH, Et a O, C 6 H 6 . 

Picrate : m.p. 146. 

Kippenberg, Ber., 1897, 30, 1133. 

3'-Amino-4-methylbenzophenone (m- 

Aminophenyl p-tolyl ketone). 
Prisms from EtOH. M.p. 111. Sol. EtOH, 



104 4-Amino-5-methyl-2 : 6-diethyl- 

pyrimidine 

(Phenyl 2-Amino-2-methyl-n-butane (tert.-J.m^Z- 
amine, 2-aminoisopentane) 

CH 3 -CH 2 -C(CH 3 ) 2 -NH 2 

C 5 H 13 N MW, 87 

B.p. 77-8. Misc. with H 2 0. Dl 0-756, DJ 5 
0-731. 

Wyschnegradsky, Ann., 1874, 174, 60. 

3-Amino-2-methyl-n-butane (3-Aminoiso - 
pentane) 

CH 3 -CH(N-H 2 )-CH(CH 3 )-CH 3 



B,HCl : needles. M.p. 198. 
BvfltaOi : needles. M.p. 142. 
yC~Ac&yl : prisms from EtOH. M.p. 139. 
Oxime : prisms from EtOH. M.p. 146. 
Limpricht, Lenz, Awn., 1895, 286, 312. 

4'-Am.inO"4-metliylbeiizoplxenone (p- 

Aminophenyl p~totyl ketone). 

Cryat. from C 6 H . M.p. 186-7. Sol. EtOH, 
CHCLj, CS 8 . Spar. sol. pot. ether. 
BtoH 2 80t : plates. M.p. 210-16 dooomp. 
N-Acelyl : plates from Et 2 0. M.p. 155. 
PhenylJiydrazone : brownish-red cryst, from 
KtOH. M.p, 163. 

Limpricht, Samiote, Ann., 1895, 286, 325. 
Limpricht, Lorn;, Ann., 1895, 286, 312. 

l-Amino-2metlxylbutaiie . 

See 2-Methyl-n-bxitylamino. 



C 5 H 13 N 

B.p. 84-7. D 19 0-7574. HN0 2 
Isopropylcarbinol. 

B<,(COOH) Z : cryst. M.p. 220. 

Trasciatti, Gazz. chim. itaL, 
II, 95. 



MW, 87 
> methyl- 

1899, 29, 
(Isoamyl- 



4~Amino-2-methyl-n-butane 

amine, 4-aminoisopentane, isopentylamine) 

H 2 N-CH 2 -CH,-CH(CH 3 ) 2 
C 5 H 13 N * MW, 87 

B.p. 95. Misc. with H 2 0. D 18 0-751. ng 
14096. 4 = 5 X KHat25. 

'N-Acetyl: JV-isoamylacet amide. B.p. 230-2 
(238). 

Erickson, Ber., 1926, 59, 2665. 

1 - Amino-1 -meth.yl-i-butyric Acid . 

See Isovaline. 

1- Amino-1 -methylcyclopentane ( 1 -Methyl- 
cydopentylamine) 



MW, 99 

B.p. 120-2. Sol. H 8 0. D 20 0-8025. 
BjHAuClft : m.p. 173 dooomp. 

Markownikow, Ann., 1899, 307, 371. 

2- Amino-1 -methy Icy clopent ane ( 2 -Methyl- 

cydopentylamine) . 

B.p. 123. Spar. sol. H 2 0. J>3 0-801. 
Markownikow, Ann., 1899, 307, 371. 

3- Amino-1 -methylcy clopentane ( 3 -Methyl- 

cydopentylamine) . 

B.p. 124. Misc. with H 2 0. J)J 0*8422. 

]$-Benzoyl : needles from EtOll.Aq. M,p. 
115-17. Very sol. KtOH. 

Markownikow, Ann., 1899, 307, 340 

4-Amino-5-metliyl-2 : 6-dietliylpyriiaid- 
ine (* 

Cyanethim) 




N?..OC,H B 

MW, 166 



a-Aminometliyl-3 : 4-dihydroxypIienyI~ 1 05 

carbinol 

Cryst. from H 2 or EtOH. M.p. 189. B.p. 
280 decomp. Aq. sol. weakly alkaline. Sol. 
18 parts EtOH at 17. Acid KMn0 4 ^ formic 
acid -f ammonia. Forms cryst. nitrate and 
hydrochloride. Gives add. comp. with AgNO*. 

'N-Acetyl : m.p. 59. 

Meyer, J. praJct. Chem., 1888, 38, 584. 



a - Aminometliyl -3:4- di&ydroxyphenyl- 
carbinol. 

See Arterenol. 

6-Amino-2-met]iyldiphenyl (Phenyl-6- 
amino-o-tolyl) 

H 3 C 



MW, 183 

Sol. most 




B.p. 144-5/2 mm. 



M.p. 43-4 
org. solvents. 

Sadler, Powell, J. Am. Ghem. Soc., 1934, 
56, 2652. 

4-Ammo~3-methyldiphenyl (Phenyl-4:- 
amino-m-tolyl). 

M.p. 43. B.p. 190-1/15 mm. Misc. with 
most solvents. FeCl 3 >- green col. 

'N-Acetyl: cryst. from EtOH. M.p. 165-5 
(158). Sol. most org. solvents. Spar. sol. cold 
C 6 H 6 , pet. ether. 

N-Benzoyl : m.p. 189. 

Benzylidene : yellow leaflets from EtOH. 
M.p. 108-5. 

I.G., P.P., 739,052, (Chem. Zentr., 1933, 

II, 1255). 
Pummerer, Binapfl, Schuegraf, Ber., 1922, 

55, 3099. 

2-Amino-4-methyldiphenyl (Phenyl~2- 
amino-p-tolyl) . 
B.p. 183/11 mm. 
N-Acetyl : m.p. 150-5-1-5 . 
N-Benzoyl : needles. M.p. 92. 
Picrate : golden needles. M.p. 161 decomp. 

Petrow, J. Chem. Soc., 1945, 18. 
Ritchie, Chem. Abstracts, 1946, 40, 880. 

2'-Amino-4-methyldiphenyl (2-Amino- 
phenyl-p-tolyl). 

N-Benzoyl : cryst. M.p. 121. 

v. Braun, Chem. Zentr., 1909, II, 1993. 



4'-Amino-4-methyldiphenyl ( 

phenyl-p-tolyl). 

Cryst. from ligroin. M.p. 99. B.p. 190 / 
18 mm. Very sol. EtOH, Et 2 0, Me 2 CO, C 6 H 6 , 
AcOH. Spar. sol. CC1 4 , CS 2 , ligroin. 

B,HCl : cryst. M.p. 280-3. 

'N-Acetyl : cryst. from AeOH. M.p. 221. 

Kliegl, Huber, Ber., 1920, 53, 1650. 



2 / -Amino-4-metliyldiplieiiylainine 



4-Amino-2-metliyldiplienylaniine (o- 

Anilino~m-toluidine, 2-'N-phenyl-2 : 5-tolylenedi- 
amine) 




C 13 H 14 N 2 MW, 198 

Needles from pet. ether. M.p. 49-50. B.p. 
196-9/4 mm. Sol. most org. solvents. Cone. 
H 2 S0 4 > reddish-violet col. 

B,HCl : m.p. 185-7. 

N-Acetyl : needles from hot H 2 0. M.p. 139- 
40. 

Joszt, Lesnianski, Chem. Zentr., 1930, II, 
3275. 

5-Amino-2~methyldiphenylamine (o- 
Anilino-p-toluidine, 2-"N-phenyl-2 : 4:-tolylenedi- 
amine). 

Cryst. from H 2 0. M.p. 93-5. 

Weiss, Katz, Monalsh., 1928, 50, 230. 

4 / -Amino-2-methyldiphenylamine (p- 
Aminophenyl-o-tolylamine, o-tolyl-p-phenylenedi- 
amine). 

Leaflets from ligroin. M.p. 58-9. Sol. EtOH, 
Et 2 0, C 6 H 6 . Spar. sol. ligroin. Insol. H 2 0. 

UUmann, Dahmen, Ber., 1908, 41, 3750. 

4-Ammo-3-methyldiphenylamiixe (m- 

Anilino-O'toluidine, 5-'N-phenyl-2 : 5~tolylenedi- 
amine). 

M.p. 77-8 (70-1). 

I. G., D.R.P., 592,201, (Chem. Abstracts, 

1934, 28, 3419). 

Gen. Aniline Works, U.S.P., 1,900,426, 
(Chem. Abstracts, 1933, 27, 2963). 

6-Amino-3-methyldiphenylamme (m- 

Anilino-p-toluidine, 3-'N-phenyl-3 : 4-tolylenedi- 
amine). 

Needles from ligroin. M.p. 87-8. Sol. EtOH, 
Et 2 0, C 6 H 6 . Spar. sol. ligroin. 

Schraube, Ber., 1893, 26, 581. 

2-Amino-4-methyldiphenylamme (N-4- 
Phenyl-% : 4c-tolylenediamine, p-anilino-m-toluid- 
ine] . 

Needles from 20% EtOH. M.p. 140. 

B,HCl : needles. M.p. 200-1. 

N-Benzoyl : cryst. from EtOH. M.p. 161. 

Borsche, Feise, Ber., 1907, 40, 384. 

3-Amino-4-methyldiphenylamine (p- 

Anilino-o-toluidine, &~'N-phenyl-2 : 4c-tolylenedi- 
amine). 

Prisms from ligroin. M.p. 76-7. 

Bayer, D.R.P., 80,977. 

2 / -Amino-4-methyldiplienylaniine (o- 

Aminophenyl-p-tolylamine, p-tolyl-o-phenylenedi- 
amine). 



4 / -Amino-4-methyldipIieiiylainine 



106 



4-Ammo-2-methyl-n-pentane 



Leaflets from ligroin. M.p. 77. Sol. EtOH, 
Et 2 0, C 6 H 6 . Spar. sol. hot H 2 0. FeCl 3 on 
HC1 sol. >- reddish -violet col. 

*N-Benzoyl : needles. M.p. 143-4. 

Borsche, Feise, Ber., 1907, 40, 383. 

4 / -Arnino-4-methyldiplienylainine (p- 

Aminophenyl-p-tolylamine, p-tolyl-p-phenylenedi- 
amine). 



5-Amino~4-metliyl-l-hexe:ae 

CH 3 -CH(NH 2 )'CH(CH 3 )-CH 2 -CH:CH 2 
C 7 H 15 lSr MW, 113 

B.p. 133-6. D 15 0-793. 

B 2 ,H 2 PtCl 6 : orange plates. M.p. 157-8 de- 
comp. Sol. H 2 0. 

Jacobi, Merling, Ann., 1894, 278, 12. 

6-Amino-4-methyl-l-liexene or 6-Amino- 



Ullmann, Dahmen, Ber., 1908, 41, 3751. 
Gen. Aniline Works, U.S.P., 1,900,426, 
(Ghem. Abstracts, 1933, 27, 2963). 

3-Ammomethylenecamplior 

*3 




C U H 17 ON 



MW, 179 



Trans or x-form : 

Prisms from EtOH. M.p. 157. Sol. MeOH, 



H 2 N-CH 2 -CH 2 -CH(CH 3 )-CH 2 -CH:CH 2 

or 

H 2 N-CH 2 -CH 2 -CH(CH 3 )-CH:CH-CH 3 
C 7 H 15 N MW, 113 

B.p. 145-50. 

B,(COOH) 2 : cry^t. + |H 2 from EtOH. 
M.p. 150. 

Wohl, Maag, Ber., 1910, 43, 3289. 

Aminomethylhy dr indene . 

See Methylhydrindamine and Neomothyl- 
hydrindamine. 

Arninometliyl hydrogen sulphite 

H 2 N-CH 2 -0-S0 2 H 



EtOH, CHC1 3 , C 6 H 6 . Insol. ligroin. [aft CH 5 3 NS 



+ 257-32 in EtOH. Distil at 153~4/10-5 mm. 

> (5 -form. 

N-Benzoyl : needles from EtOH. M.p. 208. 
Insol. H 2 0, ligroin. 

J3-p-Nitrobenzoyl : yellow leaflets from C 6 H 6 . 
M.p. 180-1. 

Gis or $-form : 

Prisms from EtOH. M.p, 156. [a]^ + 
313-76 in EtOH. More sol. than a-form. 
Very labile. 

N-Benzoyl : cryst. from EtOH. M.p. 112. 

'N-p-Nitrobenzoyl : orange needles with violet 
reflex from EtOH. M.p. 161-2. 

Z-. 

Prisms from EtOH. M.p. 152. 

dl.- 

Plates. M.p. 165. Sol. hot H 2 0, EtOH, 
C 6 H 6 , CHCLj. 
N-Me: m.p. 131. 
TS-lSt : m.p. 118. 

Singh, Bhadhuri, J. Indian Ghem. Soc., 

1932, 9, 112. 
Bupe, Seiberth, Kussmaul, Helv. Ghim. 

Ada, 1920, 3, 50. 

Aminomethylethylacetic Acid. 
See Isovaline. 

Aminomethyletliylbenzene - 
flee Ethyltoluidine. 
Aminomethylf uran . 
See Ifurfurylamine. 
4-Aminomethylgly oxaline - 
See 4-Iminazolylmothylamino, 



MW, 111 



Cryst. from H 2 0. Decomp. at 193. Spar, 
sol. cold H 2 0. Prac. insol. EtOH. Docomp. 
by NaOH or boiling H 2 0. 

Reinking, Dehnel, Labhardt, Ber., 1905, 
38, 1077. 

3-co-Aminomethylindole . 

See Indolylmothylamino. 
1-Aminoxnethylrnalonic Acid. 
See Isoaspartic Acid. 
AmmomethylnapMhalene . 
See Mothylnaphtliylamino and Naphthyl- 
methylaminc. 
1 -Amino-2-raethyl-n-octane 

OH s -[Cty 5 -OH(GH 3 )-OH 2 NH iJ 
C 9 H 21 N MW, 143 

B.p. 185-6. 

B,IIOl: noodloH. M.p. 130. 

Jftround, Schoufeld, Ber., 1891, 24, 3355. 

1 -Amino~2-methylpentan,e - 

See 2-Methyl-w-amylamitxo, 
4-Ammo-2-Knethyl-n-pentane (4-/1 mino* 
isohexane) 

CH 3 'CH(NH 2 )-(Jll 2 -(JE(()H a ) 2 
C 6 H 16 N MW, 101 

B.p. 100-3. 

B%,II%PtGl% : orango-yollow loafletn frotn H 2 0. 
M.p. 205 clocomp. 
Bto(QOOH)t : crynt, M.p. 219, 

Kerp, Ann,, 1896, 290, 149. 

Gulewitsch, Wasmus, Jer., 1906, 39, 1192* 



5-Amino-2-methyl-w-pentane 



107 



4-Amino-2-nietIiylpyTiniidiiie 



5-Amino-2-metliyl-n-pentane . 
See Isohexylamine. 
l-Amino-S-methylpentane . 
See 3-Methyl-7i-amylamine. 
2-Amino-2-methylpentanone-4. 
See Diacetonamine. 

2-Amino-3-methyl-2-pentenone-4 . 
See 2-Imino-3-methylpentanone-4. 
Aminomethylphenanthrene . 
See Phenanthrylmethylamine. 
Aminomethylphenylcarbinol. 
See a-Hydroxy- (3-aminoethylbenzene. 
4-Amino-3-meth.yl-l-phenylpyrazole 



2-Amino-6-methylpurine 



HC* 2 N 

N-C 6 H 5 
Cio H ii^3 MW, 173 

Needles from C 6 H 6 -pet. ether. M.p. 88. 
B.p. 312-13. Sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . 
Spar. sol. H 2 0. Insol. pet. ether. Sol. dil. 
acids. 

B,HCl : plates from EtOH-Et 2 O. M.p. 209. 
Sol. H 2 0. 

B 2 ,H 2 PtCl 6 : yeUow needles. M.p. 226. 

Pier ate : yellow needles from EtOH. M.p. 
138 decomp. 

N-Formyl : needles + 1H 2 from EtOH.Aq. 
M.p. 81, anhyd. 112-13. 

l$-Acetyl : needles + 1H 2 0. M.p. 94-5, an- 
hyd. 120. 

N-Benzoyl : needles from C 6 H 6 -pet. ether. 
M.p. 181. 

Michaelis, Schafer, Ann., 1915, 407, 238. 

5-Amino-3-methyl-l-phenylpyrazole (3- 

Methyl-l-phenylpyrazolone-5-imide) 



H 2 N-Cs 



or HN'.C 




-C 6 H 5 
C 10 H n N 3 MW, 173 

Needles or prisms from H 2 0. M.p. 116. 
B.p. 333, 197/16 mm. Sol. 50 parts boiling 
H 2 0, 20 parts boiling Et 2 0, 2 parts boiling 
CJEL. Sol. acids. Insol. alkalis. 

B,HCl : m.p. 199-200. Sol. H 2 0, EtOH. 

B,HAuCL: m.p. 90. Sol. EtOH. Insol. 
H 2 0. 

iS-Acetyl : cryst. M.p. 110. 

Picrate : m.p. 160-2 



5-N-JW: C 12 H 15 N 3 . 



315. 



MW, 201. Oil. B.p. 



: C 16 H 15 N 3 . MW, 249. Needles 
from EtOH.Aq. M.p. 124. B.p. 365-6. 
B } HG13H^O: m.p. 67, anhyd. 118. 
B 2) H^PtCl 6 .5H 2 : orange needles. M.p. 135. 
Mohr, J. praJct. Chem., 1909, 79, 16. 
Crippa, Caracci, Oazz, Mm. ital, 1940, 
70, 389. 




C 6 H 7 N 5 MW, 149 

Needles. M.p. above 300 decomp. Sol. hot 
H 2 0. Spar. sol. hot EtOH. 

Gabriel, Colman, Ber., 1901, 34, 1256. 



2-Amino-7-metliylpurme . 

Needles from H 2 0. M.p. 283. 
H 2 0. Spar. sol. EtOH, C 6 H 6 . 

Fischer, Ber., 1898, 31, 2555. 
2-Amino-9-methylpurine 



Sol. hot 



& : 



CH 3 
C 6 H 7 N 5 MW, 149 

Needles from H 2 0. M.p. 247. Sublimes. 
Sol. 2 parts boiling H 2 0, 6-8 parts boiling 
EtOH. Mod. sol. hot CHC1 3 , hot C 6 H 6 . 

B,HCl : plates. Sol. H 2 0. 

Fischer, Ber., 1898, 31, 2570. 

6-Amino-methylpurine . 

See Methyladenine. 

8- Amino-9-methylpurine . 

Prisms from H 2 0. Decomp. before melting. 
Aq. sol. neutral. 

B,HCl : needles. Sol. H 2 0. 

Fischer, Ber., 1897, 30, 1857. 

Aminomethylpyridine . 

See AminopicoHne. 

4-Amino-2-methylpyrimidiae (2-Methyl- 
pyrimidone-4:-imide ) 




C 5 H 7 N 3 MW, 109 

Cryst. from Me 2 CO. M.p. 205. Sol. H 2 
with alk. reaction. Sol. EtOH, Me 2 CO, C 6 H 6 . 

BflCl : pale yellow. M.p. 230. 

B,HNO^: prisms. Decomp. at 2 13-14. Mod. 
sol. H 2 0. 

B,HAuClt : needles. M.p, 203 decomp. Sol. 
hot H 2 0. 

Bt,H 2 PtCl e : m.p. 248-50 decomp. Sol. H 2 0. 

N-p-Aminobenzenesulphonyl : m.p. 207-8, 

Gabriel, Ber., 1904, 37, 3641. 



2-Ainino-4-rnetIiylpyriiiiidine 



108 



5-Arnino-6-niethylquinoline 



2-Amino-4-methylpyrImidine (4-Methyl- 
pyrimidone-2-imide) 

Plates from H 2 0. M.p. 159-60. 

N-jy-Aminobenzenesulphonyl : m.p. 236-8. 
W-Acetyl : m.p. 248. 

Gabriel, Colman, Ber., 1899, 32, 2925. 

Senary, Ber., 1930, 63, 2601. 

Northey, U.S.P., 2,378,318, (Chem. 

Abstracts, 1946, 40, 369). 
Dvornikoff, U.S P., 2,391,882, (Chem. 

Abstracts, 1946, 40, 1889). 

5-Amino-4~methylpyrimidine (4-Methyl- 
pyrimidone-5-imide) . 
M.p. 151-1-5. 

'N-p-Aminobenzenesulphonyl : m.p. 233-5-5 
decomp. N^-Acetyl : m.p. 246-7-5 decomp* 

Backer, Grevenstuk, Eec. trav. chim., 
1942, 61, 291. 



6-Amino-4-methylpyrimidine ( 

pyrimidone-Q-imide) . 

Prisms from H 2 0. M.p. 197-7-5 (194r-6). 
Sublimes. Sol. H 2 0. 

N-Phenyl : needles from H 2 0. M.p. 146. 

N-ip-Nitrobenzenesulphonyl : m.p. 204-5-6-5 . 

N-ip-Aminobenzenesulphonyl : m.p. 209-11. 

Gabriel, Colman, Ber., 1899, 32, 2928. 

2-Amino-5-methylpyrimidine (5-Methyl- 

pyrimidone-2-imide) . 

Prisms from H 2 0. M.p. 193-5. Sol. EtOH. 
Mod. sol. C 6 H 6 , ligroin. Insol. Et 2 0. 

Bt,HJPtCl e : plates. Decomp. at 255. 

2-N-Jfe : C 6 H 9 N 3 . MW, 123. Prisms from 
ligroin. M.p. 102. Sublimes above 100. Sol. 
H 2 O, Et 2 0, C 6 Hg. 

Gerngross, Ber., 1905, 38, 3398. 

4-Amino-5-methylpyrimidine (5-Methyl- 

pyrimidone-4r-imide) . 

Plates from EtOH. M.p. 176. Sol. C 6 H fl . 
Spar. sol. Et 2 0, CHC1 8 , ligroin, 

Picrate : needles. M.p. 219-21. 
Gerngross, Ber., 1905, 38, 3403. 

6-Aniiixo-4-raethylpyrirnidone-2 

Nf=C-NH 2 




O B CH 

iOCH 3 
C 5 H 7 ON 3 MW 3 125 

Prisms from H 2 0. M.p. above 310. Sol. 
250 parts H 2 at 24. Sol. AcOH 3 ammonia. 

Picrate : yellow needles from H 2 0. Decomp. 
at 265. 

6-N-Jfe : C 6 H 9 ON S . MW, 139. Cryet. from 
BLO. Decomp, at 290. Sol. AcOH. Mod. 
sol* hot H 2 0. Spar. sol. EtOH. 

6JNT-JB : 7 H U ON 8 . MW, 153. Prisms from 
H 2 0. M.p. 245-80 docomp, Sol. hot EtOH, 



acids, alkalis. Insol. Et 2 O. Hydrochloride : 
plates. M.p. 214-15. 

Johns, Am. Chem. J., 1908, 40, 352. 

4- Arnino-5-methylpyriniidoM,e-2 . 
See 5-Methylcytosine. 
6-Amijio-2-inethylpyrimidone-4 

N ONHo 



H 3 C-C 



CH 



6 H 6l hot 
Insol. 



C 5 H 7 ON 3 MW, 125 

Cryst. from H 2 0. M.p. 298-300 decomp. 
Sol. AcOH, min. acids, alkalis. Spar. sol. H 2 O, 
EtOH, Et 2 0, C 6 H 6 . 

Traube, D.R.P., 135,371, (Chem. Zentr., 
1902 II, 1229). 

2-Arnino-5-methylpyrimidone-4 . 

Prisms from H 2 0. M.p. 320-1 decomp. 
Sol. 250 parts H 2 at 25. Sol. alkalis. 

B^H^PtCL : leaflets + 2H 2 0. M.p. 254-5. 

2-N-Jfe : C 6 H 9 ON 3 . MW, 139. Cryst. + 
1H 2 from H 2 0. M.p. 213. Sol. ~ " " 
EtOH. B,H Z SO^ : m.p. 202. Sol. H 2 0. 
EtOH. Picrate : m.p. 240 decomp. 

Johnson, Clapp, Am. Chem, J., 1904, 32, 135. 
Scherp, J. Am. Chem. Soc., 1946, 68, 912. 

2-Ammo-6-methylpyrimidone-4. 

Needles from H 2 0. M.p. 297-9 decomp. 
Sol. acids, alkalis. Spar. sol. H 2 0, EtOH, 
CHC1 3 , pet. ether. Tnsol. Et 2 0. Aq" sol. reacts 
alkaline. 

B,HCl : needles. M.p. 295. 

B,ff 2 flf0 4 : m.p. 180. 

2-N-Jfe: plates from H 2 (). M.p. 202. Sol 
EtOH, acids, alkalis. BJiCl^H^O ; m.p. 253. 

N-f-Aminobenzene^ulphonyl: m.p, 253-4, 
T$*~Acetyl : m.p. 273. 

Gabriel, Colman, Ber., 1899, 32, 2924, 

Amino-2-methylquinoliB,e . 

See Aminoqixinaldino. 
Anaino-4-methylqiiinolin,e . 
See Aminolc])idine. 
8-Amino-5-niethylq;xiinoline 




C 10 H 10 N 2 

M.p. 137-8-5 (40-7). 

Elderfield et al, J. Am. (Jhem. 
68, 1524. 

S-Amino-S-methylquinoline . 

Yellow needles from H 2 0. M.p. 
limes. Sol. common or#. solvents. 



MW, lf>B 
<5., 1946, 



145, Sub- 
Spar. soL 



8-Amino-6-metliylqiiinoline 



109 



l-Amino-5-metiiyl~l : 2 : 3-triazole 



'N-Acetyl: needles from H 2 O. M.p. 160. 
Spar. sol. H 2 0. 

Noelting, Trautmann, Ber., 1890, 23, 
3657. 



H 2 0. 



8-Amino-6-methylquinoline . 

Needles. M.p. 73 (62-4). Sublimes. Sol. 

Mod. volatile in steam. 

N-Acetyl : plates from Et OH. Aq. M.p. 91-2. 
1:3: 5-Trinitrobenzene add. comp. : red 
needles from EtOH. M.p. 139. 

Noelting, Trautmann, Ber., 1890, 23, 
3670. 

4- Amino-7-rneth.ylqTiinoline . 

Cryst. from toluene. M.p. 163-4. 

Hamsey, Baldwin, Tipson, J. Am. Chem. 
Soc., 1947, 69, 67. 

8- Amino-7-rnethylquinoline . 

Golden yellow. M.p. (+ 1H 2 0) 41-3 (38- 
40), anhyd. 61-2. Volatile in steam. 
N-Acetyl : m.p. 155. 
N-Benzoyl : m.p. 145-6. 

Elderfield et al, J. Am. Chem. Soc., 1946, 

68, 1524. 
Bradford, EUiott, J. Chem. Soc., 1947, 

437. 
Capps, J. Am. Chem. Soc., 1947, 69, 179. 

2-Amino-8-methyl<ptinolme . 

Pale yellow needles from H 2 0. 

Fischer, Ber., 1902, 35, 3679. 



5-Amino-8-methylquino]ine . 

Yellow needles from H 2 0. M.p. 143. 
N-Acetyl : needles from H 2 0. M.p. 187. 

Noelting, Trautmann, Ber., 1890, 23, 
3674. 

6- Amino-8-methylquinoline . 

Needles from benzene. M.p. 129. 
N-Acetyl : plates. M.p. 174-4-5. 

Hutchinson, Kermack, J. Chem. Soc., 
1947, 678. 

7- Amino-8-metbylqmnoline . 

Prisms from EtOH.Aq. M.p. 129. B.p. 
304. Sol. EtOH, Et 2 0, Me 2 CO, C 6 H 6 . Spar, 
sol. H 2 0, ligroin. 

Markwald, Ann., 1893, 274, 360. 



2-Aminometh.yl-quinoline 

amine) 



!H 2 NH 2 




N 



(2-Quinaldyl- 



MW, 158 



c 10 H 10 isr 2 

B.p. 104/10 mm. 

B,%HCl : yellow plates from ale. HCL M.p. 
245-6 decomp. (205). 



Chloroplatinate : decomp. at 220-5. 

Ziinrner, D.E.P., 279,193, (CJiem. Zentr., 

1914, II, 1174). 
Graf, Perattioner, Tatzel, J.prakt. Chem., 

1936, 146, 101. 

4-Aminometliyl-qTiinoline (4:-Quinaldyl- 
amine). 

B.p. 172/8 mm. Sol. H 2 0, EtOH, Et 2 0. 

B,HCl: cryst. from EtOH. M.p. 206-8 
decomp. Sol. H 2 ? EtOH. Insol. Et 2 0. 

Zimmer, D.B.P., 279,193, (Chem. Zentr., 

1914, II, 1174). 
Graf, Perattioner, Tatzel, J.prakt. Chem., 

1936, 146, 101. 

1-Amino-l-methylsuccinic Acid. 

See Homoaspartic Acid. 
1 -Amino-1 -methylsuccinic Monoaniide . 
See Homoasparagine. 

2-Aminometliyltliiopliene (Thenylamine, 
thienylmethylamine ) 



HC 



S 



C 5 H 7 ONS MW, 129 

Liq. B.p. 88/26 mm., 58/5 mm. DJ 5 1-1370. 
< 1-5678, n$ 1-5589. 
B,HCl : m.p. 193-4. 

Blicke, Burckhalter, /. Am. Chem. Soc., 

1942, 64, 477. 
Lukasiewicz, Murray, J. Am. Chem. Soc., 

1946, 68, 1389. 
Putokhin, Egorova, Chem. Abstracts, 

1941, 35, 4377. 

l~Ammo-4-methyl-l : 2 : 3-triazole (N- 

Amino-$-methylpyrrodiazole) 



C aN 

N-NH 2 
C 3 H 6 N 4 MW 5 98 

N-Benzoyl : needles and leaflets from 
EtOH.Aq. M.p. 202. Sol. EtOH, hot C 6 H 6 , 
alkalies and alk. carbonates. Almost insol. 
H 2 0, Et 2 0. 

~$-Dibenzoyl : needles from EtOH or C 6 H 6 . 
M.p. 152. Spar. sol. Bt 2 O. 

Benzylidene deriv. : yellowish leaflets from 
EtOH.Aq. M.p. 94. Sol. EtOH, Et 2 0. Insol. 
H 2 0. 

Stoll6, Ber., 1926, 59, 1746. 

l-Amino-5-methyl-l : 2 : 3-triazole (N- 

Amino~a~methylpyrrodiazole) . 

Leaflets from C 6 H 6 . M.p. 70. Sol. H 2 0, 
EtOH, CH01 3 . Spar. sol. Et 2 0. Reacts neutral. 
Poes not reduce NHg.AgN^ or Fehling's. 



5-Amiao-3-inetiiyl-l : 2 : 4-triazole 



110 



4-AminonaphthaIic Acid 



B,HCl : needles from EtOH. M.p. 138 de- 
comp. Aq. sol. reacts acid and reduces Fehling's. 

N-Benzoyl: cryst. from C 6 H 6 . M.p. 158. 
Sol. hot EtOH. Spar. sol. H 2 0, Et 2 0, C 6 H 6 . 

N-Dibenzoyl : cryst. from EtOH. M.p. 136. 
Sol. hot EtOH. Spar. sol. Et 2 0. Insol. H 2 0. 

Benzylidene deriv. : cryst. from pet. ether. 
M.p. 67-8. B 9 HOl : needles. M.p. 135-40 
decomp. 

Stolle, Ber. t 1926, 59, 1746. 
Wolff, Hall, Ber., 1903, 36, 3617. 

5-Amino-3-methyl-l : 2 : 4-triazole 



H 2 N-C 



C 3 H 6 N 4 MW, 98 

Needles from AcOEt. M.p. 148. Sol. H 2 0, 
EtOH. 

B,HNO Z : m.p. 171. 

Pier ate : yellow needles. M.p. 225 decomp. 

Acetyl deriv. : cryst. from H 2 0. M.p. above 
270. 

Benzoyl deriv. : cryst. from EtOH. M.p. 285- 
90 decomp. 

"N-j)-Aminobenzenesulphonyl : m.p. 244-5. 
W-Acetyl: m.p. 298. 

Thiele, Heidenreich, Ber., 1893, 26, 2599. 
Morgan, Reilly, J. Chem. Soc., 1916, 109, 
155. 

1-Amino-l-methyl-n-valeric Acid 




CH 3 -CH 2 -CH 2 -C(NH 2 )-COOH 
C 6 H 13 2 N MW, 131 

Needles from H 2 0. M.p. 295 (sealed tube). 
Very sol. H 2 0. Mod. sol. EtOH, MeOH. Insol. 
Et 2 6, Me 2 CO, CHC1 3 , C 6 H 6 , toluene, ligroin. 

Gu salt : dark blue. Chars at 200. Very 
sol. H 2 0. Mod. sol. MeOH, EtOH, hot amyl 
ale. Insol. Me 2 CO. 

u-Naphthylurethane : needles from EtOH.Aq. 
M.p. 196. 

Kurono, Biochem. Z., 1922, 134, 434. 

4-Amino-l-rn.eth.yl-w-valeric Acid 

H 2 N-CH 2 -CH 2 -CH 2 -CH(CH 3 )-COOH 
C 6 H 13 2 N" MW, 131 

Leaflets from EtOH. M.p. 170-2 ^3- 
methyl-2-piperidone. Sol. H 2 0. Insol. EtOH, 



orange-yellow leaflets from 
EtOH. M.p. 202-3 decomp. Very sol. H 2 0. 
Spar. sol. EtOH. 

Llpp, WIdnmann, Ann., 1915, 409, 143. 

lAmmo-2-metb.yl-n*" valeric Acid. 

See leoleucine. 



1-Aminomyristic Acid 

CH 3 -[CH 2 ] n -CH(NH 2 )-COOH 
C 14 H 29 2 N MW, 

Cryst. powder from AcOH. M.p. 253. 
Insol. H 2 0, EtOH, Et 2 0, C 6 H 6 , ligroin, dil. acids. 
Me ester : C 15 H 31 2 N. MW, 257. B,HCl : 
m.p. 105. 

Et ester: C 16 H 33 2 N. MW, 271. B,HCl : 
cryst. from EtOH. M.p. 83. Sol. H 2 0, EtOH. 
Spar. sol. Et 2 0. 'N-CMoroacetyl : m.p. 58. 
Sol. EtOH, Et 2 0, CHC1 3 . 
'N-Chloroacetyl : m.p. 97. 
'N-Glycyl : m.p. 205. Spar. sol. H 2 0. 
N~Leucyl : m.p. 218. Insol. cold H 2 0, org. 
solvents. 

Abderhalden, Tanaka, Chem. Zentr., 1924, 

I, 551. 
Hell, Twerdomedow, Ber., 1889, 22, 1747. 

Aminonaplithalene - 1 : 8 - dicarboxylic 
Acid. 

See Aminonaphthalic Acid. 

5-Ammonaphthalene -2:3- dicarboxylic 
Acid 

" ,COOH 
'COOH 




C 12 H 9 4 N MW, 231 

Needles from 75% AcOH. M.p. above 360. 
Anhydride : N- Acetyl : needles. M.p. 290. 

Baker, J. Chem. 8oc., 1934, 1413. 

3-Ammonaphthalic Acid (3-Aminonaphth- 
alene-l : B-dicarboxylic acid) 

HOOC COOH 




C 12 H 9 4 N MW, 231 

Anhydride: C 12 H 7 B N. MW, 213. Yellow 
cryst. M.p. above 360. TS- Acetyl: yellow 
needles from AcOH. Spar. sol. KtOH, C C H C . 

Methylimide : yellow noodles from xylono. 
M.p. 278-80. TS-Awfyl: noodloa from nitro- 
benzene. M.p. 329-30 6 . 

Francis, Simonson, J. Chem. Soc., 1935 y 

496. 
I.G., F.P., 743,104, (Chem. Zentr., 1034, 

I, 1249). 

^Aminonaphthalic Acid (4Aminonaphth~ 
alene-l : S-dicarboxylic acid), 

M.p. 200. Na salt diet, with OaO -> 1- 
naphthylamine. 

Chlorostannite : needles. M.p. 274 . 

Chlorostannate : pale yellow oryst. M.p, 182. 

2VT/4 salt ; m.p, 222 decomp. 

Anhydride : m.p. above 360 . 



2-Amino-l-naphthoic Acid 



III 



S-Amino-2-naplitlioic Acid 



Imide: m.p. 325. Sol. cone. H 2 S0 4 with 
yellow fluor. 

Methylimide : m.p. 256-8. 

Graebe, Briones, Ann., 1903, 327, 83. 

2-Amino-l-napkthoic Acid (2-Amino-a- 
naphthoic acid 

CO OH 
[NH 



C n H 9 2 N MW, 187 

Needles from EtOH.Aq. M.p. 126 decomp. 

Sol. EtOH, Et 2 0, hot C 6 H 6 . Spar. sol. H 2 0. 

Loses C0 2 on heating alone or with HC1. 
'N-Acetyl : needles from EtOH. M.p. 195-6. 

Sol. alkalis. 

Friedlander, Littner, Ber., 1915, 48, 328. 
M.L.B., B.P., 252,820, (Chem. Abstracts, 
1927, 21, 2477). 

3-Amino-l-naph.thoic Acid. 

Yellowish-brown needles. M.p. 181-2. 
'N-Acetyl: needles. M.p. 254-5. 

Leuch, Perkins, Whitmore, J. Am. Chem. 
Soc., 1929, 51, 1834. 

4-Ammo-l-napb.thoic Acid. 

Needles from hot H 2 0. M.p. 177. Spar. sol. 
C 6 H 6 , ligroin, cold H 2 0. Heat with HC1 > 
1-naphthylamine + C0 2 . 

Et ester: C 13 H 13 2 N. MW, 215. M.p. 80. 

Amide: C n H 10 ON 2 . MW, 186. Needles. 
M.p. 175 decomp. Sol. EtOH, ligroin, hot 
H 2 0. Spar. sol. Et 2 0. 

Nitrile: C n H 8 N 2 . MW, 168. Cryst. from 
H 2 0. M.p. 174. Sol. EtOH, CHC1 3 . Spar, 
sol. Et 2 0, C 6 H 6 . 

N-Acetyl : needles from EtOH. M.p. 189. 

Weisberg, Ber., 1895, 28, 1842. 
Sergievskaya, Preobrazhenskaya, /. Gen. 
Chem. U.8.S.R., 1940, 10, 950. 

5-Amino-l-naph.tlioic Acid. 

Needles from EtOH. M.p. 212. Mod. sol. 
EtOH, AcOH. Spar. sol. Et 2 0, hot H 2 0. 
Sublimes in needles, m.p. 196. Turns violet 
when fused. 

Et ester : m.p. 92. 

Nitrile: needles from EtOH. M.p. 139. 
Sol. hot EtOH, C 6 H 6 . Spar. sol. H 2 0, ligroin. 

N-Acetyl : needles from EtOH. M.p. above 
296. 

Ekstrand, J. prakt. Chem., 1888, 38, 

244. 

Friedltader, Heilpern, Spielfogel, Chem. 
Zentr., 1899, I, 289. 

6-Ammo-l-naphthoic Acid. 

Pale yellow needles from EtOH. M.p. 
206-6. Sol. AcOH. Green or blue fluor. in sol. 



N-Acetyl : needles from AcOH. M.p. 170-2 
(252-3). 

Harrison, Eoyle, J. Chem. Soc., 1926, 87, 
Dziewonski, Otto, Chem. Zentr., 1936, II, 
78. 

7-Amino-l-naphthoic Acid. 

Light brown prisms from EtOH. M.p. 223- 
4. Shows green or blue fluor. in sol. 

'N-Acetyl: needles from EtOH. M.p. 229- 
30. 

Harrison, Eoyle, J. Chem. Soc., 1926, 87. 

8-Amino-l-naphthoic Acid. 

Needles. Heat with H 2 > naphthastyril. 

"N-p-Toluenesulphonyl : needles from EtOH. 
M.p. 158-9. Sol. boiling EtOH, C 6 H 6 . Spar. 
sol. Et 2 0. Insol. ligroin. 

Lactam : see Naphthastyril. 

Ullmann, Cassirer, Ber., 1910, 43, 441. 
Corbellmi, F.P., 774,472, (Chem. Abstracts, 

1935, 29, 2179). 
I.G., D.E.P., 531,889, (Chem. Abstracts, 

1932, 26, 155). 

l-Amino-2-naphthoic Acid (l-Amino-$- 
naphthoic acid] 

NH 9 



C n H 9 2 N ~ v MW, 187 

Needles from EtOH.Aq. or AcOH. M.p. 205 
(rapid heat.). Loses C0 2 at m.p. Shows blue 
fluor. in sol. Sol. EtOH, Et 2 0, AcOH. Insol. 
H 2 0. Heat with cone. HC1 >- 1-naphthyl- 
amine. 

Nitrile : C 1:L H 8 N 2 . MW, 168. Needles from 
H 2 or C 6 H 6 . M.p. 191-2. Sol. EtOH, 
AcOH. Spar. sol. hot H 2 0, Et 2 0. Stable to 
alkalis. 

Friedlander, Littner, Ber., 1915, 48, 328. 
I.G., D.R.P., 622,308, (Chem. Abstracts, 
1936, 30, 1391). 

3-Amino-2-naplitlioic Acid. 

Yellow cryst. from EtOH.Aq. M.p. 214. 
Sol. EtOH, Et 2 to yellow sols, with green fluor. 
Na salt spar. sol. H 2 0. 

Me ester: C 12 H n 2 N. MW, 201. M.p. 
104-5. 

Et ester: C 13 H 13 2 N. MW, 215. Yellow 
needles from EtOH. M.p. 117-18. Sol. ord. 
org. solvents. 

Isopropyl ester : m.p. 85. 

Butyl ester : m.p. 100-1. 

Isobutyl ester : m.p. 99-100. 

Phenyl ester : m.p. 135. 

Benzyl ester : m.p. 105-6. 

Amide : m.p. 234-6. 

Hydrazide : yellowish-green cryst. M.p. 206- 
10 decomp. 



4-Amino-2-naplitlioic Acid 



112 



4-Aminc-l-naphtliol 



N-Acetyl : prisms from EtOH.Aq. M.p. 238. 
Hydrazide: m.p. 225. 

Gen. Aniline Works, U.S.R, 1,903,880, 

(Chem. Abstracts, 1933, 27, 3343); 

1,871,990, (Chem. Abstracts, 1932, 26, 

5971). 
LG., B.P., 315,661, (Chem. Abstracts, 

1930, 24, 1748). 
Eierz, Tobler, Helv. Chim. Ada, 1922, 5, 

557. 
Allen, Bell, Organic Syntheses, 1942, 

XXII, 19. 

4-Arnino-2-napMIioic Acid. 

Needles from EtOH.Aq. M.p. 215-16 (204-^ 
6). 

Nitrile : C l:L Si s N 2 . MW, 168. Needles from 
EtOHAq. M.p. 123-4. 

Butler, Boyle, J. Chem. Soc., 1923, 123, 

1652. 
Cason, J. Am. Chem. Soc., 1941, 63, 828. 

5-Amino-2-naplithoic Acid. 

Yellow leaflets from EtOH. M.p. 291-2 
(232). Mod. sol. hot EtOH. Prac. insol. H 2 0. 
Insol. Et 2 0, C 6 H 6 . 

Diethylaminoethyl ester : yellow. M.p. 207- 
8. 

Nitrile : yellow needles. M.p. 142. Sol. 
Et a O, hot EtOH, C 6 H 6 . 

N-Acetyl: plates from AcOH. M.p. 291. 
Spar. sol. EtOH. 

Harrison, Boyle, J. Chem. Soc., 1926, 87. 
Ekstrand, J. prate. Chem., 1890, 42, 280. 
Cason, /. Am. Chem. Soc., 1941, 63, 828. 

6-Ammo~2~naplithoic Acid. 

Pale yellow needles from EtOH.Aq. M.p. 225. 
N-Acetyl : needles from EtOH.Aq. M.p. 
230-2. 

Harrison, Boyle, /. Chem. Soc., 1926, 87. 

7-Amino-2-napMhoic Acid. 

Pale yellow leaflets from EtOH. M.p. 245. 

Nitrile : yeUow leaflets, M.p. 192-5 (186, 
170-1). Sol. boiling EtOH, C 6 H 6 . Spar. sol. 
Et 2 0. 

'N-Acetyl : palo yollow cryst. from EtOH.Aq. 
or AcOH. Mp. 287-90 (200-1 decomp.). 

Hopper, Sym, Wilson, J. Soc. Dyers 
Colourists, 1942, 58, 93. 

8-Amino2-naphtlioic Acid. 

Greenish-yellow needles from AcOH. M.p. 
220. Sol. EtOH. Heat with lime > 1- 
naphthylamine. 

B 9 EFCl : prisms. M.p. 260 decomp. 

Nitrile : greenish-yellow leaflets. M.p. 133' 



J3-Diacetyl : yellow needles from EtOH. M.p. 
181. 

Ekstrand, J.prakt. Chem., 1890, 42, 295. 
Harrison, Boyle, J. Chem. Soc., 1926, 87. 

2- Amino-1 -naphthol ( 1 -Hydroxy- p -naphthyl- 
amine) 

OH 



C 10 H 9 ON 



MW, 159 



Needles from H 2 0. Spar. sol. H 2 0. HN0 2 
> p-naphthoquinone. 

Me ether : C n H n ON. MW, 173. Leaflets. 
M.p. 48-9. Sol. org. solvents with blue fluor. 
Spar. sol. warm H 2 0. N-Acetyl: cryst. from 
EtOH.Aq. M.p. 132. 

Et ether: C 12 H 13 ON. MW, 187. Leaflets. 
M.p. 48-9. TS-Acetyl : cryst, from EtOH.Aq. 
M.p. 148-9. 

sS~Acetyl: needles from EtOH.Aq. M.p. 
128-9. Sol. EtOH, Et 2 0. Spar. sol. cold 
ligroin. O-Benzoyl : needles from McOH. M.p. 
185. 

(M-Diacetyl : needles from EtOH.Aq. M.p. 
117. 

^-Benzoyl : leaflets from AcOH. M.p. 190. 

(M-Dibenzoyl : needles from EtOH. M.p. 
180. 

0-Benzenesulphonyl : prisms from EtOtLAq. 
M.p. 118-19. 

Grandmougin, Ber., 1906, 39, 2496; of. 

Auwers, Eckardt, Ann., 1908, 359, 381. 
Nolting, Grandmougin, Froimann, Ber., 

1909, 42, 1383. 

4- Amino-l-napMhol (4t-Hydroxy- oc-naphlhyl- 
amine). 

Needles. Turns blue in air. Ox, ~> 1:4- 
naphthoquinone. 

Me ether: N-Acetyl : priamfl from 'BIOH. 
M.p. 180-1. 

Et ether: needles from EtOH. M.p. 96. 
Sol. usual org. solvents. Fo01 3 givoa indigo-blue 
ppt. yf-Acetyl : naphthacotin. Loallotn from 
EtOH.Aq. M.p. 192. Diacelyl: leaflets or 
prisms. M.p. 138. TS-Benzayl : needles from 
EtOH. M.p. 214-15. 

"N-Formyt: noedlos from hot H 2 0. M.p, 
168. Sol. EtOH. 

TS-Acefyl: naphthacotol. Needles from EtOH. 
M.p. 187. Sol EtOH. Spar. BO!. H a (). 

'N-Chloroacetyl : noodles from EtOH . M.p. 
200-4. Sol. EtOH, Et 2 0, boiling ILO. Spar- 
sol CHC1 3 . 

N-BenaoyZ: noodles from KtOfL M.p. 228-9. 



A O-Benzoyl : m.p, 107, JB 9 ltOl : m.p. 268- 

(117). SoL BtjO, 6 H e . Spar. sol. H a O. 63 decomp. 

]$~Acetyl: needles from EtOH. M.p. 258. Dibenzoyl 



Sol. EtOH. 



215 



deriv. ; oryst. from 6 H 6 . M.p. 



5-Amino-l-naplithol 



113 



4-Amino-2-naphtlioI 



Diacetyl deriv. : m.p. 158. 

Fieser, Fieser, J. Am. Chem. Boc., 1935, 

57, 493. 
Conant, Lutz, Corson, Organic Syntheses, 

Collective Vol. 1,41. 



amine). 

Pink needles from H 2 O. M.p. 192. 

Dibenzoyl deriv. : leaflets from AcOH. M.p. 
276. Sol. EtOH, Me 2 CO, AcOH, hot CHC1 3 . 

Vorozhtzov, Kulev, Chem. Abstracts, 1929, 
23, 3697. 

6-Amino-l -naphthol (5-Hydroxy-$-naphthyl- 
amine). 

N-Acetyl : needles from H 2 O. M.p. 100. 
Sander, Ber., 1925, 58, 829. 



amine). 

Plates. M.p. 158. 

N-Acetyl : needles. M.p. 210-11. Me ether 
HCl : needles. M.p. 163-4. 

Friedlander, Zinberg, Bar., 1896, 29, 40. 
Mueller, Hamilton, J. Am. Chem. Soc., 
1944, 66, 860. 



amine). 

Needles from C 6 H 6 -ligroin. M.p. 95-7. 
Sol. hot H 2 0. Turns grey in air. 

Me ether : b.p. 180-5/14 mm. T$-Acetyl : 
needles from EtOH.Aq. M.p. 128. B.p. 138- 
40/14 mm. Sol. EtOH, AcOH. Mod. sol. 
Et 2 0. Picrate : greenish-yellow needles from 
C 6 H 6 . M.p. 172. 

Et ether : "N-acetyl. Leaflets from EtOH.Aq. 
M.p. 154. 

"N-Formyl: needles from EtOH.Aq. Decomp. 
at 140-50. 

*N-Acetyl : needles or plates from EtOH. M.p. 
181 (169). B.p. 170~2/16 mm. Sol. EtOH, 
AcOH. Spar. sol. Et 2 0, CHC1 3 , C 6 H 6 . 

(M-Diacetyl : needles from EtOH.Aq. M.p. 
118-5. 

N-Benzoyl : needles from EtOH.Aq. M.p. 
193-4. 

Dibenzoyl deriv. : needles from EtOH.Aq. 
M.p. 206-7. 

N--$-Toluenesulphonyl : cryst. from EtOH.Aq. 
M.p. 189. 

Picrate : m.p. 163-4. 



Fichter, Gageur, Ber., 1906, 39, 3331. 



amine) 



C 10 H 9 ON 

Diet, of Org. Oomp. I. 



, 159 



Leaflets from Et 2 0. Spar. sol. boiling H 2 O, 
Et 2 0. Sol. NH 3 .Aq. to yellow sol. Ox. > 
1 : 2-naphthoquinone. 

Me ether: C U H U ON. MW, 173. Needles 
from H 2 0. M.p. 54. Turns pink in air. Sol. 

usual org. solvents. FeCl 3 > blue col. N- 

Acetyl : prisms from EtOH.Aq. M.p. 178. 

Et ether: C 12 H 13 ON. MW, 187. Plates from 
pet. ether. M.p. 51. B.p. 300-2. Very sol. 

org. solvents. FeCl 3 + HCl > blue col. N- 

Acetyl : needles from H 2 0. M.p. 145. 

Propyl ether: C 13 H 15 ON. MW,201. Needles 
from H 2 O. M.p. 45. Sol. usual org. solvents. 

Isopropylether : leaflets from H 2 0. M.p. 50. 

Isobutyl ether : C 14 H 17 ON. MW, 215. Leaf- 
lets from H 2 O. M.p. 61-2. 

N-Formyl : needles from EtOH. M.p. 204. 
Spar. sol. H 2 0, EtOH. 

N-Acetyl : leaflets from MeOH. M.p. 235. 
Sol. EtOH, Et 2 0, Me 2 CO, C 6 H 6 , CS 2 . 

OT$-Diacetyl : prisms from EtOH. M.p. 206. 
Sublimes. 

Triacetyl : m.p. 119-5. 

N-Chloroacetyl : yellowish leaflets from EtOH. 
M.p. 192-3 decomp. 

N-Benzoyl : leaflets from MeOH. M.p. 248-9. 

ON -Dibenzoyl : needles from EtOH. M.p. 
235*5 (226). 

Fieser, Fieser, J. Am. Chem. 8oc., 1935, 

57, 493. 
Conant, Corson, Organic Syntheses, 1931, 

XI, 8. 
Charrier, Ferreri, Gazz. chim. ital., 1912, 

42, ii, 121. 

3-Araino-2-naphth.ol (3-Hydroxy-$-naphthyl- 
amine) . 

Needles from H 2 0. M.p. 234. Sol. EtOH, 
hot H 2 0. Spar. sol. Et 2 0, C 6 H 6 . 

~N-Benzoyl : leaflets from EtOH. M.p. 233-5. 
Sol. Me 2 CO, hot AcOH. Spar. sol. C 6 H 6 . 

O'N-Diacetyl : m.p. 188. 

I.G., B.P., 379,862, (Chem. Abstracts, 
1933, 27, 4094) ; F.P., 645,919, (Chem. 
Abstracts, 1929, 23, 2304). 

Friedlander, Zakrzewski, Ber., 1894, 27, 
763. 

4- Amino-2-naphth.ol ( 3 -Hydroxy- <x.-napMhyl>- 
amine) . 

Needles from EtOH. Decomp. at 185. Sol. 
EtOH, hot xylene. Spar. sol. CHC1 3 , C 6 H 6 . 

^Acetyl : needles. M.p. 179. 

ON -Dibenzoyl : yellowish leaflets from AcOH. 
M.p. 309-10. Sol. Me 2 CO, hot AcOH, CHC1 3 , 
C 6 H 6 . 

Q-p-Toluenesulphonyl : pale yellow prisms 
from EtOH. M.p. 137. Mod. sol. boiling EtOH. 

ChaUenor, Ingold, J. Chem. Soc., 1923, 

123, 2080. 
Morgan, Evans, J. Chem. Soc. t 1919, 115, 

1133. 

8 



5-Amino-2-napIithoI 



amine). 

Needles from 
usual solvents, 
with blue fluor. 



H 2 0. M.p. 190 
Barkens in air. 



FeCL 



violet col. 



(185). Sol. 
Sol. NH 3 .Aq. 



dark red cryst. 

"S-Acetyl : needles from EtOH Aq. M.p. 218. 
OTS-Diacetyl : cryst. from AcOH. M.p. 187. 
N-Benzoyl : needles from EtOH.Aq. M.p. 
152. 

(M-Dibenzoyl : needles from EtOH. M.p. 
223. 

Picrate : yellow needles. M.p. 170 corr. 
(185). 

Brown, Hebden, Withrow, /. Am. CTiem. 

Soc., 1929, 51, 1767. 
Sachs, Ber., 1906, 39, 3016. 

6-Amino-2-naplitliol (6-Hydroxy~ $-naphthyl- 
amine). 

Brown cryst. from EtOH.Aq. Decomp. at 
212-13. 

Me ether : m.p. 78. 'N-Acetyl : m.p. 183. 

Et ether : cryst. from pet. ether. M.p. 91. 
B.p. 330. Sol. ord. org. solvents. TX-Acetyl: 
needles from EtOH. M.p. 184-5. 

QN-Dibenzoyl : cryst. from AcOH. M.p. 
228-30. 

Ruggli, Knapp, Merz, Zimmermann, 
Helv. CUm. Acta, 1929, 12, 1046. 



114 l-Amino-8-naphthol~4 : 6-disulphonic 

Acid 

yt-Benzoyl: cryst. M.p. 208-9. 
Q*N-Dibenzoyl : cryst. from AcOH. M.p. 
208. 

Brown, Hebden, Withrow, J. Am. Chem. 

Soc. 9 1929, 51, 1767. 

Friedlander, Zinberg, Ber., 1896, 29, 41. 
Kehrmann, Engelke, Ber., 1909, 42, 351. 

1- Amino -2 -naphthol -3 : 6-disulphonic 
Acid 

NH 2 



amine). 

Needles from EtOH. M.p. 201. Sol. EtOH, 
Et a O. Spar. sol. H 2 0. 

N-Acetyl: plates from EtOH. M.p. 232. 
Q-Benzoyl : needles from EtOH. M.p. 177. 

ON-Diacetyl : pale brown leaflets or needles 
from EtOH.Aq. M.p. 156. 

N-Benzoyl : m.p. 243-6. Q~Acetyl : cryst. 
from EtOH. M.p. 177. 

QN-Dibenzoyl : needles from AcOH. M.p. 
181. 

l&^Phenyl : 7-anilmo-2-naphthol, phenyl-7- 

hydroxy-2-naphthylamine. Needles. M.p. 160. 

Raiford, Talbot, J. Am. Chem. Soc., 1927, 

49, 560. 

Franzen., Deibel, J. prakt. Chem., 1908, 
78, 155. 



amne). 

Needles from EtOH or H 2 0. M.p. 205-7. 
Sol hot H 2 0, EtOH. Mod. sol. Et 2 0. Sub- 
limes. Sol. acids and alkalis with blue fluor. 
3?eCl 3 >- greenish -blue col. 

Me ether ; prisms. M.p. 79-80. N-Acetyl : 
noodles. M.p. 161-5-2-5 . 

Wt ether : prisms from pet. ether. M.p. 67. 
B.p. 315. Sol. usual org. solvents. TS-Acetyl : 
needles from EtOKAq. M,p. 139. 

W-Acetyl : needles from AcOH.Aq. M*p* 
165. Sol. EtOH, Spar. Hoi. cold H 2 0. 




C 10 H 9 7 NS 2 MW, 319 

Sols, give dark brown col. with FeCl 3 . Boil 
aq. sol. >- 1 : 2-dihydroxynaphthalene-3 : 6- 
disulphonic acid. Reduces NH 3 .AgNO 3 . Does 
not couple with diazo-comps. Mono-Na salt is 
the developer Diogen. 

Witt, Ber., 1888, 21, 3479. 

1 - Amino - 8 - naphthol -2:4- disulplioBic 
Acid (8 - Amino - 1 - naphthol -5:7- disulphonic 
acid, 28 Acid). 

Easily sol. H 2 0. Sols, give greenish-black 
col. with FeCl 3 . Alkaline sols, show green fluor. 
HN0 2 > reddish-yellow sol. diazo-comp. 
Couples in AcOH or alk. sol. with 1 mol. diazon- 
ium salt, in acid with 2 mols. Intermediate for 
azo dyestuffs. 

Mono-Na salt : needles + 1H 2 0. Easily sol. 
H 2 0. Ppd. by HC1 from aq. sol. 

Ca salt : mod. sol. 

Dressel, Kothe, Ber., 1894, 27, 2141. 
Bayor, D.R.P., 80,668. 
Vcndelshtein, Chem. Abstracts, 1932, 26, 
4599. 

l-Ammo-8-naplitliol-3 : G-disnlplionic 
Acid (BAinino-l-naphthol-3 : G-dimiphonic acid 9 
HAcid). 

Colourless cryst. Spar. sol. cold IJUO. Sols, 
give brownish -red col. with FoCl 3 . HN0 2 >- 
sol. yellow diazo-comp. Couples with diazon* 
ium salts in acid or alk. sol. Widely used inter- 
mediate for mono- and poly-azo dyostuffs, 

Mono-Na salt : needles + 1 JH 2 0. Spar. sol. 

JBa salt : needles + 4&H 2 0. Spar. sol. 

TS-Acetyl dichloride : m.p. 188-9. 

Wiilard, Color Trade Journal (U.S.A.), 

1924, 15, 40, (Otom. Abstract^ 1924, 

18, 3374). 
I.G., U.S.P., 1,939,026, (Chem. Abstracts, 

1934, 28, 1302). 
Gubelmann, Tinker, U.S.P., 1,070,406, 

(Chem. Abstracts, 1928, 22, 2378). 

1 - Amino - 8 naphthol -4:6- dis tiljfhonic 
Acid (&-Amino~l*naphthol3 : 5di$ulphonic acid* 
K Acid). 



2-Amino-8-naphthol-3 : 6-disulphonic 1 15 

Acid 



Sols.giveyellowish-greeneoLwithFeCl 3 . HN0 2 
> yellow sol. diazo-comp. Couples with 
diazonium salts in acid or alk. sol. Inter- 
mediate for mono- and poly-azo dyestuffs. 

N-Acetyl dichloride : yellow cryst. from Et 9 0. 
M.p. 145-7. 2 

Kalle, D.R.P., 99,164, (Chem. Zentr., 

1898, II, 1230). 
I.G., U.S.P., 1,939,025, (Chem. Abstracts, 

1934, 28, 1362). 

2 - Amino - 8 - naphthol - 3 : 6-disulphonic 
Acid (7-Amino-I-naphthol-3 : -disulphonic acid, 
2R Acid). 

Free acid and alkali salts readily sol. H 2 0. 
FeCl 3 >- dark green col. Aq. sols of acid 
salts fluoresce bluish- violet, addn. of alkalis > 
bluish-green. Intermediate for azo dyestuffs. 
yellow cryst. Darkens above 



Dichloride 
250. 

N-Phenyl 
phonic acid. 



2-anilino - 8 - naphthol -3:6- disul- 
Alkali salts readily sol. H 2 O. 



Hochst, 

1889. 



D.R.P., 52,023; B.P., 15,175/ 



1 - Amino - 2 - naphthol - 4 - sulphonic Acid 

(1:2: 4- Acid) 




C 10 H 9 4 NS MW, 239 

Fine grey needles turning rose col. on exposure 
to light. Spar. sol. H 2 0. Insol. cold EtOH, 
Et 2 O, C 6 H 6 . Alk. sol. turns brown in air. Ox. 
> 1:2- naphthoquinone - 4 - sulphonic acid. 
Intermediate for azo dyestuffs. 

O : N-Diacetyl : pyridine salt, m.p. 194-5. 
p-Toluidine salt : m.p. 213-14. 

Fieser, Organic Syntheses, 1931, XI, 12. 
Bogdanov, Chem. Abstracts, 1932, 26, 

5297. 
Fieser, Fieser, J. Am. Chem. Soc., 1935, 

57, 494. 

l-Amino-2-naphthol-6-sulphonic Acid. 

Needles. Spar. sol. H 2 0. Prac. insol. EtOH. 



Insol. Et 2 0. FeCl 3 



brown col. Couples 



with diazo-comps. Na salt (+ 2^H 2 0) is the 
developer Eikonogen. Alk. sols, decomp. by 
air. 

: T$-Diacetyl : p-toluidine salt, m.p. 209-10 

Witt, Ber., 1888, 21, 3475. 
Feldmann, Chem. Zentr., 1926, 1, 84. 

1 - Amino-5-naphthol-7-sulphpnic Acid 

(&-Amino-l-naphthol~3'Sulphonic acid, M Acid). 

Leaflets. Spar. sol. H 2 0. FeCl 3 > black 
col. HN0 2 ^ orange-yellow spar. sol. diazo- 
comp. Couples in alk. sol. with diazonium salts. 



4-Amino-l : 2-naphthoqmn.one 

Na salt : leaflets. Spar. sol. H 2 O. 

Badische, D.E.P., 117,471, (CJiem. Zentr., 

1901,1,349); D.R.P., 73,276. 
Cassella, D.B.Ps., 85,058, 188,505. 

l-Amino-8-naphthol-4-sulphonic Acid 

(&-Amino-l-naphthol-5-sulphonic acid, S Acid). 

Needles. Spar. sol. H 2 0. FeCl 3 >- eme- 
rald-green col. HNOg > spar. sol. orange 
diazo-comp. Couples in acid or alk. sol. with 
diazonium salts. Intermediate for azo dye- 
stuffs. 

Na salt : sol. H 2 with bluish-green fluor. 

O : N-Diacetyl : pyridine salt, m.p. 203-4. 

Brandt, Chem. Abstracts, 1928, 22, 2665. 
Bucherer, J. praJct. Chem., 1904, 70, 349. 

2-Ammo-5-naphthol-7-sulphonic Acid 
(6-Amino-l-naphthol-S-sulphonic acid, J Acid). 

Spar. sol. H 2 0. Hot sol. with FeCl 3 > 
brownish-black col. HN0 2 > yellow spar, 
sol. diazo-comp. Couples in acid or alk. sol. 
with diazonium salts giving two series of mono- 
azo dyes. Intermediate for azo dyestuffs. 

Na salt : easily sol. H 2 with blue fluor. 

N-Acetyl : pyridine salt, m.p. 190-1. 

Battegay, Wolff, Bull. soc. chim., 1923, 

33, 1481. 
I.G., U.S.P., 1,939,325, (Chem. Abstracts, 

1934, 28, 1362). 

2-Amino-8-naphthol-6-sulphonic Acid 

(7-Amino-l-naphthol-3-sulphonic acid, Gamma 
Acid, Y-Acid). 

Needles. Spar. sol. H 2 0. FeCl 3 > dirty 
claret col. HN0 2 > spar. sol. yellow diazo- 
comp. Couples in acid or alk. sol. with diazon- 
ium salts giving two series of mono-azo dyes. 
Intermediate for many azo dyestuffs. 

Na salt : easily sol. H 2 0. 

Pb salt : needles. Spar. sol. H 2 0. 

"N-Acetyl chloride : swells about 180, but does 
not melt below 290. 

: N-Diacetyl : p-toluidine salt, m.p. 230-1. 

I.G., U.S.P., 1,939,025, (Chem. Abstracts, 

1934, 28, 1362). 
Bucherer, J. praJct. Chem., 1904, 69, 89. 

4~Ammo-l : 2-naphthoquinone (4-Amino- 

(3 -naphthoquinone, 2 -hydroxy- a~naphthoquinonim~ 
ine) 





or 



NH 
C 10 H 7 2 N MW, 173 

Bed needles from H 2 . Decomp . at 270 with 
charring. Sol. EtOH. Spar. sol. hot H 2 0. 
Insol. Et 2 0. Red. > 3 : 4-dihydroxy-l- 





2-Amino-l : 4-napMhoqrdnone 



116 



2-Amino-w-octane 



naphthylamine. Cone, alkalis or H 2 S0 4 > 2- 
hydroxy-1 : 4-naphthoquinone. 

Acetyl deriv. : orange-red cryst. Decomp. 
above 220. Sol. AcOH, hot EtOH. Insol. 
C 6 H 6 . 

Fieser, Hartwell, J. Am. Chem. Soc., 
1935, 57, 1483. 

2-Amino-t : 4-naphthoquino3ie (2-Amino- 
a.-naphthoquinone) 






C 10 H 7 2 N MW, 173 

Orange-red needles from EtOH, Et 2 0, or 
AcOH. M.p. 204-5. 

TS-Acetyl : yellow plates from EtOH. M.p. 
202. 

TS-Phenyl : 2-anilino -1:4- naphthoquinone. 
Red needles. M.p. 191. Sublimes. 

!N"-p- Aminobenzenesulphonyl : m.p. 226-7. 

Reser, Hartwell, J. Am. Chem. Soc., 1936, 
57, 1483. 

5-Amino-l : 4~naphtho(juinone (5~Amino- 

a-naphthoquinone) . 

Cryst. from AcOH. M.p. 180 decomp. 
N-Acetyl : m.p. 171-2 (162). 

Eriedlander, Ber. y 1899, 32, 3630. 
Pierz -David, Blangey, von Krannichfoldt, 
Helv. Chim. Acta, 1947, 30, 816. 

2-Aminonicotinic Acid (2-Aminopyridine- 
3-carboxylic acid) 



H 2 0. 



M.p. 



MW, 138 

310 ^ 2- 





C 6 H 6 2 N 2 

Prisms. Sol. hot 
aminopyridine + C0 2 . 

Me ester: C 7 H 8 2 N 2 . MW, 162. Needles 
from EtOH.Aq. M.p. 85. Sol. EtOH, Et 2 0, 
C 6 H 6 . N- Acetyl : yellowish leaflets from ligroin. 
M.p. 88. Sol. H 2 0, EtOH, Et 2 0, AcOEt. 

Amide: C 6 H 7 OJST 3 * MW, 137. Needles from 
H 2 0. M.p. 195. N-p- Aminobenzenesulphonyl : 
m.p. 210. 

Anhydride : cryst. from H 2 0. M.p. 384. 
Sol. hot AcOH. Mod. sol. hot H 2 0. Spar, sol 
usual org. solvents. 

N-Benzenesulphonyl : m,p. 178. 

nobenzenesulphonyl ; m.p. 176-9. 
m.p. 175. 

Soldo, Ber., 1924, 57, 1807. 
Kirpal, Monatsh., 1900, 21, 962. 
Philips, Ann., 1896, 288, 269. 



4-Aminonicotinic Acid (4:-Aminopyridine- 
%~carboxylic acid). 

Prisms from H 2 0. Heat at 340 > 4- 
aminopyridine + C0 2 . 

B,HCl : needles. Decomp. at 270. 

Me ester : cryst. from H 2 0. M.p. 173. Sol. 
EtOH, hot CHCLj. Mod. sol. Et 2 0. Hyd. by 
acids or alkalis. 

Kirpal, Monatsh., 1902, 23, 243. 

5-Aminonicotinic Acid (5-Aminopyridine- 
3-carboxylic acid). 

Leaflets from hot H 2 0. M.p. 288-90 de- 
comp. Mod. sol. hot H 2 0. Spar. sol. cold H 2 O. 

Me ester : needles from H 2 0. M.p. 137. 
Graf, J. prakt. Chem., 1933, 138, 247. 

6-Ammonicotinic Acid (6-Aminopyridine- 
3-carboxylic acid). 

Needles + 2H 2 from AcOH.Aq. Decomp. 
at 312 > 2-aminopyridine + C0 2 . 

B } HNO B : light brown cryst. M.p. 242. 
Sol. H 2 0. 

Amide : m.p. 239-40 (200). 

Nitrile: C 6 H 5 N 3 . MW, 119. Cryst. from 
H 2 0, MeOH, or C 6 H 6 . M.p. 163-4. B.p. 
240--50 /15 mm. 

Picrate : yellow needles. M.p. 248. 
Bath, Prange, Ann., 1928, 467, 4. 
Marckwald, Ber. y 1894, 27, 1319. 

1 -Amino-n-nonane . 
See Ti-Nonylamine. 
2-Amino-n-nonane (seQ.-n-Nonylamine) 

CH 3 -[CH 2 1 6 -CH(NH 2 )-CH 3 
C 9 H 21 N MW, 143 

Oil. B.p. 69-9-5/ll mm. 
B 2) H^PtCl 6 : needles from dil. HCL Decomp. 
at 210. 

Picrate : yellow noodles and leaflets from 
EtOH.Aq. M.p. 109. 

Thorns, Mannich, JBer,, 1903, 36, 2555. 

l-Amino-n-octane . 

/S y ec n-()ctylatninc. 
2-Ammo-n-octane (mc.-n-Odylamine) 

OH 3 -|OH a l 5 -OH(NH 2 )-CH 3 

C 8 H 19 N % " MW, 129 

<0r. 

B.p. 163-5/760 mm., BS-fl^/lS mm. 3)J 
0-7745. g 142319. 

d-CampJborsulphonate : m.p. Ki25* 
d-^Sromocamphorsulphonate : m.p. 180~6 f \ 



J3,HOl: m.p. 90-1. 
Benzoate : m.p. 101-2, 

dk 

B.p. 70/25 mm. [M] X) 8*62. 

Kislinor, Ohm. Zentr., 1900, 1, 653. 

Mann, Porter, J. Ohm. S0G, 9 1944, 466, 



4-Amino-n-octane 



117 



4-Amino-ii-octane 

CH 3 -[CH 2 ] 3 -CH(NH 2 )-CH 2 -CH 2 -CH 3 
C 8 H 19 N MW, 129 

B.p. 64r-5/18 mm. Absorbs C0 2 . 
B,HCl : needles from pet. ether. M.p. 194-5. 
Freylon, Ann. cfiim. phys., 1908, 15, 287. 

w-Amino-oxanilic Acid (m-Aminophenyl- 
oxamic acid] 

NH-CO-COOH 




C 8 H 8 3 N 2 ~ MW, 180 

Needles + H 2 from H 2 0. M.p. anhyd. 

245. Spar. sol. H 2 0. 

Amide : C 8 H 9 2 N 3 . MW, 179. Leaflets from 

H 2 0, needles from EtOH. M.p. 191. Sol. 

Me 2 CO, hot H 2 0. Spar. sol. hot CHC1 3 . Insol. 

C 6 H 6 . N-Chloroacetyl : reddish needles from 

H 2 0. Decomp. at 281. Sol.hotAcOH. Spar. 

sol. H 2 0. 

^-Acetyl : needles from AcOH.Aq. M.p. 209 

decomp. Sol. H 2 0, EtOH. Spar. sol. Et 2 O. 

Jacobs, Heidelberger, J. Am. Ghem. Soc., 
1917, 39. 1447. 

^p-Amino-oxanilic Acid (p-Aminophenyl- 
oxamic acid). 

Needles from EtOH. Darkens at 250, but 
does not melt below 280. Spar. sol. EtOH, 
H 2 0. 

Me ester : C 9 H 10 3 N 2 . MW, 194. Greenish- 
yellow needles from H 2 0. M.p. 129-30. Sol. 
EtOH, CHC1 3 . Spar. sol. H 2 0, cold C 6 H 6 . 

M ester: C 10 H 12 3 N 2 . MW, 208. N-Acetyl: 
needles. M.p. 193 decomp. 

Amide : pale violet cryst. from H 2 O. M.p. 
217-18. Sol. hot H 2 0, EtOH, Me 2 CO. FeCl 3 
> purple col. "N-Chloroacetyl : cryst. from 
AcOH. M.p. above 280. Spar. sol. usual 
solvents. 

Anilide : prisms from C 6 H 6 . M.p. 215. Sol. 
AcOH, boiling EtOH, C 6 H 6 . Insol. H 2 0. 

TS-Acetyl: needles from EtOH. Aq. M.p. above 
270. Sol. EtOH. Spar. sol. H 2 0. 

N-Chloroacetyl : decomp. about 235. Spar, 
sol. usual solvents. 

Jacobs, Heidelberger, /. Am. Chem. Soc., 

1917, 39, 1447. 
Koller, Ber., 1903, 36, 413. 

1 -Amino-oxindole 



C 8 H 8 ON 



NH 2 



MW, 148 

Plates from C 6 H 6 . M.p. 50. Very sol. 
EtOH. Sol. AcOEt, C 6 H 6 . Spar. sol. pet. 
ether. Very labile. Lactam ring readily opened 
on heating with alkali. 



5-Aminopelargonic Acid 

needles + H 2 from H 2 0. M.p. 



2 2 . 

Reduces AgN0 3 .NH 3 only slowly 



in 



186-7 
cold. 
N-Benzoyl : plates from EtOH.Aq. M.p. 189. 

Neber, Keppler, Ber. } 1924, 57, 778. 
Neber, Ber. 9 1922, 55, 841. 

3-Amino-oxindole . 

Not isolated in free state. Ox. > isatin. 

B,HCl : cryst. Decomp. at 170. Decomp. 
byH 2 0. 

'N-Phenyl : 3-anilino-oxindole. Prisms from 
C 6 H 6 . M.p. 192. Very sol. Me 2 CO. Sol. 
EtOH, CHC1 3 . Spar. sol. Et 2 O, C 6 H 6 . Insol. 
pet. ether. 

Picrate : yellow. Darkens at 150. 

Baeyer, Knop, Ann. 9 1866, 140, 37. 
Pummerer, Gottler, Ber. 9 1910, 43, 1380. 

6~Amino -oxindole . 

Needles from H 2 0. M.p. about 200. Sol. 
hot H 2 0, EtOH. Spar. sol. C 6 H 6 , CS 2 . 

Gabriel, Meyer, Ber., 1881, 14, 832. 
1-Aminopalmitic Acid 

CH 3 -[CH 2 ] 13 -CH(NH 2 )-COOH 
Ci 6 H 33 2 N MW, 271 

Cryst. from hot AcOH. Insol. EtOH, Et 2 0, 
C 6 H 6 . 

~N-Phenyl: 1-anilinopalmiticacid. Cryst. from 
EtOH-AcOEt. M.p. 142-3. 

Hill, Jordanow, Ber., 1891, 24, 941. 
1-Aminopelargonic Acid 

CH 3 -[CH 2 ] 6 -CH(NH 2 )-COOH 
C 9 H 19 2 N MW, 173 

M.p. 273 decomp. Spar. sol. H 2 0. 
N-Benzoyl : m.p. 128. 

Albertson, J. Am. Chem. Soc., 1946, 68, 
450. 

2-Aminopelargonic Acid 

CH 3 -[CH 2 ] 5 -CH(NH 2 )-CH 2 -COOH 
C 9 H 19 2 N MW, 173 

M.p. 205-5-5 . 
B,HCl : m.p. 135-5-136. 
N-Benzoyl : m.p. 129-5-131. Amide : m.p. 
185-6. 

Urethane : m.p. 80. 

Bodianov, Zvorykina, Chem. Abstracts, 
1944, 38, 1473. 

5-Aminopelargonic Acid 

CH 3 -[CH 2 ] 2 -CH(NH 2 )-[CH 2 ] 4 -COOH 
C 9 H 19 2 N MW, 173 

M.p. 198-5-199. 

McLaren, Pitzl, J. Am. Chem. Soc., 1945, 
67, 1625. 



8-Aminopelargonic Acid 



118 



o-Aminopiienacyl Alcohol 



8-Aminopelargonic Acid 

H 2 N-CH 2 -CH 2 -[CH 2 ] 5 -CH 2 -COOH 
C 9 H 19 2 N MW, 173 

S 9 HCl : cryst. from Me 2 CO. M.p. 115-18. 
Sol. H 2 0, Me 2 CO. 

N-Carbomethoxyl : cryst. from EtOH.Aq. 
M.p. 77. Sol. usual org. solvents. Spar. sol. 
cold H 2 0. Insol. pet. ether. 

~N-Benzenesulphonyl : prisms from H 2 0. M.p. 
85. Mod. sol. warm Et 2 0, AcOEt, toluene, 
hot H 2 0. Insol. cold H 2 0, pet. ether. 

Jegorow, J. prakt. Chem., 1912, 86, 530. 
Flaschentrager, Gebhardt, Z. physiol. 

Chem., 1930, 192, 249. 
Flaschentrager, Halle, Z. physiol. Chem., 
1930, 192, 253. 

1-Amino-M-pentadecane . 

See Pentadecylamine. 
Aminopentametliylbenzene . 
See Pentamethylaniline, 
1 -Amino-w-pent ane . 
See ft-Arnylamine. 
2-Amino-n-pentane (sec. n-Amylamine) 

CH 3 -CH 2 -CH 2 -CH(NH 2 )-CH 3 
C 5 H 13 lSr MW, 87 

B.p. 89-5-91 /752 mm. Df 0-7384. Misc. 
with H 2 0, EtOH, Et 2 0. 
B,HCl : needles. M.p. 168. Sol. H 2 0, EtOH. 
B,HAuC\ : leaflets + |H 2 0. M.p. 82-3. 
B,(COOH\ : m.p. 226 (131). 
Loffler, Ber., 1910, 43, 2034. 
Sabatier, Mailhe, Ann. chim,, 1909, 16, 
105. 

3-Amino-n-pentane 

CH 3 -CH 2 -CH(NH 2 )"CH 2 -CH 8 
C 6 H 13 N MW, 87 

B.p. 91. D'f 0-7487. 
B,HCl : needles. M.p. 216-17. 
Wallach, Ann., 1905, 343, 59. 

5-Amino-w-pentanol-l (5-Hydroxy-n-amyl- 
amine, 5-amino-n-amyl alcohol, 5-pentanolamine) 

H 2 N-CH 2 1CH 2 1 3 -CH 2 OH 
C 5 H 13 ON MW, 103 

Cryst. M.p. 38-9. B.p. 221-2, 79-81/l mm. 
Misc. in all proportions with H 2 0> EtOH. 
Di 7 0-9488. n$ 14618. Readily absorbs H 2 
and C0 2 from air. 
, BJlflOt : m.p. 102^-3. 

Putochin, Lissizin, Ber. f 1926, 59, 629. 
Woods, Sanders, J. Am. Ghem. See,, 1946, 
68, 2111. 

3-Amino-ra~pentanol-2 (Methyl- 1 -amino- 
propylcarbinol, 3-ammo-soc. n-amyl alcohol, 2- 
pentanolamine~3) 



B.p. 174/765 mm. Sol. EtOH. Spar. sol. 
H 2 0. D 18 0-906. 

B 2 ,(COOH) 2 : m.p. 166. 

B,(COOH) 2 : m.p. 204. 

*N-Chloroacetyl : m.p. 52-60. B.p. 126-8 / 
0-3 mm. Sol. H 2 0, EtOH, Me 2 CO, CHC1 3 . 
Spar. sol. C 6 H 6 , ligroin. 

Stienon, Chem. Zentr., 1902, I, 717. 
Jacobs, Heidelberger, J. Biol. Chem., 
1915, 21, 429. 



5-Amino-w-pentanol-2 ( 

amyl alcohol, 4-pentanolamine) 

H 2 N-CH 2 -CH 2 -CH 2 *CH(OH)-CH 3 
C 5 H 13 ON MW, 103 

B.p. 119-21 /8 mm. 
B,HCl : m.p. 107-10. 

Wojcik, Adkins, J. Am. Chem. Soc., 1934, 
56, 2422. 

2-Amino-n~pentanol-3 (Ethyl-} -aminoethyl- 
carbinol, 3-pentanolamine-2 3 2-aminodiethyl- 
carbinol) 

CH 3 -CH 2 -CH(OH)-CH(NH 2 )-CH a 
C 5 H 13 ON MW, 103 

B.p. 174/760 mm. Sol. H 2 0, EtOH. Spar. 
sol. C 6 H 6 . Insol. Et a O. D 235 0-9289. %> 
14458. 

B 2) H^PtCl Q : yellow cryst. M.p. 154. 

Picrolonate : yellow needles. M.p. 215. 

Janecke, J5er., 1899, 32, 1099. 
4-Amino-l-pentene (4- Amino-l ~am,ykne) 



C 6 H U N 



MW, 85 



B.p. 85. Sol. H 2 0, EtOH. 

Gal, Compt. rend, 1873, 76, 1355. 

5-Amino-l-pentene (ft-Amino-l-amylenv, 4- 
pentenylamine) 



5 H U N MW, 85 

B.p. 91-4. Absorbs G() a and H 2 0. 
B 9 HAuOl^: yellow. M.p. 195. Sol H a <). 

On warming sol. depositw Au. 
B%,H$PtClQ : rod leaflets from H a O, M'.p. 

166 (lecomp. Sol hot H a O. 

v. Braun, Awn.., 1911, 382, 43. 

Aminopentenone . 

See Acotylacetonamino. 
o-Aminophenacyl Alcohol (oAminobwwoyl m 
carbinol, 



00-OH,OH 

^ 



C 5 H 18 ON 



MW, 103 G a H 2 N 




MW, 



2?-Aininophenacyl Alcohol 



119 



9-Aminophenanthrene 



Pale yellow cryst. from H 2 0. M.p. 98. 
Almost odourless when cold, evolves sweetish 
odour/wlien heated. Reduces Fehling's imme- 
diately. Becomes reddish-violet above m.p. 

N-Acetyl : needles from H 2 0. M.p. 141. 
Sol 2NNaOH > indoxyl on heating. 

Diacetylderiv. : cryst. fromMeOH. Spar. sol. 
H 2 0. Gives no indoxyl on heating. 

Dibenzoyl deriv. : needles from AcOEt. M.p. 
167-8. 

Phenylhydrazone : pale yellow needles from 
EtOH. M.p. 198. Turns red in air. 

Arndt, Eistert, Partaie, Ber., 1928, 61, 
1114. 

2>-Aminophenacyl Alcohol. 

YeUow needles from C 6 H 6 . M.p. 165. Sol. 
EtOH, min. acids. Spar. sol. H 2 O. Reduces 
AgN0 3 and Fehling's. 

'N-Acetyl : leaflets. M.p. 176-7. Sol. EtOH, 
CHC1 3 . Prac. insol. Et 2 0, C 6 H 6 . 0-Benzoyl: 
needles. M.p. 200-1. Sol. EtOH. Phenyl- 
hydrazone : yellow needles. M.p. 223. 

0-Acetyl : pale yellow prisms from hot H 2 0. 
M.p. 129-30 (135). Sol. MeOH, EtOH. Spar, 
sol. C 6 H 6 . Reduces Fehling's, slowly in cold, 
rapidly on warming. Readily diazotisable. 

ON-Diacetyl : needles from H 2 0. M.p. 162. 
Sol. H 2 0, EtOH. Spar. sol. Et a O, C 6 H 6 . 

0-Benzoyl: m.p. 188. Sol. EtOH. Spar. 
sol. Et 2 0, C 6 H 6 . Insol. H 2 0. 

Phenylhydrazone : yellow needles. M.p. 199. 

Kunckell, Ber., 1900, 33, 2646. 
Robinson, Robinson, J. Chem. Soc., 1932, 
1441. 

2-Aminophenanthraquinone 



C 14 H 9 2 N 




>NH 



MW, 223 



Dark violet needles from H 2 0. Sinters at 205- 
10, does not melt at 300. Sol. hot EtOH. 
Spar. sol. H 2 0. Cone. H 2 S0 4 > reddish- 
brown sol. 

N-Acetyl : dark reddish- violet cryst. from 
PhN0 2 . M.p. 324. Spar. sol. most solvents. 
Cone. H 2 S0 4 > yellowish-brown sol. 

"N-Benzoyl : brownish-red plates from PhN0 2 . 
M.p. 297-8. Sol. H 2 S0 4 with greenish-brown 
col. 

McMaster, Wobus, J. Am. Chem. Soc., 

1934, 56, 164. 
Brass, Ferber, Ber., 1922, 55, 548. 

3~ Aminophenanthraquinone . 

Dark reddish-brown needles from EtOH. 
M.p. 254. 



Monoxime : reddish-brown prisms. M.p. 247 
decomp. 

Schmidt, Soil, Ber., 1908, 41, 3694. 

4r-Aminophenanthra(jTiinone . 

Black cryst. from EtOH. Softens at 207, 
does not melt at 340. Sol. usual solvents > 
intense red sols. Cone. H 2 S0 4 > yellowish- 
olive sol. 

Brass, Ferber, Ber., 1922, 55, 551. 



2 - Aminophenanthrene 

amine) 



(2 - Phenanthryl- 




M H U N MW, 193 

Pale yellow cryst. from ligroin. M.p. 85. 
^-Acetyl : leaflets from xylene. M.p. 225-6. 

Sol. EtOH, AcOH, xylene. Spar. sol. ligroin. 
*N-Benzoyl : needles from xylene. M.p. 21 6-5. 

Werner, Ann., 1902, 321, 318. 

3 - Aminophenanthrene (3 - Phenanthryl- 
amine). 

Exists in two forms, 
a-. 

Leaflets from ligroin. M.p. 143. Labile. 
Yields [3 -form on standing. 

P- 

Cryst. from ligroin. M.p. 87-5. Sol. EtOH. 
Spar. sol. H 2 0, xylene. Sols, show violet fluor. 
Cone. H 2 S0 4 >- green sol. >- yellow on 
warming. 

B,HI : exists in two forms. 1. Needles from 
H 2 0. M.p. 244-5. 2. Cryst. from H 2 0. M.p. 
140. Both yield p-form of base with NaOH. 

N-Acetyl : leaflets from xylene. M.p. 200-1. 
Sol. 20 parts hot xylene. 

"N-Benzoyl : needles from EtOH. M.p. 213- 
14 (211). 

Schmidt, Sauer, Ber., 1911, 44, 3241. 
Werner, Ann., 1902, 321, 313. 

4 - Aminophenantlirene (4 - PJienanthryl - 
amine). 

Grey cryst. from ligroin. M.p. 105. Very 
sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . Spar. sol. 
ligroin. Sol. cone. H 2 S0 4 with green fluor. 

N-Acetyl : cryst. from EtOH. M.p. 190. 

'N-Benzoyl : needles from EtOH. M.p. 224. 

Pier ate : green needles from EtOH. M.p. 
216 decomp. 

Picrolonate : needles from EtOH. M.p. 195. 
Schmidt, Heinle, Ber., 1911, 44, 1501. 

9 - Aminophenantlirene (9 - PJienanthryl - 
amine). 

Exists in two forms. M.p. 137-8 (135-6, 
139), and cryst. from EtOH, m.p. 104. 

B,HCl: prisms from EtOH HC1. M.p. 
275 decomp. 

: needles. M.p. 163 decomp. 



Aminophenanthrol 



120 



p-Aminophenol 



: needles from EtOH-H 2 S0 4 . M.p. 
230. 

B 2 ,(COOH) 2 : yellowish needles from EtOH. 
M.p. 215. 

Picrate : green needles from EtOH. M.p. 
190. 

Picrolonate : m p. 230-1 decomp. 
N-Acetyl : needles from EtOH. M.p. 207-8. 
'N-Benzoyl : needles from EtOH. M.p. 199. 
Spar. sol. Et 2 0. 

Goldberg, Ordas, Carsch, /. Am. Chem. 

Soc., 1947, 69, 260. 
Schmidt, Heinle, Ber. } 1911, 44, 1501. 

Ammophenanthrol . 

See Hydroxyaminophenanthrene. 
1-Ammophenazine 



N NH, 




C 12 H 9 N 3 MW, 195 

Red plates from EtOH. M.p. 172. SoL 
EtOH, Et 2 0. Insol. H 2 0. 

Kehrmann, Prunier, Helv. Chim. Acta, 

1924, 7, 990. 

2-Aminophenazme . 

Red needles from C 6 H 6 or xylene. M.p. 
290-1. Sublimes. SoL in C 6 H 6 fluor. green. 
'N-Acetyl : decomp. at 280. 

Kehrmann, Mermod, Helv. Chim. Acta, 

1927, 10, 65. 
Kehrmann, Hoehn, Helv, Chim. Acta, 

1925, 8, 218. 

Aminoplienetole . 
See Phenetidine. 

o - Aminophenol (o - Hydroxyaniline, I - 
hydroxy-2-aminobenzene) 

OH 




C 6 H 7 ON ' MW, 109 

Needles. M.p. 174. SoL 59 parrs H 2 at 
0, 23 parts EtOH, SoL Et 0. Spar. sol. C 6 H 6 . 
* = 2-18 X JO 10 at 25." Sublimes. Turns 
brown on long standing. 

B,H.CQOH : leaflets. M.p. 119-20. 

B,OHfOOOH : m.p. 150, SoL AcOH. 

Bz 9 (COOH) 2 : needles. M.p. 167-5 decomp. 

Me ether : see o-Anisidine. 

Et ether : see o-Phenetidine. 

Phenyl ether : see o-Aminodiphenyl Ether. 

"N-Phenyl : me 2-Hydroxydiphonylamiao, 

yt-Formyl: needloa from H 2 0. M.p. 129- 
9-5. Very sol. EtOH, AcOEt, CHOL Mo 2 CO, 
hot H 2 0. SoL Et a O. Spar. Hoi. (! 6 H e> ligroin. 

N-Acetyl: see o-ffydroxyacotanilide. 



IS-CKloroacetyl : leaflets. M.p. 138-40. 
N-Benzoyl : see o-Hydroxybenzanilide. 

Brown, Warner, J. Phys. Chem., 1923, 

27, 455. 
Kirkhgof, Spektor, Russ. P., 39,117, 

(Chem. Abstracts, 1936, 30, 3339). 
Micewicz, Chem. Abstracts, 1928, 22, 4111. 

m- Aminophenol . 

Prisms from toluene. M p. 123. Very sol. 
Et 2 0, EtOH. Sol. hot H 2 0. Spar. sol. C 6 H 6 , 
ligroin. Stable in air. 

B,HCl : prisms from H,0. M.p. 229. 

B,HBr: prisms. M.p. 224. 

B,HI : prisms. M.p. 209. 

B.H^SO^ : plates or needles. M.p. 152. 

Me ether : see m-Anisidine. 

Et ether : see m-Phenetidine. 

Phenyl ether : see m-Arninodiphenyl Ether. 

Benzyl ether: C 13 H 13 01Sr. MW, 199. B,HCl : 
plates. M.p. 149. 

N -Phenyl : see 3-Hydroxydiphenylamine. 

~N-Acetyl : see m-Hydroxyacetanilide. 

Diacetyl deriv. : plates from C 6 H 6 -pet. ether. 
M.p. 101. 

N-Chloracetyl : plates from H 2 0. M.p. 135-6 
corr. 

1^-Benzoyl : see w-Hydroxybenmnilide. 

Bantlin, Ber., 1878, 11, 2101. 

Meyer, Sundmachor, Ber., 1899, 32, 2113. 

Ikuta, Am. Chem. J., 1893, 15, 40. 

p - Aminophenol (Eodinal, Ursol P), 

Plates. M.p. 186. SoL 90 parts H 2 0, 
22 parts EtOH at 0. Insol. CH01 3 , H 6 . 
SoL alkalis, sols, turning violet rapidly in, air. 
Sublimes part, decomp. Heat of cxmib, (L 
763-3 OaL k = 6-6 X 10~ 9 at 15. Or0 3 - > 
jp-benzoquinone. Photographic developer. 

B,HCl : prifimH. M.p. 306 dooomp. 

B,(COOH)z : m.p. 183. 

Me ether : see jp-Anisidino. 

Et ether : see p-Phonotidino. 

Propyl ether: 9 H 13 ()N. MW, 161. Oil. 



m.p. 171. Picrate : yollow noodles 
from H 2 0. Darkens 162, m.p. 170, 

Phenyl ether : see p-Amitiodiphonyl Kthor. 

Benzyl ether: C 13 H W ON. MW, 191). Plates 
from H 2 or ItOH.Xq. M.p, 66. BJlOl: 
m.p. 222-3. Picrate : yellow noedlon. Mp. 
165 decomp. 

W-hopropyl: C 9 H 13 ON. MW, 151. M.p. 
165-6. 



10 H W ON. MW, 



Cryst. 



M.p. 118-19. 

^"Phenyl : see 4-Hydroxydiphonylattiiuo. 
"N-Formyl : needloa from'H a (X M.p. 139-40* 
W-Acdyl : see jp-Hydroxyaoetaiiilido. 

JX-Diacetyl : m.p. 118. 

ON -Diacetyl: see under ^Hydroxyaootanil* 
ide. 

Dichloroacetyl deriv* : m.p. 148. 



2-Aminoplienol-4-arsonic Acid 



121 



4-Ammophenol-3-sulpkonic Acid 



Trichloroacetyl deriv. : m.p. 166. 
N-Benzoyl : see ^-Hydroxybenzanilide. 
0-Benzoyl : plates. M.p. 153-4. 
~N--p-Toluenesulphonyl : m.p. 252-4. 
0-p-Toluenesulphonyl : prisms. M.p. 142-5. 

Porai-Koshitz, Chem.-Ztg., 1925, 49, 59. 

Bertsch, U.S.P., 2,035,292 (Chem. Ab- 
stracts, 1936, 30, 2993). 

2-Aminophenol-4-arsonic Acid 
OH 




C 6 H 8 4 NAs "' MW, 233 

Darkens above 170. Decomp. about 290. 
Spar. sol. H 2 O, most org. solvents. Reduces 
NH 3 -AgN0 3 . Sol. in alkaH + NaOCl > dark 
olive-green col. Acid sol. + K 2 Cr 2 O 7 > red 



salt : cryst, + 1 or 2H 2 0. Spar. sol. 



acetylarsan. Trypan- 



col. 

Na 
H 2 0. 

N-Me: C 7 H 10 4 NAs. MW, 247. Needles 
+ iH 2 from H 2 0. M.p. 263-263-5. Sol. 
EtOH, hot AcOH. Spar. sol. Me 2 CO. Insol. 
Et 2 0. 

N:N-Di-Me: C 8 H 12 4 NAs. MW, 261. 
Cryst. from H 2 0. M.p. 119-21 decomp. 

'N-Acetyl : acetarsone, stovarsol, spiroziod. 
OoH 10 5 NAs. MW, 275. M.p. 220-21. One 
of the least toxic of the arsenical drugs. Used 
in syphilis therapy. 

Diethylamine salt : 
ocidal drug. 

$-Hydroxyethylamine salt : solvarsin. Sol. 
H 2 0. Spar. sol. Me 2 CO, Et 2 O, C 6 H 6 . Used in 
syphilis therapy. Toxic, especially to the optic 
nerve. 

EhrHch, Bertheim, Ber., 1912, 45, 757, 

765. 

Fargher, J. Chem. Soc., 1919, 115, 991. 
Jacobs, Heidelberger, Rolf, J. Am. Chem. 

Soc., 1918, 40, 1590. 
Gaebel, Archiv. der Pharmazie, 1911, 249, 

242. 

Streitwolf et al, U.S.P. 1,859,683, (Chem. 
Abstracts, 1932, 26, 3877). 

2-Aminophenol-4-sulphonic Acid 
OH 



3 H 
C 6 H 7 4 NS MW, 189 

Rhombohedra + |H 2 0. Sol. to 1% in cold 
H 2 0. Does not melt. (M.p. 155-6). * = 9-41 

x io- 5 . 

Anilide : needles from EtOH.Aq. M.p. 205 
(172). 



: "N-Diacetyl : pyridine salt, m.p. 162. 
Chloride : m.p. 143. Anilide : m.p. 205. 

Post, Ann., 1880, 205, 51. 

Minevitch, Chem. Abstracts, 1922, 16, 

2994. 
Popov, Chem. Abstracts, 1934, 28, 1671 ; 

1936, 30, 7554. 
Williams, J. Chem. Soc., 1942, 708. 

2-AminopIienol-5-sulphonic Acid. 

Needles. Mod. sol. H 2 O. 

Cassella, D.R.P., 197,496, (Chem. Zentr., 
1908, 1, 1656). 

3-Aminophenol-4~sulphonic Acid. 

Cryst. from BUO. Sol. hot H 2 0. FeCl 3 > 
red col. H 2 S0 4 - at 100 > 3-aminophenol-6- 
sulphonic acid. 

Oehler, D.R.P., 74,111. 

Colour Trade Journal, 1921, 9, 240. 



3-Aminophenol-5-sulplioiuc Acid. 

Needles from H 2 0. Mod. sol. H 2 0. 

-> brownish-red col. Stable to HC1 at 200 

Oehler, D.R.P., 79,120. 



3-Aminoplienol-6-sulp]ionic Acid. 

Plates or needles from H 2 0. FeCl 3 > red 
col. 

Anilide : m.p. 184. 

: N-Diacetyl : anilide, m.p. 213-14. 

N-Chloroacetyl : plates and needles. M.p. 
above 275. 

Jacobs, Heidelberger, Rolf, /. Am. Chem. 

Soc., 1919, 41,471. 
Bayer, D.R.P., 84,143. 

4-Aminophenol-2~sulphonic Acid. 

Plates or needles + H 2 from H 2 0. Anhyd. 
at 100. Darkens on heating but does not melt 
below 300. Spar. sol. H 2 0. Insol. EtOH, 
Et 2 0. Tc = 8-3 x 10- 6 at 25. Turns brown 
in air. FeCl 3 > bluish- violet col. Reduces 
NH 3 .AgN0 3 and Fehling's. PeCl 3 
quinone. 

Amide : m.p. 202 decomp. 

Anilide : m.p. 159 (98). 

'N-Acetyl : amide, m.p. 215. 

: TS-Diacetyl : pyridine salt, m.p. 
Chloride : m.p. 148-9. Anilide : m.p. 150 
decomp. 

Bauer, Ber., 1909, 42, 2107. 
Post, Ann., 1880, 205, 49. 
Williams, J. Chem. Soc., 1942, 708. 

4-Aminophenol-3-sulphonic Acid. 

Needles + 1H 2 from hot H 2 0. M.p. 285 
decomp. Sol. 50 parts H 2 O at 14. Insol. 
EtOH,Et 2 0. Reduces NH 3 .AgN0 3 . FeCl 3 > 
brownish-violet col. Ox. > js-benzoquinone. 

Schultz, Stable, J. prakt. Chem., 1904, 
69, 334. 



2-Amiiiop3aenoxyacetic Acid 

2-Aminoplienoxyacetic Acid 
OCEo-COOH 



122 



o-Aminoplxenylacetic Acid 



C 8 H 9 3 N MW, 167 

N-Acetyl : cryst. from xylene. M.p. 153-4. 
Heat with HC1 > lactam. 

Lactam : phenmorpholone. Prisms from 
EtOH. M.p. 173. Sol. H 2 0, EtOH, Et 2 0, 
C 6 H 6 , alkalis. Sublimes in needles. 

Heidelberger, Jacobs, J. Am. CJiem. Soc., 

1917, 39, 2188. 
Thate, J. prakt. Chem., 1884, 29, 161, 

175. 

3- Aminoplienoxy acetic Acid. 

Plates from AcOH.Aq. M.p. 207-8 decomp. 
Spar. sol. common solvents. 

Et ester : B,HCl : m.p. 135-136-5. 

Amide: C 8 H 10 2 N 2 . MW, 166. Needles from 
EtOH. M.p. 119-24. Insol. C 6 H 6 . 

"N-Acetyl : micro-cryst. M.p. 170-2. 

Heidelberger, Jacobs, J. Am. Chem. Soc., 
1917, 39, 2192. 

4-Aminophenoxyacetic Acid. 

Prisms from H 2 O. M.p. 220 decomp. 

Me ester: CoH l:L 3 N. MW, 181. Needles 
from H 2 0. M.p. 65-6. Sol. EtOH, C 6 H 6 . 
Spar. sol. cold H 2 0. FeCl 3 > reddish- violet 
col. B,HCl : needles from EtOH. M.p. 223-5 
decomp. 

Et ester: C 10 H 13 3 N. MW, 195. Prisms from 
pet. ether. M.p. 58. Sol. H 2 0, EtOH, Et 2 0, 
C 6 H 6 . 

Amide : plates from H 2 0. M.p. 128. 

He-amide : needles from toluene. M.p. 110- 
11. 

Anilide : needles from C 6 H 6 . M.p. 104-^5. 

Heidelberger, Jacobs, /. Am. Chem. Soc., 
1917, 39, 2196. 

a-Aminophenylacetic Acid (C-Phenylgly- 
cine, (t-amino-a-toluic acid) 

C 6 H 5 -CH(NH 2 )-COOH 
C 8 H 9 2 N MW, 151 

til-. 

Pearly leaflets. Sublimes without melting at 
256. Spar. sol. most ord. org. solvents. Heat 
of comb. C, 957-8 Cal. Decolorises KMn0 4 and 
Br sols. Dist. -> benzylamine + C0 2 , HN0 2 
> mandelic acid. 

Me ester: C 9 H n 2 N. MW, 165. Needles 
from ligroin. M.p. 32. Sol. EtOH, Et 2 0, C 6 H e . 
B,HCl : cryst. M.p. 224. 

Et ester : C 10 H 13 2 N. MW, 179. B.p. 257, 
149/16 mm., 114-15/5 mm. < 1-500. B,HCl : 
m.p. 202. B,HNO 2 : needles. M.p. 59. 
m.p. 65-6. 



Amide : C 8 H 10 ON 2 . MW, 150. Plates from 
EtOH-C 6 H 6 . M.p. 132. Sol. H 2 0, EtOH. 
Spar. sol. Et 2 0. Insol. C 6 H 6 . 

Nitrile : see a-Aminobenzyl cyanide. 

~$-Plienyl : see a-Anilinophenylacetic Acid. 

T3-Formyl : m.p. 180 decomp. 

"N-Acetyl : prisms from H 2 0. M.p. 198*5 
corr. 

T$~Chloroacetyl : cryst. from H 2 or EtOH, 
M.p. 170. 

\ : see 1-Phenylhippuric Acid. 



Plates from H 2 0, needles from EtOH.Aq. 
M.p. 305-10. Spar. sol. EtOH. [oc] D 111-0 
in H 2 0, OR - 157-8 in dil. HCL Boil. dil. 
HC1 > dl-. 

B,HCl: needles from dil. HCL M.p. 246 
decomp. 

Et ester: B,HC1 3 m.p. 203 decomp. N- 
Acetyl : cryst. from ligroin. M.p. 69-70. 

Nitrile : see a-Aminobenzyl cyanide. 

'N-Formyl : plates from H 2 0, needles from 
EtOH. M.p. 190 decomp. [a]?? - 259-9 in 
EtOH. 

N-Acetyl : needles from H 2 0. M.p. 191 corr. 
[a] + 1974 in H 2 0. 

OB? + 112*6 in H 2 0. 

Me ester : BJELOl, m.p. 202. [If ] p - 247 
inH 2 0. N-Acetyl: m.p. 114-17. Hygroscopic. 
[M] 5893 363 in MeOH. N-Benzoyl : m.p. 
101-5. [M] 5893 238 in MeOH. 

Amide : B,HCl, decomp. above 150. CM]J 98 
188. ^-Acetyl : m.p. 175. \M.] D 465 
inCHC! 3 . *N-Benzoyl : m.p. 217-5. [M^ 302 
in CHC1 3 . 

N-Formyl : OS + 259-3 in EtOH. 

"N-Acetyl : needles from H 2 0. M.p. 191 corr. 
[a]|> + 197-4 in H 2 0. 

Marvel, Noyes, J. Am. Chem. Soc., 1920, 

42, 2264. 

Fischer, Weichhold, Ber., 1908, 41, 1286. 
Zelinsky, Stadnikoff, Ber., 1906, 39, 1725. 

o-Aminophenylacetic Acid ( 
toluic acid) 

CH 2 -COOH 




C 8 H P 2 N MW, 151 

Needles. M.p. 119 decomp. Sol. hot H 2 0. 
Readily forms oxindole. Diazotises and couples. 

Me ester : "N-acetyl, powder. M.p. 90. 
^-Benzoyl : needles from EtOH. M.p. 108. 

Et ester : pale red liq. TS-Acetyl : needles, 
M.p. 66. N-Benzoyl: needles from EtOH. 
M.p. 82. 

Amide : "S-Acetyl, needles from H0. M.p, 
203. 

Nitrile : see o-Aminobenzyl cyanide. 



m-Arainop}ienylacetic Acid 



123 



l-Amino-3-phenylbutyric Acid 



TS-Formyl : cryst. from EtOH. M.p. 110. 
N-Acetyl : cryst. M.p. 158 (rapid heat.). 
'N-Benzoyl: needles from EtOH. Softens 
at 170. M.p. 179. 

Neber, Ber., 1922, 55, 826. 

m-Aminopkenylacetic Acid. 

Needles from H 2 0. M.p. 151. 
Me ester : oil. B,HCl : plates from EtOH- 
Et 2 0. M.p. 167-70 decomp. 

Amide : prisms from H 2 0. Plates from 
EtOH. M.p. 164-6 corr. N-Chloroacetyl : 
needles from EtOH.Aq. M.p. 187-8. 
Nitrile : see m-Aminobenzyl cyanide. 

Jacobs, Heidelberger, J. Am. Chem. Soc. 3 
1917, 39, 2420. 

p-Aminophenylacetic Acid. 

Plates from H 2 O. M.p. 199-200 decomp. 
Mod. sol. hot H 2 0. 

Me ester : b.p. 140~50/17 mm. 

Et ester : plates from H 2 O. M.p. 51 corr. 

Amide : m.p. 161-2. N-Acetyl : amorphous. 
M.p. 235. N-Chloroacetyl : plates from AcOH. 
M.p. 191-2 corr. ~N-Benzoyl : plates from 
EtOH. M.p. 248. 

Nitrile : see _p-Aminobenzyl cyanide. 

N-Acetyl : cryst. M.p. 168-70. 

N-Chloroacetyl : needles from H 2 O. Yellow 
plates from AcOH. M.p. 158-60. 

N-Benzoyl : needles from EtOH. M.p. 205-6. 
Robertson, Organic Syntheses? Collective 
Vol. I, 44. 

5-Amino-l-phenylacridine 



NH 



o-Aminopkenylarsonic Acid (o-Amino- 
pTienylarsinic acid, o-arsanilic acid) 

0:As(OH) 2 




C 19 H U N 2 " ~ MW,270 

Yellow. M.p. 210-11, 

Albert, G-ledhill, /. Soc. Chem. Ind., 1945, 
64, 169. 

5-Amino-3-phenylacridine . 
Yellow. M.p. 215-16. 

Albert, Gledhill, J. Soc. Chem. Ind., 1945, 
64, 169. 

3- Amino-5-phenylacridine . 

Yellow needles from EtOH. M.p. 204. Sol. 
Et 2 0, CHC1 3 . Mod. sol. EtOH. Spar. sol. 
ligroin. Insol. H 2 0. Sols, yellow with green 
fluor. Sol. AcOH > red col. Sol. cone. H 2 S0 4 
>- yellow sol. with green fluor. 

TS-Acetyl : yellow cryst. from C 6 H 6 . M.p. 
256. 

"N-Benzoyl : yellow prisms from EtOH. M.p. 
246. 

Kehrmann, St6panoff, JSer., 1908, 41, 
4135. 



C 6 H 8 3 NAs " MW, 217 

Needles. M.p. 153 decomp. Very sol. H 2 0, 
EtOH. Spar. sol. Et 2 0. Very sol. acids and 
alkalis. Aq. sol. turns Congo paper violet. 

Benda, J5er., 1911, 44, 3307. 
Jacobs, Heidelberger, Rolf, J. Am. Chem. 
Soc., 1918, 40, 1583. 

m-Ammopkenylarsonic Acid (m-Arsan- 
ilic acid) . 

Prisms from H 2 0. M.p. 215. Sol. 50 parts 
of boiling H 2 0, 200 parts cold. Spar. sol. org. 
solvents. Very sol. alkalis and alk. carbonates. 

'N-Acetyl : m.p. 208-9. 

Bcehringer Sohne, D.R.P., 286,547, 
(Chem. Zentr., 1915, II, 731). 

Bertheim, Benda, Ber., 1911, 44 3 3299. 

Andres, Hamilton, J. Am. Chem. Soc., 
1945, 67, 946. 

j)-Aminophenylarsonic Acid. 
See Arsanilic Acid. 
1-Ammo-l-phenylbutyric Acid 

9eH 5 
CH 3 -CH 2 -C(NH 2 )-COOH 

C 10 H 13 2 N " MW, 179 

Prisms or needles from H 2 + a little NH 3 . 

M.p. 275 (corr.) decomp. Sol. AcOH. Insol. 

most other solvents. 
B,HCl : m.p. 271 (corr.) decomp. 

Herbst, Johnson, J. Am. Chem /Soc., 1932, 

54, 2468. 
Jawelow, Ber., 1906, 39, 1199. 

2-Amino-2-phenylbutyric Acid 

9eH 5 
CH 3 -C(NH 2 )-CH 2 -COOH 

Ci H 13 2 N MW, 179 

Cryst. powder from EtOH. M.p. 255 
decomp. 

Posner, Ann., 1912, 389, 76. 

l-Ainino-3-plienylbutyric Acid 

C 6 H 5 -CH 2 -CH 2 -CH(NH 2 )-COOH 
C 10 H 13 2 lSr MW, 179 

&. 

[oc] D + 33-0 in20%HCl. 
IS-Acetyl : needles or leaflets from H 2 0. M.p. 
178. [oc] B + 19-5 in 



. 

Decomp. at about 305 Q . [a] D 29-6 i 
20% HC1. 



3-Amino-3-phenylbutyric Acid 



dl-. 



Leaflets or needles from H 2 0. M.p. 293-5 
decomp. 

Et ester G I2 S. l7 0^. MW, 207. B.p. 161- 
2/16 mm. BJ&Cl : m.p. 121-3 decomp. 

Knoop, Hoessli, Ber., 1906, 39, 1478. 
Darapsky, J. praJct. Chem., 1936, 146, 285. 
Fischer, Schmitz, Ber., 1906, 39, 2213. 

3-Amino-3-phenyIbutyric Acid 

C 6 H 5 "CH(NH 2 )-CH 2 *CH 2 *COOH 
CiflH^OaN - MW, 179 

Prisms from H 2 0. M.p. 216. 
B,HCl : prisms. M.p. 180 decomp. 
Kohl, Ber., 1903, 36, 174. 

l-p-Aminophenylbutyric Acid 

ethylphenylacetic acid) 



1 24 m-Aminophenylglycine 

3-p-Aminophenylbutyric Acid. 



MW, 179 

[a]*? + 12-2 in EtOH. 
1-. 
[a]g> - 12-4 in EtOH. 



d-. 

M.p. 138-40. 



. 

Cryst. from C 6 H 6 . M.p. 142-3. 
Et ester : b.p. 101-2/0-05 mm. n% 1-524. 

Chu, Marvel, J. Am. Chem. Soc., 1933, 
55, 2847. 

2-p-Aminophenylbutyric Acid 



Ci H 13 2 N 



MW, 179 



Cryst. from EtOH.Aq. M.p. 176. 
Schroeter, Ber., 1907, 40, 1596. 

3-o-Aminophenylbutyric Acid 
NH 



C 10 H 13 2 N MW, 179 

Leaflets from H 2 or C 6 H 6 . M.p. 125-6. 

B,HCl: leaflets from EtOH-Et<>0. M.p. 
201. 

B 2 ,H 2 PtClfi : orange cryst. M.p. 208. 

"N-Benzoyl : cryst. from EtOH.Aq. M.p. 
156. HP 

N-p-ToluenesulpJionyl : m.p. 177-8. 
Et ester: C 12 H 17 2 N. MW, 207. Viscous 
oil. B.p. 191/10 mm. Not volatile in steam. 
TS-Benzoyl: leaflets from MeOH. M.p. 128. 
N-p-Toluenesulphonyl : cryst. from AcOEt. 
M.p. 115-6. 

Briggs, De Ath, J. Chem. Soc., 1937, 456. 
v. Braun, Ber., 1907, 40, 1843. 
Schroeter, Ber., 1930, 63, 1324. 



Plates from H 2 0. M.p. 130-1. Sol. EtOH, 
Me 2 CO. Mod. sol. CHC1 3 . Insol. cold H 2 0, 
Et 2 ? C 6 H 6 , pet. ether. 

van der Scheer, J. Am. Chem. Soc., 1934, 
56, 744. 

2-o-Aminophenyletliyl Alcohol (o-Amino- 
phenethyl alcohol) 

CH 2 -CH 2 OH 



C 8 H n ON 






MW, 137 

mm. 



< 



Viscous liq. B.p. 147-8/3-5 
1-5849. Sol. cold H 2 0. 

B,HCl: cryst. from EtOH-Et 2 0. M.p. 
126-5. 

N-Acetyl : cryst. from C 6 H 6 or CHCl 3 -pet. 
ether. M.p. 103-5. 

N-Benzoyl : m.p. 168. 

N-Benzenesulphonyl : prisms. M.p. 89. 

Sabetay, B16ger, de Lestrange, Bull. soc. 
chim., 1931, 49, 3. 

2-p-Aminophenylethyl Alcohol (p-Amino- 
phenethyl alcohol). 

Needles from EtOH. M.p. 108. 

B,HCl : cryst. from EtOH-Et 2 0. M.p. 171 
(163). 

Et ether : m.p. 69-71. B.p. 164-7/4 mm. 
Darkens in air. 

N-Acetyl : m.p. 105. 

N-Benzoyl : plates. M.p. 139-40. 

N-Benzenesulphonyl : prisms. M.p. 93. 

0-Benzoyl : needles from ligroin. M.p. 59- 
60. 

QN-Dibenzoyl : needles from EtOH.Aq. 
M.p. 136. 

Ferber, Ber., 1929, 62, 190. 
Ehrlich, Distschimuka, Ber., 1912, 45, 
2433. 

Aminophenylethyl Alcohol. 

See also Hydroxy-aminoethylbenzene. 
Aminophenylethyl chloride. 
See Chloro-aminoethylbenzene. 
tn-Aminophenylglycine (m-Aminoanilino- 
acetic acid) 

NH-CH 2 -COOH 




C 8 H 10 2 N 2 v MW, 166 

Light brown cryst. from dil. AcOH. M.p. 

193-4 decomp. Sol. hot H 2 0. Spar. sol. most 

org. solvents. Eeadily oxidised in aq. sol. FeCl 3 

> brown col. 
Me ester : oil. B,2HCl, cryst. from MeOH- 

Et 2 0. M.p. 196-7 decomp. 



p-Aminophenylglycine 



125 



2-p -Aminophenylpyridine 



Amide : C 8 H n ON 3 . MW, 165. Needles from 
EtOH. M.p. 145-5-146-5 decomp. 

Jacobs, Heidelberger, J. Am. Chem. Soc., 
1917, 39, 1447. 

p-Aminophenylglycine . 

Plates + 1H 2 from dil. AcOH. M.p. 222-3 
decomp. Sols, in dil. acids or alkalis turn violet 
in air. FeCl 3 > green to violet col. 

B,HCl : turns brown at 200, decomp. at 250. 

B,2HCl : m.p. above 280. 

Et ester: B,2HCl, m.p. 201-2 decomp. 
N-Acetyl: needles from C 6 H 6 . M.p. 124-5 
corr. 

Amide : brown plates from EtOH. M.p. 



Nitrite: G B #JX 3 . MW, 147. Plates. M.p. 
168. 
N-Acetyl : m.p. 241-2. 

Jacobs, Heidelberger, J". Am. Chem. Soc., 
1917, 39, 1447. 

l-Amino-2-phenylliydracrylic Acid. 

See 2 - Hy droxy - 1 - amino - 2 - phenylpropionic 
Acid. 

3-p-Aminophenylisobutane . 
See ff-Isobutylarn'line. 
l-Amino-2-phenylisobutyric Acid 



C 10 H 13 2 N MW, 179 

Needles from H 2 0. M.p. 293-4 (corr.) 
decomp. Sol. AcOH. Insol. most other org. 
solvents. 

B,HCl : m.p. 244-6 (corr.) decomp. 

Herbst, Johnson, J. Am. Chem. Soc., 
1932, 54, 2468. 

2-Amino-2-phenylisobutyric Acid 



C 6 H 5 -CH(NH 2 )-CH-COOH 
C 10 H 13 2 N MW, 179 

Cryst. from EtOH.Aq. M.p. 243 decomp. 
Spar. sol. cold H 2 0, EtOH. Insol. Et 2 0, 
ligroin, C 6 H 6 . 

B,HCl : cryst. from EtOH-Et 2 0. M.p. 227 
decomp. 

N-Benzoyl : cryst. from MeOH. M.p. 205. 

Posner, Ann., 1912, 389, 72. 

2-p-Aminophenyl-lactic Acid. 

See 1 - Hydroxy - 2 -p - aminophenylpropionic 
Acid. 

2-Amino-2-phenyl-lactic Acid. 

See 1 - Hydroxy - 2 - amino - 2 - phenylpropionic 
Acid. 

2-p- Aminophenyl-lepidine . 

See Flavaniline. 

Aminophenyl Mercaptan. 

See Aminothiophenol. 



Aminoplienyl metliyl sulpMde. 
See under Aminothiophenol. 
Aminoplienyloxamic Acid, 
See Amino- oxanilic Acid. 
o-Aminophenylpropiolic Acid (o-Amino- 
phenykbcetylene-carboxylic acid) 
C:C-COOH 




C 9 H 7 2 N ^ MW, 161 

Yellow needles. M.p. 123 > o-amino- 
phenylacetylene + C0 2 . Spar. sol. Et 2 0. In- 
sol. H 2 0, C 6 H 6 , CHC1 3 , pet. ether. Boiling H 2 
>- o-aminoacetophenone. 

Et ester: G^-fi^Q^S . MW, 189. YeUow 
needles from EtOH. M.p. 55. T&-Farmyl: 
needles from EtOH. M.p. 83. TS-Acetyli 
needles. M.p. 124. 

Eichter, Ber. } 1883, 16, 679. 

m-Ammophenylpropiolic Acid. 
Needles irom EtOH.Aq. M.p. 183. 

Reich, Chem. Abstracts, 1918, 12, 1876. 

Aminophenylpropionic Acid. 

See Aminohydrocinnaniic Acid and Amino- 
hydratropic Acid. 

2-m- Aminophenylpyridine 




C n H 10 N 2 MW, 170 

B.p. 213/20 mm. 
TS-Acetyl : needles. M.p. 141-2. 

Heilbron, Hey, Lambert, /. Chem. Soc., 
1940, 1279. 

3-m- Aminophenylpyridine . 

Cryst. from CHCl 3 -pet. ether. M.p. 77-8. 
N-Acetyl : needles. M.p. 135-6. 

Heilbron, Hey, Lambert, /. Chem. Soc., 
1940, 1279. 

4-m-Aminophenylpyridine. 

Needles from benzene-pet, ether. M.p. 165-6. 
N-Acetyl : needles. M.p. 171-2. 

Heilbron, Hey, Lambert, /. Chem. Soc., 
1940, 1279. 

2-p- Aminophenylpyridine . 

Prisms from EtOH.Aq. M.p. 97-8. Sol. 
EtOH. Spar. sol. Et 2 0. Insol. H 2 0. 

B,2HCl: cryst. from EtOH-Et 2 0. M.p. above 
310. 

'N-ip-Aminobenzenesulphonyl : m.p. 257-5. 
W-Acetyl: m.p. 241. 

Picrate : yellow plates from EtOH. M.p. 
218-19 decomp. 

Forsyth, Pyman, J. Chem. Soc., 1926, 
2917. 



5-Amino-2-p]ienylpyridiiie 
5-Aimno-2-phenylpyridine 



126 



2-Amino-3-phenylquinoline 




c n H 10 N 2 MW, 170 

Needles from C 6 H 6 -ligroin. M.p. 105-6. Sol. 
dil. acids and most org. solvents except ligroin. 
Insol. H 2 0. 

B,HAuCl^ : reddish-brown needles. M.p. 169 
decomp. 

N-Acetyl : needles from EtOBLAq. M.p. 
148-9. 

N-Benzoyl: cryst. from EtOH. Aq. M.p. 201. 

Nienburg, Ber., 1934, 67, 877. 

2-m-Aminop3ie:aylqmnoliae 

NH 2 

2J_ ' 




C 15 H 12 N 2 MW, 220 

Needles from H 2 0. M.p. 120. Sol. MeOH, 
Et 2 0, C 6 H e . Spar. sol. H 2 0, ligroin. 

Miller, Kinkelin, Ber., 1885, 18, 1904. 

2-jp-AininopIieiiyl(Tuinoliiie . 

Needles from H 2 0. M.p. 138. Sol. EtOH, 
Et 2 0, CHC1 3 , C 6 H 6 . 

Methiodide : orange micro-needles. M.p. 220 
decomp. 

^Formyl : cryst. M.p. 160. 

N-Acetyl : plates from EtOH. M.p. 189. 

l$-Diacetyl : cryst. from MeOH. M.p. 153-5. 

N-Benzoyl : plates from toluene. M.p. 234. 

N-Jfe: C 16 H 14 N 2 . MW, 234. M.p. 82. 
Picrate : needles from EtOH. M.p. 183. 

N-ffi: C 17 H 16 N 2 . MW,248. YeUow needles 
from pet. ether. M.p. 110. 

Picrate : m.p, 194-5. 

John, J. prakt. Chem., 1934, 139, 183. 
Glaus, Ber., 1881, 14, 1940. 

4-tn-Aminophenylquinoline . 

Prisms from EtOH. M.p. 198. Mod. sol. 
CHC1 3 . Spar. sol. EtOH, C 6 H 6 . Prac. insol. 
Et 2 with bluish- violet fluor. 

Koenigs, Nef, Ber., 1887, 20, 628. 

4-^-Amiaophenylquinoline . 
Plates from EtOH. M.p. 150. Sol. CHC1 3 , 
C 6 H 6 . Spar. sol. Et 2 with bluish-violet fluor. 
Koenigs, Nef, Ber., 1887, 20, 627. 

3-Ammo-2-phenylquinoline 




C 15 H 12 N 2 MW, 220 

M.p. 115-16 (120-1). B.p. 223-5/3 mm. 
B,HCl : yellow cryst. M.p. 280-300. 



Methiodide : needles from EtOH. M.p. 238. 

Ethiodide : orange-yellow prisms. M.p. 202. 

T$-Acetyl : m.p. 124. 

~N-Diacetyl : prisms. M.p. 173. Mefho- 
chloride : pale yellow. M.p. 230 decomp. 
Meihiodide : m.p. 221 decomp. Metho- 
sulphate : pale yellow. M.p. 200-1. 

'N-Benzoyl : m.p. 179-80. 

'N-p-Nitrobenzoyl : pale yellow. M.p. 223. 

-N-Phenyl : C 21 H 16 N 2 . MW, 296. M.p. 137. 

Picrate : cryst. from EtOH. M.p. 194-5. 
John, Ottawa, J.praJct. Chem., 1931, 131, 
346. 

4-Amino-2-phenylquinoline . 

Needles from C 6 H 6 . M.p. 168. Sol. MeOH, 
EtOH, AcOH, Me 2 CO, AcOEt, CHC1 3 , C 6 H 6 , 
C 6 H 5 C1, toluene. Mod. sol. Et 2 0, CC1 4 . Insol. 
petrol. 

B,HCl : needles. M.p. 272. 

Nitrate : m.p. 206. 

MetModide : cryst. from MeOH. M.p. 274. 

Ethiodide : prisms from EtOH. M.p. 244. 

N-Formyl: cryst. from C 6 H 6 . M.p. 275 
decomp. 

TS-Acetyl : prisms from EtOH. M.p. 108. 

"K-Diacetyl : cryst. from EtOH. M.p. 117. 

N-Benzoyl : needles from C 6 H 6 . M.p. 182. 

N-jy-Aminobenzenesulphonyl : N^-acetyl, m.p. 
269-70. 

N-Phenyl: cryst. from C 6 H 6 . M.p. 190. 
B,HCl : yeUow cryst. from AcOH. M.p. 265-6. 
Nitrate : yellow cryst. from EtOH. M.p. 195 
decomp. N-Acetyl : m.p. 160. Picrate : m.p. 
235-6. 

Bergstrom, J. Org. Chem., 1938, 3, 429. 
John, Ber., 1926, 59, 1447. 
Dziewonski, Moszew, Chem. Abstracts, 
1933, 27, 3937. 

6-Ammo-2-phenylqiiinoliiie . 

Cryst. from EtOH.Aq. M.p. 122-3. 

Chem. Fabr. Schering, D.R.P., 312,098, 
(Chem. Zentr., 1919, II, 852). 

7- Ammo-2-phenylquinoline . 

Yellow needles. M.p. 134. 

Borsche, Weigner-Roemmich, Ann., 1940, 
544, 287. 

8- Amino-2-phenylqmnoline . 

Cryst. from EtOH.Aq. M.p. 111-11-5. 

Elderfield et al, J. Am. Chem. Soc., 1946, 
68, 1589. 

2-Amino-3-phenylquinoliae . 

Cryst. from EtOH. M.p. 155-6. Sol. EtOH, 
Et 2 0, Me 2 CO, AcOH, AcOEt, CHC1 3 , C 6 H 6 . 
Spar. sol. H 2 0, ligroin. 

N-Acetyl : m.p. 107-8. 

'N-Benzoyl : m.p. 124. 

Picrate : needles from EtOH. M.p. 234. 
Pschorr, Ber., 1898, 31, 1293. 



6-Amino-4-plienylquinoliiie 
6- Amtao-4-phenylquinoliae . 



Needles from CHC1 3 . M.p. 205. Sol. EtOH EU). 



127 l-Amino-4-plienyi-n-valeric Acid 

Needles from H 2 0. M.p. 150. Sol. EtOH, 



with bluish-green fluor. Sol. Et 2 O with blue 
fluor. 

Picrate : yellow needles. M.p. 233-4. 

Koenigs, Meimberg, Ber., 1895, 28, 1044. 

Ammophenyltolylamine. 
See Aminomethyldiphenylamine. 
Aminophenyl tolyl Ketone. 
See Aminomethylbenzophenone. 
1-p-Amiaophenyl-l : 2 : 3-triazole 



>NH 



N 



C 8 H 8 N 4 MW, 160 

Cryst. from H 2 0. M.p. 138-9. Sol. hot 
C 6 H 6 . Spar. sol. hot EtOH, AcOEt. 

Michael, Luehn, Higbee, Am. Cliem. /., 
1898, 20, 392. 

4-Amino-l-pheuyl-l : 2 : 3-triazole 



MW, 160 



HC 5 2 N 

N-C 6 H 5 
C 8 H 8 N 4 

Cryst. from EtOH. M.p. 110. 
N-Acetyl : cryst. from EtOH. M.p. 143. 
KleinfeUer, Bonig, J. praJct. Chem., 1931, 
132, 196. 

5-Amino-l-plienyl-l : 2 : 3-triazole. 
Needles from H 2 0. M.p. 110. Sol. EtOH. 
Spar. sol. Et 2 0. Insol. ligroin. 
5-N-Jf e : C 9 H 10 N 4 . MW, 174. Prisms from 

TT TVT v, 102. 

u-jLN-jr/yZ: C 14 H 12 N 4 . MW, 236. Plates 
from EtOH. M.p. 142. 

Dimroth, Ann., 1909, 364, 211. 
4-Ammo-2-phenyl-l : 2 : 3-triazole 

HC N-CJSL 



c 6 H. 



B,HCl : needles + 1H 2 from dil. HCL M.p. 
187. 

B,HNO S : needles from H 2 O. M.p. 181. 

Picrate : yellow needles from H 9 0. M.p. 
220. 

3-TS-Acetyl : cryst. from EtOH. M.p. 168. 

3-H3-Diacetyl : needles. M.p. 118. 

Cuneo, Gazz. chim. Hal., 1899, 29, 16. 

5-Amin.o-l-plaenyl-l : 2 : 4-triazole. 

Needles. M.p. 157. Sol. EtOH. Spar. sol. 
H 2 O, C 6 H 6 . 

B 2 ,H 2 PtCl e : cryst. M.p. 197. 

Picrate : yellow needles from HoO. M.p. 
175. 

Pellizzari, Roncagliono, Gazz. chim. ital., 
1901, 31, 524. 

o-Aminoplieiiyliiretliaiie (Carbethoxy-o- 
phenylenediamine, o-aminoanilinoformic etJiyl 
ester) 

NH-COOC 2 H 5 

(r- 

C 9 H 12 2 N 2 MW, 180 

Needles from,Et 2 0-ligroin. M.p. 86. 

Karrer, Schopp, Benz, Pfaehler, Helv. 

CUm. Acta, 1935, 18, 69. 
Rudolph, JBer., 1879, 12, 1295. 

p-Aminoplieiiyluretliaiie (Carbethoxy-p- 
phenylenediamine, -p-aminoanilinoformic ethyl 
ester). 

Needles from H 2 0. M.p. 73-4. Spar. sol. 



C 8 H 8 N 4 



B 3 HCl : needles. M.p. 242-4 decomp. 

p-N-Acetyl : prisms from EtOH. M.p. 202-5 
(181). 

p-'N-Benzoyl : violet needles from EtOH. 
M.p. 230. 

SchifT, Ostrogovich, Ann. 9 1896, 293, 375. 

2-Amino-2-plienyl-n-valeric Acid 
CH 3 -CH 2 -C(NH 2 )-CH 2 'COOH 



MW,160 C X1 H 15 2 N 



MW, 193 



Needles from H 2 0. M.p. 70. Sol. EtOH, Needles + 1-|H 2 from H 2 0. Sinters at 95, 



C 6 H 6 , CHCL. 
4-N-Acetyl : needles. M.p. 166. 

Thiele, Schlaussner, Ann., 1897, 295, 157. 

3-Ammo-l-phenyl-l : 2 : 4-triazole 



HC 8 



m.p. anhyd. 217 decomp. Mod. sol. cold 
EtOH. 

Posner, Ann. 9 1912, 389, 87. 
l-Amino-4-phenyl-n-valeric Acid 



C 8 H 8 N 4 



N< 



C 6 H 5 



C 6 H 5 -CH 2 -CH 2 -CH 2 -CH(NH 2 )*COOH 
C U H 15 2 N MW, 

Leaflets from H 2 0. M.p. 203-6. Mod. sol, 
MW, 160 EtOH. Very spar. sol. cold H 2 0. 



4-o-AminophenyIvaleric Acid 



128 



6-Amino-a-picoline 



'N-$-Naphthalenesulphonyl : cryst. from 
EtOBLAq. M.p. 83. 

v. Braun, Kruber, Ber., 1912, 45, 389. 

4-o-Aminophenylvaleric Acid 

CH 2 *CH 2 -CH 2 -CH 2 -COOH 




C n H 15 2 N ~ MW, 193 

Needles from EtOELAq. M.p. 60-2, 
N-Acetyl : m.p. 126-8. 
N-Benzoyl : cryst. from very dil. EtOH. 
M.p. 127. Nitrite: cryst. from EtOH.Aq. 
M.p. 114. 

v. Braun, Bartsch, Ber., 1912, 45, 3386. 
v. Braun, Ber., 1907, 40, 1841. 
Diehl, Einhorn, Ber., 1887, 20, 385. 

3-Aminoph.tlialic Acid 
COOH 



MW, 181 



Spar. 
CHC1 3 , 

M.p. 



Cryst. M.p. ,231-2 (191-2 decomp.; 
sol. EtOH, Et 2 0, cold H 2 0. Insol. 
C 6 H 6 , ligroin. 

Mono-NH^ salt : cryst. from EtOH.Aq. 
117-18 decomp. 

Di-Hg salt : decomp. at 200. Spar. sol. H 2 0. 

B,HCl : m.p. 225 decomp. 

l-Me ester : B,HCl, cryst. from cone. HC1. 
M.p. 153 decomp. 

Di-Me ester : B,HCl : needles. M.p. 172-4 
decomp. N-Acetyl : cryst. from AcOH.Aq. M.p. 
92-3. 

Imide : 3-aminophthalimide. Yellow needles 
from H 2 or EtOH. M.p. 266-7. Spar. sol. 
most solvents > fluor. sols. Hydrochloride: 
m.p. 268 decomp. 3-J$-Acetyl : needles from 
H 2 0. M.p. 242. yf-Di-acefyl: prisms from 
EtOH. M.p. 152-4. 

Phenylimide : yellow needles from EtOH. 
M.p, 186-8. N-Acetyl : needles from EtOH. 
M.p. 195-5. 

o-Tolylimide : yellow prisms from MeOH. 
M.p. 214-15. 

~N-Benzoyl : m.p. 186-7 decomp. 

Kenner, Mathews, J". Chem. Soc., 1914, 

105, 2477. 

Scott, Cohen, J. Chem. 8oc., 1921, 664. 
Gisvold, J. Am. Pharm. Assocn., 1942, 31, 

202. 

4-Aminophthalic Acid. 

Cryst. from AcOH.Aq. 
B 2 ,H 2 8nCl^ : needles. M.p. 274. 
B%,H 2 8nClQ : yellow cryst. M.p. 182. 
l-Me ester : C 9 H 9 4 N. MW, 19J5. Yellow. 
Decomp. at 140. 



Di-Me ester: C 10 H u 4 lSr. MW, 209. Plates 
from EtOH or C 6 H 6 . M.p. 84. Sol. CHC1 3 , 
Py. Spar. sol. H 2 0, Et 2 O, pet. ether. "N-Acetyl : 
plates from EtOH.Aq. M.p. 136-5. N-Pro^p- 
ionyl : needles from C 6 H 6 ~pet. ether. M.p. 
110-5. N-Benzoyl : needles from C 6 H 6 . M.p. 
132. N-m-Nitrobenzoyl : m.p. 147. N-p- 
Nitrobenzoyl : yellow cryst. from 'EtOH. M.p. 
202. 

Di-Et ester : C 12 H 15 4 N. MW, 237. Prisms 
from EtOH. M.p. 95. Insol. H 2 0. N-Acetyl : 
plates from H 2 or EtOH. M.p. 122. 

Imide : 4-aminophthalimide. Yellow needles 
from H 2 0. M.p. 294. Sublimes. Sol. EtOH, 
Me 2 CO. Spar. sol. H 2 0, Et 2 0, CHC1 3 . 

Me-imide : yellow cryst. M.p. 242-3. 

Phenylimide : yellow needles from EtOH or 
AcOH. M.p. 205-5. 

Bogert, Benshaw, J. Am. Chem. Soc., 
1908, 30, 1136, 

Aminophthalimide . 

See under Aminophthalic Acid. 
5-Amino - a - picoline (5 - Amino - 2 - methyl- 
pyridine) 




C 6 H 8 N 2 MW, 108 

Cryst. from C 6 H 6 -pet. ether. M.p. 96. 
Spar. so]. H 2 0. 

B$HCl: needles from EtOH-Et 2 0. M.p. 
215-18. 

Picrate : m.p. 201. 

T$-Acetyl : needles from CHCL-pet. ether. 
M.p. 126 (122-3). 

N-Benzoyl : needles from EtOH.Aq. M.p. 
110-11. 

Graf, J. praJct. Chem., 1932, 133, 19. 

6 - Amino - a - picoline (6 - Amino - 2 - methyl- 
pyridine}. 

M.p. 41. B.p. 208-9. Very sol. H 2 0. Sol. 
common org. solvents except ligroin. 

B,HCl : m.p. 155. 

B,HBr : m.p. 149-50. 

B,HI : m.p. 162. 

B,HNO Z : m.p. 168. 

B^HzPtClQ : orange cryst. from dil. HN0 3 . 
M.p. 218 decomp. (209). 

Picrate : m.p. 202. 

N-Acetyl : m.p. 90 (88). 

N-Benzoyl : m.p. 90. 

1^-p-Aminobenzenesulphonyl : ra.p. 219. 
B,HCl : m.p. 220. TX*-Acetyl : m.p. 21S-47 . 

Meyer, Rec. trav. chim., 1925, 44, 323. 
Seide, Chem. Zentr., 1923, III, 1022, 
Schering A.G., D.R.P., 663,891, (Chem, 
Zentr,, 1938, II, 2843). 



2-Amino-p-picoline 



2 - Amino - p - picoline (2 - Amino - 3 - methyl- 
pyridine) . 

M.p. 26-26-4. B.p. 222/748 mm., 102-3/ll 
mm. (corr.), 95 /8 mm. Sol. H 2 O, org. solvents 

B,HCl,H 2 O: needles from EtOH-Et 9 0. 
M.p. 68-75. 

B^H z PtCl Q : orange prisms from BLO. M.p. 
209 decomp. 

Picrate : yellow prisms from Me 2 CO. M.p. 
229. 

N-Formyl : m.p. 138. Picrate : bright yel- 
low. M.p. 167-8. 

N-Acetyl : rhombic cryst. from C 6 H 6 . M.p. 
64. Picrate : bright yellow. M.p. 157-9. 

N-Benzoyl : needles from EtOH. M.p. 220. 
Seide, Ber., 1925, 58, 1733; 1924, 57, 
1803. 

2 - Amino - y - picoline (2 - Amino - 4-methyl- 
pyridine). 

Leaflets from ligroin. M.p. 98. B.p. 200- 
250. Sublimes. Sol. H 2 0, most org. solvents. 

B,HCl: prisms from EtOH. M.p. 176-7 
(sealed tube). 

leaflets from EtOH. M.p. 139. 

orange cryst. from H 2 0. M.p. 
208. 

Picrate : yellow needles from Me 2 CO or AcOH. 
M.p. 227 decomp. 

Iti-Acetyl : prisms from C 6 H 6 . M.p. 102-3. 

N-Benzoyl : prisms from ligroin. M.p. 114. 

^-Dibenzoyl : needles from EtOH.Aq. M.p. 
182-3. 

N-p-Aminobenzenesulphonyl : m.p. 225-6. 
Seide, Ber., 1924, 57, 791. 

3- Amino -y- picoline (3 - Amino - 4 - methyl- 
pyridine). 

Prisms from C 6 H 6 -pet. ether. M.p. 106. 
B.p, 254/735 mm. Sol. H 2 0, EtOH, Et 2 0, 
CHC1 3) Me 2 CO, C 6 H 6 . Insol. Hgroin. Volatile in 
steam, 

B,HCl: prisms. M.p. 180. 

B z ,HoPtCl 6 : orange prisms from HCL M.p. 
227. 

Picrate: yellow prisms from EtOH. M.p. 
179-80. 

"N-Acetyl : leaflets from Me 2 CO-ligroin. M.p. 
84. Picrate : m.p. 194. 

13-Benzoyl : plates from Me 2 CO-ligroin. 
M.p. 81. Picrate : needles. M.p. 164. 

Koenigs, Fulde, Ber., 1927, 60, 2109. 



2-pyridylmethylamine, x-picolylamine) 



129 3-AmmopicoHnic Acid 

B,H^PtCl 6 ,3H 2 : golden leaflets. M.p. 245 
decomp. 

B,2AuCl 3 : yellow cryst. M.p. 186 (204). 
Picrate : needles from EtOH. M.p. 162 de- 
comp. 

"N-Benzoyl : rosettes from pet. ether. M.p. 
53. B.p. 235/15 mm. 

~N-p-Nitrobenzoyl : pale yellow needles from 
EtOH. M.p. 136. 

J$-ip-Aminobenzenesulphonyl : m.p. 131. N 4 - 
Acetyl : m.p. 124. 

Craig, Hixon, J. Am. Chem. Soc., 1931, 

53, 4368. 
Graf, Perathoner, Tatzel, J. prakt. Chem., 

1936, 146, 88. 

Kolloff, Hunter, J. Am. Chem. Soc., 1941, 
63, 490. 

co-Amino-p-picoline (3-Aminomethylpyridine t 
S-pyridylmethylamine, p -picolylamine) . 

B.p. 112/18 mm., 102~3/14 mm. Misc. 
with H 2 O, EtOH, Et 2 0. 

B,2HCl : m.p. 224 (219-20). 

J3,H 2 PtCl G : cryst. from very dil. HCL M.p. 
above 320 (decomp. at 280). 

B,2HAuClt,H 2 : golden leaflets. M.p. 201- 
2 decomp. 

Picrate: plates from EtOH. M.p. 211 
(193). 

~N-p-Nitrobenzoyl : needles from EtOH. M.p. 
188-9. 

N-ip-Aminobenzenesulphonyl : m.p. 133. N 4 - 
Acetyl : m.p. 181. 

Craig, Hixon, J. Am. Chem. Soc., 1931, 

53, 4369. 
Erlenmeyer, Epprecht, Helv. Chim. Acta, 

1937, 20, 690. 

Graf, Perathoner, Tatzel, J. prakt. Chem., 

1936, 146, 88. 
Ad kins, Wolff, Pavlic, Hutchinson, /. Am. 

Chem. Soc., 1944, 66, 1293. 

co - Amino - y - picoline (4 - Aminomethyl - 
pyridine, 4-pyridylmethylamine, ^-picolylamine), 

B.p. 103/11 mm. 

B,HBr : m.p. 240 decomp. 

B,2HBr : m.p. 253 decomp. 

B,2HAuCL : yellow cryst. powder. M.p. 
190. 

N-Benzoyl : rosettes from CHC1 3 . M.p. 108. 
B.p. 240/12 mm. 

"N-p-Aminobenzenesulphonyl : m.p. 183. N" 4 - 
Acetyl : m.p. 196. 

Graf, Perathoner, Tatzel, J. praJct. Chem., 
1936, 146, 88. 

3-Ammopicolinic Acid (3-Aminopyridine- 
2-carboxylic acid) 



C 6 H 8 ]Sr 2 MW, 108 

B.p. 91/15 mm., 82/12 mm. Sol. H 2 0. 
B,2HBr: m.p. 234. 

Diet, of Org. Oomp. I. 



CH0ISr 



( JCOOH 

N 



622 



MW, 138 
9 



5-Aminoprekoitene 



130 



m-Aminopropiophenone 



Faintly coloured plates + iH 2 0. M.p. 210 
decomp. Heat above m.p. >- 3-aminopyrid- 
ine. 

Sucharda, Ber., 1925, 58, 1727. 

5-AmiiiopreIiiiitene . 

See Prehnidine. 
Aniinopropane. 

See Propylamine and Isopropylamine. 
Aminopropsuiol. 

See Aminopropyl Alcohol and Aminoisopropyl 
Alcohol. 

y-Aminopropenylbenzene . 

See Cinnamylamine. 

1-Airdnopropionic Acid. 

See Alanine. 

2-Amiziopropionic Acid ($-Alanine) 

H 2 N-CH 2 -CE 2 -COOH 
C 3 H 7 2 K MW, 89 

Cryst. from H 2 0. M.p. 200. Sol. H 2 0. 



Spar. sol. EtOH. Insol. Et 2 O, Me 2 CO. Heat neec n es . ]$!p. 163. 
> acrylic acid. 

B,HCl : plates. M.p. 123. 

B,HBr : needles. M.p. 105-15. 

B,HI : needles. M.p. 199. 

B^H^SO^ : prisms. M.p. 150 decomp. 

B,HAuCl : needles. M.p. 144-5. SoLH 2 0, 
EtOH, Et 2 O. 

B 2 ,H 2 PtCl G : yellow plates from EtOH-HCl. 
M.p. 210 decomp. Sol. H 2 0. Spar. sol. EtOH. 

Me ester : C 4 H<0 2 N. MW, 103. B.p. 58/ 
15mm. Sol.H 2 0. DJ 6 1-0346. B,HCl : scales. 
M.p. 94-5. B 2 ,H z PtCls : needles. M.p. 192. 

m ester : C^IL^O^. MW, 117. B.p. 58/ n -o- OT<r 
14 mm. B,HCl: plates from EtOH-Et 2 0. ^^n^ 
M.p. 69-70. B 2 ,H 2 PtCl Q : needles. M.p. 196. 



Picrate : yellow needles from EtOH. M.p. 
1645. 

TS-Acetyl : cryst. from C 6 H 6 . M.p. 90-1. 
N-Benzoyl : prisms from Et 2 0. M.p. 104-5. 

Eberhard, Arch, pharm., 1915, 253, 81. 
Gabriel, Ber., 1908, 41, 1127. 

y - Aminopropioplienone (2 - Aminoethyl 
pTienyl Jcetone) 

C 6 H 5 -CO-CH 2 -CH 2 ]S[H 2 
C 9 H U ON MW, 149 

B,HCl : prisms from EtOH. M.p. 128 de- 
comp. 

B,HAuCl^ : m.p. 125 decomp. 

B^H 2 PtOl & : yeUow needles. M.p. 215 de- 
comp. 

Picrate : needles. M.p. 155 decomp. 

N-Acetyl : plates from C 6 H 6 -pet. ether. M.p. 
76. 

^Benzyl: leaflets. M.p. 67. B,HCl: 



*N-Benzoyl : prisms from C 6 H 6 . M.p. 94-5- 
95-5. 

Hale, Britton, J. Am. Chem. Soc., 1919, 

41, 846. 
Mannich, Hieronimus, Ber., 1942, 15B, 49. 

o-Arninopropiophenone (Ethyl o-amino- 
phenyl ketone) 

CO-CH 2 -CH 3 

A 



.U. VCr~ t\J . JLJnjAJLnJ. t/Wfg . 1XOC/UJLCJD. -"* I/* * v\J . 

Amide : C 3 H 8 ON 2 . MW,88. Needles. M.p. 93 / rr 8 ^? im - 



Leaflets from pet. ether. 



MW, 149 
M.p. 47. B.p. 



41. Spar. sol. Et 2 0. Hydrochloride : m.p. 149. 
B 2 ,H 2 PtClQ : orange-yellow prisms. M.p. 213 
decomp. Picrate : m.p. 156. 

"S-Phenyl : see 2-Amlinopropionic Acid. 

^-Benzyl: m.p. 181. B,HCl : m.p. 175 
decomp. 

*N-Benzoyl : leaflets or prisms from H 0. 
M.p. 120. 

Lactam : see p-Propiolactam. 

Holm, J. Chem. Soc., 1905, 88, 29. 
Buggli, Bussinger, Helv. Chim. Acta, 

1942, 25, 35. 
Galat, /. Am. Chem. Soc., 1945, 67, 1414. 

|3 - Arninopropiophenone (1 - Aminoethyl 
phenyl ketone) 

C 6 H 5 -COCH(NH 2 )-CH 3 



Unstable. 
B,HCl: 
187. 



(M.p. 112-14). 



needles from EtOH-Et 9 0. 



MW,149 
M.p. 



m.p. 151. 

: orange-red cryst. M.p. 205-6. 
: cryst. from HC1. M.p. 219-20. 



B,HOl : m.p. 184-5 (200) decomp. 

N-Formyl : m.p. 39-41. 

N-Acetyl : plates from EtOH. M.p. 71, 

N-Propionyl : cryst. from EtOH. M.p. 51. 

N-n-Butyryl : cryst. from EtOH. Mp. 39- 
40. 

N-Benzoyl : needles from EtOH. M.p. 130. 

!$-ip-Toluene$ulphonyl : prisms from EtOH. 
Softens at 125. Decomp. over range. 

Oxime : silky needles from H 2 0,, stout 
needles from C 6 H 6 . M.p. 88-9. 

Semicarbazone : prisms from EtOH. M.p. 
190 decomp. 

Auwers, Dtiesberg, Ber., 1920, 53, 1179. 
Elson, Gibson, Johnson, J. Chem. Soc., 

1930, 1128. 

Wohnlich, Arch, pharm., 1913, 251, 531. 
Zenitz, Hartung, J. Org. Chem., 1946, 11, 

444. 

m-Ammopropiophenone (Ethyl m-amino- 
phenyl ketone). 

Yellow cryst. M.p. 42. B.p. 168-9 /] 5 mm. 
B,HCl : m.p. 198-9 (170) decomp. 
N-p-Toluenesulphonyl : needles from EtOH. 



$?-Aminopropiophenone 



131 



3-Axninopropyiene Giycol 



M.p. 102-3 (97). 
Oxime : m.p. 112-13. 

Elson, Gibson, Jolinson, J. Chem. Soc., 
1930, 1128. 

p-Aminopropiophenone (Ethyl p-amino- 
phenyl Jcetone). 

Needles from H 2 0. M.p. 140, Sol. H0 S 
EtOH. 2 

B,ECl : needles. M.p. 225. 

B 2 ,H Z SO^: plates from EtOH. M.p. 225 
decomp. 

N-Acetyl : needles from H 2 O. M.p. 172-3 
(161). Oxime : m.p. 156-7 decomp. 

*N-Propionyl : needles from H 2 O. M.p. 151 
corr. 

N-Benzoyl : plates from EtOH. M.p. 190. 
Oxime : m.p. 164-5. 

Oxime : needles from EtOH. M.p. 153. 

Kunckell, Chem. Abstracts, 1912, 6, 1432 ; 
Chem. Zentr., 1912, I, 134. 

2-Aminopropyl Alcohol (2-Hydroxyisopro- 
pylamine, $-propanolamine, 2-aminopropanol-l) 

CH 3 -CH(NH 2 )-CH 2 OH 
C 3 H 9 ON MW, 75 

dl-. 

B.p. 173-6. Sol. H 0, EtOH, Et 2 0. 

B,HCl : plates from EtOH~Me 2 CO. M.p. 86- 
87-5 decomp. 

B 2 ,H 2 PtClQ : brownish-yellow plates. M.p. 
198-9 decomp. 

N-Benzyl : b.p. 155-7/20 mm. M.p. 70-2. 
B,HCl : m.p. 111-13. Picrate : m.p. 135-7. 
Acid oxalate : m.p. 176-8. 

d-. 

B 2 ,(COOH) 2 : [og? -18-8. 

^Benzyl: m.p. 47-9. [oc]^ -44-25. 
B,HCl : m.p. 136-8. [a]g -14-75. Picrate : 
m.p. 73-5. Acid oxalate : m.p. 187-9. 

1-. 

Colourless oil. B.p. 72-3/ll mm. D! 0-965. 
[a] 2 ,? + 15-8. B 2 ,(COOH) 2 : m.p. 171. [op 
+ 18-8. 

^Benzyl : gum. [a]?> + 44. 

Karrer et al., Helv. Chim. Acta, 1921, 

4,98. 

Gabriel, Ber., 1916, 49, 2121. 
Stoll, Peyer, Hofman, Helv. Chim. Acta, 

1943, 26, 929. 

3-Aminopropyl Alcohol (2-Hydroxypro- 
pylamine, propanolamine, y-propanolamine, 3- 
aminopropanol- 1 ) 

H 2 N-CH 2 -CH 2 -CH 2 OH 
C 8 H 9 ON MW, 75 

B.p. 188. Df 5 0-9824. <' e 14570. 

B 2 ,H%PtCl e : yellow plates. M.p. 199. 

Picrate : m.p. 222 decomp. 



N-Di-Jfe : C 5 H 13 OjSL MW, 103. B.p. 163- 
4. Sol. H 2 0. Me ether: C 6 H 15 ON. MW, 
117. B.p. 129-30. Df 0-8123. Picrate of 
Q:N-Tri-Me : m.p. 203-4. 

TS-Di-Et : C 7 H 17 ON. MW, 131. B.p. 189-5, 
87/16 mm. Sol. H 2 O. Styphnate : m.p. 103. 

N-Phenyl : see y-Hydroxypropylaniline. 

Putochin, Chem. Abstracts, 1929, 23, 2939 ; 

Ber. 9 1926, 59, 625. 
Henry, Ber., 1900, 33 S 3169. 

co-Arninopropyl-oo-arninobutyl-ainine . 
See Spermidine. 
a-Aminopropylbenzene . 
See 1-Ph.enylpropylamine. 
p-Aminopropylbenzene . 
See 2-Phenylisopropylamine. 
y-Aminopropylbenzene . 
See 3-Phenylpropylamine. 
o-Aminopropylbenzene (o-Propylaniline) 



C 9 H 13 N MW, 135 

B.p. 222-4, 116/15 mm. 

BMCl : m.p. 173. 

Picrate : m.p. 151. 

N-jK-Jfe : C n H 17 ]Sr. MW, 163. B.p. 104- 
S/17 mm. B 2 ,H 2 PtCl 6 : red powder from H 2 0. 
M.p. 146. Picrate: m.p. 150. 

J3-Acetyl : o-propylacetanilide. Needles from 
EtOH.Aq. M.p. 104-5. 

IX-Benzoyl : needles from EtOH.Aq. M.p. 
119. 

GottHeb, Ber., 1899, 32, 962. 

pAminopropylfoenzene (p-Propylaniline). 
B.p. 225. Spar. sol. H 2 0. 
B,HCl: plates. M.p. 203-4. 
B,HBr: plates. M.p. 213. 
N-JM-JMe : b.p. 230. 

N-Acetyl: ^p-propylacetamlide. Plates from 
EtOHAq. M.p. 95-6 (87). 

N-Benzoyl : plates from EtOH. M.p. 115. 

WUlgerodt, Sckerl, Ann., 1903, 327, 301. 

3-Aminopropylene Giycol (2 : 3-Dihydroxy- 
propylamine) 

H 2 N-CH 2 -CH(OH)-CH 2 OH 
C 3 H 9 2 N MW, 91 

dl-. 

B.p. 264-5/740 mm. part, decomp. Sol. 
H 2 0, EtOH. Insol. Et 2 0, C 6 H e . Df 1-1752. 
rig 1-49. Hygroscopic. Absorbs C0 2 . HN0 2 
> glycerol. 

B 2 ,H 2 PtCl Q : yeUow needles. M.p. 185. 

N-Jfe: C 4 H^0 2 N. MW, 105. B.p. 239- 
41/748 mm. Picrolonate : orange prisms from 
EtOH. M.p. 212. 



4-cD-AmiaopropylglyoxaHne 



132 



1-Aminopyrene 



C 5 H 13 2 N. 



MW,119. B.p. 216- 

yellow cry st. from EtOH. 



"8-Di-Me : 
17. Picrolonate : 
M.p. 160 

K-Et : C 5 H 13 2 K MW, 119. B.p. 244-7 / 
750 mm., 141-2/18 mm. Picrolonate : yellow 
cryst. from EtOH. M.p. 237 decomp. 

N-Di-jB* : C 7 H 17 2 N. MW, 147. B.p. 233- 
5. Picrolonate : orange yellow needles from 
EtOH. M.p. 116-18. 

: 0-Dibenzoyl : B,HCl : needles. M.p. 
about 203 decomp. Nitrate : needles. M.p. 
185 decomp. Nitrite : needles from EtOH.Aq. 
Decomp. about 70. Picrate : needles from 
EtOH.Aq. M.p. 187 decomp. 

: N-Dibenzoyl deriv. : hexagonal tables from 
EtOH.Aq. M.p. 109. 

0:0: N-Tribenzoyl : cryst. M.p. 113-14. 

: Q-Di-ip-nitrobenzoyl : hydrochloride, plates 
or needles from dil. HC1. Decomp. about 
216. 

: ]$-Di-p-nitrobenzoyl : needles. M.p. 139. 

Picrolonate : prisms from EtOH. M.p. 219- 
20 decomp. 



d-. 

B.p. 163/15 mm., 134/0-1 mm. 
in H 2 0, + 17-7 in dil. HC1. 



[a]j> 8 + 24 



B.p. 95-8/0-003 mm. [a] D 28-4 in dil. 
HC1, -2-4 in H 2 0. 

Knorr, Ber., 1899, 32, 752. 
Abderhalden, Eichwald, Ber., 1914, 47, 

2880. 
Bergmann, Brand, Dreyer, Ber., 1921, 54, 

936. 
Sowden, Fischer, J. Am. Chem. Soc., 

1942, 64, 1291. 

4-co-Ammopropylgly oxaline . 

See 3-[4-Iminazolyl]-w-propylamine. 

3-cD-Aminopropylradole . 

See 3 - [3 -Indolyl] -7i-propylamine . 

3-Aminopropyl Mercaptan. 

See 3-Mercaptopropylamine. 

Aminoprotocatechnic Acid. 

See 3 : 4-Diliydroxy-2-aminobenzoic Acid, 
4 : 5-Dihydroxy-2-aminobenzoic Acid, and 
4 : 5-Dihydroxy-3-aminobenzoic Acid, 

6-Ammopurine . 

See Adenine. 

2-Aminopurpnroxanthin (1 : 3-Dihydroxy- 
2-aminoanthraquinone) 

CO OH 



NH* 




18-Benzylidene : brown prisms from benz- 
aldehyde. M.p. 257-8. 

Bock, MonatsTi, 1905, 26, 575. 

v. Georgievics, Monatsh., 1885, 6, 755. 

4-Aininoptirpiiroxantliin (1 : S-Dihydroxy- 

4:-aminoanthraquinone) . 

Brown needles with metallic reflex from EtOH. 
Mod. sol. hot HoO. 

3-Jfe ether: - C 15 H n 4 N - MW ? 269 - M -P- 
224r-6. 

Di-Me ether: C 16 H 13 O 4 N. MW 3 283. Cryst. 
from AcOH. M.p. 224-6. 

Di-phenyl ether : yellow needles from C 6 H 6 . 
M.p. 184. 

Liebermann, Ann., 1876, 183, 211. 
Stenhouse, Ann., 1864, 130, 337. 

3-Aminopyrazole (3-Amino-l : 2-diazole. 
]^"ote. The pyrazole ring is sometimes num- 
bered from the other nitrogen atom, in which case 
the compound is 5-aminopyrazole) 



C 3 H 5 N 3 



NH 

or desmotropic form 



MW, 83 

Colourless, viscous, hygroscopic oil. B.p. 
282/753 mm., 218/122 mm. Sol. H 2 0, EtOH. 
Spar. sol. Et 2 0. 

N-p-Aminobenzenesulphonyl : m.p. 227-8. 

Knorr, Ber., 1904, 37, 3522. 

4-Aminopyrazole (4-Amino-l : 2-diazole). 

M.p. 80-2. Very sol. H 2 0. Sol. EtOH, 
AcOEt, CHC1 3 . Spar. sol. Et 2 0, C 6 H 6 , ligroin. 
Sols, darken in air. Hygroscopic. Sublimes. 
Forms stable diazo-salts. 

Picrate : m.p. 193-4. 

Picrolonate : m.p. 242. 

N-Dibenzoyl deriv. : needles from EtOH. 
M.p. 173. 

N-'p-Aminobenzenesulphonyl : m.p. 185. 
Knorr, Ber., 1904, 37, 3522. 



1-Aminopyrene 



NIL 




C 14 H 9 4 N 



Black needles with green lustre, or reddish- 
brown cryst. powder. Sol. hot Py, PhN0 2 , 
aniline. Spar. sol. EtOH, Bt a O, AcOH, C 6 H 6 . 
Sol. alkalis with blue col. HC1 > anthragallol. 



C 16 H U N v MW, 217 

Pale yellow prisms from toluene. M.p. 182. 
MW, 255 Cone. H 2 S0 4 > yellow sol. with bluish-green 
fluor. 

N-Acetyl : needles from C 6 H 5 CL M.p. 276. 
VoUmann, Becker, Corel!, Streeck, Ann., 
1937, 531, 155. 



3-Aminopyrene 133 



4-Aminopyrimidine 



3- Aminopy rene . 

Pale yellow needles from hexane. M.p. 
117-18. Cone. H 2 S0 4 > colourless sol. with 
violet-blue fluor. 

N-Acetyl : needles from AcOH. M.p. 260. 
N-BenzyUdene : m.p. 122-3. 
NJfe : m.p. 82-3. 

Vollmann, Becker, Corell, Streeck, Ann., 
1937, 531, 109. 

4- Aminopy rene . 

Yellow leaflets from xylene. M.p. 207. 
'N-Acetyl : yellow needles or plates from 
AcOH. M.p. 229. 

Vollmann, Becker, Corell, Streeck, Ann., 
1937, 531, 138. 

2-Aminopyridine (a-Pyridylamine) 



C 5 H 6 N 2 MW, 94 

Leaflets from ligroin. M.p. 57-5. B.p. 204, 
104-6/20 mm. Sol. most org. solvents. Spar. 
sol. ligroin. Sublimes. Bitter taste. Anaes- 
thetic action. 

B,HGl : cryst. + 2H 2 0. M.p. 86. 

Ghloroaurate: red needles. M.p. 231. 

BfrH^PtGls : orange prisms. M.p. 231. 

Picrate : yellow needles. M.p. 216-17. 

N-Jf e : C 6 H 8 N 2 . MW, 108. Picrate : needles. 
M.p. 190. 

N-Di-Me : C 7 H 10 N 2 . MW, 122. B.p. 196. 
Picrate : yellow plates. M.p. 182. 

N-m : C 7 H 10 N 2 . MW, 122. B.p. 79-82/4 
mm. B 3 H^80^: m.p. 111-13. Ghloroaurate: 
m.p. 125-6. 

N-Phenyl : see 2-Anilinopyridine. 

N-Acetyl : prisms from ligroin-C s H 6 . 
71. 

N-Thioacetyl ; m.p. 108. 

N-Dibenzoyl: needles from EtOH. 
165. Picrate : m.p. 146. 

N-p-Nitrobenzoyl : m.p. 244. 

N-Tp-Aminobenzoyl : m.p. 166-7. 

N-p-Aminobenzenesulphonyl : m.p. 
W-Acetyl: m.p. 224-6. 

Mscher, Bar., 1899, 32, 1301. 
Tschitschibabin, Seide, CJiem. 

1915, 1, 1065. 
Blicke, Tsao, J. Am. GTiem. Soc., 1946, 

68, 905. 
Whitmore, Mosher, Goldsmith, Ilytina, 

J. Am. Ghem. Soc., 1945, 67, 393. 

3-Aminopyridme ($-Pyridylamine). 
Leaflets from C 6 H 6 -ligroin. M.p. 64. B.p. 
250-2. Sol. H 2 0, EtOH, Et 2 0. Insol. ligroin. 
B,2HGl : hygroscopic plates. M.p. 175. 
red cryst. M.p. 218. 



M.p. 

M.p. 

190. 

Zentr., 



B 2) H z PtGl G : orange-red prisms or plates. 
Deeomp. at 225. 

N-Acetyl: plates from C 6 H 6 . M.p. 133. 
B.p. 326. Sol. H 2 0, EtOH, CHC1 3 , 

N-Diacetyl : needles from C 6 H 6 . M.p. 88. 

N-Benzoyl : leaflets from C 6 H 6 . M.p. 119. 
B,HGl : decomp. at 206. 

13-p-Aminobenzenesulphonyl : m.p. 256. N 4 - 
Acetyl : m.p. 280. 

Friedl, Ber., 1912, 45, 429. 
Binz, Bath, Ann., 1931, 4<86, 95. 

4-Azninopyridine (y-Pyridylamine). 

Needles from C 6 H 6 . M.p. 158. Sol. H 2 0, 
EtOH. Mod. sol. Et 2 0, C 6 H 6 . Spar. sol. 
ligroin. 

B,HGl: m.p. 240. 

BLAuC\-. m.p. 283-^. 

B 2) H 2 PtGl Q : ni.p. 251-2. 

Picrate: m.p. 215-16. 

N-Acetyl : needles + H 2 from H 2 0. M.p. 
anhyd. 150. 

^Benzoyl: m.p. 202. 

N--p-Aminobenzenesulp7ionyl : m.p. 240. 
W-Acetyl: m.p. 256. 

Koenigs, Kinne, Weiss, Ber., 1924, 57, 
1172. 

Aminopyridine-carboxylic Acid. 

See Aminopicolinic, Aminonicotinic and 
Aminoisonicotinic Acids. 

2-Aminopyrimidine (Pyrimidone-2 - imide) 



C 4 H 5 N 3 MW, 95 

Cryst. M.p. 127-8. Sol. H 2 0. Sublimes. 

B } HGl : cryst. M.p. 196. 

GUoroplatinate : yellow needles. M.p. 216 
decomp. 

Picrate: yellow needles. M.p. 237~8 . Q 

'N-'p-AminobenzenesulpJwnyl : m.p. 252. N 4 - 
Acetyl: m.p. 255. 

T8--p-Nitrobewoyl : m.p. 206-5-207-5. 

IS.-p-Aminobenzoyl : m.p. 240-1. 

Biittner, Ber., 1903, 36, 2229. 
Dvornikoff, U.S.P., 2,391,822, (Ghem. 

Abstracts, 1946, 40, 1888). 
Moos, Price, U.S.P., 2,375,735, (Chem. 

Abstracts, 1945, 39, 4633). 

4-Aminopyrimidine (Pyrimidone-^imide). 

Plates from AcOEt. M.p. 151-2. Sol. H 2 0, 
EtOH. 

B,HCl : prisms from H 2 0. M.p. 257 decomp. 

B\H^SO^ : prisms from EtOH. M.p. 143. 

Picrate: yellow needles. M.p. 226. 

Picrolonate : yellow needles from H 2 0. M.p. 
261 decomp. 

N-Me: C 5 H 7 N 3 . MW, 109. M.p. 74-5. 



4-Arnmopyrimidone-2 



134 



5-Arninoqiiiiiizariai 



Ns. MW,171. M.p. 142-3. 
N-Acetyl: needles from H 2 0. M.p. 202. 

Wheeler, J". jBfoZ. Chem., 1907, 3, 189, 290. 



4-Amizxopy rimidone-2 . 

$ee Cytosine. 
2-Aminopyrimidoiie-4 . 

See Isocytosine. 

3~Aminoqizizialdiiie ($-Aminoquinaldine, 3- 
amino-2 -meihylgumoline} 




C 10 H 10 N 2 MW, 158 

Yellow needles from Et 2 or pet. ether. M.p. 
159-60. B.p. 270, 198/16 mm. Sol. EtOH, 
Me 2 CO, C 6 H 6 , CHC1 3 . Spar. sol. Et 2 0, ligroin. 
Insol. H 2 0. Acid sols, fhioresce. KMn0 4 > 
aeetylanthranilic acid. 

Picrate : needles from H 2 0. Decomp. about 
235. 

N~Formyl : needles from H 2 or C 6 H 6 . M.p. 
163. 

"N-Acetyl : needles from Et 2 or C 6 H 6 . M.p. 
165. Methosulphate : pale yellow. M.p. 190-1. 
Methochloride : yellow. M.p. 236 decomp. 
Methiodide : yellow. M.p. 241 decomp. 

N-Acetoacetyl : m.p. 149. 

N-p-Toluenesulphonyl : m.p. 202-3. 

N-Di-Me : methochloride : yellow. M.p. 230 
decomp. Methiodide : bright yellow. M.p. 
240-1. 

N-Benzoyl : needles from Me 2 CO, AcOEt, 
C 6 H 6 , or toluene. M.p. 161. 

Stark, Ber., 1907, 40, 3425. 

4-Aminoquinaldine (y-Aminoquinaldine) . 

Needles from C 6 H 6 ~ligroin. M.p. 168. B.p. 
333. Sol. EtOH, Et 2 0, Me 2 CO, hot C 6 H 6 . 
Prac. insol. H 2 0, ligroin. 

B 2 ,H z PtCl Q : orange cryst. M.p. 223 de- 
comp. 

Picrate : yellow needles. M.p. 197-9. 

N-Acetoacetyl : m.p. 256 decomp. 

N-PAenyZ: C 16 H 14 N 2 . MW, 234. Prisms. 
M.p. 150-1. 

Marckwald, Ann., 1894, 279, 18. 
Meyer, Monatsh., 1907, 28, 52. 

5-Aminoquinaldine . 

Greenish plates or needles + 1H 2 from 
H 2 0. M.p. anhyd. 117-18. Sol. EtOH, 
C 6 H 6 , hot H 2 0. Spar. sol. Et 2 0. 

N-Acetyl : m.p. 204-5. Methiodide : orange 

cryst. M.p. 250-60 decomp. Very sol 

Sol. EtOH. 

N-Cinnamoyl : yellow prisms. M.p. 257. 
Hamer, /. Chem. Soc. t 1921, 119, 1435. 



6- Aminocjninaldiiie . 

Pale brown cryst. from H 2 0. M.p. 187-8. 
Very sol. EtOH, CHC1 3 . 

CJilorostannate : plates. M.p. 224-5. 

Chlorostannite : deliquescent cryst. from H 2 0. 
Decomp. about 180. 

N-Acetyl: m.p. 168-9. Methiodide: yellow 
cryst. Decomp. at 254. 

N-Cinnamoyl : cryst. M.p. 257. 

"N-p-Aminobenzenesulphonyl : m.p. 252. 

Hamer, J. Chem. Soc., 1921, 119, 1435. 

7-Aminoquinaldine . 

Needles + 1H 2 from H 2 0. M.p. anhyd. 
148. Sol. EtOH, C 6 H 6 . Mod. sol. ligroin. 
Spar. sol. Et 2 with bluish-green fluor. Volatile 
in steam. 

Picrate : yellow needles. M.p. 213-14 de- 
comp. 

"N-Acetyl : yellow needles from AcOEt or 
EtOH-Et 2 0. Methiodide : yellow cryst. M.p. 
267. Sol. EtOH, hot H 2 0. 

'N-Benzoyl : needles + 1H 2 from EtOH.Aq. 
M.p. 172-3. 

Alber, J. prakt. Chem., 1905, 71, 39. 

S-Aminocpiinaldiaae . 

Prisms from ligroin. M.p. 56. Sol. EtOH, 
Et 2 0, hot ligroin. Spar. sol. H 2 0. Volatile in 
steam. 

Dobner, Miller, Ber., 1884, 17, 1701. 

2-Aniinoqiiinizarin (1:4- Dihydroxy - 2 - 
aminoanthraquinone) 

CO OH 

,NH 9 




C 14 H 9 4 N MW, 255 

Greenish-yellow needles with metallic lustre 

from PhN0 2 . M.p. 313-4. Sol. H 2 S0 4 with 

orange-red col. Sol. alkalis with bluish-red col. 
N-Phenyl : needles from aniline. M.p. 255- 

6. 
N-p-Tolyl: m.p. 220. 

Marschalk, Bull. soc. chim., 1937, 4, 629. 

5 - Aminoquinizarin (1:4- Dihydroxy - 5 - 
aminoanthraquinone) . 

Brownish-red cryst. from toluene, M.p. 212- 
3. Sol. H 2 S0 4 with red col. Sol. alkalis with 
reddish- violet sol. 

Di-Me ether: C IB E^O^. MW,283. Orange- 
red needles from AcOH. M.p. 242-3. N~p* 
Toluenesulphonyl : orange needles from chloro- 
benzene or AcOH. M.p. 197, 

"N-Phenyl : blackish- violet cryst. from toluene. 
M.p. 223. 

Waldmann, Hartisch, J, prakt. Chem., 
1931, 130, 92. 



2-Aminoqriinoline 



135 



7-Ammoqnmoline 



2-Aminoqiainoliae 

quinolylamine) 



( a-Aminoquinoline, 




MW, 144 

M.p. 129. Sol. EtOH, 
Spar. sol. C 6 H 6 , ligroin. 



C 9 H 8 N 2 

Leaflets from H 2 0. 
Et 2 O, CHC1 3 , hot H 2 0. 
Sublimes. 

B,HCl: m.p. 226-7. 

~N-p-Nitrobenzoyl : m.p. 283-5. 

'N-p-Aminobenzoyl : m.p. 156-8. 

'N-p-Aminobenzenesulphonyl : m.p. 198. 

sym.-Trinitrobenzene add. comp. : red needles. 
M.p. 186. 

Picrate : cryst. Decomp. at 255-6. 

Methochloride : + 1H0. M.p. 268. Sol. 



m.p. 



Sol. EtOH, 



'WLt/MV/VUtV . -j~ JLJULjjV-'. - LY - i --M- *J\J< 

H 2 0. Spar. sol. EtOH. B 2 ,HJPtCL 
268. 

Methiodide : prisms. M.p. 247 
hotH 2 O. 'N-Acetyl: m.p. 213. 

Ethiodide : m.p. 232. Sol. EtOH, hot H 2 0. 
TS-Phenyl: C 15 H 12 lSr 2 . MW, 220. Plates 
from EtOH. M.p. 98. 

Diepolder, Deuerlein, J. praJct. Chem., 

1923, 106, 54. 

Tschitschibabin, Ber., 1921, 54, 822. 
Tschitschibabin, Witkovsky, LapscMn, 
Ber., 1925, 58, 805. 

3-Aminoquinoline (fi-Aminoquinoline, P- 
quinolylamine) . 

Two modifications, (i) Cryst. from toluene, 
m.p. 84. (ii) Cryst. from H 2 O or EtOH.Aq., 
m.p. 94 > first mod. Sol. Et 2 0, EtOH, 
CHCla- Sols, show slight blue fluor., intensified 
by addition of acids, even C0 2 , and sols, turn 
yellow. Both forms give same acetyl deriv. 
Picrate : softens at 200. M.p. 210 decomp. 
TS-Acetyl: cryst. from H 2 O. M.p. 166-7. 
Methosulphate : yellow prisms. M.p. 171. 
"N-p-Aminobenzenesulphonyl : m.p. 185. 
Methochloride : yellow. M.p. 190. 
Methiodide : orange yellow prisms. M.p. 
187. 

Mills, Watson, /. Chem. Soc. 9 1910, 97, 

746. 

Bargellini, Settimj, Gfazz. chim. ital., 1923, 
53, 601. 

4-Aminoquinoline (y-Aminoguinoline, y- 
quinolylamine) . 

Needles + 1H 2 from H 2 O or EtOH.Aq. 
M.p. 70, anhyd. 154. Sol. H 2 0, EtOH, CHC1 3 , 
hot C 6 H 6 . Spar. sol. ligroin, CS 2 . 

B,HN0 3 : plates or needles. M.p. anhyd. 
214. 

B^H^PtCL : orange-yellow needles + 2H 2 
from dil. HOI. M.p. 266-70 decomp. 

Bvm.-Trinitrobenzene add. comp. : red prisms. 
M.p. 111. 



Picrate : needles from H 2 O. M.p. 274. 

MethocJiloride : m.p. 310. 

Methiodide : needles from EtOH. M.p. 224. 

Mhiodide : m.p. 232. 

N-Phenyl : needles. M.p. 198. B,Hd : yel- 
low prisms from EtOH. M.p. 244. 

T3- Acetyl : needles + 1H 2 O from H 2 O. M.p. 
anhyd. 176. Methiodide : m.p. 291 decomp. 

N-p-Aminobenzenesulphonyl : m.p. 248. 

Claus, Frobenius, J. praJct. Chem., 1897, 

56, 181. 
Tschitschibabin, Witkovsky, Lapschin, 

Ber., 1925, 58, 806. 

5-Aminoquinoline (5-Quinolylamine). 

Needles from EtOH. M.p. 110. B.p. 310, 
184/10 mm. Sol. EtOH, Et 2 0. Mod. sol. 
C 6 Hg. Spar. sol. cold H 2 O. Prac. insol. ligroin. 
Sublimes. 

'N-Acetyl : needles. M.p. 178. 

N-p-Aminobenzenesulphonyl : m.p. 230. 

N-p-Toluenesulphonyl : needles from EtOH. 
M.p. 203-4. 

Hamer, J. Chem. Soc., 1921, 119, 1436. 
Dikshoorn, Rec. trav. chim., 1929, 48, 147. 

G-Aminoqiiinoline (6-Quinotylamine). 

Cryst. + 2H 2 from H 2 0, prisms from Et 2 0. 
M.p. anhyd. 114. B.p. 146/0-3 mm. Sol. 
EtOH, Et 2 0, NH 3 . Spar. sol. H 2 0, ligroin. 
Sublimes. 

B,HCl: yeUow needles from EtOH. M.p. 
109. 

B,2HCl : prisms. M.p. 250. 

B,SQz : yellow cryst. M.p. 124. 

Methochloride. : lemon-yeUow needles. M.p. 
242-3. 

Methiodide : reddish-brown needles from 
EtOH. M.p. 199. 

N-ZH'-Jfe: C U H 12 N 2 . MW, 172. YeHow 
cryst. M.p. 56-8. B.p. about 335. Picrate : 
reddish-yellow needles from H 2 0. M.p. 215 
decomp. 

N-Acetyl : needles from H 2 0. M.p. 138. 
Methiodide : yellow cryst. from H 2 O. M.p. 
317 (268). 

N-Diacetyl : needles. M.p. 75. 

"N-Chloroacetyl : prisms from C 6 H 6 -toluene. 
M.p. 153-5. 

N-Benzoyl: leaflets. M.p. 169. 

N-p-Nitrobenzoyl : m.p. 248-50. 

'N-p-Aminobenzoyl : m.p. 96-8. 

N~p-Aminobenzenesulphonyl : m.p. 208 (200). 
^-Acetyl : m.p. 283 (275). 

N-p-Tolu&nesulphonyl : cryst. from EtOH. 
M.p. 193. 

Knueppel, Ann., 1900, 310, 75. 
Hamer, J. Chem. Soc., 1921, 119, 1436. 

7-Ammoqinnoline (7-Quincdylamine). 
YeUow needles + H 2 0. M.p. 73-5, anhyd. 
93-5-94. Sols, fluoresce. 



R-. Am inQcpiim oily*. 6 



136 



4-Aminoresorcinol 



B 2 ,H<ftCl Q : yellow cryst. M.p. about 225 
decomp. 

N-Acetyl : m.p. 167-5. Methiodide : yellow 
prisms. Darkens at 267. M.p. 295-310. 

'N-Benzoyl : m.p. 189. 

N-p-AmiTiobenzenesulpkonyl : m.p. 206. 

^-^-Toluenesulphonyl : m.p. 184-5. 

"N-Cinnamoyl : m.p. 202. 

Hamer, J. Chem. Soc., 1921, 119, 1436. 

8-Aininoquiiioline (S-Quinolylamine). 

Yellow cryst. from EtOH or ligroin. M.p. 
70 (65). B.p. 157~62/20-4 mm. SoL H 2 0. 
Volatile in steam. Forms red salts. 

B,HCl: dark red. M.p. 208-9. 

"N-Acetyl : needles from EtOH. M.p. 103. 

N-Benzoyl : needles from EtOH. M.p. 98. 

~N-p-Nitrobenzoyl : m.p. 178-80. 

N-p-Amiiwbenzoyl : m.p. 160-2. 

N-p-AminobenzenesulpJwnyl : m.p. 195 (188). 
W-Acetyl : m.p. 194. 

~N-p-Toluenesulphonyl : needles. M.p. 154-6. 
Seka, Monatsh., 1924, 45, 290. 
Dikshoorn, Rec. trav. chim., 1929, 48, 147. 
Kaufmann, Zeller, Ber., 1917, 50, 1627. 

2-Aminoquinoline-3-carboxylic Acid 



C 10 H 8 2 N 2 MW, 188 

Amorphous. M.p. 290-2 decomp. 
Me ester : C n H 10 2 N 2 . MW, 202. Yellow 
cryst. M.p. 140-1. 

Et ester: C 12 H 12 2 lSr 2 . MW, 216. YeUow 
needles from EtOH. M.p. 135. Sol. EtOH, 
AcOEt, AcOH, C 6 H 63 CHC1 3 . Insol. H 2 0, 
Et 2 0, ligroin. "N-Benzoyl : yellow needles from 
EtOH. M.p. 160. Picrate: golden yeUow 
cryst. from EtOH. M.p. 177. 

Eupe, Heckendorn, Helv. Chim. Acta, 

1926, 9, 980. 
Kollier, Strang, Monatsh., 1928, 50, 144. 

5-Ammoqmnoline-4-carboxylic Acid (5- 

Aminocinchoninic acid). 

Euby-red needles from H 2 0. Ag and Ba salts 
are yellow. 

Lactam: C 10 H 6 ON 2 . MW, 170. YeUow 
needles from EtOH. M.p. 254-5. 

Koenigs, Lossow, Ber., 1899, 32, 719. 

5-Amino(juinolme-6-carboxylic Acid 

Cryst. from AcOH.Aq. M.p. 218. Sol. 
AcOH, Py. Mod. sol. H 2 0, EtOH, Me 2 CO. 
Spar. sol. C 6 H 6 . Insol. Et 2 0, CHC1 3 , CCJ 4 , pet. 
ether. 

B,HCl: red needles. M.p. 265. 

Me ester : red needles + 2H 2 from H 2 0. 
M.p. anhyd. 245 decomp. Sol. H 2 0, EtOH, 
AcOH. 



TS-Acetyl : yellow needles. M.p. 237 de- 
comp. 

Bogert, Fischer, J. Am. Chem. Soc., 1912, 
34, 1572. 

2-Aminoquinoxaline 

N 




C 8 H 7 N 3 MW, 145 

M.p. 155-6. Sublimes in vacua. 

N-Acetyl : yellow. M.p. 192 5-3-5. 

IS-Benzenesulphonyl : m.p. 259-60. 

'N-p-Aminobenzenesulphonyl : m.p. 247-8. 
N*-Acetyl: m.p. 243-4. 

Weijlard, Tishler, Erickson, J. Am. Chem. 
Soc., 1944, 66, 1957. 

6-Aminoquinoxaline . 

YeHow needles from Et 2 0. M.p. 159. Sol. 
H 2 0, EtOH, CHC1 3 . Mod. sol. Et 2 0, C 6 H 6 . 
Et 2 sol. shows greenish-yellow fluor. Sub- 
limes. Cone. min. acids >- deep violet sols, 
changing to reddish-brown on dilution. 

B,HCl : brownish-red plates with green lustre. 
Decomp. at 215. 

Hinsberg, Ann., 1887, 237, 345. 

2-Arainoresorcinol (2 : 6-Dihydroxyaniline) 
OH 



C 6 H 7 2 N MW, 125 

Free base unstable . Reduces NH 3 . AglSf 3 and 
Fehling's. 

Di - Me ether : 2:6- dimethoxyanilinel 
C 8 H n 2 N. MW, 153. Leaflets from pet. 
ether. M.p. 75. B.p. 146/23 mm. N-Acetyl : 
plates from H 2 or AcOH. M.p. 81. 

Di - Et ether : 2:6- dicthoxyaniline. 
C 1(0 H 15 2 N. MW, 181. Needles from pet. 
ether. M.p. 57. 

0:0: N-Triacetyl : cryst. from MeOH-Et 2 0. 
M.p. 164-5. 

'N-Benzoyl : leaflets from EtOH. M.p. 187. 

Turner, J. Chem. Soc., 1915, 107, 469. 
Kauffmann, de Pay, Ber., 1906, 39, 

323. 
Kauffmann, Franck, Ber., 1907, 40, 3999. 

4-Aminoresorcinol (2 : ^Dihydroxyaniline). 

Unstable. Forms stable hydrochloride with 
2 mols. H 2 of cryst. 

1-Me ether: C 7 H/) 2 N. MW, 139. Unstable. 
Eeduces NH 3 .AgN0 3 . B,HCl : needles from 
dil. HCL M.p. 205-6. $t-Acetyl: needles 
from H 2 0. M.p. 164-5. i^-Triaeetyl : 



5-Aminoresorcinol 



137 



5-Aminosalicylic Acid 



~H-Benzoyl : cryst. 



cryst. from C 6 H 6 . M.p. 92 
from C 6 H 6 . M.p. 163. 

3-Me ether : reddish-brown needles from 
toluene. M.p. 175-80. N-Acetyl : red needles 
from toluene. M.p. 150-6. N-Chloroacetyl : 
plates from AcOEt. M.p. 166. 

Di - Me ether : 2:4- dim ethoxy aniline. 
C 8 H n 2 N. MW, 153. Plates from ligroin. 
M.p. 32-5-33-5 corr. B,HCl : sublimes at 110. 
M.p. 224 decomp. N-Acetyl : cryst. from 
Me 2 CO.Aq. M.p. 117. N-Chloroacetyl : needles 
from EtOH.Aq. M.p. 90 corr. TS-Benzoyl: 
cryst. from EtOH. M.p. 173. 

1-M ether : C 8 H n 2 N. MW, 153. Needles. 
M.p. 148. Spar. sol. H 2 0. O :N-Diacetyl: 
prisms from ligroin. M.p. 91-3. N-Benzoyl : 
cryst. from C 6 H 6 . M.p. 187. 

S-Et ether : grey leaflets from CS 2 .Aq. M.p. 
152^. N-Acetyl : prisms from AcOH. M.p. 
172-5-1 74-5. "N-Chloroacetyl : grey plates from 
toluene. M.p. 158-5-161. 

Di - Et ether : 2:4- diethoxyaniline. 
C 10 H 15 2 N. MW, 181. Brownish-red needles 
and plates from C 6 H 6 -ligroin. M.p. 34 corr. 
250-2. B,HCl : cryst. M.p. 198. 
greenish-yellow needles + 2H 2 0. 
"N-Acetyl : needles from EtOH.Aq. 
(121). N-Chloroacetyl : needles 
M.p. 102-3. N-Benzoyl : needles. 
N-Dibenzoyl : prisms from AcOH. 



jgj 

M.p. 169-5. 
M.p. 117-18 
from EtOH. 
M.p. 113-5. 
M.p. 171. 

l-Me-Z~Et ether: C 9 H 13 2 N. MW, 167. 
Plates. M.p. 22-5. B.p. 144-5/9 mm. N- 
Acetyl : red needles from ligroin. M.p. 100-5- 
101. 'N-Chloroacetyl : plates from toluene. 
M.p. 126-7. 

3-Me-I-Et ether: red cryst. from C 6 H 6 - 
ligroin. M.p. 27-5-28-5 corr. B.p. 152/12 
mm. N-Acetyl : red plates from C 6 H 6 -ligroin. 
M.p. 118. N-Chloroacetyl : plates from ligroin. 
M.p. 98. 

N-Acetyl : m.p. 164-5. 

O : : N-Triacetyl : m.p, 113. 

0-Benzoyl;. m.p. 177-8. 

O : : 'N-Tribenzoyl : needles. M.p. 172. 

"N-ip-Aminobenzenesulphonyl : m.p. 176. 

Heidelberger, Jacobs, /. Am. Chem. Soc., 

1919, 41, 1466. 

Bechhold, Ber., 1889, 22, 2378. 
Henrich, Wagner, Ber., 1902, 35, 4195. 

5-Aminoresorcinol (3 : 5-Dihydroxyaniline, 
phloramine). 

Fine needles. M.p. 146-52. Sol. EtOH. 
Spar. sol. cold H 2 0. Prac. insol. Et 2 0. Oxidises 
rapidly in air. Boiling H 2 > phloroglucinol. 

Di-Me etfier : 3 : 5-dimethoxyaniline. Cryst. 
M.p. 46. B.p. 177/12 mm. B 2 ,H 2 PtCl Q : yel- 
low cryst. M.p. 223. B, HCl : m.p. 210. 
Picrate : yellow needles from EtOH. M.p. 
167-70 decomp. T$-Benzoyl : m.p. 139. 



Triacetyl deriv. : cryst. powder. M.p. 119- 
21. 

Pollak, Monatsh., 1893, 14, 419. 
Seka, Fuchs, Monatsh., 1931, 57, 67. 

Aminoresorcylic Acid. 

See 3 : 5-Dihydroxy-2-aminobenzoic Acid, 
4 : 6-Dihydroxy-3-aminobenzoic Acid, and 3 : 5- 
Dihydroxy-4-aminobenzoic Acid. 

3-Aminpsalicylic Acid (o-Hydroxy-m- 
aminobenzoic acid) 

COOH 



C 7 H 7 3 N " MW, 153 

M.p. 235 decomp. Prac. insol. EtOH. 

B,HCl : needles + 1H 2 0. Decomp. at 150. 

Me ester: C 8 H 9 3 N. MW, 167. Needles 
from C 6 H 6 -ligroin. J$-Chloroacetyl : needles 
from EtOH. M.p. 106. 

Et ester: C 9 H U 3 N. MW, 181. Needles 
from EtOH.Aq. M.p. 47. 

Nitrile : o - hydroxy - m - aminobenzonitrile. 
C 7 H 6 ON 2 . MW, 134. Prisms. M.p. 145 de- 
comp. Phototropic. B 3 HOl : plates from 
EtOH-Et 2 0. Decomp. at 130. 

Me ether: C 8 H 9 3 K MW, 167. Needles 
from CC1 4 . M.p. 82. N-Acetyl : needles + 
H 2 from H 2 0. M.p. anhyd. 137-8. 

"N-Formyl : needles from H 2 0. Decomp. 
at 215. 

N-Benzoyl : needles. M.p. 189. 

"N-Benzenesulphonyl: cryst. fromEtOH-C fi H fi . 
M.p. 194. 

Zahn, J. prakt. Chem., 1900, 61, 532. 
Einhorn, Pfyl, Ann., 1900, 311, 42. 

4-Aminosalicylic Acid (o - Hydroxy -p - 
aminobenzoic acid). 

Reddish-brown cryst. powder from EtOH- 
Et 2 0. M.p. 150-1 decomp. Sol. H 0, EtOH. 
Mod. sol. Et 2 0. 

B,HCl: m.p. 220: 

Nitrile : o - hydroxy-p - aminobenzonitrile. 
C 7 H 6 ON 2 . MW, 134. YeUowish needles from 
AcOEt-C 6 H 6 . M.p. 182. : N-Dibenzoyl : 
cryst. from EtOH.Aq. M.p. 198-9. 

Siedel, Bittner, Monatsh., 1902, 23, 415. 
Borsche, Ann., 1912, 390, 16. 
McGhie et al, J. Soc. Chem. Ind., 1949, 
68, 328. 

5 - Aminos alley lie Acid ( 2 - Hydroxy - 5 - 
aminobenzoic acid). 

Needles from H 2 0. M.p. 283 (280 decomp.). 
Spar. sol. hot H 2 0. Insol. EtOH. FeCl 3 > 
red col. Dist. > jp-aminophenol + C0 2 . 

B z ,H 2 SnClQ : brown prisms. M.p. 128. 

Me ester: C 8 H 9 3 N. MW, 167. Needles 
fromC 6 H 6 . M.p. 96. TS-Acetyl : needles from 



6-Aminosalicylic Acid 



138 



4'-Ammo-y~stiIbazole 



EtOH. M.p. 147 (102). B.p. 169-70/2 mm. 
~N-Chloroacetyl : cryst. from EtOH. M.p. 157. 
Q~Benzoyl : prisms or plates from EtOH. M.p. 
180. 

m ester: C 9 H n 3 N. MW, 181. Needles 
from EtOH. M.p. 145. N-Chloroacetyl : 
needles from EtOH. M.p. 131*5. 

Amide: C 7 H 8 2 N 2 . MW, 152. Needles from 
dil. NH 3 . M.p/ 194-7 decomp. N-Acetyl: 
m.p. 204-6. ~N~Chloroacetyl : plates from 
EtOH.Aq. M.p. 225-7. 

Nitrile : 2 - hydroxy - 5 - aminobenzonitrile. 
C 7 H 6 ON 2 . MW, 134. Needles. M.p. 158-60 
decomp. Phototropic. B,HCl : prisms from 
EtOH-Et 2 0. Decomp. at 180. 

Me ether: C 8 H 9 3 N. MW, 167. Prisms 
from H 2 0. M.p. 153-4. B^H^O.: plates 
from EtOH. Decomp. at 242. N-Acetyl: 
plates from AcOH. M.p. 208-9. 

Et ether : N-acetyl, needles from H 2 0. M.p. 
189-90. 

'N-Acetyl : cryst. + JH 2 from EtOH.Aq. 
M.p. 218. 

TS-Chloroacetyl : cryst. + 1H 2 from AcOH. 
M.p. 233-4 decomp. 

Diacetyl deriv. : m.p. 184. 

N-Benzoyl : amorphous. M.p. 252. 

N-p- ArMnobenzenemlphonyl : m.p. 224. 
W-Acetyl: m.p. 242-5. 

Weil, Traun, Marcel, Ber., 1922, 55, 2664. 
Norris, Cummings, 2nd. Eng. Chem., 1925, 
17, 305. 

6-Aminosalicylic Acid. 

See 6-Hydroxyanthranilic Acid. 
5 - Aminosaligenin (2 - Hydroxy - 5 - amino 
benzyl alcohol, 5-aminosaligenol) 

CH 2 OH 




C 7 H 9 2 N MW, 139 

Cryst. M.p. 139. Sol. hot H 2 0, EtOH, 
Et 2 0. Decomp. in air when moist. Hydro- 
chloride is the developer Edinol. 

x-Me ether: C 8 H n 2 N. MW ? 153. Cryst. 
M.p. 124-6. Sol. hot H 2 0, EtOH. Spar. sol. 
EtgO. 

*-Et ether: C 9 H 13 2 N. MW, 167. Cryst. 
M.p. 76-8. 

K-Acetyl : cryst. M.p. 136-7. 

Tribenzoyl deriv. : m.p. 187. 

Bayer, Chem. Zentr., 1904, 1, 699. 

1-Aminostearic Acid 

CH 3 -CH 2 -[CH 2 ] 13 -CH 2 -CH(NH 2 )-COOH 
Ci 8 H 37 2 N MW, 299 

Cryst. powder from hot AcOH. M.p. 222. 
Insol. EtOH, Et 2 0, C 6 H 6 . 



Me ester: C 19 H 39 2 N. MW, 313. B,HCl : 
needles from AcOEt. M.p. 112 corr. N- 
Chloroacetyl : needles from pet. ether. M.p. 
78 corr. 

Et ester: C 2Q H 41 2 N. MW, 327. B,HCl : 
needles from AcOEt. M.p. 89 corr. N-Chloro- 
acetyl : needles from pet. ether. M.p. 68 corr. 

~N-Chloroacetyl : needles from Et 2 0-pet. ether. 
M.p. 103-7. 

Hell, Sadomsky, Ber., 1891, 24, 2395. 
Fischer, Kropp, Awn,., 1908, 362, 339. 



2 / ~Amino-a-stilbazole 

pyridine) 

-CHICH 



(2-[2-Aminostyryl]- 




MW, 196 
needles from EtOH-HCl. M.p. 



C 13 H 12 N 2 

B,2HCl 
250-4. 

^-Diacetyl : m.p. 111-12. 

Feist, Arch: pharm., 1902, 240, 256. 
Simpson, J. Chem. Soc., 1946, 673. 

S'-Amino-a-stilbazole (2- [3- Aminostyryl]- 
pyridine). 

Needles + H 2 0. M.p. 85. Sol. EtOH, Et 2 0, 
CHC1 3 . Prac. insol. cold H 2 0. 

B,2HCl: cryst. + 2H 2 0. M.p. 240. Turns 
red in air. 

Feist, Arch, pharm., 1902, 240, 254. 
Schuftan, Ber., 1890, 23, 2717. 



^-Amino-a-stilfoazole ( 
pyridine). 

Pale yellow needles from EtOH.Aq. M.p. 
138-9. Sol. EtOH, Et 2 0, CHC1 3 , Insol. H 2 O. 

B,2HCl : cryst. from dil. HC1. M.p. above 
260. 

B,H 2 Sn 2 Cls : m.p. 198-9. 

"N-Acetyl: needles from EtOH.Aq. M.p. 
170-1. 

Feist, Arch, pharm., 1902, 240, 251. 
Baumert, Ber., 1906, 39, 2972. 

2 / -Ammo-y-stilbazole (4- [2-Aminostyryl]- 
pyridine). 

B,2HCl: needles, M.p. 205. 
Sulphate : from H 2 0. M.p. 140. 
B,H 2 Sn z Cl Q : from H 0. M.p. 155. 
B 3 H 2 PtCL: m.p. 238. 
B 2 ,C0 2 ,H 2 0: m.p. 76. 

Lowensohn, Ber., 1907, 4)0, 4861. 

4 / -Amino-y-stilbazole (4- [4b-Aminostyryl]- 
pyridine). 

M.p. 275 (138-9). Sol. EtOH, Et 2 0, CHC1 3 . 
Prac. insol. H 2 0. 

B,2HCl : cryst. from EtOH-HCL M.p. 257- 
8 decomp. 



2-AminostiIbene 



139 



AminoterepMhalic Acid 



B,H 2 Sn%Cl & : m.p. 198-9. 
B,H%PtCl 6 : m.p. above 300. 

Baumert, Ber. } 1906, 39, 2973. 

Royer, J. Chem. Soc., 1947, 560. 

2-Amiaostilbe:ae 

H 2 N 



C 14 H 13 N MW, 195 

Plates from EtOH.Aq. M.p. 106. Sols. 

exhibit blue fluor. 

TS-Acetyl : needles from EtOH. M.p. 140. 
Sachs, Hilpert, Ber., 1906, 39, 904. 

3-Aminostilbene . 

Blocks from butyl acetate. M.p. 119-20. 

T$-Acetyl : tablets. M.p. 191-2. 

Bergmann, Schapiro, J. Org. Chem., 1947, 
12, 57. 

2-Amiixostilbeae-4-carl)oxylic Acid 
H 2 N 

C 15 H 13 2 N MW, 239 

Yellow cryst. powder from xylene-ligroin. 

M.p. 197-8. Sol. EtOH, Et 2 0, AcOH. Spar. 

sol. C 6 H 6 . Sols, exhibit bluish-green fluor. 
Nitrile: C 15 H 12 N 2 . MW, 220. Yellow 

nodules from EtOH-ligroin. M.p. 123. 2-N- 

Acetyl: needles. M.p. 220. 

UUmann, Gschwind, Ber., 1908, 41, 2295. 

o-Aminostyrene (o-Aminophenylethylene, o- 
aminovinylbenzene ) 



CHICHo 




C 8 H 9 N MW, 119 

Colourless oil. B.p. 97-8/8 mm. Dg 1-015. 
Tin 1-6130. Polymerises readily. Turns yellow 
in air. 

N-Acetyl : needles from C 6 H 6 . M.p. 129. 
Sabetay, Mintsou, Bull. soc. chim., 1929, 

45, 842. 
Komppa, Ber., 1893, 26, 677 (Eef.). 

m- Aminostyrene 

Yellow oH. B.p. 112-15/12 mm. Df, 1-0216. 
Readily polymerises. 

B,HCl : needles. M.p. 144-5. Prisms + 
1H 2 from EtOH.Aq. M.p. 181. 

TS-Acetyl : needles from C 6 H 6 -Hgrom. M.p. 
74-5. 

TS-Benzoyl : leaflets from C 6 H e -ligroin. M.p. 
90-1. Plates + 1H 2 from EtOH.Aq. M.p. 
126-7. 

Tutin, Caton, Hann, J. Chem. Soc., 1909, 

95, 2125. 
Komppa, Ber., 1893, 26, 677 (Eef.). 



p-AjxdHostyrene (p-Aminophenylethyle7ie, p- 
aminovinylbenzene) . 

M.p. 23-5. B.p. 98-100/4 mm. Dg 1-012. 
Tig 5 1-6250. Turns yellow in air. Polymerises 
to product, m.p. 81. 

B,HCl : needles from dil. HC1. Darkens at 
170. 

N-Acetyl : plates from C 6 H 6 . M.p. 142. 
N-Benzoyl : cryst. from EtOH. M.p. 160-1. 
Sabetay, Mintson, Bull. soc. chim., 1929, 

45, 842. 
Komppa, Ber., 1893, 26, 677 (Eef.). 

o-Aminostyryl chloride. 
See (3-Chloro-o-aminostyrene. 
Aminostyrylpyridine . 
See Aminostilbazole. 
Amiaaosuccinic Acid. 
See Aspartic Acid. 
Amino-sulphopropionic Acid. 
See Cysteic Acid and Isocysteic Acid. 
Aminotereplithalic Acid (Z-Aminobenzene- 
1 : 4:-dicarboxylic acid) 

COOH 




COOH 
C 8 H 7 4 N MW, 181 

Yellowish cryst. from H 2 O. M.p. 324-5 
decomp. (corr.). Spar. sol. cold H 9 0, EtOH, 
Et 2 0. Insol. Me 2 CO, AcOH, CHCl 3 rC 6 H 6 , pet. 
ether. Sols, show blue fluor. Jc = 2-65 X 10- 4 
at 25. 

1-Jfe ester: C 9 H 9 4 N. MW, 195. Yellow 
cryst. from MeOH. M.p. 216-17 corr. Sols, 
show violet-blue fluor. "N-Acetyl : cryst. from 
C 6 H 6 . M.p. 254-5 decomp. (corr.). 

4t-Me ester : colourless needles from MeOH. Aq. 
M.p. 217 corr. *N-Acetyl : needles from MeOH. 
M.p. 207-8 corr. 

Di-Me ester: C 10 H U 4 N. MW, 209. Cryst. 
from EtOH. M.p. 134. Volatile in steam. 
N-Acetyl : cryst. from C 6 H 6 or MeOH. M.p. 
167 corr. N-Diacetyl : tablets from MeOH. 
M.p. 74-6. 

Dibenzyl ester: C 22 H 19 4 N. MW, 361. 
Needles from Et 2 0-pet. ether. M.p. 99-101. 

N-Jtfe : C 9 Ho0 4 N. MW, 195. Yellow cryst. 
from EtOH. M.p. 271-2 corr. 1-Me ester: 
yellow plates from C 6 H 6 . M.p. 208-9 corr. 
4-J4" e ester : yellow needles from MeOH or 
Cj}H 6 . M.p. 187. Di-Me ester: cryst. from 
MeOH, EtOH, or C 6 H 6 . M.p. 93. Volatile in 
steam. TS-Acetyl : cryst. from AcOH. M.p. 
217 decomp. 

N-IH'-Jfe: C 10 H U 4 N. MW, 209. Needles 
from H 2 0. M.p. 281 corr. 1-Me ester : yellow 
needles from CH 6 . M.p. 132-3. 4-Jfe ester : 
cryst. from MeOH or C 6 H 6 . M.p. 178-9. Di- 
Me ester : yellow plates from MeOH. M.p. 
70-5. 



1 -Aminotetradecane 



140 



~N-Acetyl: cryst. from EtOH. Decomp. at 
272 eorr. 

Cahn-Speyer, Monatsh., 1907, 28, 803. 
Wegscheider et &l., Manatsh., 1912, 33, 
194,143; 1910,31,1299. 

1 - Aminotetradecane . 

See Tetradecylamine. 

4 - Amino - 2 : 3 : 2' : 3' - tetramethylazo - 
benzene (o-Xyleneazo-o-3-xylidine, o-3-aminoazo- 
xyletie) 

H 3 C_CH 3 H 3 C CH 3 




C 16 H 19 N 3 MW, 253 

Yellow leaflets from C 6 H 6 . M.p. 110-11. 
Sn + HC1 > o-3-xylidine + 3 : 6-diamino-o- 
xylene. 

Nolting, Ford, Ber., 1885, 18, 2684. 

4 - Amino - 2 : 5 : 2' : 5' - tetrametLylazo- 
benzene (p-Xyleneazo-p-xylidine, ip-aminoazo- 
xylene). 

Red leaflets from EtOH. M.p. 150. Sn + 
HC1 > #-xylidine + 2 : 5-diamino-p-xylene. 

Nolting, Forel, Ber., 1885, 18, 2685. 

4 - Amino - 2 : 6 : 3' : 5' - tetrametliylazo- 
benzene (m-Xyleneazo~m-5-xylidine, m.-5-amino- 
azoxylene). 

Yellow leaflets from EtOH. M.p. 95. Sn + 
HC1 > m 5 - xylidine + 2:5- diamino - m - 
xylene. 

Nolting, Forel, Ber., 1885, 18, 2684. 

6 - Amino - 3 : 4 : 3' : 4 7 - tetramethylazo- 
benzene (o-Xyleneazo-o-^-xylidine, o-4:-amino- 
azoxylene). 

YeUow leaflets from EtOH. M.p. 179. 

Nolting, Forel, Ber., 1885, 18, 2685. 

2 - Amino - 3 : 5 : 2' : 4" - tetramethylazo- 
benzene (m-Xyleneazo-m-k-xylidine, m-4-ammo- 
azoxylene). 

Orange-yellow leaflets. M.p. 78. Spar. sol. 
cold EtOH, Sol. CgHe. Sn + HC1 > m-4- 
xylidine + 4 : 5-diamino-m-xylene. 

Nolting, Forel, Ber., 1885, 18, 2682. 

4 - Amino - 3 : 5 : 2' : 6 X - tetramethylazo- 
benzene . 

Yellow plates from EtOH.Aq. M.p. 77-5. 
Sol. EtOH, C 6 H 6 . 

Nolting, Forel, Ber., 1885, 18, 2684. 

4 - Amino - 3 : 6 : 2' : 4 / - tetramethylazo- 
b enzene (m-Xyleneazo-p-xylidine) . 

Dark orange leaflets. M.p. 110-11. Sol. 
EtOH, Et 2 0. Sn + HC1 > m-4-xylidine + 
2 : 5-diamino-jp-xylene. 

Nolting, Forel, Ber., 1885, 18, 2684. 



4 - Amino-m-tliiocresol 

5-Amino-l : 2 : 3 : 4-tetramethylbe:azene. 

See Prehnidine. 

4-Ami2io-l : 2 : 3 : S-tetramethylbenzene. 

See Isoduridine. 

3-Amino-l : 2 : 4 : 5-tetramethylbenzene. 

See Duridine. 

co-Aminotetrametliylbenzene . 
See Trimethylbenzylamine. 
2-Aminothiazole (Abadole) 



C-NH, 




C 3 H 4 N 2 S ^W ? 100 

Yellow tablets from EtOH. M.p. 90. Spar. 
eol. H 2 0, EtOH, Et 2 0. Decomp. on dist. 
-8-Acetyl : needles from H 2 0. M.p. 203- 
Traumann, Ann., 1888, 249, 36. 
Eritton, Harding, U.S.P., 2,387,212, 

(Chem. Abstracts, 1946, 40, 1179). 
Short, Kelly, B.P., 558,956, (Chem. 

Abstracts, 1945, 39, 4632). 
Morren, Bupont, Chem. Abstracts, 1944, 
38, 3284. 

5-Aminothiazole . 

TX-Acetyl : anhyd. needles from H 2 0, EtOH, or 
C 6 H 6 or as plates containing solvent of cryst. 
M.p. 162. 

HeUsing, Ber., 1903, 36, 3550. 

4-Amino-o-thiocresol (o-Mercapto-p4olui~ 
dine, 4:-amino-o-tolyl mercaptan) 
CH 



MW, 139 
M.p. 47. 



V 

NH 2 
C 7 H 9 NS 

Needles from C 6 H 6 ~pet. ether. 
Slowly volatile in steam. Sol. EtOH, Et 2 0. 

S-Me : methyl p-&mino~o-t>Qlyl sulphide. 
C 8 H n NS. MW, 153. Plates from ligroin. 
M.p. 47. N-Acetyl : needles from C 6 H 6 . M.p. 
126 P . 

N:S-Tri-Me: C 10 H 15 NS. MW, 181. Yel- 
low oil. B.p. 159/17 mm. Volatile in steam. 
Methiodide : plates from H 2 or EtOH. M.p. 
200-2 decomp. 

TS-Acetyl : needles from EtOH. M.p. 95. 

N : S-Diacetyl : yellow cryst. from C 6 H 6 -pet. 
ether. M.p. 125. 

Zincke, RoUhauser, Ber., 1912, 45, 1500. 

4 - Amino - m -tMocresol (m - Mercapto - p - 
toluidine, 4c-amino-m~tolyl mercaptan). 

Thick oil. Pormic acid ^ 6-methylbenztM- 
azole. 

Hess, Ber. t 1881, 14, 492. 



2-Amino-p-tMocresol 



141 



m-AminotMoplienol 



2-Amino-p-tMocresol (p-Mercapto-o-tolui- 
dine, 2-amino--p-tolyl mercaptan). 

S-Me : methyl o-amino-j>-tolyl sulphide. 
Needles. B.p. 130/20 mm. N-Acetyl : needles 
from C 6 H 6 ~pet. ether. M.p. 114. 

Eichter, Bernoulli, Ber., 1909, 42, 4310. 
Zincke, Kose, Ann., 1914, 406, 135. 



3 - AminotMonaplitliene 

naphthene) 



- Aminothio - 




GE 



C 8 H 7 NS MW, 149 

Oil. Besi.nifi.es in air. Sol. dil. min. acids. 
Volatile in steam. Boiling H 2 > thio- 
indoxyl. 

Zn salt : greyish-brown needles from C 6 H 6 - 
EtOH. M.p. 204. 

N-Acetyl : tablets from H 2 or MeOH. M.p. 
169. 

13-Benzoyl : cryst. from EtOH. M.p. 132. 

Komppa, J. praJct. Chem., 1929, 122, 324. 

4- Amino-1 -thionaphtliol (<i-Amino-l -mer- 
captonaphthalene, -mercapto-\-naphthylamine) 

SH 




C 10 H 9 NS MW, 175 

Yellow needles from EtOH. M.p. 91-3. 
Sol. EtOH, Et 2 0, AcOH, CHC1 3 . Mod. sol. 
C 6 H 6 . Spar. sol. ligroin. Vac. dist. > 1- 
naphthylamine. 

S-Me : C n H u NS. MW, 189. Needles from 
C 6 H 6 . M.p. 54. *N-Acetyl: needles from 
AcOH. M.p. 193. 

S-p-Nitrophenyl : ochre needles from EtOH. 
M.p. 168. 

TS-Acetyl : needles from AcOH. M.p. 173. 

Zincke, Schiitz, Ber., 1912, 45, 473. 

8- Amino-2-tMonapMhol (8 -A mino-%-mer- 
captonaphthalene, 1 -mercapto-l-naphthylamine) 
H 2 N _ 




C 10 H 9 NS ' " MW, 175 

Needles + |EtOH from EtOH. M.p. 127. 

Cleve, Ber., 1888, 21, 3267. 
2-Aminothiopliene (2-Thiophenine) 



C 4 H 6 NS 



S 



Pale yellow liq. B.p. 77-9/ll mm., 61-2/l 
mm. Eapidly oxidises and polymerises. 

N-Me : C 5 H 7 NS. MW, 113. B.p. 88-92/15 
mm. "N-Acetyl : leaflets from H 2 0. M.p. 60. 

TS-Et : C 7 H 9 NS. MW, 127. B.p. 85-9/2-3 
mm. 

N-Acetyl : leaflets. M.p. 161-2. 

N-Propionyl : plates from H 2 O. M.p. 111. 

N-Benzoyl : needles from EtOH.Aq. M.p. 
172-3. 

N-o-Toluenesulphonyl : cryst. from EtOH. 
M.p. 183-4. 

Steinkopf, Ann., 1913, 403, 17. 
Seemann, Lucas, Can. J. Research, 1941, 
19,291. 

3-Aminothiopliene (3-Thiophenine). 

Eree base is unstable. 

N-Acetyl : leaflets from H 2 0. Needles from 
C 6 H 6 ~CHC1 3 . M.p. 145-8. 

N-Benzoyl : leaflets from C 6 H fi -CHCL. M.p. 
153-5. 

Steinkopf, Hopner, Ann., 1933, 501, 183. 

o-Aminothiophenol (o-Mercaptoaniline, o- 
aminophenyl mercaptan) 
SH 



MW, 99 



C 6 H 7 NS MW, 125 

Needles. M.p. 26. B.p. 234, 125-7/6mm- 
HI > aniline + H 2 S. Ox. >- 2 : 2'-diamino- 
diphenyl disulphide. 
B,HCl: cryst. M.p. 217 decomp. 
S-Me : methyl o-aminophenyl sulphide, o- 
thioanisidine. C 7 H 9 NS. MW, 139. B.p. 234 
part, decomp., 133-4/15 mm. "N-Formyl : 
prisms from C 6 H 6 -3igroin. M.p. 53-4. N- 
Acetyl: leaflets from EtOH. M.p. 102-3. 
~N-Benzoyl : needles from EtOH. M.p. 96. 

Tri-Me: VJI^S. MW, 167. B.p. 130 / 
20 mm. Methiodide : prisms from H 2 0. M.p. 
162-3 decomp. 

S-PJienyl : see o-Aminodiphenyl sulphide. 
N:S-Diacetyl: prisms from EtOH. M.p. 135. 
N : S-Dibenzoyl : needles from EtOH. M.p. 
154-5. 

Hofmann, Ber., 1887, 20, 2260. 
Zincke, Siebert, Ber., 1915, 48, 1242. 
Claasz, Ber., 1912, 45, 1030. 
Eaprianoo et aL, Chem. Abstracts, 1946, 

40, 1829. 

Gardner, B.P., 558,887, (Chem. Abstracts, 
1946, 40, 7237). 

m-Aminothiophenol (m-Mercaptoaniline, 
m~aminophenyl mercaptan). 

Pale yellow oil. B.p. 180-90/16 mm. Sol. 
H 2 0, EtOH. Insol. Et 2 0, pet. ether. Easily 
oxidised. FeCl 3 > 3 : 3'-diaminodiphenyl di- 
sulphide. 



p-AininotMoplieiiol 



142 



3-Amino-o-toltiic Acid 



B,HCl: cryst. M.p. 232. 

S-Jkf e : methyl ra-aminophenyl sulphide^ m- 
thioanisidine. Pale yellow oil. B.p. 163-5/16 
mm. TS'Acetyl: needles from H 2 (X M.p. 75. 

Tri-Me: yellow oil. B.p. 165-7/16 mm. 
Methiodide: cryst. from H 2 0. M.p. 183-5 
decornp. 

N : S-Diacetyl : cryst. from C 6 H 6 -4igroiii. M.p. 
97. 

Zincke, Midler, Ber., 1913, 46, 775. 

p-AminotMopliejiol (p-Mercaptoaniline, p- 
aminophenyl mercaptan). 

White cryst. mass. M.p. 46. B.p. 140-5 / 
16mm. Sol.E 2 0. Volatile in steam. Eeadily 
OXi ^ 4 : 4'-diaminodiphenyl disulphide. 

S-Me : methyl p-aminophenyl sulphide, p- 
thioanisidine. B.p. 272-3, 140/15 mm. Dg 
1-1425. Volatile in steam. N-Acetyl : needles 
from H 2 0. M.p. 130-5 (128). 

Tri-Me : leaflets from MeOH.Aq. M.p. 23. 
Methiodide: leaflets from H 2 0. M.p. 180-4 
decomp. 

S-Et : ethyl ^-aminophenyl sulphide, jp-thio- 
phenetidine. CoH^NS. MW, 153. Yellow oil. 
B.p. 280-1, 165/12 mm. Dgl-1010. BJSOl: 
cryst. M.p. 188 decomp. N-Acetyl: cryst. 
from H 2 or EtOHAq. M.p. 116-17. N- 
Benzoyl : leaflets from EtOH. M.p. 145. 

S-Phenyl : see ^-Aminodiphenyl sulphide. 

N-Acetyl : two forms, (i) White scales, (ii) 
Yellow leaflets. Both forms, m.p. 154 (150). 
(i) ^ (ii) at about 137 in sunlight. 

N : S-Diacetyl : two forms, (i) Leaflets. M.p. 
144. (ii) M.p. 132. (i) ^ (ii) at 155-66. 

N-Benzoyl : two forms, (i) Colourless. Sin- 
ters at 165, m.p. 180. (ii) Yellow needles. 
M.p. 182. (i) > (ii) on heat, or by recryst. 
from EtOH. 

Hinsberg, J5er., 1906, 39, 2427. 
Zincke, Jorg, Ber., 1909, 42, 3362. 

l-Aminothioxanthone 
CO 




C 13 H 9 ONS MW, 227 

Plates from C 6 H 6 . . M.p. 202-3. Green fluor. 

inH 2 S0 4 . 

TS-Ace&yl : cryst. from AcOH. M.p. 233-4. 
Mayer, Ber., 1909, 42, 3063. 

2-AminotMoxanthone . 
Cryst. from AcOH. M.p. 246. 
TS-Acetyl : m.p. 267. 

Mayer, Ber., 1909, 42, 3067. 

3-Aminothioxanthone . 

Yellowish -brown needles from PhN0 2 . M.p. 
221-2. Sol. CHCL, AcOH. Less sol. C 6 H 6 . 
Spar. sol. EtOH. Green fluor. in H 2 SO 4 . 



B,HGl: hygroscopic needles. Decomp. at 
230. 

~8-Acdyli plates from Ac 2 0. M.p. 236-7. 

Mayer, Ber., 1909, 42, 3056. 

4-AminotMoxantIione . 
Greyish-brown needles. M.p. 249-50. Green 
fluor. in H 2 S0 4 . 

N-Acetyl: needles from AcOH. M.p. 273. 

Mayer, Ber., 1909, 42, 3065. 

2-Amiaothymol (S-Hydroxy-2-amino-l- 
meihyl-4:-isopropylbenze,ne) 

CH 3 



,NH 2 
1JOH 

CH(CH 3 ) 2 
C 10 H 15 ON MW, 165 

Eree base not known. 

Et ether : B,HCl : needles from dil. HCL 
M.p. about 204 decomp. B 2 ,H 2 PtCl 6 : reddish- 
yellow needles. M.p. 169-70 decomp. N- 
Acetyl: needles from EtOHAq. M.p. 109. 
N-Benzoyl : leaflets from EtOH.Aq. M.p. 144. 

Gaebel, Ber., 1902, 35, 2798. 

6-Ammotliy mol . 

Scales from C 6 H 6 . M.p. 178-9. Ox. in 
acid sol. > thymoquinone. 

B } HCl: cryst. M.p. 255. 

Me ether : B,HCl : m.p. 250 decomp. N- 
Acetyl : cryst. from EtOH. M.p. 139. 

M ether: C 12 H 19 ON. MW, 193. Unstable 
oil. B,HCl: needles from dil. HCL M.p. 
227-30 decomp. 'N-Acetyl : thymacetin. 
Needles from EtOH. M.p. 136. N-Chloro- 
acetyl: cryst. from EtOH. M.p. 154. 3ST- 
Bromoacetyl : m.p. 145. 'N-Benzoyl : needles 
from EtOHAq. M.p. 151-2. 

TX-Acetyl : m.p. 174-5. 

Triacetyl : leaflets from EtOH. M.p. 91. 

TS-Benzoyl : needles from EtOH.Aq. M.p. 
178-9. 

: ~N-Dibenzoyl : needles from EtOH.Aq. 
M.p. 166-7. 

Wallach, Neumann, Ber., 1895, 28, 1663. 
Kremers, Wakeman, Hixon, Organic Syn~ 
Collective Vol. I, 498. 



a-Aminotoluene-jp-sulplionic Acid. 
See 4-Homosulphanilic Acid. 
co-Aminotoluic Acid. 
See Benzylamine-carboxylic Acid. 
3-Amino~o~toluic Acid 

CH 3 



C 8 H 9 2 N 



MW, 161 



4-Amino-o-toIuic Acid 



143 



Needles. M.p. 125-6 decomp. 
Nitrile: C 8 H 8 N . MW, 132. Cryst. from 
M.p. 127-8: 

Gabriel, Thieme, Ber., 1919, 52, 1079. 

4-Amino-o-toluic Acid. 

Prisms from H 2 0. M.p. 196. Sol.hotHX), 
hot EtOH. 

Nitrile : needles from pet. ether. M.p. 88. 
Spar. sol. hot H 2 0. B,HCl: needles from 
EtOH. M.p. about 220. Picrate: needles 
from EtOH. M.p. 178-9. 

N-Acetyl : needles from EtOH. M.p. 177. 
Landsberger, Ber., 1898, SI, 2881. 

5-Amino-o-toluic Acid. 

Needles from EtOH. M.p. 165 decomp. 
(153). Sublimes. Heat. > m-toluidine. 

Nttrile : rhombic cryst. from EtOH. M.p. 
90. 

N-Acetyl : reddish-yellow cryst. from H 2 O. 
M.p. 243. 

Gabriel, Thieme, Ber., 1919, 52, 1079. 

6-Ammo-o-toluic Acid. 

M.p. 191. 

Nitrile : needles from H 2 0. M.p. 95-5. 

Nolting, Ber. y 1904, 37, 1025. 

2-Amino-m-toluic Acid 

CH 



MW, 151 
Heat, at 




H 2 0. 



M.p. 172 
MW, 150. Cryst. from 
Cryst. M.p. 



C 8 H 9 2 N 

Prisms from 
200 > o-toluidine. 

Amide : C 8 H 10 ON 2 . 
H 2 0. M.p. 149. 

Nitrile: C 8 H 8 N 2 . MW, 132. 
39. Volatile in steam. 

TS-m : C 10 H 13 2 N. MW, 179. Prisms from 
ligroin. M.p. 71-2. 

N-Acetyl : needles from H 2 0. M.p. 194. 

"N-Benzoyl : m.p. 178. 

Findeldee, Ber. t 1905, 38, 3553. 
Gabriel, Thieme, Ber., 1919, 52, 1091. 

4-Amino-m-toluic Acid. 

Leaflets from EtOH. M.p. 175. Sol. Et 2 0. 
Mod. sol. hot H 2 0. 

Me ester : C 9 H 1]L 2 ]Sr. MW, 165. Columns 
fromH 2 0. M.p. 62. 

Amide : prisms from CHCL. M.p. 179. 

Nitrile : oryst. from EtOH.Aq. M.p. 63. 

Anilide : tablets from EtOH. M.p. 240. 

N-JIfe : CH U 2 N. MW, 165. Cryst. from 
pet. ether. M.p. about 128. 

N-ZW-Jfe : B,HCl : m.p. 202. B 2 ,H 2 PtOl Q : 
yellow cryst. M.p. 217-18. 

N-J27* : yellow leaflets from H 2 0. M.p. 191. 



3-Amino-p-toluic Acid 
N-Acetyl: needles from EtOH.Aq. M.p. 
Findeklee, Ber., 1905, 38, 3553. 



5-Amino-m~toluic Acid 
Needles from CgHg. M.p. 183. Bist. with 
CaO > m-toluidrae. 
Nitrile : needles from ligroin. M.p. 75. 

Muller, Ber., 1909, 42, 433. 

Gabriel, Thieme, Ber., 1919, 52, 1091. 

6-Amino-m-toluic Acid. 

Needles from H 2 0. M.p. 169. Dist. with 
CaO > o-toluidine. 

Me ester : prisms from EtOH. M.p. 118. 

Et ester : needles from EtOH.Aq. M.p. 79. 

Amide : cryst. + 1H 2 from H 2 0. M.p. 
anhyd. 115. 

Nitrile : needles from H 2 O. M.p. 95. 

N-Jtfe: needles from H 2 O. M.p. 201. 

$-Et: needles from H 2 0. M.p. 169-70. 
N-Acetyl : cryst. from H 2 0. M.p. 228. 

N-Benzoyl : yellow needles from Et 2 0. M.p. 
about 100. 



Muller, Ber., 1909, 42, 433. 

Gabriel, Thieme, Ber., 1919, 52, 1091. 

2-Amino-p-toluic Acid 
CH 3 

^VH, 



MW, 151 



Mod. sol. H 2 0. 



C 8 H 9 2 N 

Needles. M.p. 165. 

Nitrile: C 8 H 8 N 2 . MW, 132. Prisms from 
EtOH. M.p. 81-2. Spar. sol. H 2 0. Intense 
sweet taste. 

N-Acetyl : needles from AcOH. Cryst. from 
Et 2 0. M.p. 279-81 corr. 

Banse, Ber., 1894, 27, 2163. 
Ahrens, Z. Chem., 1869, 104. 

3-Ammo-j)-toliiic Acid (Homoanthranilic 
acid). 

Needles from EtOH. M.p. 177 decomp. Sol. 
Et 2 0, C 6 H 6 , hot EtOH. Spar. sol. ligroin, CS 2 , 
hot H 2 0. 

Amide: C 8 H 10 ON 2 . MW, 150. Leaflets. 
M.p. 146-7. 

Nitrile : leaflets from EtOH.Aq. M.p. 94. 
Sol. EtOH, Me 2 CO, CHC1 3 > C 6 H 6 . Volatile in 
steam. N-Acetyl : needles from EtOH. M.p. 
133. N-Benzoyl : needles from C 6 H 6 . M.p. 
145 corr. 

N-Formyl : needles from EtOH. M.p. 186-7 
decomp. 

N-Acetyl : needles. M.p. 183. 

Niementowski, J. prdkt. Chem., 1889, 
40,1. 



a-Aminotoluidine 



144 



co-Amino-1 : 3 : 5-trimetliylbenzene 



a-Amdnotoluidine . 
See Aminobenzylamine. 
2-Amino-m-toluylformic Acid. 
See 3-Methylisatic Acid. 
4-Amino-m~toluyHormic Acid (4:-Amino- 
3-methylp7ienylglyoxylic acid) 

COCOOH 



1-Amino-l : 3 : 4-triazole 




KEL 



C 9 H 9 3 N MW, 179 

Yellow needles from H 2 0. M.p. 163-4 
decomp. Sol. EtOH, Me 2 CO, AcOH. Spar, 
sol. CHC1 3) Et 2 0. 

IS-lBt : C n H 13 3 ]SL MW, 207. Yellow 
prisms from H 2 0. M.p. 132-4 decomp. 

Phenylhydrazine deriv. : m.p. 179 decomp. 

Boehringer, D.R.P., 117,021, (Ohem. 
Zentr., 1901, I, 237). 

6-Amino-m-tolnylformic Acid. 
See 5-Methylisatic Acid. 
Aminotolyl Mercaptan. 
See Aminothiocresol. 
1-Amino-l : 2 : 3-triazole 

Hfi 4 - 



G 2 H 4 N 4 MW, 84 

Hygroscopic cryst. from EtOH-Et 2 or 
CHCla-ligroin. M.p. 51. 

B,HOl : yellow plates. M.p. 114 decomp. 

"N-Benzoyl : needles from H 2 0. M.p. 151. 

Picrate : m.p. 130 decomp. 

Pechmann, Bauer, Ber., 1909, 42, 669. 
StoU6, Ber., 1926, 59, 1743. 

3-Amino-l : 2 : 4-triazole 



NH 
C 2 H 4 N 4 MW, 84 

Cryst. from H 2 0, EtOH or AcOEt. M.p. 
159. Sol H 2 0, EtOH, CHC1 3 . Spar. sol. 
AcOEt. Insol. Et 2 0, Me 2 CO. Eeacts neutral. 

B,HCl: cryst. from EtOH. M.p. 153. 

B 3 HNO Z : m.p. 174 decomp. 

N-Monoacetyl : m.p. 295-300 decomp. 

N-Diacetyl : cryst. from EtOH or toluene. 
M.p. 190-1. 

Picrate : yellow needles from H 2 . M.p . 23 1 
decomp. 

Thiele, Manchot, Ann., 1898, 303, 33. 
Darapsky, Mliller, Ber., 1907, 40, 818. 
Allen, Bell, Organic Syntheses, 1946, 
XXVI, 11. 



C 2 H 4 N 4 MW, 84 

Hygroscopic needles from EtOH or GHC1 3 . 
M.p. 82-3. Sol. EtOH. Spar. sol. CHC1 3 , pet. 
ether. Eeacts slightly acid. 

B,HCl : leaflets from EtOH. M.p. 153. 

B,HBr : leaflets or needles from EtOH. M.p. 
136 slight decomp. 

B,HI: needles from EtOH. M.p. 134-5 
decomp. 

BtHAuOl^ : cryst. + 1H 2 0. M.p. 120, 
anhyd. 170. 

B 2 ,H 2 PtClQ : orange-red cryst. powder from 
HC1. M.p. 230 decomp. 

TX-Formyl: cryst. from EtOH-Et 2 O. M.p. 
117. 

Picrate : yellow needles. M.p. 194-5 de- 
comp. 

Curtius, Darapsky, Miiller, Ber., 1907, 40, 

835, 1196. 

Billow, Ber., 1909, 42, 2715. 
Allen, Bell, Organic Syntheses, 1944, 

XXIV, 12. 

1-Aminotridecane . 
See Tridecylamine. 
12-Aminotridecylic Acid 

H 2 N-CH 2 -CH 2 -[CH 2 ] 8 -CH 2 "CH 2 -COOH 
13 H 27 2 N MW, 229 

Cryst. powder. M.p. 177 decomp. Sol. 
EtOH, hot H 2 0. Insol. Et 2 0, C 6 H 6 . 

EMCl : m.p. about 151. 

Et ester : C 15 H 31 2 N. MW, 257. Cryst. from 
EtOH.Aq. M.p. 73. B,HCl: needles from 
EtOH. M.p. 145. 

TS-Bemzoyl : cryst. from EtOH.Aq. M.p. 111 
(105). 

N-Benzenesulphonyl : prisms from EtOH.Aq. 
M.p. 102. 

Ghloroplatinate : yellow leaflets. M.p. about 
207 decomp. 

MiiUer, Krauss, Ber., 1932, 65, 1357. 
Baruch, Ber., 1893, 26, 1870. 

5-Amino-l : 2 : 3-trimethylbeiizene. 

See 5-Aminohemimellitene. 

oo-Amino-1 : 2 : 4-trimethylbenzene. 

See 2 : 4-Dimethylbenzylamine. 

3-Amino-l : 2 : 4-trimethylbenzene. 

See 3-Amino-i/r-cumene. 

5-Amino-l : 2 : 4-trimethylben2ene. 

See ^-Cumidine. 

6-Amino-l : 2 : 4-trimethylbenzene, 

See 6-Amino-^-cumene. 

co-Amino-1 : 3 : 5-trimethylbenzene. 

See 3 : 6-Dimethylbenzylamine. 



Aminotrimetliylcarbinol 



145 



a-Aininotriplienytoietliane 



Aminotrimetiiylcarbiiiol . 

See Anodno-fer.-butyl Alcohol. 
Aminotrimethyleiie . 
See Cyclopropylamine. 
o-Aminotriphenylami:ae 

pkew/lenediamine) 




C^H 
C, 

C 18 H 16 N 2 MW, 260 

Plates from EtOH. M.p. 145. Sol. EtOH, 
C 6 H 6 . Mod. sol. Et 2 0, ligroin. 
N-Acetyl : needles. M.p. 130. 

Piccard, Brewster, J. Am. Chem. Soc., 
1921, 43, 2630. 

m-Aminotriphenylamine (N-Diphenyl-m.- 

phenylenediamine) . 

M.p. 116. Sol. EtOH, Et 2 0, C fi H. 
TX-Acetyl : m.p. 167. 

Piccard, Brewster, J. Am. Ohem. Soc.. 
1921, 43, 2630. 

p-Aminotriphenylamine (N-Diphenyl-p- 
phenylenediamine) . 

Needles from EtOH. M.p. 145-8. Sol. 
Me 2 CO, C 6 H 6 . Mod. sol. EtOH, MeOH, CC1 4 . 
Spar. sol. ligroin. 

N-Acetyl : silvery plates. M.p. 195. 

Gambarjan, Ber., 1908, 41, 3507. 
o-Aminotriphenylcarbinol 




C 19 H 17 ON 



MW,275 
Sol. C 6 H 6 , 



Plates from Et 2 0. M.p. 121-5 
EtOH. Spar. sol. Et 2 O, ligroin. Heat, above 
m.p. > 9-ph.enylacridine. 

B,HOl: needles + PI 2 0. Turns brown at 
140, m.p. 164 decomp. 

T$-Di-Me: C 21 H 21 ON. MW, 303. Prisms 
from EtOH or ligroin. M.p. 156-60. B,HGl : 
prisms + 1H 2 0. M.p. (anhyd.) 187 deeomp. 

N-Phenyl: C 25 H 21 01Sr. MW, 351. Prisms 
from ligroin. M.p. 127-8. 

"N-Acetyl : prisms. M.p. 192 decomp. 

Picrate : yellow plates + JC 6 H 6 from C 6 H 6 . 
M.p. 122-3 decomp. 

Baeyer, Villiger, Ber., 1904, 37, 3193. 

m-Aminotriphenylcarbinol. 

Cryst. from Et 2 0. M.p. 155. 

N-Di-M e : tablets from EtoO or ligroin. M.p. 
110. B,HCl : leaflets from H 2 0. M.p. 181. 

0:N-Tn-lfe:C 22 H 23 ON. MW,317. Tablets 
and prisms from ligroin. M.p. 81. 

N-Acetyl : leaflets from Et 2 0. M.p. 164. 

Tschacher, Ber., 1888, 21, 190. 

Diet, of Org. Oomp.--I. 



l>-Aniinotriplienylcarbinol. 

Cryst. from toluene or Et 2 O-ligroin. M.p. 
116. Sol. EtOH, Et 2 O, C 6 H 6 . Spar. sol. 
ligroin. 

N-Dfc-Jfe : needles from Et 9 0-ligroin. M.p. 
92-3. 

"N-Acetyl : needles from C 6 H 6 -ligroin. M.p. 
176. 

Baeyer, Lohr, Ber., 1890, 23, 1625. 
Baeyer, Villager, Ber., 1904, 37, 599. 

o-Aminotriphenylmethane 

^> 

C 19 H 17 N MW, 259 

Leaflets from Et 2 O. M.p. 129. Cryst. + 
1C 6 H 6 from C 6 H 6 . M.p. 94-5. 

N-Jfe: C 20 H 19 N. MW, 273. Cryst. from 
C 6 H 6 . M.p. 130-2. B,HCl: prisms. M.p. 
210 decomp. T$-Acetyl : prisms from AcOEt. 
M.p. 147-8. 

N-Acetyl : prisms from AcOEt. M.p. 154-5. 

Baeyer, Villiger, Ber., 1904, 37, 3198. 

m-Aminotriphenylmethane . 
Needles from Et 2 0. M.p. 120. 
N-Acetyl : pearly scales from Et 2 0. M.p. 
115. 

Tschacher, Ber., 1888, 21, 189. 

p-Aminotraphenylmethane . 

Prisms or leaflets from Et 2 or ligroin. 
Prisms + 1C 6 H 6 from C 6 H 6 . M.p. 84. B.p. 
about 248/12 mm. 

Sulphate : needles or plates from H 2 O. M.p. 
211. 

IX-Di-Me: C 21 H 21 N. MW, 287. Needles 
from EtOH. M.p. 132. B 2 ,H 2 PtCl Q : yellow 
needles. Decomp. at 186-7 corr. Methiodide : 
leaflets from H 2 0. M.p. 184-5. 

J$-Acetyl : needles from EtOH. M.p. 168. 

T$-Benzoyl : needles from C 6 H 6 . M.p. 198. 

Busch, Einck, Ber., 1905, 38, 1768. 
Baeyer, Lohr, Ber., 1890, 23, 1623. 

a- Aminotripheny Imethane (Triphenyl - 
methylamine) 



C 19 H 17 N MW, 259 

Needles from EtOH. M.p. 105. B.p. 223 / 
14 mm. Sol. EtOH, Et 2 O, C 6 H 6 . Insol. H 2 O. 

B,HCl : needles. M.p. 244. 

N-Jfe : C 20 H 19 N. MW, 273. Prisms from 
ligroin. M.p. 73. B,HCl : m.p. 216. 

N-Di-Me : C 21 H 21 N. MW, 287. Cryst. from 
ligroin. M.p. 97. 

N-Jfe : C 21 H 21 N. MW, 287. Cryst. powder 
from AcOEt. M.p. 75-7. 

10 



2-Aminotropane 



146 



4-Amino-n-valeric Acid 



C 25 H 21 N. MW, 335. Prisms 
from Et 2 0~EtOH. M.p. 149-50 (146). 

KkBenayZ: C 26 H 23 N. MW, 349. Prisms. 
M.p. 110. B,HCl : needles. M.p. 249. 

N-Acetyl : needles from EtOH. M.p. 207-8. 

~N-Chloroacetyl : cryst. from toluene. M.p. 
201-2 corr. 

N-Benzoyl : cryst. from EtOH. M.p. 160-2. 

Bibs, Ber., 1884, 17, 702. 

Hemilian, Silberstein, Ber., 1884, 17, 745. 

2-Aminotropane . 

See Isotropylamine. 
3-Aminotropane . 
See Tropylamine. 
3-Amino-vy-tropane . 
See ^-Tropylamine. 
1 - Aminoundecane . 
See Ti-Undecylamine. 
2- Aminoundecane . 
See sec.-7&-Undecylamine. 
AminoTindecylene . 
See Undecenylamine. 

Aminourazole (4:-Amino-3 : 5-diketodihydro- 
1:2: 4-triazole) 



3-Araino-n-valeric Acid 

CH 3 -CH(NH 2 )-CH 2 -CH 2 -COOH 



C 2 H 4 2 N 4 MW, 116 

Prisms from H 2 0. M.p. 270. Spar. sol. 
EtOH. Insol. Et 2 0. Reduces NH 3 .AgN0 3 . 

B,N^H^ : prisms. M.p. 197. 

Monoacetyl deriv. : leaflets. Decomp. at 235. 

DiJiydrazone : needles from EtOH.Aq. M.p. 
207 decomp. 

Dibenzoyl deriv. : needles. M.p. 201. 

Tribenzoyl deriv. : needles. M.p. 234. 

Curtius, J. prate. Chem., 1895, 52, 481. 
Stolle, Krauch, Ber., 1912, 45, 3307. 
Stolle, J. prate. Chem., 1907, 75, 416. 

l-Amino-4-ureido-ra-valeric Acid. 
See Citrulline. 

1-Amino-w- valeric Acid. 
See Norvaline. 
2-Araino-w-valeric Acid 

CH 3 -CH 2 -CH(NH 2 )-CH 2 -COOH 

C 5 H n 2 N MW, 117 

Needles from EtOH or Et 2 0. M.p. 160-5 
decomp., (178-9). Very sol. H 2 0. 

Cu salt : cryst. + 2H 2 0. M.p. anhyd. 235- 
6 decomp. 

Et ester : C 7 H 15 2 N. MW, 145. B.p. 82-4 / 
12 mm. 

N-Benzoyl : m.p. 145-6. 
13-$Naphthalenesulphonyl : m.p. 134-5. 
Dakin, /. Bid. Chem., 1933, 99, 531. 
Rodionov, Chem. Abstracts, 1946, 40, 
1785. 



MW, 117 



d-. 



Cryst. from EtOH.Aq. M.p. 214 corr. [a]*> 
+ 12-0 in H 2 0. 
'N-Benzoyl: [a]^ + 16-5 in EtOH. 

[Vgo _ 10 .7. 

TS-Benzoyl: needles from H 2 0. M.p. 133 
corr. [a]J 21-9 in EtOH. 

cHk 

Cryst. M.p. 199 (214 corr.). Sol. H 2 0. 
Prac. insol. EtOH. Insol. Et 2 O, C 6 H 6 , Hgroin. 
Dist. -> 2-metliylpyrrolidone-5. 

B,HGl : prisms from EtOH. M.p. 154. 

Et ester: B,HCl, plates from EtOH-Et 2 0. 
M.p. 92. 

N-Di-Et : Et ester, b.p. 96/8 mm. Picrate 
of Et ester : yellow cryst. from EtOH. M.p. 
90-1. 

N-Benzoyl : cryst. M.p. 132. 

Fischer, Groh, Ann., 1911, 383, 370. 
Tafel,en, 1889, 22, 1861. 

4-Amino-w-valeric Acid 

H 2 N-CH 2 -CE 2 -CH 2 -CH 2 -COOH 



C 5 H n 2 N 

Leaflets. M.p. 157-8 
Sol. H 2 0. Prac. insol. 
HN0 >- 



MW, 117 

^ piperidone + H 2 0. 
EtOH. Insol. Et 2 0. 



allylacetic acid. 

K salt : from EtOH-Et 2 0. M.p. 228-9. 

B,HCl : from CHC1 3 . M.p. 84-6. 

B,HAudA : yellow cryst. + 1H 9 0. M.p. 
106. 

Et ester : T$-Benzoyl, cryst. M.p. 26. 

Amide : TX-Benzoyl, cryst. from H 2 0. M.p. 
181-5. 

N-Jfe : C 6 H 13 2 N. MW, 131. Hygroscopic 
needles or prisms from EtOH~Et 2 0. M.p. 
121-2 corr. K salt: m.p. 280. B,HCl: 
m.p. 93. 

N-Di Jfe : C 7 H 15 2 N. MW, 145. B.p. 18ft- 
9. B,HAuCl^ : yellow prisms from EtOH. 
M.p. 75. Methobromide : tablets from EtOH. 
M.p. 184-7. 

N-JSfe : B,HCl, from Me 2 CO. M.p. 115. 

N-Propyl : B,HCl, from EtOH-Bt 2 0. M.p. 
118-19. 

TS-Isopropyl : B,HCl, from EtOH-Et 2 0. 
M.p. 123-4. 

T$-Butyl: B,HCl, from EtOH-Et s O. M.p.. 
124. 

N-Octyl: B,HCl, from EtOH-Et 2 0. M.p. 
139-40. 

^-Benzyl: B t HGl, from EtOH-EU). M.p,, 
120. 



5-Aminovanillic Acid 



147 



5-Amino-o-3-xylenol 



N-Benzoyl : cryst. from EtOH.Aq. M p 
105 (94). 

Gabriel, Aschan, Ber., 1891, 24, 1365. 
Roth, Ann., 1931, 489, 107. 
Schniepp. Marvel, J. Am. Chem. Soc., 
1935, 57, 1557. 

5-Aminovanillic Acid. 
See under 
Acid. 

2-Aminovanillin 

CHO 



3-Aminoveratrol 

OCH 3 





C 8 H n 2 N ~ MW, 153 

B.p. 137/10 mm. Darkens in air. Sol. 
4 : 5-Dihydroxy-3-aminobenzoic H 2 0. Volatile in steam. 

Picrate : needles from EtOH. M.p. 173-5. 

Gibson, Simonsen, Rau, J. Chem. Soc., 
1917, 111, 79. 

4- Amino ver atr ol . 

M.p. 85-6. B.p. 174-6. HC1 sol. + FeCl 3 
> reddish- violet > blue col. 
Platinichloride : m.p. 227-8. 
N-Acetyl : plates from EtOH. M.p. 133. 
TS-Benzoyl : needles from EtOH. M.p.^177 . 

Pollecoff, Robinson, J. Chem. Soc., 1918, 

113, 645. 

Simonsen, Rau, ibid., 28. 
Heinisch, Monatsh., 1894, 15, 232. 
Frisch, Bogert, J. Org. Chem., 1943, 8, 331. 

1-Aminoxanthone 



C 8 H 9 3 N MW, 167 

Cryst. from C 6 H 6 . M.p. 128-9. Sol. EtOH, 
Et 2 O. Spar. sol. H 2 0. 

Oxime : needles from C 6 H 6 . M.p. 151-2. 

~N-Acetyl : yellow needles from EtOH. M.p. 
97. 

Phenylhydrazone : yellow needles from EtOH. 
M.p. 165. 

Sumuleanu, Chem. Zentr., 1903, II, 31. 

2-Aminoveratric Acid (2-Amino~S : 
methoxybenzoic acid) 

COOH 



> JJNJ.J.2 

!JOCH 3 

)5CH 3 
C 9 H U 4 N 

Needles from H 2 0. M.p. 184. Sol. EtOH, 
AcOH, Me 2 CO, Spar. sol. ligroin. 
N- Acetyl : needles from EtOH. M.p. 188-90. 
Pschorr, Sumuleanu, Ber., 1899, 32, 3410. 
Kuhn, Ber., 1895, 28, 810. 
Frisch, Bogert, J. Org. Chem., 1944, 9, 338. 




MW, 211 



C 13 H 9 2 N 
MW, 197 M.p. 201-2. 

Comp. Rationale, F.P., 839,698, (Chem. 
Abstracts, 1939, 33, 8025); 821,275, 
(Chem. Abstracts, 1938, 32, 3628). 



5-Aminoveratric Acid. 

B,HCl : decomp. above 235. 
Me ester : "N-Benzoyl, cryst. from EtOH. 
M.p. 188-90. 

N-Acetyl : needles + 1H 2 from H 2 0. M.p. 
126, anhyd. 188. 

Simonsen, Rau, J. Chem. Soc., 1918, 113, 
24. 

6-Aminoveratric Acid. 
Me ester: G^H^O^. MW, 211. Plates 
from C 6 H 6 . M.p. 133. 

Et ester: C n H 15 4 N. MW,225. M.p. 88-9. 
N-Acetyl : prisms from AcOH. Decomp. 
above 228. 

Heidelberger, Jacobs, J. Am. Chem. Soc., 

1919, 41, 2142. 
Grime, Ber., 1886, 19, 2305. 
Tiemann, Matsmoto, Ber. 9 1876, 9, 942. 
Fischer, Bogert, J. Org. Chem., 1939, 
4,71. 



2-Aminoxantlione. 

Bright yellow needles from EtOH or toluene. 
M.p. 232. Very sol. EtOH, hot C 6 H 6 , hot 
toluene. Insol. pet. ether. Blue nuor. in 
EtOH. 

Ullmann, Wagner, Ann., 1907, 355, 363. 

3- Aminoxanthone . 

Yellow laminae from EtOH. M.p. 205. 
N-Acetyl : needles. M.p. 178. 

Purgotti, Gazz. chim. ital., 1914, 44, 644. 
Comp. Nationale, F.P., 839,698, (Chem. 
Abstracts, 1939, 33, 8025). 



Aminoxylene. 

See Xylidine and Xylylamine. 
5-Amino-o-3-xylenol 
o-xylene) 

CH 3 



re 

HXF 5 



C 8 H U ON 



MW, 137 



G-Amino-o-S-xylenol 



148 



4-Amino-m-5-xylenol 



Orange needles from CHClg or C 6 H e . M.p. 
179. Sol. Me 2 CO, warm H 2 0, EtOE. 

Crossley, J. Chem. Soc., 1913, 103, 2181. 

6-Amino-o-3-xylenol (3-Hydroxy-6-amino- 
o-xylene). 

Needles from AcOEt. M.p. 175. Sol. EtOE, 
warm H 2 O. Oxidises rapidly in air. 

Hinkel, Collins, Ayling, J. Chem. Soc., 
1923, 123, 2971. 



3-Amino-o-4-xylenol 

o-xylene) 




MW, 137 

Cryst. from C 6 H 6 . M.p. 126. 

Hinkel, Ayling, Bevan, /. Chem. Soc., 
1928, 131, 2531. 

5-Amino-o-4-xylenol (k-Hydroxy-S-amino- 
o-xylene). 

Plates from Et 2 0. Turns brown at 165. 
M.p. 173-5. Sol. EtOH. Spar. sol. C 6 H 6 . 
Prac. insol. H 2 0, pet. ether. Sublimes. Slowly 



CrO a 



4 : 5-dimetliyl-o- 



volatile in steam. 
benzoquinone. 

B,HCl : silky needles from H 2 O. M.p. 250 
decomp. 

N-Acetyl : plates from EtOH. Sinters at 
184. M.p. 191. 

: 1$-Diacetyl : needles or prisms from EtOH. 
M.p. 157. 

Tri-acetyl : tablets from EtOH. M.p. 100-1. 

N-Benzoyl : m.p. 195-6. 

Dibenzoyl deriv. : needles. M.p. 152-3. 

Crossley, Bartlett, J. Chem. Soc., 1913, 

103, 1299. 
Hinkel, Collins, Ayling, J. Chem. Soc., 

1923, 123, 2973. 

5-Amino-m-2-xylenol (2-Hydroxy-5-amino- 
m-xylene) 

CH 3 




C 8 H U ON MW, 137 

Leaflets from H 2 O or C 6 H 6 . M.p. 137-8 
decomp. 
Me ether: C 9 H 13 ON. MW, 151. Needles 



5- Amino-m-4-xylenol (4-Hydroxy-5-amino- 
m-xylene) 

CH, 



OH 



C 8 H n ON 



MW, 137 
134-5. Sol. 



Leaflets from EtOH. M.p. 
EtOH, Et 2 0. Spar. sol. C 6 H 6 . 

Me ether : C 9 H 13 ON. MW, 151. B.p. 239- 
40. 

Et ether : C 1Q H 15 ON. MW, 165. B.p. about 
146/30mm. JS-Acetyl : m.p. 65-6. 

N-Formyl : needles or prisms from EtOH.Aq. 
M.p. 68. 

N-Acetyl : cryst. from EtOH.Aq. M.p. 96. 

: N-Dibenzoyl : m.p. 153-5. 

Bamberger, Eeber, Ber., 1913, 46, 808. 
Prancke, Ann., 1897, 296, 200. 



6-Amino-m-4-xylenol 

m-xylene). 

Needles or plates from EtOH. M.p. 166-7. 
Sol. EtOH, Et 2 0, hot H 2 0. Spar. sol. C 6 H 6 , 
ligroin. 

Bamberger, Reber, Ber., 1907, 40, 2267. 

2-Amino-m-5-xylenol (5-Hydroxy-2-amino- 
m-xylene) 

GBL 



HO 



CH 3 



C 8 H U ON MW, 137 

Needles from H 2 or CHC1 3 . M.p. 181 . Sol. 
EtOH. Spar. sol. H 2 0, Et 2 0, CHC1 3 , ligroin. 
Boiling dil. min. acids > 2 : 6-dimethylhydro- 
quinone. 

j5 2 ,# 2 $0 4 : leaflets, M.p. 268. 

Me ether: C 9 H 13 ON. MW, 151. Leaflets 
from pet. ether. M.p. 43. Volatile in steam. 

N-J : C, H 15 ON. MW, 165. M.p. 161-2. 

^-Benzyl: C 15 H 17 ON. MW, 227. M.p. 
104-5. 

'N-Acetyl : needles. M.p. 178-80. 

Bamberger, Rising, Ann., 1901, 316, 300. 

4-Ammo-m-5-xylenol (S-HydroxyA-amino- 
m~xylene). 

Needles from C 6 H 6 . M.p. 163. Sol. EtOH, 
AcOH, hot H 2 0. Reduces NH 3 .AgN0 3 . 

B,HCl : cryst. from H 2 or dil. HC1. M.p. 
270-80. 

Me ether : IS-Acetyl, prisms from 



M.p.66 
M.p. 136-7 . 
D^tyldenv.: m.p. 160. 

Howe, Bannister, Storey, /. Soc. Chem. 
Ind., 1931, 50, 79. 



. 

pnsmsfrom needles from MeH.Aq., or C 8 He- M.p. 80-1. 
X-Acetyl : scales from H,0 M.p. 186-7. 
Diacet yl deriv. : m.p. 87-8. ? 
~S-Benzoyl : cryst. from MeOH or EtOH Aq. 
M.p. 211-12. 



* 3~Amino-p-2-xylenol 



149 



Ammoresinoi 



O : "N-Dibenzoyl : needles from MeOH. M.p. 
148-9. Alc.KOH >- ^-benzoyl. 

Auwers, Borsehe, Ber., 1915, 48, 1698. 

3-Amino-p-2-xylenol (2-Hydroxy-%-amino- 
GEL 



C 8 H n ON 



f 2]UJ=L 

I 6 . 3 JNH 



Leaflets from C 6 H 6 . M.p. 



MW, 137 

M A 149-50. Sol. 
EtOH, CHC1 3 . Spar. sol. H 2 0. 

N-Benzoyl : needles. M.p. 210-11. 
Dibenzoyl deriv. : needles. M.p. 178-9. 

Auwers, Murbe, Sauerwein, Deines, 
Schornstein, Ghem. Zentr., 1924, EL 
2269. 

5-Amino-p-2-xylenol (Z-Hydroxy-S-amino- 
p-xylene). 

Leaflets from EtOH. M.p. 242 decomp. 
FeCl 3 or Cr0 3 > p-xyloquinone. 

Et ether: C 10 H 15 ON. MW, 165. M.p. 69-5. 

N-Acetyl: octahedra from EtOH. M.p. 177-9. 

Jacobs, Heidelberger, J. Am. Chem. Soc. 9 

1917, 39, 2204. 

Sutkowski, Ber., 1887, 20, 979. 
Gattermann, Ber., 1894, 27, 1930. 
Smith, Opie, J. Org. Chem., 1941, 6, 427. 

G-Amino-p-2-xylenol (2-Hydroxy-6-amino- 
p-xylene). 

Plates from H 2 0. M.p. 155. 

Me ether : B,HCl, needles + 1H 2 from 
H 2 0. M.p. anhyd. 250-1 decomp. CKbro- 
stannate : needles from dil. HC1. Decomp. 
(anhyd.) about 250. 

Sonn, Ber., 1916, 49, 2590. 
Hobertson, Stephenson, J. Chem. Soc., 
1930, 133, 315. 

Ammelide (Melanuric acid, cyanuric acid 
monoamide) 

c-NH 2 C:NH c-NH 2 



or 



H 



HOC C-OH 



NH 
CO 



or 



00 CO 



Y 



NH 
C 3 H 4 2 N 4 MW, 128 

Microscopic prisms from H 2 0. Decomp. at 
high temps, without melting. Spar. sol. hot 
H 2 0. Insol. usual org. solvents. Sol. alkalis 
and min. acids. Hot min. acids > cyanuric 
acid + NH 3 . 

Werner, /. Ghem. Soc., 1913, 103, 2275. 



Ammeline (Cyanuric acid diamide) 

C:NH 

Hx/\H or /\ 

oc C:NH HO-C C-NH, 

^ Y 

C 3 H 5 ON 5 MW, 127 

Needles from aqueous Na 2 C0 3 sol. Prac. 
insol. H 2 0. Insol. EtOH, Et 2 0, AcOH. Sol. 
alkalis and min. acids. Warm cone. H 2 S0 4 > 
ammelide + NH 3 . Salts are unstable in pres- 
ence of 



Stolte, Krauch, Ber., 1913, 46, 2337. 

Amrnidin. 
See Imperatorin. 
Ammodendrine 

C 12 H 20 ON 2 ,H 2 MW, 226 

Alkaloid from Ammodendron conollyi, Bge. 
Prisms from Et 2 O. M.p. 73-4, anhyd. 50-60. 
Sol. EtOH, Me 2 CO, CHC1 3 . Spar. sol. H 2 0, pet. 
ether. 

B,HI : cryst. from EtOH. M.p. 218-20. 

Perchlorate : cryst. from Me 2 CO. M.p. 199- 
200. 

KT-Jfe : C 13 H 22 ON 2 . MW, 222. Cryst. from 
pet. ether. M.p. 65-6. B,HI : cryst. from 
Me 2 CO-EtOH. M.p. 183-5. Methiodide:cr?st. 
from Me 2 CO-EtOH. M.p. 163-5. 

Orekhov, Proskurnina, Lazurevskii, Ber., 

1935, 68, 1807. 
Or6khov, Proskurnina, Bull. soc. chim., 

1938, 5, 29. 

Ammoidin. 
See Xantho toxin. 
Ammonchelidonic Acid. 
See Chelidamic Acid. 
Ammoresinol 



C(CH 3 ) 2 



C 24 H 30 4 MW, 382 

Isolated from Dorema ammoniacum. Cryst. 
from CC1 4 . M.p. 109. Sol. dil. Na 2 C0 3 . Sol. 
most org. solvents. Insol. H 2 0. Heat in 
vacuo > resacetophenone. 

Acetyl deriv. : cryst. from MeOH.Aq. M.p. 
128-9. 

Diacetyl : cryst. from AcOH or EtOH. M.p. 
102-3. B.p. 210-2570-02 mm. 

Dibenzoyl : needles from ligroin. M.p. 75. 




AmorpMgenin 



150 



tert.-Am.jl acetate 



Di--p-chlorobenzoyl : prisms from MeOH. M.p. 
93-5. 

Raudnitz, Petru, Diamant, Neurad, Lan- 

ner, Ber., 1936, 69, 1956. 
Spath, Simon, Lintner, ibid., 1656. 
Kunz, Weidle, Fischer, J. praJct. Chem., 
1934, 141, 350. 



C 22 H 22 7 MW, 398 

From Amorpha fruticosa. M.p. 191-2 (from 
MeOH). Contains 2 OMe groups. 

Acree, Jacobson, Haller, J. Org. Chem. 
1943, 8, 572. 

AmorpMn 
C 33 H 40 16 MW, 692 

Glycoside occurring in Amorpha fruticosa. 
M.p. 151-1-5. Contains 2 OMe groups. Gives 
positive Durham and orcinol tests. 

Acree, Jacobson, Haller, J. Org. Chem., 
1943, 8, 572. 



Ampelopsin 



CO OH 



HC V : 

HO HO 
C 15 H 12 8 MW, 320 

Constituent of " Haku-tya ", a drug and 
condiment used in China. Cryst. + 2| H 2 
from H 2 O or EtOH. M.p. 245-6. Gives 
violet-red col. with Mg + HC1 ; with EtOH- 
FeCl 3 a violet col. which changes to dark orange 
on standing. AcOH sol. > yellow col. with 
H 2 S0 4 . 

Tetra-Me : m.p. 168. 

Penta-Me : m.p. 194-5. 

Hexa-acetyl : m.p. 174-5. 

Hexa-benzoyl : m.p. 174. 

Kubota, J. Chem. 8oc. Japan, 1939, 60, 
604, (Chem. Abstracts, 1942, 36, 4118). 

Amphetamine . 

v See 2-Phenylisopropylamine. 

Amygdalin (Mandelonitrile-$-gentiobioside) 




MW, 457 

Glycoside of bitter almonds (3-4%). Also in 
kernels of cherries (0-8%), peaches (2-2-5%), 
apricots, and fruits of the Amygdalacece and 



Pomacece generally. Cryst. ~f- 3H 2 from H 2 0. 
M.p. 214-16. Sol. hot EtOH. Insol. Et 2 0. 
[ a ]Jf - 40-57 in H 2 0. Hot dil. HC1 > glu- 
cose, benzaldehyde and HCN. Emulsin gives 
same end hyd. products, the amygdalase giving 
glucose and mandelonitrile-glucoside, and prun- 
ase splitting this to aldehyde, HCN and glucose. 
Bitter taste. Reacts neutral. 

Hepta-acetyl : prisms from EtOH.Aq. M.p. 
169. [a]? 36-2 in AcOEt. 

Hepta-benzoyl : needles from EtOH-CHCl 3 . 
M.p. 218. [aji 8 - 10-5. 

Hepta-p-chlorobenzoyl : needles from EtOH- 
CHC1 3 . M.p.234. 

Hepta-p-bromobenzoyl : needles from EtOH- 
CHBr 3 . M.p. 229. 

Hepta-anisoyl : amorphous. M.p. 119. 

Hepta-stearyl : amorphous. M.p. 92. [a]i 8 " 
- 84. 

Campbell, Haworth, J. Chem. Soc., 1924, 
125, 1337. 

Amygdophenine (Mandelyl-p-phenetidine) 

C 2 H 5 0-C 6 H 4 *NH-CO-CH(OH)-C 6 H 5 
C 16 H 17 3 N MW, 271 

Leaflets. M.p. 140-5. 

Acetyl deriv. : needles from ligroin. M.p. 
157. 

Wenghoffer, Chem.-Ztg., 1895, 19, 1753. 
Anschiitz, Booker, Ann., 1909, 368, 62. 

n-Amyl acetate 

CH 3 -CH 2 -CH 2 -CH 2 -CH 2 0"CO-CH 3 
C 7 H 14 2 MW, 130 

F.p. - 70-8. B.p. 148/737 mm. Dg 0-8963, 
D\l 0-8792. 

Lieben, Rossi, Ann., 1871, 159, 74. 
active Amyl acetate 



C 7 H 14 2 MW, 130 

B.p. 141-2 (139). D 12 0-8803. < 1-4012. 
MS> + 3-30. 

Hardin, Sikorsky, Chem. Zentr., 1908, I, 
2143. 

Houtman, Steems, Heertjes, Eec. trav. 
chim., 1946, 65, 781. 

ter*.-Amyl acetate 
CH 3 



CH 3 -CH 

C 7 H M 2 MW, 130 

B.p. 124. D 19 0-8738. Above 125 decomp. 
gradually to 2-methylbutylene + acetic acid. 
HOI > acetic acid + tert.-&myl chloride. 
Oddo, Gazz. chim. ital. y 1911, 41, 289, 
Kondakow, Ber., 1893, 26, 1013 (Ref.). 



active Amylacetic Acid 



151 



n-Amylbenzene 



active Amylacetic Acid (3-Methylcaproic 
acid, 3-methyl-S-ethylbutyric acid) 



C 7 H 14 2 MW, 130 

B.p. 221. Spar. sol. H 2 O. D 20 0-9149. [oR? 
+ 7-6 in MeOH. (Inactive form, b.p. 217-18.) 

Me ester: C 8 H 16 9 . MW, 144. B.p. 158- 
64. D 2 ^ 0-8764. 

Et ester : C 9 H 18 2 . MW, 158. B.p. 173-9. 
D 21 0-8644. 

Welt, Ann. chim., 1895, 6, 132. 



ra-Amylacetylene . 

See 1-Heptyne. 

n-Amylacrylic Acid. 

See 1-Octenic Acid. 

Amyl Alcohol (commercial). 

Constituent of fusel oil. A mixture of isoamyl 
alcohol and active amyl alcohol in varying 
amounts, depending on the source (potatoes, 
molasses, etc.). That from potato contains 
13-22% of the active alcohol, that from molasses 
50-60%. B.p. 130-2. D 20 0-81. Sol. H 2 0, 
EtOH, Et 2 0. 

n-Amyl Alcohol (Butykarbinol, 1-pentanol, 
primary n-amyl alcohol) 

CH 3 -CH 2 -CH 2 -CH 2 -CH 2 OH 
C 5 H 12 MW, 88 

M.p. - 79. B.p. 137/740 mm., 49-50 / 
13 mm. Insol. H 2 0. Dg 0-80915, DJ 0-8296. 
< 1-4101. 

Me ether : C 6 H 14 0. MW, 102. B.p. 99- 
100. 

Et ether: C 7 H 16 0. MW, 116. B.p. 119-20. 

n-Amyl ether : see Di-w-amyl Ether. 

3 : 5-Dinitrobenzoate : m.p. 46-4. 

Phenylurethane : tablets from pet. ether. 
M.p. 46. 

p-Nitrophenylurethane ; m.p. 86. 

u-Naphthylurethane : m.p. 68. 

Bouveault, Blanc, Chem. Zentr., 1905, 

II, 1700. 
Scheuble, Lobl, Monatsh., 1904, 25, 1096. 

sec.-w-Amyl Alcohol. 

See Methyl-7&-propylcarbinoL 
active Amyl Alcohol (sec.-Butylcarbinol, 2- 
methylbutanol-l ) 



C 5 H 12 



MW, 88 



B.p. 128. DJ 0-816. [<xg> - 5-90. Cr0 3 
> methylethylacetic acid. Eacemised by Na. 

Phenylurethane : cryst. from ligroin. M.p. 
30. [a] D + 6-4 in CHOI,. 



B.p. 128-9/742 mm. D 0-8341. 
Phenylurethane : m.p. 31. 



1-4092. 



Marckwald, Ber., 1904, 37, 1039. 
Whitmore, Vlewine, J. Am. Chem. Soc., 

1938 5 60, 2569. 
Houtman, Steenis, Heertjes, Hec. trav. 

chim., 1946, 65,781. 



tert.-Amyl Alcohol 

dimethylethylcarbinol, tert.-pentanol, " amylene 
hydrate") 



C 5 H 12 MW, 88 

M.p. - 8-4. B.p. 102. Sol. 8 parts H 2 O. 
DS 0-827, Dg 0-8069. < 1-4052. Mol. b.p. 
elevation, 24-6. O0 3 > acetone + acetic 
acid. M at 230 > ^s^m.-trimethylethyl- 
ene. Soporific. 

Et ether : G 7 H 16 0. MW, 116. B.p. 102-3 / 
742 mm. D 0-7785. 

Phenylurethane : needles. M.p. 44-7. B.p. 
146/9 mm. 

Wischnegradsky, Ann., 1878, 190, 332. 
Adams, Kamm, Marvel, J. Am. Chem. 
Soc., 1918, 40, 1950. 

Amyl Alcohol. 

See also Isoamyl Alcohol, Methyl-n-propyl- 
carbinol and Methylisopropylcarbinol. 
n-Amylamine (1-Amino-u-pentane) 

CH 3 -[CH 2 ] 3 -CH 2 NH 2 
C 5 H 13 N MW, 87 

E.p. 55. B.p. 104. D 19 0-7662. 
Picrate : m.p. 138-9. 
Picrolonate : m.p. 198. 

Menschutkin, Chem. Zentr. , 1898, 1, 702. 
Brown, Jones, J. Chem. Soc., 1946, 781. 

Amylamine. 

See also 2-Amino-7&-pentane, Methyl-n-butyl- 
amine, 2-Amino-2-methylbutane and 4-Amino- 
2 -methylbutane . 

p-tert.-Amylanisole . 

See under #-er.-Amylphenol. 

w-Amylbenzene (l-Phenylpentane) 



B.p. 201-2. CIS 0-8664. 



MW, 148 
1-4751. 



Radcliffe, Simpkin, J. Soc. Chem. Ind., 

1921, 40, 119. 
Oilman, Robinson, Organic Syntheses, 

1930, X, 4. 
Hennion, Toussaint, U.S.P., 2,390,835, 

(Chem. Abstracts, 1946, 40, 2849). 




ferf.-Amylbeiizeae 152 tert.-Amyl chloride 

terf.-Amylbenzene (2 -Methyl -2- phenyl- n-Amyl butyrate 

butane, 2-phenyli$opentane)^ CH 3 -CH 2 -CH 2 -COO-CH 2 -[CH 2 ] 3 -CH 3 

C 9 H 18 2 MW, 158 

_ Us F.p. -73-2. B.p. 185. DJ 0-8832. 

C H 3 MW, 148 Gartenmeister, Ann., 1886, 233, 269. 

B.p. 189-91, 77/15 mm. D 15 0-8736, n active Amyl butyrate 

149154. CH 3 -CH 2 -CH 2 -COO-CH 2 -CH(CH 3 )-CH 2 -CH 3 

Konowalow, Jegorow, Chem. Zentr., 1899, C 9 H 18 2 MW, 158 

A Ij I 7 : T> i i. * A in ocvr B -P- 1797765 mm. corr., 173-6/726 mm. 

Anschutz, Beckerhoff, Ann., 1903, 327, D 20 Q.862 ?4 14112. [a? + 3-51. 

HeSon, Kurtz, /. Am. Chem. Soc., 1943, * Walden > ^ ****** O7iem -> 1896 > 20 ' 573 ' 

65, 1001. tert.-Amyl butyrate 

Simons, Hart, /. Am. Chem. Soc., 1944, 

66, 1309. 01 

4-terf .-Amylbenzoic Acid G H ^ MW 158 

U 9 n 18 u 2 mw, io 

B.p. 164. D 0-8769. 

Kondakow, JSer., 1893, 26, 1012 (JBe/.). 

t ert .-Amylcarbinol (2 : 2-Dimethylbutanol- 1 , 

C(CH 3 ) 2 CH 2 *CE 3 ' 2 : 2-dimethylbutyl alcohol) 

c i2 H i62 MW, 192 CH 3 *CH 2 -C(CH 3 ) 2 -CH 2 OH 

Needles. M.p. 158. Sol. EtOH, Et 2 0. Q H MW 102 

Spar. sol. H 2 0. 6 T - 14 ... , , ^ ' 

. ,.,--.. ,^ rt ^ ^^ ^ -LiQ- "with campnoraceotis odour. B.p. 135. 

Ansctmtz, Eanff, Ann., 1903, 327, 202. po O .g 44 r r 

Kreysler^er., 1885, 18,1709. 'phenylurethane : cryst. from EtOH. M.p. 

Amyl borate. 65-6. 

See Tri-^-amyl borate. Bouveatdt, Blanc, Bull. soc. chim. : 1879, 

n-Amyl bromide (l-Bromopentane) 31 ? 749. 

CH 3 *CH 2 *GH 2 *CH 2 *CH 2 Br n-Amyl chloride (l-Chloropentane) 

C 5H u Br MW, 151 CH 3 -CH 2 "CH 2 -CH 2 -CH 2 C1 

M.p. - 95-25. B.p. 129-7. D* 5 1-22367, C 5 H n CI MW, 106-5 

DJ 1-20456. ng 1-4444. M<p> __ 99 o^ B 1084 o (105 o /764 mm>)> jjw 

Fournier, Bull soc. chim., 1906, 35, 623. 0-88657, Df 0-87163. rig 1-4119. 

sec.-n-Amyl bromide. Lieben, Bossi, Ann., 1871, 159, 72. 

See 2-Bromopentane. scc.-n-Amyl chloride. 

active Amyl bromide (l-Bromo-2-methyl- See 2-Chloropentane. 

butane, l-bromoisopentane) act ive Amyl chloride (l-CMoro-2-meihyl. 

OH 3 -CH 2 *CH(CH 3 )-CH 2 Br butane, l-chloroisopentane) 

C 5 H n Br MW, 151 CH 3 -CH 2 'CH(CH 3 )'CH 2 C1 

B.p. 120-1. D 2 4 1-221. [a + 3-68. (In- G^EL^Cl MW, 106-5 

active form, b.p. 117-18.) B,p. 97-9. DJ S 0-8868. < 1-4126. [a]Jf + 

Marchwald, Her., 1904, 37, 1046. 1-7. (Inactive form, b.p. 96-9. Dg 0-8818.) 

Jones, /. Chem. Soc., 1905, 87, 138. Aschan, Chem. Zentr., 1918, II, 939. 

tcrt.-Amyl bromide (2-Bromo-2-methyl- McKenzie, Clough, J. Chem. Soc., 1913, 

butane, 2-bromoisopentane) 1^3, 699. 

p-o- Hardin, Sikorsky, Chem. Zentr., 1908, I, 

UXlg\ > QjD /"ITT ,QTT 2143 

C 5 H u Br Hs 2 3 MW.ltt Brown^oot, J. ^lm. CAem. ^oo., 1942,, 

Yel^wliq. B.p. 108-9 deoomp. DJ 1-2439. ^.-Amyl chloride (Z-Chloro-Z-methyl. 

^ * Jw&we, 2-chloroisopentane] 

Wischnegradsky, J.?w., 1878, 190, 337. OH 

2-w-Amylbutylene . CHg^ CC1 * CH 2 *CH 8 

See 3-Methyl-2-octene. C^H-L^l M?CV, 106*6 



cc-n- Amylcinn amaldehy de 



153 



tert .-Amyl liypoclilorite 



M.p. -73. B.p. 86. Dg 0-8692. ri 
1-407. 

Brochet, Ann. chim., 1897, 10, 384. 

a-n-Amylcinnamaldehyde (Jasmine aide- 
hyde, a.-amyl-$-phenylacrolein] 



C 14 H 18 



(Bis-trimethylethylene 



CH 2 *[CH 2 ] 3 -CH 3 

MW, 202 

Used in perfumery. Pale yellow oil, b.p. 174- 
5/20 mm., 140/5mm. Dg 0-9711. rig 1-5381. 
Oxime : m.p. 72-5-73. 
Semicarbazone : m.p. 117-5-118. 
2 : 4:-Dinitrophenylhydrazone : scarlet. M.p. 
164. 

Backes, Bull. soc. chim., 1942, 9, 60. 
Butovskii, Korolev, J.praJct. Chem., 1928, 

119 272 

I.G., Swiss P. 127,159. 
Amylene,, 

See 1-Pentene, 2-Pentene, and 2-Methyl- 
butylene. 

Amylene-carboxylic Acid. 
See 2- Allylpropionic Acid, 3-Ethylidenebutyric 
Acid, Hydrosorbic Acid, and Propylacrylic Acid. 
Amylene dibromide. 
See Dibromopentane and Dibromoisopentane. 
Amylene Glycol. 
See Dihydroxypentane. 
Amylene hydrate. 
See tert.-Amyl Alcohol. 
Amylene nitrosate 
nitrosate) 

[(CH 3 ) 2 C(ON0 2 )-CH(CH 3 )^0] 2 
C 10 H 20 8 N 4 MW, 324 

Colourless cryst. M.p. 98-9. Depolymer- 
ises at m.p. > bluish-green liq. Sol. Me 2 CO, 
~ ~ Spar. sol. EtOH, AcOH, Et 2 O. 

Michael, Carlsom, J. Am. Chem. Soc., 

1937, 59, 843. 

Klingstedt, Ber., 1925, 58, 2363. 
Schmidt, Ber., 1902, 35, 2336. 

n- Amylethylene . 

See 1-Heptene. 

active Amylethylene. 

See 4-Methyl-l-hexene. 
n- Amylethylene Glycol. 
See Heptandiol-1 : 2. 
n-Amyl fluoride (l-Fluoropentane) 
CH 3 -CH 2 -CH 2 -CH 2 -CH 2 F 

MW, 90 

B.p. 63. DJ 0-788. 

Swarts, Chem. Zentr., 1921, III, 1457. 
sec.-n-Amyl fluoride (Z-Fluoropentane] 

CH 3 -CH 2 -CE 2 -CHF-CH 3 
H^F MW, 90 

B.p. 48-50/756 mm. 

Bergmann, Polanyi, Szabo, Trans. Fara- 
day Soc,, 1936, 32, 843. 



C 6 H 6 



C 5 H n F 



n - Amyl - n - hexylcarbinol ( 1 - n - Amylhex- 
anol-l t dodecanol-6) 

CH 3 -[CH 2 ] 5 -CH(OH)-[CH 2 ] 4 -CH 3 
C 12 H 26 O MW, 186 

Cryst. from pet. ether. M.p. 30. B.p. 
119/9 mm. 

Bouveault, Locquin, Compt. rend.., 1905, 
140, 1700. 

n-Amyl ra-hexyl Ketone (Lodecanone-6) 



MW, 184 

M.p. 9. B.p. 112/9 mm. 
Oxime : b.p. 147/10 mm. 

Bouveault, Locquin, Compt. rend., 1905, 
140, 1699. 

tert.-Amyl hydroperoxide 



C 5 H 12 



GEL 



MW, 104 
B.p. 26/3-5 mm. D 20 0-903. %> 1-4161. 

Milas, Sturgenor, J. Am. Chem. Soc., 1946. 
68, 642. 

2 - n -Amyl - 4 - hydroxymethylene - 5- ox - 
azolone (2-AmylA-formyl-5-oxazolone] 

HOCHin - CO 



C 9 H 13 3 N 



OH 2 -[CH 2 ] 3 -CH 3 



MW 5 183 



Colourless plates. M.p. 145-6 after darken- 
ing at 140. c^-PeniciUamme 
penilloic acid. 

Na salt : needles from Me 2 0. M.p. 228-9 
> sodium 2-amyloxazole-4-carboxylate. 

Ag salt ; m.p. 164 decomp. EtI > 2-amyl- 
4-ethoxymethylene-5-oxazolone. 

Me ether : 2-amyl-4-methoxymethylene-5- 
oxazolone. C 10 H 15 3 N. MW 5 197. M.p. 22. 
B.p. 106-8/0*15 mm. ^-Penicillamine methyl 
ester > methyl ^-amylpenicillenate. 

Et ether : 2-amyl-4-ethoxymethylene-5-ox- 
azolone. C n H 17 8 N. MW, 211. Colourless 
oil. B.p. 94/0-05 mm. ng 1-4975. 

Brown, Cqrnforth, Chemistry of Penicillin, 
Princeton University Press, 1949, pp. 
522, 804, 808, 824. 

Amyl jp-hydroxyphenyl sulphide. 
See under Thiohydroquinone. 
tert.-Amyl hypochlorite 

G *\r 



C 6 H n OCl 



MW, 122-5 



2-ra~Amyliminazole 154 tert.-Amyl Mercaptan 

Yellow liq. B.p. 76/752 mm. decomp. Df ra-Amylmalonic Acid (Hexane-l : l-di- 
0-8547. Decomp. in suilight. carboxylic acid) 

Ghattaway, Backeberg, J. Chem. Soc., 

1923,123,2999. _ __ 

A i- - i * H iA ^ 174 

-n-Amyliminazole Prisms M p g2 o gol ^ EtOH? Et2 o. 

At 140 > %-lieptylic acid. 



xISTH Hell. Schule, Ber., 1885, 18, 626. 

active Amylmalonic Acid (3-Methylpentane- 

C 8 H 14 N 2 MW, 138 1 : l-dicarboxylic acid) 

Needles. M.p. 38. B.p. 117/15 mm. CH 3 -CH 2 ^ r TT. rT T prr^COOH 

Picrolonate : yellow prisms. M.p. 190-1. CEL^ * 1 ^" UJ1< S300E[ 

Abraham et al., and Cornforth, Chemistry C 8 H 14 4 MW, 174 

of Penicillin, Princeton University jtt-ffl ester: C,JELJO. MW, 230. D 

Press, 1949, pp. 50, 705. 0-9665. 

n-Amyl iodide (l-Iodo-n-pentane) Walden, Z. physik. Chem., 1906, 55, 11. 

CH 3 -CH 2 -CH 2 -CH 2 -CH 2 I tert .-Amylmalonic Acid (2 : 2-Dimethyl- 

Q jj j MW, 198 butane-l : l-dicarboxylic acid) 

B.p. 155/740 mm., 62/20 mm. Df 1-517. OT _ ^3\ QOOH 

nff 1-4955. "' 






Lieben, Rossi, J.wn., 1871, 159, 74. C H 3 MW, 174 

active Amyl iodide (l-Iodo-2-methylbutane, Di-Et ester : C 12 H 22 4 . MW, 230. B.p. 

\-iodoisopentane) 238. 

CH 3 -CH 2 -CH(CH 3 )-CH 2 I * Bischoff, Ber. 9 1895, 28, 2628. 

CglLuI MW, 198 n-Amyl Mercaptan (n-Thioamyl alcohol, l- 

B.p. 148. DJ 5 1-523. n$ 1-4981. Fog 5 mercapto-n-pentane) 

+ 5-78. CH 3 -CH 2 -CH 2 -CH 2 -CH 2 SH 

Marckwald, Nolda, Ber., 1909, 42, 1589. C 5 H 12 S MW, 104 

Klages, Sautter, Ber., 1904, 37, 651. B.p. 126/767 mm. D 20 0-857. ri$ 1-44366. 

A , . , . ^., Hg salt : m.p. 74-5. 

tert.-Amyl iodide (2-Iodo-2-methylbutane, P 1 C L comp : m.p. 41. 

3 . ^Di n it ro benzoyl chloride comp. : m.p. 39- 

40. 

3-Nitrophthattc anhydride comp. : m.p. 131-2. 

CsHii 1 MW, 198 Pexsters, C&em. Zenr., 1907, 1, 1398. 

B.p. 128/737 mm. D 1-524. H 2 _ > Mann, Purdie, J. Ghem. Soc., 1935, 1559. 

/eri.-amyl alcohol. Wertheim, J. Am. Ghem. Soc., 1929, 51, 

Wischnegradsky, Ann., 1878, 190, 337. 366L 

active Amyl Mercaptan (%-Met"hyl-n-butyl 

active Amyl isobutyrate mercaptan, active thioamyl alcohol, Z-methyl- 

CHg^Qjj^QQQ^jj .Qjj^OHg butanthiol-1, l-mercaptoisopentane) 

CH 3 2 CH 2 *CH 3 QJJ 

C 9 H 18 2 MW, 158 CH 3 -CH^ H " CH2SH 

B.p. 171/765 mm., 168-70/730 mm. D ao C 5 H 12 S MW, 104 

0-8619. B.p. 119-21. D 23 0-8415. [oc]?> 8 + 3-21. 

Walden, Z. physik. Ghem., 1896, 20, 574. Votocek, Vesety, Ber., 1914, 47, 1515. 

fert.-Amyl isobutyrate H ' Sikorsk y> Ctem. Zentr., 1908, I, 



tert.-Amyl Mercaptan (2-Mwcaptoiso- 
CH pentane) 

MW,158 
B.p. 153-5. Dg 0-8706. OJ 

Kondakow, Ber., 1893, 26, 1012. C 5 H 12 S 3 MW, 104 



Amyl jp-methoxyphenyl sulphide 



155 



n-Amylpenicilloic Acid 



Hg salt : m.p. 159-60. 

Kheinboldt, Dewald, Diepenbruck, J. 

praJct. Chem., 1931, 130, 138. 
Backer, Eec. trav. chim., 1935, 54, 215. 

Amyl p-methoxyphenyl sulphide. 

See under Thiohydroquinone. 
ra-Amyl nitrite 

CH 3 -CH 2 -CH 2 -CH 2 -CH 9 0-NO 
C 5 H n 2 N ^ MW, 117 

Yellow liq. B.p. 104, 51-2/132 mm. D 20 
0-8528. < 1-38506. Hyd. by KOH. In- 
halation affects heart, blood pressure, etc. 

Pexsters, Chem. Zentr., 1907, I, 1398. 
*ert.-Amyl nitrite 



w-Amylpenicillenic Acid 



CH 3 / 
C 5 H n 2 N MW, 117 

B.p. 93, 62-3/345 mm. Sol. EtOH. D 19 ' 5 
0-8958. 72, 16 ' 8 1-3904. 

Bertoni, Oazz. chim. ital., 1886, 16, 515. 

Amyl nitrite. 

See also Isoamyl nitrite. 

Amylopectin . 

See Starch. 

Amylose. 

See Starch. 

2-w-Amyloxazole 

N=9-CH 2 -[CH 2 ] 3 -CH 3 
HCU ,0 



"V 

CH 



C 8 H 13 ON 



MW, 139 
Sweet-smelling oil. B.p. 172-3. 
Picrate : yellow needles. M.p. 84-5-85-8. 

Cornforth, Chemistry of Penicillin, Prince- 
ton University Press, 1949, p. 703. 

n-Amylpenaldic Acid 



C 9 H 15 4 N MW, 201 

Me ester : C 10 H 17 4 N. MW, 215. Pale yel- 
low oil. 2 : k-Dinitrophenylhydrazone : cryst. 
from MeOH. M.p. 153-5. ^-Penicillamine 
>* a-methyl amylpenicilloate. 

Et ester : C U H 19 4 N". MW, 229. OH. B.p. 
155-60 /4 mm. 2 : k-Dinitrophenylhydrazone : 
needles from EtOH. M.p. 166-7. Anil: 
needles from EtOH. M.p. 145-6. dlMPeni- 
cillamine > a-ethyl ^Z-amylpeniciUoate. 

Di-Etacetal: C 13 H 25 5 N. MW, 275. Cryst. 
from EtOKAq. M.p. 67-8. 

Brown, The Chemistry of Penicillin, 
Princeton University Press, 1949, p. 
473. 



-CH-COOH 

SH KB 



90 



CH 2 -[CH 2 ] 3 'CE 3 



314 



Me ester 
from 



: C 15 H 24 4 N 2 
O-Et0. M. 



4 NS. 



MW, 328. Cryst. 

Me 2 CO-Et 2 0. M.p. 105-6. Benzyl- 
amine ^ (3 -methyl amylpenicilloate a-benzyl- 
amide. Shows ultra-violet absorption max. at 
317-5 mju, (, 28,000). 

Cornforth, The Chemistry of Penicillin, 
Princeton University Press, 1949, p. 
831. 



w-Amylpenicillin (Flavacidin, gigantic acid, 
dihydropenicillin-F , dihydropenicillin-I ) 

H 3 C 
H 3 C 



9H-COOH 

N 




NH-CO-CH 2 -[CH 2 ] 3 -CH 3 



C 14 H 22 4 N 2 S MW, 314 

Powerful antibiotic elaborated by strains of 
Penicillium and Aspergillus. [a]^ 9 + 440 in 
H 2 0. Cold min. acids > n-amylpenillic acid. 
Hot min. acids > C0 2 + penicillamine + 
%-amylpenilloaldehyde. Alkalis > w-amyl- 
penaldic acid. 

Ba salt: (C 14 H 21 4 N 2 S) 2 Ba'2H 2 0. [a]f? 
+ 120 in H 2 0. Antibiotic activity : 1,000- 
1,400 penicillin units /mg. 

Procaine salt : m.p. 113-15. [a] + 175 
in 50% Me 2 CO.Aq. Antibiotic activity: 983 
penicilHn units /mg. 

Cook, Heilbron, The Chemistry of Peni- 
cillin, Princeton University Press, 1949, 
p. 38. 

Wintersteiner, ibid., 103. 

Adler, Wintersteiner, J. Biol. Chem., 
1948, 176, 873. 

Philpot, Nature, 1943, 152, 725. 

n-Amylpenicilloic Acid 

^H-COOHp 



CH-COOHa 
NH-CO-CH 2 -[CH 2 ] 3 -CH 3 



MW, 332 



d-. 



Cryst. from MeOH-Et 2 0. M.p. 188-90. 
HgCl 2 > w-amylpenilloaldehyde + penicilla- 



mine. 



156 



2>~e>'t.-Amylpiienol 



oL-Me ester: C 15 H 26 5 IS T 2 S. MW,346. C 
fromMeOH-EtjjO. M.p. 167-8. B,HCl : 



Di-Et acetal: C 12 H 25 3 N. MW, 231. Oil. 
B.p. 127-9/4 mm. Hyd. > caproic acid. 

2 : 4-Dinitrophenylhydrazone : yellow prisms 
from EtOH. M.p. 191. Boil with 2 : 4-di- 

ju,u 2 vy. iw-.p. a-ar^-o . nitrophenylhydrazinehydrochloride >glyoxal 

H 28 S N 2 S. MW,360. Cryst. osazone. 

Dimedone deriv. : cryst. from EtOH.Aq. M.p. 

Brown, The Chemistry of Penicillin, 
Princeton University Press, 1949, p. 
481. 

w-Amylpenilloic Acid 
K 



Cryst. 
m.p 
170" 

$-Me ester : amorphous. a-Benzylamide : 
cryst. from Me 2 CCHEt 2 0. M.p. 142-3 r 

Di-Me ester : C 16 H 28 S ~ 
from AcOEt. M.p. 128-30. 

a-Et ester: C 16 H 28 5 N 2 S. MW S 360. B,HCl: 
cryst. M.p. 167-8. 

x-Et $-Me ester: C 17 H 30 5 N 2 S. MW, 374. 
Prisms from CHCl 3 -Et 2 0. M.p. 125-7. 
dt. 

a-Et ester : prisms from Et 2 0-light petroleum. 
M.p. 114. 

BJSCl : m.p. 171-2. 

N^-Acetyl : cryst. from AcOEt-light petrol- 
eum. M.p. 125-30. 

Mozingo, ITolkers, The Chemistry of Peni- 
cillin, Princeton University Press, 1949, 
p. 535. 

H-Amylpenillainine 

3 CH-COOH 

3H JSTv 

HP/ \p-CH 2 -[CH 2 ] 3 -CH 3 

HC N 

MW, 270 
d-. 

B,HCl : needles. M.p. 170 decomp. Shows 
ultra-violet absorption max. at 218 nyc (e 6,750). 

B,HCl: needles from Me 2 CO-Et 2 0. M.p. 
167-8 decomp. [a]% + 60-0 in H 2 0. 
dZ-. 

BtHCl: prisms from Me 2 CO-MeOH-Et 2 0. 
M.p. 170. 

Cook, The Chemistry of Penicillin, Prince- 
ton University Press, 1949, p. 106. 

M-Amylpenillic Acid 



H, 



HOOC-CH 



d-. 



MW, 314 



Needles or rhombs from H 2 0. M.p. 190 
(effervescence), [a]!, 1 + 475. Shows ultra- 
violet absorption max. at 240 m/* (e 2,500). 
Hyd. ^ C0 2 + penicillamine + ^-amylpenillo- 
aldehyde. HgCl 2 ^ ft-amylpenillamine + 
C0 2 . Hot H 2 >~ ^-amylpenilloic acid. 

Cook, The Chemistry of Penicillin, Prince- 
ton University Press, 1949, p. 106. 

n - Amylpenilloaldehyde (Gaproamidoacet- 
aldehyde) 

CH 3 -[CH 2 ] 3 -CH 2 -CO'NH-CH 2 -CHO 
C 8 H 15 2 N MW, 157 



CH 2 -NH-CO-CH 2 [CH 2 ] 3 -CH 3 
C 13 H 24 3 N 2 S MW, 288 

d-. 

pK a 1-48, pK 2 5-16 in H 2 at 5. 
B,HCl: cryst. M.p. 193-4 decomp. [a]^ 1 
+ 82-0 in EtOH. 

dZ-. 

B,HCl: needles from MeOH-Et 2 0. M.p. 
201 decomp. Stable to hot dil. acids. 

Me ester : C 14 H 26 3 ISr 2 S. MW, 302. Plates 
from Et 2 0-light petroleum. M.p. 100-1. 

Diketopiperazine : plates from EtOH.Aq. 
M.p. 185-6. 

Mozingo, Folkers e The Chemistry of 
Penicillin, Princeton University Press, 
1949, p. 535. 
Cook, ibid., p. 141. 

fert.-Amyl peroxide 

CH 3 \ 
-CH 2 
CH 3 
C 10 H 22 2 MW, 174 

B.p. 58-5/14 mm., 44/10 mm. DJ 0-821. 
< 1-4095. 

Rust, Dickey, Bell, U.S.P., 2,403,758, 

(Chem. Abstracts, 1946, 40, 6092). 
Vaughan, Bust, U.S.P., 2,403,771, (Chem. 

Abstracts, 1946, 40, 5757). 
Milas, Surgenor, J. Am. Chem. Soc. } 1946, 
68, 643. 

p-tert .-Amylphenetole . 

See under jp-fer.-Amylphenol. 



2 
\CH 




Needles. 
15 mm. 



MW, 164 
B.p. 265-7, 138 / 



n-Amylp&enylcarbinol 



157 



p-Amyranol 



Me ether : 
MW, 178. B.p. 240 (217). 

Et ether : ^-ferZ.-amylphenetole. 
MW, 192. B.p. 260. 
Acetyl: b.p. 265. 

Anschiitz, Beckerhoff, Ann., 1903, 327, 
218. 

ra-Amylphenylcarbinol . 

See 1-Phenylhexyl Alcohol. 

re-Amyl piienyl Ketone. 

See Caprophenone. 

ra-Amylpropiolic Acid (l-Heptyne-l-carb- 
oxylic acid] 

CH 3 -[CH ] 4 -C:C-COOH 
C 8 H 12 2 " MW, 140 

F.p. 2-5. B.p. 148-9/19 mm., 133/10 mm. 
Decomp. at 180-220. Dl 3 0-9623. ^1-46335, 
nf? 1-4595. 

Me ester : C 9 H 14 2 . MW, 154. B.p. 107/ 
20 mm., 94/10 mm. D 20 0-926. < 1-4464. 

JK6fer:O ia H 16 O a . MW,168. B.p. 115 /16mm. 

Propyl ester: C n H 18 2 . MW, 182. B.p. 
134/17 mm. 

Isopropyl ester : b.p. 126-7 /22 mm. 

Isobutyl ester: C 12 H 20 2 . MW, 196. B.p. 
138 /23 mm. 



B.p. 143. D 15 0-8545. 

Kondakow, Ber., 1893, 26, 1012 (Eef.). 

l-Amylpropionic Acid. 

See l-Methyl-ft-lieptylic Acid. 
2-n-Amylquinoline 




C 13 H 22 2 - 



21 - B -P- 



Isoamyl ester : 
148-9 /20 mm. 

Allyl ester : C n H 16 2 . MW, 180. B.p. 124- 
8/18 mm. 

Chloride: C 8 H U OCL MW, 158'5. B.p. 
88-90/17 mm. 

Amide : C 8 H xa ON. MW, 139. Plates from [ a ] 2 B -104 in CHC1 3 . 
EtOH. M.p. Or. &-. 

Nitrile: CJSL^N. MW, 121. B.p. 194-6, 
80-1/13 mm. 

o-Toluidide: needles from pet. ether. M.p. 60 . 

p-Toluidide : cryst. from C 6 H 6 . M.p. 68. 

Anisidide : m.p. 44. 

K-Naphthylamide : m.p. 113-14. 

Moureu, Delange, Compt. rend., 1903, 136, 

553; 1901,132,988. 
Zoss, Hennion, J. Am. Chem. Soc., 1941, 

63, 1152. 
Nametkin et al, Chem. Abstracts, 1942, 36, 

3783. 



C 14 H 17 N MW, 199 

Constituent of alkaloids of Cusparla trifoliata. 
Colourless oil. B.p. 130-45/10 mm. 

Picrate: cryst. from MeOH. M.p. 125-6 
(111-12, 104-5). 

Spath, Pickl, Ber., 1929, 62, 2245; 

Monatsh., 1930, 55, 352. 
Taylor, Hobson, J. Chem. Soc., 1936, 183. 

Amylresorcinol. 

See Olivetol. 

Amyl-jS-resorcylic Acid, 
See Olivetol-carboxylic Acid. 
n-Amylsuccinic Acid. 
See Heptane- 1 : 2-dicarboxylic Acid. 
n-Amylvinylacetylene. 
See l-Nonen-3-yne. 
n-Arnylvinylcarbinol. 
See l-Octenol-3. 
a-Arnyradiene 
C 30 H 48 MW,408 

I: 

Needles from Et 2 0-EtOH. M.p. 193-4. 



AmylpropioHc Aldehyde (l-Heptyne-I- 

aldehyde) 

CH 3 -[CH 2 ] 4 -C:C.CHO 

C 8 H 12 MWi 124 

B.p. 185-7, 89/26 mm. D 0-89. Gives 
cryst. bisulphite comp. 

Moureu, Delange, Compt. rend., 1904, 138, 
1341. 



Needles from Et 2 0-EtOH. M.p. 134-5. [a]^ 1 
+109 in CHC1 3 . 
d 2 -. 
M.p. 119-120. [a] +137. 

Vesterberg, Ber., 1887, 20, 1245; 1891, 

24, 3835. 
Vesterberg, Westerlind, Ann. y 1922, 428, 

250 

Winterstein, Stein, Ann., 1933, 502, 223. 
Ewen, GUlam, Spring, /. Chem. Soc. 9 1944, 

28 

Noller, Hearst, J. Am. Chem. 8oc., 1950, 
72, 625. 

p-Amyranol (OUanan-2$~ol) 



ter*,-Amyl propionate 
CH 3 -CH 2 -COO 



!H 3 
!H 2 -CH 3 



MW, 144 C 30 H 62 




MW, 428 



a-Amyrenol 



158 



Needles from MeOH. 



+184 in CHC1 3 



Acetyl : 
284*5-5-0 



plates 



Ox.- 

from 



[a] D +21 in CHOI 



M.p. 186-0-6-5 . [a] D 
> amyranone. 
CHCl 3 -MeOH. M.p. 



p-Amyrin ($-Amyrenol, olean-I2-en-2$-ol) 



3- 



Ruzicka, Jeger, Helv. CMm. Acta, 1941, 

24, 1178. 
Barton, Holness, J.CJiem. Soc., 1952, 78. 

cc-Amyrenol. 

See a-Amyrin. 

[3-Amyrenol. 

See p-Amyrin. 

a- Amyrenone . 

See a-Amyrone. 

p-Amyrenone, 

See (3-Amyrone. 

a-Amyrin (a-Amyrenol) 




Suggested structure 
C 30 H 50 MW, 426 

Occurs in free state and as acetate in latex of 
various species of rubber tree. Needles from 
EtOH. M.p. 186. [a]J> 7 +91-6 in C 6 H 6 , 
+ 83-5 in CHC1 3 . CrO 3 > a-amyrone. 

Formyl : needles from AcOH. M.p. 190. 
[aj? + 80-4 in C 6 H 6 . 

Acetyl : leaflets from petrol. Needles from 
EtOH. M.p. 225-6 corr. More sol. than 
p-form. [] + 77 in C 6 H 6 . 

Benzoyl : needles or prisms from C 6 H 6 -Me 2 CO. 
M.p. 193-4 corr. []g + 94-6 m CHC1 3 . 

m-Nitrobenzoyl : cryst. from CHCL-EtOH. 
M.p. 233. [ag? + 97-6 in C 6 H 6 . 

Anisoyl : needles from CHCL-EtOH. M.p. 
193. [a]| + 102-2 in C 6 H 6 . 
Me ether : m.p. 221-2. [ag? + 93 in CHC1 3 . 
Ruzicka, Wirz, Helv. Chim. Acta, 1939, 

22, 948. 

Ha worth, Annual Reports of the Progress 

of Chemistry (London), 1937, 34, 338-9. 

Spring, Vickerstaff, J. Chem. Soc., 1937, 

249. 
Ruzicka, Schellenberg, Goldberg, Helv. 

Chim. Acta, 1937, 20, 791. 
Lederman, Journal and Proceedings of the 
Australian Chemical Institute, 1946, 13, 
65 (Review). 
Meisels, Jeger, Ruzicka, Helv. Chim. 

Acta, ..1949, 32, 1075. 

Jeger, tJber die Constitution der Triterpene, 
Fortschritte der Chemie Organischer 
Naturstoffe, Vol. 7, 1950, L 




C 30 H 60 MW, 426 

Occurs in free state and as acetate and pal- 
mitate in latex of various species of rubber tree. 
Needles from EtOH. M.p. 197-7-5. Sol. 
4cOH, EtoO, C 6 H 6 and hot EtOH. Mod. sol. 
petrol, [aft 9 + 99-8 in C 6 H 6 , + 88-4 in CHC1 3 . 
Cr0 3 > p-amyrone. 

Formyl: leaflets from AcOH. M.p. 240. 
[off + 49-8 in C 6 H 6 . 

Acetyl : prisms from petrol. Needles from 
EtOH-Et 2 0. M.p. 236 (238-9). [a]J> 7 + 78-6 
inC 6 H 6 , + 81-4 in CHC1 3 . 

Benzoyl : leaflets from Me 2 CO. M.p. 229-30 
(233-4). [a]i + 100-2. 

m-Nitrobenzoyl : needles from CHCl 3 ~EtOH. 
M.p. 236. [a]|> + 96-7. 

p-Nitrobenzoyl : from 95% EtOH. M.p. 257- 
8. [a]|? + 95-6 in CHC1 3 . 

Anisoyl : leaflets from Me 2 CO or AcOH. M.p. 
250. [a] 3 / + 97-4 in C 6 H e . 

Palmitoyl : m.p. 75. [a]i 6 + 54-5. 

AllopMnate : from dloxan-methyl ethyl 
ketone. M.p. 263-5. 

Toluene-p-sulphonyl : m.p. 132-8 decomp. 

Me ether : m.p. 247-8. [a] 1 ^ +98 in CHC1 3 . 

Ruzicka, Marxer, Helv. Chim. Acta, 
1939, 22, 195. 

Horrmann, Krzlaff, Arch. Pharm., 1930, 
268, 64. 

Vesterberg, Bull. soc. Chim., 1925, 37, 742. 

Haworth, Annual Reports of the Progress 
of Chemistry, (London), 1937, 34, 338-9, 

King et al, J. Am. Chem. Soc., 1943, 65, 
1168. 

Lederman, Journal and Proceedings of the 
Australian Chemical Institute, 1946, 13, 
65 (Review). 

Jeger, fiber die Constitution der Tri- 
terpene, Fortschritte der Chemie Organ- 
ischer Naturstoffe, Vol. 7, 1950, L 

Barton, Holness, J. Chem. Soc., 1952, 78. 

Klyne, J. Chem. Soc., 1952, 2916. 

epi-|3-Amyrin. 

Cryst. from MeOH. M.p. 225. |>]r> + 73-3 
in CHC1 3 . 

Acetyl: cryst. from MeOH-CHCL, M.p. 
128. 

Ruzicka, Wirz, Helv. Chim. Acta, 1941, 
24, 248. 



a-Amyrone 



159 Ajiagyrine 



a-Amyrone 
C 30 H 48 MW, 424 

Tablets from MeOH. M.p. 125-6. Na + 
EtOH or H 2 + Pt > a-amyrin. 

JSemicarbazone : cryst. from C fi H ft ~-EtOH. 
M.p. 204r-5. 

2 : 4c-Dinitrophenylhydrazone : yellowish-red. 
M.p. 218. 

Dieterle, Brass, Schaal, Arch. Pharm., 

1937, 275, 557. 
Ruzicka, Muller, Schellenberg, Helv. 

Chim. Acta, 1939, 22, 758. 

(3-Amyrone 




C 30 H 48 MW, 424 

Cryst. from MeOH. M.p. 177-9 (174, 168). 
[oc] D +107-2 in CHC1 3 . 
Oxime: m.p. 265-7. 

Semicarbazone : m.p. 244-5 decomp. (248- 
9). 

Rollett, Monatsh., 1923, 43, 413. 
B/uzicka, Schellenberg, Goldberg, Helv. 

Chim. Acta, 1937, 20, 791. 
Ruzicka, Wirz, Helv. Chim. Acta, 1941, 
24, 248. 

Anabasine (S-[2-Piperidyl]-pyridine 9 2-[3- 
pyridyl]-piperidine) 

CH 2 



C 10 H 14 N 2 



NH 



MW, 162 



Occurs in Anabasis apylla. B.p. 276, 104- 
5/2 mm. Sol. H 2 0, EtOH, Et 2 0, C 6 H 6 . 
D 1-0455. ri 1-5430. [a]g 82-20. KMn0 4 
> nicotinic acid. Boiling with Zn dust > 
2 : 3'-dipyridyl 

N-Benzoyl : needles. M.p. 82-3. B.p. 222 / 
2 mm. [a]g -127-23 in EtOH. 

Nitroso deriv. : b.p. 176/4 mm. Dig 1-1777. 
n^ 1-5698. [a]$ -155-0. 

Dinitrodiphenate : cryst. from MeOH. M.p. 
265 in vac. 

Dipicrate : m.p. 198-199-5 decomp. 

dk 

Dinitrodiphenate : cryst. from MeOH. M.p. 
264-5. 



Dipicrate : m.p. 198-9 decomp. 

dl-. ISfeonicotine. 
B.p. 280-2/775 mm. 
Dipicrate : m.p. 213-14. 

Orechoff, Menschikoff, Ber., 1931, 64, 

266; 1932,65,232. 
Roark, Chem. Abstracts, 1941, 35, 3388; 

1945, 39, 2373. 

Smith, J. Am. Chem. Soc., 1932, 54, 397. 
Spath, Kesztler, Ber., 1937, 70, 72. 
Spath, MamoH, Ber. } 1936, 69, 1084. 

Anacardic Acid 
C 22 H 32 3 MW, 344 

From cashew nut oil (Anacardium occidentale, 
Linn.). Believed to be a 2-hydroxy-6-penta- 
decadienylbenzoic acid. M.p. 26 (22-5, 21). 
< 1-5164. Sol. EtOH, Et 2 O. Insol. H 2 O. 
KMn0 4 ^ oxalic and w-heptylic acids. H 2 + 
Pd ^ 2-hydroxy-6-pentadecanylbenzoic acid. 

Me ether: C 23 H 34 3 . MW 358. n$ 1-5009. 
Me ester : b.p. 200-5/0-5 mm. 

Ruhemann, Skinner, Ber., 1887, 20, 1861. 
Pillay, J. Indian Chem. 8oc., 1935, 12, 

226. 
Backer, Haack, Rec. trav. chim., 1941, 60, 

661. 
Eichbaum, Hauptmann, Rothschild, 

Chem. Abstracts, 1946, 40, 6443. 

Anacardol 




C 21 H 32 MW, 300 

B.p. 215*2/14 mm. (220-3/4 mm.), 186- 

7/l mm. D|S 0-9399. 7^ 1-5107 (rig 1-5060). 

Sol. Me 2 CO, C 6 H 6 , AcOEt, EtOH, Hgroin. Inol. 

H 2 0. H + Pd > m-pentadecylphenol. 

Me ether: C 22 H 34 0. MW, 314. B.p. 212- 

14/5 mm., 188-5/l mm. rig 5 1-5008. 

Pillay, J. Indian Chem. Soc., 1935, 12, 226. 
Backer, Haack, Rec. trav. chim., 1941, 

60, 661. 
Wasserman, Dawson, Ind. Eng. Chem., 

1945, 37, 396. 

Anaesthesia. 

See Benzocaine. 

Anagyrine (Monolupine, rTiombinine) 




N 
CH 2 CH CH CH 2 

CH 2 

Suggested structure 



MW, 244 



Analgen 



160 



Androl 



Alkaloid present in Anagyris fortida and 
Lupinus laxiflorus var. silvicola. Pale yellow 
deliquescent glass, darkening on exposure to 
light B.p. 210-15/4 mm., 165-8 /0-3 mm. 
Sol. BtOH 5 Et 2 0, CHC1 3 , C S H 6 . Less sol. hot 
than cold E 2 0. Insol. ligroin. []g -165-3 in 
EtOH. FeCi 3 .Aq. > red col. 

Perchlorate : needles from H 2 0. Decomp. 
about 270 without melting (315 decomp.). 

B,HAuCl: golden needles from dil. HC1. 

's,E^PtCl Q : orange cryst. M.p. 278 de- 
comp. 

Picrate: cryst. from EtOH. M.p. 169*5 

(253). 

Methiodide : cryst. from MeOH. M.p. 264 
decomp. (257). 

Couch, J. Am. Chem. Soc., 1939, 61, 3327. 
Ing, J. Chem. Soc., 1933, 504. 
Marion, Quellet, J. Am. Chem. Soc., 1948, 
70, 3076. 

Analgen. 

See under 8-Hydroxy-5-aminoquinoIine. 

Analobine. 

8ee Anolobine. 

Anatabine (Tetrahydro~2 : %' -Mpyridyl} 

CH 



H 2 C 




C,,H IS N, MW, 160 

Alkaloid found in tobacco. 

dl-. 

D 20 1*086. < 1-5655. 

Diperchlorate : m.p. 129-30. 

Dipicrate : m.p. 201-0-1-5 . 

Trinitro-m-cresol add. comp. : m.p. 140-1. 

Picrolonate : m.p. 233-5. 

I-. 

B.p. 145-6/10 mm. Bf 1-091. wff 1-5676. 
[cx]i 7 177-8. Pd at 200 ^ 2 : S'-dipyridyl. 
Pd + H 2 > Z-anahasine. 

-R-Benzoyl : b.p. 160-170 (bath temp.)/0-01 
mm. Mi 5 -15-4 in MeOH. 

N-V-Nitrobenzoyl : m.p. 101-2, solidifies and 
remelts at 130-1. []}?* -174-5 in MeOH. 

Dipicrate : m.p. 191-3. 

Trinitro-m-cresol add. comp. : m.p. 191-2. 

Dinitrodiphenate : m.p. 238-0-8-5 . 

Picrolonate : m.p. 234r-5 decomp. 

d-. 

N-p-Nitrobenzoyl : m.p. 101-2, solidifies and 
remelts at 129-30. [] +168-7 in MeOH. 

Spath, Kesztler, Ser. 9 1937, 70, 239, 704. 



Anavenol. 

See 2-Hydroxyethyl 2-naphthyl Ether. 
Anduisin 
r H A MW, 540 

O 3 o-n-36 U 9 

Substituted trihydroxyanthraquinone found 
in alkanet root. Dark red powder from EtOH. 
Decomp. above 300. Dist. with Zn dust > 
2-methylanthracene . 

Triacetyl : cryst. from AcOH, M.p. 212-15 
decomp. 

Tribenzoyl : cryst. from C 6 H 6 -ligroin. M.p. 
226-8 decomp. 

Di-Me ether : cryst. from AcOH. M.p. 240- 
2 decomp. Acetyl : brown powder. M.p. 
above 330. 

Majumdar, Chakravarty, J. Indian Chem. 
jSoc., 1940, 17, 272. 

Andogenin 

C 27 E 42 4 MW,430 

Sapogeniii from Phytolacca abyssinica. M.p. 
276-9. Sol. EtOH, AcOH, CC1 4 , CHC1 3 , Et 2 O, 
AcOEt. [a]g +50 in MeOH. 

Bachstez, Cavallini, Chem. Abstracts, 
1946,40,6211. 

Andrographolic Acid 

C 20 H 32 6 MW,368 

Needles from MeOH. M.p. 188 > andro- 
grapholide. Mod. sol. EtOH. Spar. sol. H 2 O, 
Et 2 0, Me 2 CO, CHC1 3 , C 6 H 6 . [a]f? + 14-4 in 
MeOH. Warm H 2 S0 4 -EtOH > andrographol- 
ide. 

Gorter, Rec. trav. chim., 1911, 30, 151. 

Audrographolide 
C 20 H S0 6 MW, 350 

Occurs in Andrographus paniculata, Nees. 
Oryst. from MeOH. M.p. 218 decomp. Mod. 
sol. MeOH, Me a CO. Spar. sol. H 2 0, Et 2 0, 
CHC1 3 . [a]J 126-0 in AcOH. Warm, with 
alkali > andrographolic acid. 

Triacetyl deriv. : needles from EtOH. 
129. 



M.p. 



Gorter, Bee. trav. chim., 1914, 33, 239; 

1911, 30, 151. 
Moktader, Guha-Sircar, J. Indian Chem. 

Soc., 1939, 16, 333. 

Androl 

C 10 H 20 MW, 156 

Occurs in oil of water fennel. B.p. 197-8. 
D 15 0-858. n 1-44991. [a] D - 7-2. 
Phenylurethane : m.p. 42-3. 
Diphenylur ethane : m.p. 87-90. 

Schimmel, Chem. Zentr., 1904, II, 1470. 



Androsin 



161 



3//4-Androstane-3 : 4-dioic Acid 



Androsin (Gli^coacetovanillone) 
0-C 6 H n 5 



CO 



CH 3 
Ci 5 H 20 8 MW, 328 

Occurs in rhizomes of Apocynum andro- 
scemifolium, Linn. Cryst. -j- 2H 2 from H 2 (X 
M.p. anhyd. 223-4. Spar. sol. EtOH, cold 
H 2 0. Hyd. by emulsin. Boil. dil. H 2 SO 4 > 
acetovanfilone. 

Tetra-acetyl deriv. : cryst. from EtOH. M.p. 
156-7. 

Mauthner, J.prakt. Chem., 1925, 110, 123. 
A 5:7 -Androstadiene-3p :17(p)-diol 

CH 3 

)H 




C 19 H 28 2 MW, 288 

Needles from Me 2 CO. M.p. 212. One tenth 
the physiological activity of the corresponding 
A 5 -androstene-3 : 17-diol. Absorption maxima at 
270 and 280 m^. 

Diacetyl : cryst. from EtOH.Aq. M.p. 132. 
Peroxide : m.p. 221-1-5. [a]| 8 4-8 in CHC1 3 . 

Dibenzoyl : cryst. from CHCl 3 -MeOH. M.p. 
217-18. 

Butenandt et al. } Ber., 1938, 71, 1316. 
Butenandt, Paland, Ber., 1939, 72, 424. 
Goldberg et al., Helv. Chim. Acta, 1947, 
30, 1441. 

A 3 * 5 -Androstadiene-17-one 

OH, 

>0 




C 19 H 26 MW, 270 

From urine of man with adrenal tumour. 
Leaflets from MeOH.Aq. M.p. 88-9. [a] D 
31 in EtOH. Bed. > androstan-17-one. 
350-400 y ss 1 LIT. No cortical hormone ac- 
tivity. 

Oxime : needles from MeOH. M.p. 164-70. 

Semicarbazone : needles from dioxan. M.p. 
291-2. 

Burrows, Cook, Roe, Warren, Biochem. 
J., 1937, 31, 956. 

Diet, of Org. Oomp. I. 



A 4 : 16 -Androstadiene-3-one 

CH 3 




C 19 H 26 O MW, 270 

Purified by sublimation in high vacuum. 
M.p. 131*5-3-5 corr. [o:]^ 6 123 3-5 (c, 1-03 
in CHC1 3 ). Absorption maximum at 240 mpu 
Intense col. in the Kagi-Mescher test (Helv. 
CUm. Acta, 1939, 22, 683). 

Prelog, Ruzicka, Meister, Wieland, Helv. 
Chim. Acta, 1945, 28, 618. 

Androstane (Aetioallocholane) 

CH 3 




C 19 H 32 MW, 260 

Leaflets from Me 2 CO. M.p. 50-2 (50-0-50-5) . 
[]}? +2 in CHC1 3 . 

Butenandt, Tscherning, Z. physioL GJiem., 

1934, 229, 190. 
Encyclopedia of Endocrinology, Section 1, 

Vol. I. (Franks, Montreal). 

2//3-Androstane-2 : 3-dioic Acid (2 : 3-seco- 

Androstane-2 : 3-dioic acid) 

GH a 




C 19 H 30 4 



MW, 322 



Cryst. from Et 2 O-pet. ether. M.p. 237-8 
corr. [a]! 1 -8-3 2 (c, 1-089 in EtOH). 

Di-Me ester: C^H^. MW, 350. Cryst. 
from pet. ether. M.p. 44-5 corr. [a]! -8-8 
3 (c, 1-077 in CHCy. 

Buzicka, Prelog, Meister, Helv. Chim. 
Acta, 1945, 28, 1651. 

3//4-Androstane-3 : 4-dioic Acid (3 : 4-seco- 

Androstane-3 : 4-dioic acid) 

CH S 



HOO 
HOOC' 




MW, 322 
11 



Androstane-3a : 17a-diol 



162 



Androstane-3p : llp-diol-17-one 



Cryst. from Et 2 O. M.p. 242-4 corr. [a]! 1 
21-9 1-5 (c, 1-101 in EtOH). 

Ruzicka, Prelog, Meister, Helv. Chim. 
Acta, 1945, 28, 1651. 



Androstane-Sa : 17a-diol 



HO-'* 




OH 



MW, 292 
227-8 corr. 



Needles from AcOEt. M.p. 
350 y a 1 I.U. 

Ruzicka, Kagi, Helv. Chim. Acta* 1937, 
20, 1564. 

Androstane-3cc : 17(3-diol (epi-Androstane- 



HO-''" 




C 19 H 32 2 



MW, 292 



Needles from Me 2 CO.Aq. or EtOH.Aq. M.p. 
221. [a]?? + 12-6. 20 y m 1 I.U. 

%~Acetyl : cryst. from MeOH. M.p. 183-4 
corr. 20 y = 1 I.U. 

YI-Acetyl: cryst. from MeOH.Aq. M.p. 191- 
2 corr. 20 y = 1 I.U. 

Diacetyl : prisms from Me 2 CO.Aq. M.p. 159- 
60. [a$? + 12-5. Physiologically active. 
3-Acia-succinyl : m.p. 208 corr. 
Di-succinyl : cryst. from Et 2 0. M.p. 139-40 
corr. 

17-Benzoyl : cryst. from AcOEt. M.p. 203-4 
corr. Inactive. 

3-Acetyl-ll -benzoyl : cryst. from EtOH. M.p. 
198-9 corr. 

Butenandt, Tscherning, Z.physiol. Chem. 9 

1935, 234, 225. 
Euzicka, Goldberg, Meyer, Helv. Chim. 

Acta, 1935, 18, 210. 
Buzicka, Goldberg, Helv. Chim. Acta, 

1936, 19, 99. 

Ruzicka, Wettstein, Helv. Chim. Acta 9 
1936, 19, 1146. 

Androstane-3p : 17oc-diol 



-OH 




Prisms from MeOH. M.p. 218-20. 
Diacetyl : prisms from di-isopropyl ether. 
M.p. 146-147-5. 

Ruzicka, Kagi, Helv. Chim. Acta, 1936, 

19, 847. 
Marker, J. Am. Chem. Soc., 1936, 58, 480. 

Androstane-3|3 : 17p-diol 




C 19 H 32 2 MW, 292 

Leaflets from EtOH.Aq. Cryst. from AcOEt. 
M.p. 164. Sublimes at 140/0-01 mm. [a]g 
+ 4-2. 550 y ^ 1 I.U. 
11-Acetyl : m.p. 148. 

Diacetyl: needles from EtOH.Aq. M.p. 
123-4. 

Ruzicka, Goldberg, Rosenberg, Helv. 

Chim. Acta, 1935, 18, 1487. 
Butenandt, Tscherning, Hanisch, Ber,, 
1935, 68, 2098. 

Androstane-3a : llp-diol-17-one 
HO, 

X. s ^ m 

r'.O 

OH,! I 

y'\. 

T^ 



HO- 




MW, 306 
197-8. [a]^ 
Isolated from 



C 19 H 30 3 

Cryst. from Me 2 CO. M.p. 
+96-6 d=2 (c, 0-590 in EtOH). 
urine, in increased amounts from patients with 
adrenal cortical tumours. 

Z-Acetyl : cryst. from Me 2 CO. M.p. 238-40. 
Mason, Kepler, /. Biol. Chem., 1945, 161, 

235. 
Shoppee, J. Chem. Soc., 1946, 1134. 

Androstane~3p : llp-diol-17-one 




MW, 292 



C 19 H 30 3 MW, 306 

Cryst. in needles from Me 2 CO-Et 2 0, M.p. 
233-5 corr. 

3-Acetyl : purified by sublimation in high 
vacuum, cryst. in needles from Me 2 CO-Et 2 0. 
M.p. 228-9 corr. 

Reichstein, Helv. Chim. Acta, 1936,19,402. 
Shoppee, Helv. Chim. Acta, 1940, 23, 740. 
v. Euw, Reichstein, Helv. Chim, Acta, 
1942, 25, 988. 



Androstane-3 : 17-dione 



163 



Andr ostane-1 7-ol-3-one 



Androstane-3 : 17-dione 

OH S 




C 19 H 28 2 MW, 288 

Leaflets from Me 2 CO or hexane. M.p. 132-3. 

[o& + 111 in EtOH. 130 y s 1 I.U. Brom- 

ination > 2-monobromide. Qemmensen red. 

> androstane. 

Dioxime : m.p. 255-60. 

Ruzicka, Rosenberg, Helv. Chim. Acta, 

1936, 19, 366. 
Butenandt, Tscherning, Hanisch, Ber., 

1935, 68, 2102. 
Butenandt, Tscherning, Z. physiol. Chem., 

1934, 229, 185. 

Androstane-6 : 17-dione 

CH 8 

/N fo 




C 19 H 28 2 MW, 288 

M.p. 134-5. 

Dioxime : m.p. 288-90. 

Butenandt, Suranyi, Ber., 1942, 75, 591. 



Androstane-3oc-ol 



CH 8 




ol) 



Androstane-17(a)-ol (Androstane-11 '-' cis '- 




MW, 276 

Cryst. in needles from MeOH. M.p. 152-3. 
Hexahydrobenzoyl : C 26 H 42 2 . MW 386 
M.p. 138-9. 

Kagi, Miescher, Helv. Chim. Acta, 1939, 

22, 683. 
See also Goldberg et al. } Helv. Chim. Acta, 

1947, 30, 1441. 



Androstane - 17(p) - ol 
* trans ! -0Z) 



(Androstane - 17 - 



C 19 H 32 O MW, 276 

Cryst. from Et 2 O-pentane. M.p. 164-6. 

Mf? +13-1 (c, 1*160 in CHC1 3 ). 
Propionyl : m.p. 80-1. 

Kagi, Miescher, Helv. Chim. Acta, 1939, 

22, 683. 
Marker, J. Am. Chem. Soc., 1940, 62, 

2543. 
See also Goldberg et al., Helv. Chim. Acta, 

1947, 30, 1441. 



Androstane-3-ol-17-one . 

See Androsterone. 
Androstane-17oc-ol-3-one 

testosterone) 




(epi~Dihydro- 
-OH 



HO ^i Q ^ 

C 19 H 32 MW, 276 

M.p. 145-6 corr. [a]* 7 +2 2 (c, 1-276 in c i9 H 3(Ai MW > 29 

CHC1 3 ). Needles from MeOH. M.p. 180 corr. 300 y 

Prelog, Ruzicka, Wieland, Helv. Chim. 



Acta, 1944, 27, 66. 
Androstane-3p-ol 



OH 3 




Acetyl : cryst. from hexane. M.p. 150-1 
corr. 

Ruzicka, Kagi, Helv. Chim. Acta, 1937, 
20, 1563. 



Androstane-17|3-ol-3-one 

sterone) 



C 19 H 32 O MW, 276 

M.p. 147-5148 corr. [oft 7 + 0-9 0-9 (c, 
2-22 in CHClg). 

Prelog, Ruzicka, Wieland, Helv. Chim. 
Acta, 1944, 27, 66. 




(Dihydrotesto- 



OH 



MW, 290 



Androstane-3-oiie 

Cryst. from AcOEt or Me 2 CO.Aq. M.p. 178 
(182). [a]S + 32-4 in EtOH. Sublimes at 135 / 
0-01 mm. 20 y 1 I.U. Bromination > 
2-monobromide. 

Acetyl : needles from Me 2 CO.Aq. M.p. 157 
corr. 

Benzoyl : cryst. from petrol-AcOEt. M.p. 
200-1 corr. 

Oxime : needles from EtOH.Aq. M.p. 209 . 
Semicarbazone : cryst. from EtOH. M.p. 
237-43. 

Butenandt, Tscherning, Hanisch, Her., 

1935, 68, 2100. 
Ruzicka, Goldberg, Helv. Chim. Acta, 

1936, 19, 105. 

Ruzicka, Goldberg, Grob, Helv. Chim. 
Acta, 1941, 24, 1151. 



Androstane-3-one 




C 19 H 30 MW,274 

Purified by sublimation in high vacuum, 
cryst. from hexane. M.p. 104-5-5*5 corr. 
[a]! +254 3 (c, 0-710 in CHC1 3 ). 

Prelog, Ruzicka, Meister, Wieland, Helv. 
GUm. Acta, 1945, 28, 618. 

Androstane-17-one 




I 19 H 30 MW, 274 

Cryst. from AcOEt-pet. ether. M.p. 122. 

x ]16 + 87 . 8 o fc Q HCl3 

Semicarbazone : m.p. 275 decomp (284-5). 
Fernholz, Chakravorty, Ber., 1935, 68, 

353. 

Butenandt, Dannenbaum, Z. physiol. 
Chem., 1934, 229, 192. 

Androstane-3p : 16 (a) : 17(a)-triol 




HO 



C 19 H 32 3 MW, 308 

Cryst. from EtOH.Aq. M.p. 251-3. [] 
+18 (c, 0-53 in 95% EtOH). 



, 308 



: 17(3-diol 



Huffman, Lott, J. Am. Chem. Sac., 1949, 

71 719. 
See also Goldberg et al, Helv. Chim. Acta, 

1947, 30 5 1441. 

Androstane-3|3 : 16(P) : 17(cc)-triol 
C 19 H 32 3 

M.p. 256-60. 

Tnacetyl: m.p. 175-176-5. [aft 6 -44 (c, 
0-45 in EtOH). 

Hirschmann, J. Bid. Chem., 1943, 150, 

363. 

Marrian, Butler, Nature, 1944, 154, 19. 
Goldberg et al., Helv. Chim. Acta, 1947, 
30, 1441. 

Androstane-3p : 16(P) : 17((3)-triol 
C 19 H 32 3 MW, 308 

Purified by sublimation in high vacuum, cryst. 
from EtOH. M.p. 265-6 corr. [a] -19 4 
(c, 55 in EtOH). 

Triacetyl : needles from MeOH. M.p. 165 
corr. No physiological activity. 

Ruzicka, Prelog, Wieland, Helv. Chim. 

Acta, 1945, 28, 1609. 
Huffman, Lott, J. Am. Chem. Soc., 1947, 

69,1835; 1949,71,719. 
Goldberg et al., Helv. Chim. Acta, 1947, 
30, 1441. 

Androstane-3 : 11 : 17-trione 

OH 3 

o: 




C 19 H 26 3 MW, 302 

Leaflets from Et 2 0. M.p. 178 corr. (182-3). 
[a]g +152 in Me 2 CO. Sublimes at 165 /O-l 
mm. Obtained by ox. of many of the con- 
stituents of the adrenal cortex. One-third as 
active as androsterone. 

3 : Yl-Dioxime : cryst. from EtOH. M.p. 
274-6 corr. 

Reichstein, Helv. Chim. Acta, 1936, 19, 

404. 
Euw, Reichstein, Helv. Chim. Acta, 1942, 

25, 988. 

Mason, Kepler, J. Biol Chem., 1945, 161, 
235. 

A 4 -Androstene-3a : 17p-diol 

OH, 




C 19 H 30 2 



MW, 290 



A 4 -Androstene-3(3 : 17p-diol 



165 



A 2 -Androstene-6 : 17-dione 



Needles from EtOH or AcOEt. M.p. 202-6. 
[a]? + 187-5 in Py. 150-200 y m I LU. 
Diacetyl : leaflets from EtOH.Aq. M.p. 121. 
Butenandt, Heusner, Ber., 1938, 71, 202. 

A 4 -Androstene-3p : 17p-diol 

OH, 

OH 




MW, 290 
Cryst. from Me 2 CO. M.p. 153-4. [ofe 9 

+ 48-5 in EtOH. Pptd by digitonin. 150- 

200 y ^ 1 I.U. 

Diacetyl : leaflets from EtOH.Aq. M.p. 

101-2. 

Butenandt, Heusner, Ber., 1938, 71, 202. 
A 5 -Androstene-3oc : 17(3-diol 




HO- 

MW, 290 

Prisms from AcOH. M.p. 200. After sub- 
limation in high vacuum, m.p. 208-9 corr. 
[<x] D 56 in EtOH. 35 y = 1 I.U. 

3-Acetyl : leaflets from MeOH. M.p. 183. 

Diacetyl : leaflets from MeOH-pet. ether. 
M.p. 155 corr. 

Huzicka, Goldberg, Bosshard, Helv. Chim. 
Acta, 1937, 20, 544. 

A 5 -Androstene-3(3 : 17cc-diol 

OH 8 




C 19 H 30 2 MW, 290 

Needles from AcOEt. M.p. 198-198-5 corr. 
850-1000 y m I I.U. 

Diacetyl : prisms and needles from MeOH. 
M.p. 170 corr. 

%-Acetyl-ll-benzoyl : needles from. EtOH. 
M.p. 133-4 corr. 

ll-B&nzoyl : prisms from di-isopropyl ether. 
M.p. 150-1 corr. 

Ruzicka, Kagi, Helv. Chim. Acta, 1936, 
19, 842. 




A 5 -Androstene-3|3 : 17(3-diol 

CH 3 

r- OH 



HO- 



c i9 H 3<A MW, 290 

Cryst. from MeOH or AcOEt. M.p. 184. 
[a] D - 50 in EtOH. 500 y = 1 I.U. Has 
cestrogenic properties. 

3-Acetyl : cryst. from hexane. M.p. 147-8 
corr. 

Yl-Acetyl : needles from Me 2 CO. M.p. 146-5- 
148-5 corr. [ag> 8 56*6 in EtOH. 

Diacetyl : leaflets from hexane. M.p. 165-6. 
MS 56-5 in EtOH. 

3-Acetyl-I7-benzoyl: leaflets from EtOH. M.p. 
180-2 corr. 

17-Benzoyl : needles from di-isopropyl ether. 
M.p. 221-2. 

Butenandt, Hanisch, Z. physiol. CJiem., 

1935, 237, 89. 
Ruzicka, Wettstein, Helv. Chim. Ada, 

1935, 18, 1264. 
Ruzicka, Kagi, Helv. Chim. Acta, 1935, 

18, 1481. 

A^Androstene-S : 17-dione 




C H MW, 286 

Needles from EtOH.Aq. M.p. 139-40. MB 
+ 148-5 in EtOH. Absorption band at 238 m^. 
No male hormone activity but gives positive 
Allen-Doisy test. 

Dioxime : cryst. from EtOH.Aq. M.p. 258- 
64 decomp. 

Butenandt et al, Ber., 1939, 72, 1622, 
Butenandt, Dannenberg, Ber., 1936, 69, 

1161. 
Miescher, Wettstein, U.S.P., 2,260,328, 

(Chem. Abstracts, 1942, 36, 873). 

A 2 -Androstene-6 : 17-dione 

OHj, 




C 19 H 26 2 MW, 286 

Purified by sublimation in high vacuum, 
cryst. from AcOEt-hexane. M.p. 190-2. [a] D 



A 4 -Androstene-3 : 17-dione 



166 



A 16 -Androstene-3|3-ol 



CH a 





+ 123 2 (c, 1-6 in CHC1 3 ). Yellow col. with A 5 -Androstene-3(3-ol 
C(N0 2 ) 4 . 

Blunsehy, Hardegger, Simon, Helv. Chim. 
Acta, 1946, 29, 199. 

A 4 -Androste*ie-3 : 17-dione 

CH S 

1U 

MW, 274 

" JL 5U ~ 

Purified by sublimation in high vacuum, m.p. 
135-136-5 corr. [a] D -68-3 2 (c, 0-71 in 
dioxan). 

C 19 H 26 2 MW, 286 .^ceft/Z : purified by sublimation in high 

Cryst. from hexane. M.p. 173-4 corr. [a]i 8 vacuum, cryst. from Me 2 CO.Aq in platelets. 
+ 185 in EtOH, + 199 in CHCL. Absorption M.p. 93-4 corr. Yellow, col. with C(JNO 2 ) 4 . 

band at 235 mp. 130 y - 1 I.U. - ~ * " 

Dioxime : cryst. from EtOH. M.p. 143. 
Enol-acetyl: needles from MeOH. M.p. 127-9 
corr. 

Enol-benzoyl : cryst. from Me CO. M.p. 176- 
80 corr. 

Ruzicka, Wettstein, Helv. Chim. Acta, 

1935, 18, 993. 
Ruzicka, ^Fischer, Helv. Chim. Acta, 1936, 

19, 1373. 
Butenandt, Kudsus, Z. ghysiol. Chem., 

1935, 237, 85. 
Julian et al., J. Am. Chem. Soc., 1945, 67, 

1728. 

Marker, Wittle, U.S.Rs, 2,397,424-6, 
(Chem. Abstracts, 1946, 40, 3571). 

A 5 -Androstene-3 : 17-dione 



Heard, McKay, /. Biol. Chem., 1946, 165, 
677. 

A 5 - Androstene-1 7-ol 

CH 3 





MW, 274 

M.p. 163-5 (161-2). 

Acetyl : cryst. from MeOH. M.p. 135-6. 
Kuwada, Tutihasi, J. Pharm. Soc. Japan, 
1939, 59, 352, (Chem. Abstracts, 1939, 
33, 8209). 

Marker, Wittle, Tullar, J. Am. Chem. Soc., 
1940 3 62, 223. 



A 1 6 - Andr ostene-3a-ol 



OH, 



C 19 H 26 2 MW, 286 

Needles from EtOH. M.p. about 158. Acids 
> A 4 -androstene-3 : 17-dione. 300 y B 1 I.U. 
Dioxime : cryst. M.p. 180-205. 

Butenandt, Schmidt-Thome", Ber., 1936, 

69, 886. 
Oppenauer, Eec. trav. chim., 1937, 56, 137. 

A 4 -Androstene-17-ol 

OH S 




OHJ 
J/ 

HO" ^H 

MW, 274 
Purified by sublimation in high, vacuum., cryst. 




2 (c, 0-936 in CHC1 3 ). Blue col. in the Kagi- 
Miescher test (Helv. Chim. Acta, 1939, 22, 683)* 
Prelog, Ruzicka, Wieland, Helv. Chim. 
Acta, 1944, 27, 66. 

A 16 -Androstene-3(3-ol 



C 19 H 30 ' MW,274 

Cryst. from MeOH. M.p. 146-9. 
Acetyl : m.p. 97-100. 

Marker, Wittle, Tullar, J. Am. Chem. Soc. y 

1940, 62, 223. 

See also B.P.s, 550,684; 550,478, (Chem. 
Abstracts, 1944, 38, 1611, 1612). 




MW, 274 



A 3 -Androstene-3-ol-2 : 17-dione 



167 



A 9 : 11 -Androstene-3p-ol-17-one 



Purified by sublimation in high vacuum, cryst. 
from Me 2 CO. M.p. 125-7. [a] 11-2 2-5 
(c, 0-761 in CHC1 3 ). Blue col. in the Kagi- 
Miescher test (Helv. Chim. Acta, 1939, 22, 683). 

Prelog, Ruzicka, Wieland, Helv. Chim. 
Acta, 1944, 27, 66. 

A 3 -Androstene-3-ol-2 : 17-dione 

CH 3 

>o 




C 19 H 26 3 MW, 302 

Cryst. from hexane. M.p. 165-75. [a]f? 

+ 149-8. 

Acetyl: cryst. from EtOH. M.p. 208-10. 

Toluene--p-sulphonyl : cryst. from Me 2 CO- 
hexane. M.p. 206-8. [a] 2 D + 1334. 

Djerassi, Yashin, Rosenkranz, /. Am. 
Chem. Soc., 1950, 72, 5750. 

A 4 -Androstene-17a-ol-3-one (epi-Testoster- 

one) 

OH, 

-OH 




C 19 H 28 2 ~ " ^ MW,288 

Pale yellow tablets from AcOEt or Me 2 CO. 
M.p. 220-1 corr. [at + 71-7 in EtOH. 25 
times less active than testosterone. 

Acetyl : cryst. from hexane. M.p. 116 corr. 

Benzoyl : cryst. from EtOH. M.p. 136-5-138 
corr. 

Oxime : cryst. from EtOH.Aq. M.p. 220-5 
corr. 

Semicarbazone : cryst. from MeOH. M.p. 
221-2 corr. decomp. 

Ruzicka, Kagi, Helv. Chim. Acta, 1936, 
19, 848. 

A 4 -Androstene-17|3-ol-3-one. 

See Testosterone. 

A 5 -Androstene-3a-ol-17-one (Dehydro- 
androsterone) 

OH, 



Acetyl : cryst. from MeOH. M.p. 173*5- 
174-5 corr. 

Oxime : leaflets from MeOH.Aq. M.p. 204-6 
corr. 

Ruzicka, Goldberg, Helv. CMm. Ada, 
1936, 19, 1410. 

A 5 -Androstene-3-ol-17-one. 

See Dehydro-epiandrosterone. 
A 5 -Jkndrostene-17|3-ol-3-one (^-Testoster- 
one) 




HO-** 
C 19 H 28 2 MW, 288 

Cryst. from AcOEt. M.p. 221 corr. 100 y j 
1 I.I 




Acetyl : leaflets from 



MW, 288 

M.p. 130- 

> testo- 
sterone acetate. 125 y s 1 I.U. 

Propionyl : cryst. from pet. ether. M.p. 
about 135. [oc] D - 17 in EtOH. 

Benzoyl : cryst. from cyclohexane. M.p. 170- 
80. [at + 23 in C 6 H 6 . 

Butenandt, Hanisch, JBer., 1936, 69, 2775. 
Ruzicka, Goldberg, Bosshard, Helv. CMm. 
Acta, 1937, 20, 541. 

A 9 : 11 -Androstene-3o-ol-17-one 




HO 

C 19 H 28 2 MW, 288 

Cryst. from AcOEt. M.p. 189-90. MD 
140 2. 

Acetyl: m.p. 190-2. [a] 2 D 5 +135 3. 
Isolated from pathological urine. 

Mason, Kepler, /. Biol. Chem., 1945, 161, 

235. 

Shoppee, J. Chem. Soc., 1946, 1134. 
Miller, Dorfman, Sevringhaus, Endo- 
crinology, 1946, 38, 19. 

A 9 : 11 -Androstene-3p-ol-17-one 

OH, 

>o 




C 19 H 28 2 

Purified by sublimation in high vacuum, cryst. 
from MeOH.Aq. M.p. 170-2-5 corr. []? 
+125-5 2 (c, 0-534 in EtOH). 



A 11 ?-Androstene-3a-oI-17-<me 



168 



A 5 -Androstene-3p : 16 (a) : 17(a)-triol 



Acetyl : purified by sublimation in high Purified by sublimation in high vacuum, 
vacuum, cryst. in prisms from pentane. M.p. cryst. from EtOH. M.p. 78-80. 

Marker, Wittle, Tullar, J. Am. Chem. Soc. 9 

1940, 62, 223. 

Lee, Stirn, U.S.P., 2,398,185, (Chem. 
Abstracts, 1946, 40, 3569). 



102 corr. [aft 4 110-8 4 (c, 1-255 in Me 2 CO). 
Yellow col. with C(N0 2 ) 4 . 

Shoppee, Helv. Chim. Acta, 1940, 23, 740; 

J. Chem. Soc., 1946, 1134. 
Reich, Lardon, Helv. Chim. Acta, 1947, 
30, 329. 



A 11 ?-Andjrostene-3cc-ol-17-one 

OH, 




HO* ~ H 
C 19 H 28 2 MW, 288 

Purified by sublimation in high vacuum, cryst. 
from MeOH.Aq. M.p. 181-3 corr. [a]??' 6 
+122 2 (c, 0-364 in 95% EtOH). Isolated 
from urine of patient with adrenal cortical 
tumour. 

Acetyl : m.p. 178-80 corr. [oc]| 65 +114 
5 (c, 0-314 in EtOH). 

Benzoyl : m.p. 162-4 corr. 

Semicarbazone : m.p. 279-80 decomp. 

Wolfe, Fieser, Eriedgood, J. Am. Chem. 

Soc., 1941, 63, 582. 
Shoppee, J. Chem. Soc., 1946, 1134. 
Lieberman et al., J. Biol. Chem., 1948, 

172, 263. 

A 2(or 3) -Androstene-17one 

CHa 




C 19 H 28 MW, 272 

Purified by sublimation in high vacuum, 
cryst. in leaflets from MeOH. M.p. 104*5- 
5-5 corr. (110, 111-14). [aft 7 146 9 (c, 
040 in EtOH). 

Hirschmann, /. Biol. Chem., 1940, 136, 

492. 
Prelog, Ruzicka, Meister, Wieland, Helv. 

Chim. Acta, 1945, 28, 618. 
Lieberman et al., J. Biol. Chem., 1948, 

172, 263. 

A 4 -Androstene-17-one 

OH a 



C 19 H 28 




A 5 -Androstene-17-one 

CH 3 




) MW, 272 

M.p. 105-7. 

Semicarbazone : m.p. 285-7. 

Marker, Wittle, Tullar, J. Am. Chem. Soc., 
1940, 62, 223. 

A 16 -Androstene-3-one 




C 19 H 28 MW, 272 

Purified by sublimation in high vacuum, 
cryst. from pentane. M.p. 140-1 corr. [a]JJ 
+38 1 (c, 2-079 in CHC1 3 ). Intense blue 
col. in the Kagi-Miescher test (Helv. Chim. Acta, 
1939, 22, 683). 

Prelog, Ruzicka, Wieland, Helv. Chim. 
Acta, 1944, 27, 66. 

A 5 -Androstene-3p : 16 (oc) : 17(a)-triol 

OH 8 

-OH 




C 19 H 30 3 



MW, 306 



MW, 272 



Needles from Py.Aq. M.p. 273-5. 
Acetone condensation product : C 22 H 34 00. 
MW, 346. Needles from MeOH. M.p. 163-4*. 
Triacetyl : cryst. from EtOH. M.p. 208-9-5, 

Butenandt, Schmidt-Thome*, Weiss, Ber., 

1939, 72, 417. 
Huffman, Lott, J. Am. CJiem. Soc., 1949, 

71, 719. 
See also Goldberg et al., Helv. Chim. Acta, 

1947, 30, 1441. 



A 5 -Androstene-3p : 16oc : 17p-triol 



169 



Anethole 



A 5 -Androstene-3p : 16cc : 17(3-triol 

-, OH 



HO 





OH 



Ci 9 H 3 o0 3 MW, 306 

From normal human urine and patient with 
adxenocarcinoma. Cryst. from EtOH, MeOH. 
M.p. 265-70 (270, 257-5-60-5). Purple col. 
in Liebermann test. 

Triacetyl: m.p. 184-5 (187-8-5). [a]* 6 
-102 (c, 1-0 in EtOH). 

Hirschmann, J. Biol. Chem., 1943, 150, 363. 
Ruzicka, Prelog, Wieland, Helv. CJiim. 

Acta, 1945, 28, 1609. 
Huffman, Lott, J. Biol. Chem., 1946, 164, 

785. 
See also Goldberg et al. } Helv. Chim. Acta, 

1947, 30, 1441. 

A 4 -Androstene-3 : 11 : 17-trione. 

See Adrenosterone. 

Androsterone (Androstane-3a-ol-I7 -one) 




HO" 



C 19 H 30 2 MW, 290 

Secondary sex hormone isolated from male 
urine. Leaflets or prismatic needles from 
EtOH or Me 2 CO. M.p. 178 (184-5 corr.). 
Sol. prac. all org. solvents. Very spar. sol. 



H 2 0. 



[QC] D + 94-6 in EtOH, + 103-5 in 
MeOH. Produces male sex characteristics in 
immature animals. Physiologically active in 
doses of 150-200 y on Butenandt (capon comb) 
test and 60 y on Tschopp (seminal vesicle) test. 
100 y is equivalent to one International Unit 
(I.U.). 

Acetyl : prismatic needles from EtOH.Aq. 
M.p. 160-1. 100 y - 1 I.U. Oxime : needles 
from EtOH.Aq. M.p. 219-20. Semicarbazone : 
cryst. from EtOH. M.p. 272-3. 

Propionyl : needles from EtOH.Aq. M.p. 
145 (151-2). 

Acid succinyl : m.p. 184-5 corr. 

Benzoyl : prisms from C 6 H 6 -ligroin or MeOH. 
M.p. 178. 

Oxime : needles from EtOH.Aq. M.p. 215- 
16, 500 y w 1 I.U. 

Semicarbazone : needles from EtOH. M.p. 
276 (260-4). 

Phenylhydrazone : m.p. 153-4. 



2 : 4-Dinitrophenylhydrazone : yellow cryst. 
from EtOH.Aq. M.p. 232-5-4-0 . 

Ruzicka, Naturmssenschaften, 1935, 23, 

44. 
Ruzicka, Goldberg, Meyer, Briingger, 

Eichenberger, Helv. Chim. Acta, 1934, 

17, 1395. 
Butenandt, Tscherning, Z.physiol. Chem., 

1934, 229, 167, 185. 
Ruzicka, Goldberg, Wirz, Helv. Ghim. 

Acta, 1935, 18, 61. 

epi- Androsterone ( Androstane-%$-ol-YI -one ) 



CH. 




C 19 H 30 2 MW, 290 

Cryst. from EtOH.Aq. M.p. 170-1 (175-6 
corr.). [a] D + 89 in MeOH. Physiologically 
active in doses of 1400 y on Butenandt and 
500 y on Tschopp tests. 

Acetyl : cryst. from MeOH.Aq. M.p. 96-7. 
Semicarbazone : m.p. 261-2 corr. 

Oxime : m.p. 185-6 corr. 

Semicarbazone : m.p. 282-3 corr. 

Ruzicka, Goldberg, Briingger, Helv. Chim. 

Acta, 1934, 17, 1389. 
Ruzicka, Eichenberger, Helv. Chim. Acta, 

1935, 18, 430. 

Dirscherl, Z. physiol. Chem., 1935, 235, 1. 
Cardwell, Cornforth, Duff, Holtermann, 

Robinson, Chemistry and Industry f 

1951, 389. 



Anemonin 



-- CO or 



CH 9 -C-CH:CH 

^o co 



CH 2 -C-CHICH 



C 6 H 4 2 (C 10 H 8 4 ) MW, 96 (192) 

Needles or prisms. M.p. 157-8. Sol. EtOH. 
Reduces Fehling's and NH 3 .AgN0 3 . Ox. > 
oxalic and succinic acids. 

Asahina, Fujita, Chem. Abstracts, 1920, 

14, 1384. 
Kipping, J. Chem. Soc., 1935, 1145. 

Anethole (p-Propenylphenyl methyl ether , p- 
propenylanisole) 

OCH 3 




C 10 H M 



MW, 148 



Anetliole Glycol 



170 



Angelic Acid 



From anise and fennel oils. Leaflets from 
EtOH. M.p. 22*5. Setting point 21-4. B.p. 
235, 114/14 mm. Sol. Et 2 0, Me 2 CO, CHOj, 
C 6 H 6 . Sol. 5 parts 96% EtOH. Very spar, 
sol. H 2 0. Di 0-9936. ng 1-5624. Cr0 3 or 
HN0 3 > anisaldehyde -f anisic acid. Red. 
> 2>-propylanisole. ZnCl 2 > metanethole, 
CgoH^Og, m.p. 133. Slowly decomp. in sun- 
light. 

Dibromide : needles from Et 2 0. M.p. 67. 

Pier ate : orange-red needles from EtOH. 
M.p. 70 decomp. 

Behal, Tiffeneau, Bull. soc. chim., 1908, 

3, 304. 

Cahours, Ann., 1842, 41, 57. 
Quelet, Compt. rend., 1936, 202, 956. 
Bert, Compt. rend., 1941, 213, 873. 

Anethole Glycol (p-Metlioxyphenylpropylene 
glycol, p-a : $-dihydroxypropylanisole) 



C 10 H U 3 

a-Form : 



MW, 182 



Cryst. + 3H 2 0. M.p. 31, anhyd, 63. 
Diacetyl : b.p. 203/20 mm. Sol. H 2 0. 



M.p. 115-16. 

Diacetyl: b.p. 210/41 mm., 187/12 mm. 
Insol. H 2 0. 

$-Me ether: C n H 16 O v MW, 196. B.p. 171- 
5/65-70mm. 

Balbiano, J. Chem. Soc., 1907, 92, i. 522. 
Tiffeneau, Daufresne, Compt. rend.. 1907, 

144, 1355. 

Giuliano, Chem. Abstracts, 1941, 35, 2872. 
Schulz, Treibs, Ber., 1944, 77, 377. 
Doeuvre, Chervet, Compt. rend., 1947, 

224, 660. 

Aneurin (Vitamin B l9 anti-beri-beri or anti- 
neuritic vitamin, torulin, oryzanin, thiamin) 



r 



,HC1 



/ 

H 3 OC CH 

v 

C 12 H 18 ON 4 C1 2 S MW, 337 

Rice husks are chief source. Variable constitu- 
ent of yeast, milk, green leaves, roots and tubers. 
Cryst. from MOH-Et 2 0, m.p. 233-4. Plates 
from MeOH-EtOH or H 2 0-EtOH, m.p. 250. 
Very sol. H 2 0. Spar. sol. EtOH, Me 2 CO. Insol. 
Et 2 0, C Q H 6 . Generally more sol. than lacto- 
flavine. It is also more thermolabile and more 



readily decomp. by alkalis than the latter. Sol. 
in H 2 or EtOH shows absorption bands at 
235 mt/, and 267 rnpL Bromide-hydrobromide 
has equal physiological activity. 

0-Acetyl : leaflets from EtOH, M.p. 205-7. 
Picrate : m.p. 176. 
Nitrate : m.p. 164-5. 

Sulphate : two forms. M.ps. 203 and 276-8, 
Picrolonate : m.p. 165 or 229. 

Todd, Bergel, J. Chem. Soc., 1938, 26; 

1937, 364. 

Williams et al., J. Am. Chem. Soc., 1937, 
59, 216; 1936, 58, 1063; 1935, 57, 
517, 536, 1093, 1751, 1849, 1856. 
Itter, Orent, McCollum, J. BioL Chem., 

1935, 108, 571. 
Kinnersley, O'Brien, Peters, Biochem. J., 

1935, 29, 701, 716. 

Williams, Ergebnisse der Vitamin-und 
Hormonforschung ( Akademische Verlag, 
Leipzig), 1938, I, 213. 
Ohdake, Chem. Zentr., 1935, I, 3677. 
Windaus et al,, Z. physioL Chem., 1932, 

204, 123. 

Veen, Z. physioL Chem : , 1932, 208, 125. 
Harris, Vitamins and Vitamin Deficiencies, 

Vol. I (Churchill, London, 1938). 
Gravin, Chem. Abstracts, 1944, 38, 1239. 
Chelintsev, Benevolenskaya, Chem. 

Abstracts, 1946, 40, 4069. 
Williams et al., The Biochemistry of B 
Vitamins, (E-einhold Publishing Cor- 
poration, New York), 1950. 
Robinson, The Vitamin B Complex, 
(Wiley & Sons, Inc., New York), 1951. 

Angelic Acid (l-Methylcrotonic acid, trans- 
1 : 2-dimethylacrylic acid, l-ethylidenepropionic 
acid) 



CH0 



H 3 C-C-COOH 



582 



MW, 100 

Constituent of roots of Angelica archangelica, 
Linn., and Roman cumin oil. Monoclinic prisms. 
M.p. 45-6. B.p. 185, 88~9/10 mm. Mod. 
sol. H 2 0. DJ 6 0-9539. < 7 1-4434. Heat of 
comb. 635-1 Cal. k = 5-01 x 10~ 5 at 26. 
Volatile in steam. Isomerises to tiglic acid 
on boiling, or with cone. H 2 S0 4 at 100, 
or with boiling dil. NaOH. KOH fusion > 
acetic and propionic acids. HI at 180 
> methylethylacetic acid. 

Me ester : CeHj/V MW, 114. B.p, 127-6- 
127-8/764 mm. D5 0-94130. < 144620. 

Et ester: C 7 H 12 . MW, 128. B.p. 141, 
48-9/ll mm. D* 0-9347. 

Isobutyl ester: C 9 H 16 2 . MW, 156. B.p. 
177. 

Isoamyl ester: C 10 H 18 2 . MW, 170. B.p. 
200-1. 

Anilide : cryst. from C 6 H 6 . M.p. 126. 



Angelica lactone 



171 



Anlialiiiiiie 



$-Naphthylamide : cryst. from C JBL. M p 
135. e e * 

Wislicenus, Ann., 1893, 272, 9. 

Young, Dillon, Lucas, J. Am. Chem. 

Soc.> 1929, 51, 2532. 
Fittig, Kobig, Ann. 9 1879, 195, 98. 

Angelica lactone (Angelic lactone) 
C 5 H 6 2 MW, 98 

Two forms. 

(I) a or A 2 . 

CH 3 *9=CH-CH 2 
- CO 

Needles. M.p. 18. B.p. 55-6/12 mm. Sol. 
20 parts H 2 at 15. Df 1-084. Volatile. 
Readily reverts to p-form. n^ 1-4476. 

(II) porA 1 . 







CO 



F.p. 17. B.p. 208-9 /751 mm., 86-5 / 
10 mm. DJ 1-076. n 1-4603. < 1-4532. 
Auwers, Ber., 1923, 56, 1672. 
Haynes, Jones, J. Chem. 8oc., 1946, 954. 

Angelicixi 




C n H 6 3 MW, 186 

Constituent of root of Angelica archangelica, 
Linn. Cryst. from MeOH.Aq. M.p. 138-9-5. 
Sol. Et 2 0. Spar. sol. petrol. H 2 2 > furan- 
2 : 3-dicarboxylic acid. 

Spath, Pailer, Ber., 1934, 67, 1212; 1935, 

68, 943. 
Spath, Pesta, Ber., 1934, 67, 853. 

Angliceric Acid (Anglyceric acid, 1 : 2-di- 
methylglyceric acid, 1 : 2-dihydroxy-I-methyl- 
butyric acid) 

9 H 3 

CH 3 -CH(OH)-C(OH)-COOH 
C 5 H 10 4 MW, 134 

Needles. M.p. 111. Sol. H 2 0, EtOH, Me 2 CO. 
Spar. sol. Et 2 0. Insol. C 6 H 6 , CHCL,, ligroin. 
Non-volatile in steam. Ca salt sol. H 2 0. 

Fittig, Penschuck, Ann., 1894, 283, 114. 

Angustione 




Alkali-soluble constituent of essential oil of 
Backhousia angustifolia, Muell. Viscous oil with 
faint unpleasant odour. B.p. 129/15 mm. 
DfS 1-089. wg> 1-5137. [aUi - 5-56. FeCl 3 
> orange-red col. 

Cu derw. : blue prisms. M.p. 192-3- 

Gibson, Penfold, Simonsen, J. Chem. 

Soc., 1930, 1184. 
Birch, J. Chem. Soc., 1951, 3026. 

Anhalamine (8-Hydroxy-6 : 1-dimethoxy- 
1:2:3: 4-tetrahydroisoquinoline) 

CH 2 

CH 3 0/ V \H 2 
CH 3 0'\A /NH 

HO CH 2 
C U H 15 3 N MW, 209 

From Mexican Anhalonium Lewinii, Hen- 
nings. Spherical aggregates of needles from 
EtOH. M.p. 187-8. Sol. H 2 0, alkalis, hot 
EtOH. Spar. sol. Et 2 0, C 6 H 6 , CHClg, pet. 
ether. FeClg > blue > green col. 

B,HCl : m.p. 257-8 (in vacuo). 

M e ether : see Anhahnine. 

N-Me : see Anhalidine. 

N-Benzoyl : m.p. 167-8. 

Dibenzoyl : m.p. 128-9. 

"N-m-Nitrobenzoyl : m.p. 174-5. 

Picrate : m.p. 234-6. 

Spath, Becke, Ber., 1934, 67, 2100. 
Spath, Koder, Monatsh., 1922, 43, 93. 
Heffter, Ber., 1901, 34, 3004. 

Anhalidine (N-Methylanhalamine) 
CH 2 



C 12 H 17 3 N 




H 



MW, 223 



Cactus alkaloid from Anhalonium Lewinii, 
Hennings. Cryst. by sublimation. M.p. 131-3. 

Spath, Becke, Ber., 1935, 68, 944; 
Monatsh., 1935, 66, 335. 

Anhaline. 

See Hordenine. 

Anhalinine (Anhalamine methyl ether) 

CH 2 



C 12 H 17 3 N 




MW, 223 



MW, 196 



Cactus alkaloid from Anhalonium Lewinii, 
Hennings. Cryst. by sublimation. M.p. 61-3. 

Spath, Becke, Ber., 1935, 68, 501; 
Monatsh., 1935, 66, 327. 



A nlialonidine 



172 



Anhydrofructose 



Anhalonidine (6(S)-Hydroxy-7(6) : S(7)-di- 
methoxy-I-mefhyl-l : 2 : 3 : 4z-tetraliydroisoquinol- 
ine) 



or 



HO CH-CH 3 



HO 
CH 3 OI 

ca 




C 12 H 17 3 N 



MW, 223 

M.p. 160. Sol. H 2 3 EtOH, CHOj. Spar, 
sol. Et 2 0. InsoL petrol. 
N-Me : see Pellotine. 
!$-Benzoyl : m.p. 189. 
^-m-Nitrobenzoyl : m.p. 201-2. 

Spath, Monateh., 1922, 43, 477. 

Anhalonine (6-Met7wxy-7 : 8-methylenedioxy- 
\-metkyl-\ : 2 : 3 : ^tetrahydroisoquinoline) 

CH 2 



C 12 H 15 3 N 




MW,221 



M.p. 85. Sol. H 2 0, EtOH, CHCL, Et 2 0. 

BJSCli [a]i 7 -41<9inH 2 0. 

N-Me : lophophorine. Sol. most org. sol- 
vents. InsoL H 2 0. B,HGl : [oft 7 9-47 in 
H 2 0. Mefhiodide m.p. 238-40 (racemic form, 
m.p. 242-3). 

Spath, Gangl, Monatsh, 1923, 44, 103. 

Anhydroberberilic Acid. 

See Berberilic Anhydride. 
Anhydrobrazilic Acid 



CH 2 -COOH 




C 12 H 10 5 MW, 234 

Cryst. from H 2 0. M.p. 197. Eeadily sol. 

EtOH. Spar. sol. Et 2 0, CHC1 3 , C 6 H 6 . InsoL 

pet. ether. 

Oxime : needles from H 2 0. M.p. 175-80. 
Perkin, J. Ohem. Soc., 1902, 81, 230. 

Anhydrocamplioronic Acid 



G 9 H 12 5 MW, 200 

M.p. 139. Sol. H 2 O, EtOH s Et 2 0. Sub- 

limes. [<xg - 5-56 in CHC1 3 . 

Me ester: C 10 H U 5 . MW, 214. Two forms. 

(a). M.p.l38. B.p. 166-7/12 mm. (p). M.p. 

45. B.p. 156/10 mm. 



Chloride: C 9 H n 4 CL MW, 218*5. Two 
forms, (a). M.p. 137-8. B.p. 164-5/13mm., 
> p-form. [ag + 6-25 in CHC1 3 . ( p). M.p. 
38-9. B.p. 151/10 mm. [a]i -4-21 in 
CHC1 3 . 

Anilide : m.p. 202-3. 

Goebel, Noyes, J. Am. Chem. Soc., 1923, 

45, 3064. 
Bredt, Ann., 1896, 292, 87. 

Anhydrocarboxyglycine . 

See 2 : 5-Oxazolidinedione. 
Anhydroecgonine (Ecgonidine) 

CH 2 9H p-COOH 

| N-CH 3 9H 

CH 2 6n CH 2 

C 9 H 13 2 N MW, 167 

Cryst. + 1H 2 0. M.p. 226-30 decomp. Sol. 
H 2 0. Spar. sol. EtOH. 

Me ester : mefhiodide, m.p. 180. 

I-. 

Cryst. from MeOH-Et 2 0. M.p. 235 decomp. 
BJELGl : needles from EtOH. M.p. 240-1. 
Me ester: C 1Q H 15 2 N. MW, 181. B.p. 



107/7 mm. B,HBr : m.p. 147. 

M ester: C u Hi 7 2 N. MW, 195. B.p. 136-9 / 
16 mm. Sol. cold, spar. sol. hot H 2 0. Meth- 
iodide : leaflets. M.p. 177. 

B 2i H 2 PtCl 6 : reddish-yellow prisms. M.p. 223 
decomp. 

WiUstatter, Wolfes, Mader, Ann., 1923, 

434, 137. 
Einhoen, Ber., 1890, 23, 1338. 

Anliydroforrnaldehydeaniline (Methylene- 
aniline, triphenylhexahydrotriazine) 

X CH 2 - N-OJa 5 
C 6 H 5 -N< >CH 2 

\CH 2 -N-C 6 H 5 
C 21 H 21 N 3 MW, 315 

Silky needles. M.p. 143. Sol. Et 2 0, C 6 H , 
toluene, CHC1 3 . Spar. sol. EtOH. Prac. insol. 
H 2 0. Decomp. by boiling H 2 or EtOH. Sol. 
cone. min. acids > reddish-brown sols. HCN 
> phenylglycine nitrile. Zn + HC1 - 
methylaniline. 

Bischoif, Ber., 1898, 31, 3251. 

Anhydrofructose 

9H 2 OH 
, mar 

I V H 

H09H 
HQOH 




C 6 H 10 5 



H 2 C>0 



MW, 162 



3 : 6-Anh.ydrogaiactose 



178 



1 : 5-Aahydro-B-sorbitol 




Spheroids from EtOH-Et 2 0. M.p. 143-5. 
[CC]D + 30-2 in H 2 0. Very hygroscopic. Does 
not reduce Fehling's. 

Tri-acetyl : needles + |EtOH from EtOH. 
M.p. 123. 

Schlubach, Eisner, Ber., 1932, 65, 519. 
Irvine, Stevenson, J. Am. CJiem. Soc., 
1929, 51, 2197. 

3 : 6-Anhydrogalactose 

9HO 
H90H 
9H 

H09H 
H90H 

i CH 2 

C 6 H 10 5 MW, 162 

[a] D + 24 in H 2 0. 
Mono-acetone, deriv. : m.p. 92. 
Phenylosazone : yellow needles from MeOH. 
M.p. 217 (213-4 decomp.). [a]i 6 +71 in MeOH. 
Di-Me acetal : [a]J? + 36*5 in H 2 0. 

Haworth, Jackson, Smith, J. Chem. Soc., 

1940, 630. 
Ohle, Thiel, Ber., 1933, 66, 532. 

Anhydrogitalin. 

See Gitoxin. 

Anhy droglucochloral . 

See p-Glucochloralose. 

3 : 6-Anhydro-d-glucose 



9HOH 
i Cl 



4 9 

I 9HOH 

1 CHOH 

C 6 H 10 5 MW, 162 

Needles from AcOEt or EtOH-petrol. M.p. 
119. Sol. H 2 0, Me 2 CO. [a]*, +55-39 in 
H 2 0. [a] + 39-67 > 30-8 after 10 mins. 
inPy. 

Tri-Me ether: C 9 H 16 5 . MW, 204. B.p. 
111-13 /0-2 mm. [<x]# + 70-6 in CHC1 3 . 

5-Acetyl : syrup. [a]J? + 91-18 in CHC^. 

Tri-acetyl : b.p. 165/0-2 mm. [a]i> 8 + 178-93 
in CHC1 3 . 

Mono-acetone deriv. : needles from Et 2 0- 
petrol. M.p. 56-7. [a]?? +29-33 in H 2 0. 
Acetyl deriv. : needles. M.p. 31. B.p. 125- 
30/0-05 mm. [a]J? + 35-7 in CHGLj. Benzoyl 
deriv. : needles from petrol. M.p. 58-9. [ag? 
+ 22-28 in CHClg. Toluene-^-sulphonyl : m.p. 
132-4. 

Phenulosazone : yellowish-red needles from 
EtOELAq. M.p. 187-8 (198-200). [a& 7 ~~150 
in MeOH. 




o-Tolylosazone : yellow needles from EtOH. 
M.p. 168-70. 

p-Tolylosazone : yellow needles from aceto- 
nitrile. M.p. 202. 

Phenylhydrazone : yellow needles from ILO. 
M.p. 157. 

p-Bromophenylhydrazone : yellow leaflets from 
Py-Et 2 O. M.p. 184. [ajg 5 -18-89 > 
10-86 in 6 hours in Py. 

Diels, Meyer, Onnen, Ann,, 1936, 525, 94. 
Fischer, Helferich, Ostmann, Ber., 1920, 

53, 880. 

Ohle, Vargha, Ber., 1928, 61, 1208. 
Ohle, Euler, Ber. } 1930, 63, 1796. 
Kess, Mcheel, Ann., 1928, 466, 100. 
Seebeck, Meyer, Reichstein, Helv. Chim. 

Acta, 1944, 27, 1142. 
Haworth, Owen, Smith, J. Ohem. 8oc., 

1941, 88. 

1 : S-AnJiydro-D-nianiiitol. 

See Styracitol. 
1 : 4-Anhydro-D-sorbitoL 
See Sorbitan. 

1 : 5-Anhydro-D-sorbitol (Polygatitol, 

aceritol) 



H90H 
H09H 



9H- 
CH 2 OH 

C 6 H 12 5 MW, 164 

Found in Polygala tenuifolia, vulgaris, amara, 
senega. Prisms or plates from MeOH. M.p. 
142-3 (140-1). [>] +42-86 in H 2 0. 
NaOBr + phenylhydrazine >- 1 : 5-anhydro- 
fructosazone. H 2 2 + phenylhydrazine > 
glucosazone. 

Tetra-acetyl : cryst. from ether-isopentane. 
M.p. 73-6-74-8. [og? +38-9 in CHC1 3 . 

Tetra-Me ether : b.p. 80 (bath temp.)/2 mm. 
D 1-0571. ng 1-4444. [og +67-67. 

Picard, Chem. Abstracts, 1927, 21, 3385. 
Shinoda, Sato, Sato, Ber., 1932, 65, 1219. 
Carr, Krantz, J. Am. PJiarm. Assocn., 

1938, 27, 318, (CJiem. Abstracts, 1938, 

32, 5785). 
Freudenberg, Bogers, J. Am. CJiem. Soc., 

1937, 59, 1602. 
Freudenberg, Sheehan, J. Am. Chem. 

Soc., 1940, 62, 558. 
Bichtmeyer, Hudson, J. Am. CJiem. Soc., 

1943, 65, 64. 
Bichtmeyer, Carr, Hudson, J. Am. CJiem. 

Soc., 1943, 65, 1477. 
Fletcher, J. Am. Chem. Soc., 1947, 69, 

706. 



Anhydrovitamin 



174 



AnHine-p-sulphonic Acid 



Anhydrovitamin A l 
Ha<\ /CH 3 



!$-Allyl: phenylaUylamine. 
736 mm. D 25 0-982. 



B.p. 217-18 / 



Suggested structure 
C 20 H 28 MW 5 268 

Orange prisms. M.p. 76-7, Shows max. 



*^ 
*^ 



2500), 
3180). 



ultra-violet absorption at 351 (EJ 
371 (El'La 3650) and 392 mfz. (EJ 
SbCl 3 - blue col. 

Shantz, Cawley, Embree, J. Am. Chem. 

Soc., 1943, 65, 9301. 
Edisbury, Gillam, Heilbron, Morton, 

Biochem. J., 1932, 26, 1164. 
Meunier, Dulou, Vinet, Compt. rend., 

1943, 216, 907. 



Anil-alloxan 



C0 



>C(OH)-C 6 H 4 -NH 2 



C 10 H 9 4 N 3 MW, 235 

Needles from EtOH. M.p. 248 decomp. 
Sol. hot. H 2 O. Heat. > CO 2 , NH 3 and 
2>-toluidine. Cone. H 2 S0 4 > ^-aminobenz- 
aldehyde. 

Pellizzari, Gazz. chim* ital., 1887, 17, 412. 

Anil-diacetic Acid. 

See Phenyliminodiacetic Acid. 
Aniline (Aminobe'>uene, phenylamine) 

C 6 E 5 -NH 2 
C 6 H 7 N MW, 93 

F.p. - 6. B.p. 184, 92/33 mm., 71/9 mm. 
Vapour pressures : 600 mm./175, 500 mm./ 
169, 400 mm./162, 300 mm./151, 200 mm./ 
139, 100 mm./119, 50 mm./102, 15 mm./77. 
Misc. in all proportions with EtOH, Et 2 s C 6 H 6 . 
Sol. most org. solvents. 100 parts H 2 diss. 3-4 
parts at 20, 64 parts at 90. DJJ 1-0268. 
n$ 1-5863. Sp. heat 0-518 at 20-5. Latent 
heat of vap. 113-9 cal./gram. Heat of comb. 
C p 815 Cal. Flash point 76. k = 4-6 x 10~ 10 
at 25, 7-6 X 10' 10 at 40, 1-7 X 10~ 9 at 60. 
Volatile in steam. Dissolves many metals ,(K, 
Na, Mg, Ca, etc.), giving metal anilides, e.g., 
C 6 H 5 NHNa. Pure aniline is a colourless liq., 
but turns brown on exposure to air. Cr0 3 > 
^-benzoquinone. H]TO 2 + min. acid -> diazo 
salt. Ale. KOH + CHC1 3 > phenyl iso cyan- 
ide (carbylamine reaction). Ale. KOH + CS 2 
> thiocarbanilide. 

B,HCl : known in commerce as aniline salt. 
White cryst. M.p. 198. B.p. 245. Sol. H 2 0, 
EtOH. 

B } HBr : m.p. 286. 

B,HN0 3 : b.p. 190 decomp. 
\ : m.p. 140. 



Henke,Brown,J.P%5.C f Aem.,1922,26,631. 
Wedekind, Ber., 1903, 36, 3791. 

Aniline-2 : 4-disulphonic Acid 




C 6 H 7 6 NS 2 MW, 253 

Cryst. + 2H 2 0. Decomp. at 120. Sol H 2 O, 
EtOH, alkalis. Insol. Et 2 0. 

Diamide : C 6 H 9 4 N 3 S 2 . MW, 251. Leaflets 
from H 2 0. M.p. 235. 

Fischer, Ber., 1891, 24. 3806. 

Aniline -phthalein. 

See Diaminophthalophenone. 

Aniline Salt. 

See under Aniline. 

Aniline-o-sulphonic Acid (Orthanilic acid) 

NH 



C 6 H 7 3 NS 






Cryst. + JH 2 0. 
3-3 x 10- 3 at 25. 



MW, 173 

Spar. sol. cold H 2 0. Jc = 
Mod. ox. with KMn0 4 > 
azobenzene-2 : 2 r -disulphonic acid. Warm cone. 
H 2 S0 4 > sulphanilic acid. 

Amide: C 6 H 8 2 N 2 S. MW, 172. Needles. 
M.p. 153. B,HCl : m.p. 201. Benzoyl deriv. : 
needles. M.p. 198. 

Wertheim, Organic Syntheses, 1935, XV, 

55. 

Gerilowsky, Ber., 1896, 29, 1075. 
Schrader, J. prakt. Chem., 1917, 95, 392. 

Aniline-m-sulphonic Acid (Metanilicacid)* 
Prisms + 1-|H 2 0, or needles. Sol. 68 parts 
H 2 at 15. k = 1-8 X 10~* at 25. KOH 
fusion > resorcinol. 

Amide : leaflets or needles. M.p. 142. Spar, 
sol. cold H 2 0. "N-Acetyl : cryst. from 50% 
EtOH. M.p. 216-19. 

Jacobs, Heidelberger, J. Am. Chem. Soc. y 

1917, 39, 2428. 
Doolittle, Chem. Abstracts, 1924, 18, 791. 

Aniline-p-sulphonic Acid (Sulphanilic 
acid). 

Rhombic plates or monoclinic cryst. + 2H 2 0. 
Sol. 166 parts H 2 at 10. k = 5-81 X 10~ 4 afc 
25. Ox. > ^p-benzoquinone. 

Amide : see Sulphanilamide. 

Hydrazide : m.p. 131 decomp. 

Anilide : m.p. 200. TX-Acetyl : m.p. 214. 

o-Toluidide : needles. M.p. 132. 

m-Toluidide : needles. M.p. 136. 



Aniline-co-sulplionic Acid 



175 



1-Anilmoisobutyric Acid 



p-Toluidide : needles. M.p. 109. 
d-Naphthylamide : needles. M.p. 196. 
$-Naphthylamide : needles. M.p. 203. 
Gelmo, J. prakt. Chem., 1908, 77, 369. 
Jacobs et al., Ind. Eng. Ghem., 1943, 35, 

321 

TursM, U.S.P., 2,401,525, (Chem. 
Abstracts, 1946, 40, 5451). 

Aniline-co-sulphonic Acid. 

See Phenylsulphamic Acid. 
Anilinoacetic Acid. 
See Phenylglycine. 

co-Anilinoacetophenone (Phenacylaniline) 
C 6 H 5 *CO-CH 2 -KH-C 6 H 5 

MW, 211 

Tom EtOH. M.p. 93. Sol. EtOH, 
Et 2 0, C 6 H 6 , CHCL, CS 2 . Insol. cold H 9 0. 



2~Anilinobutyric Acid 



C 14 H 13 ON 



Volatile in steam. Heat at 100 > 3-phenyl- 
indole. Cone. min. acids or alkalis in the hot 
> phenylcarbylamine + aniline. 

Bischler, Ber., 1892, 25, 2860. 
1 - Anilinoanthraquinone 

CO NH-C 6 H 5 




C 20 H 13 2 N MW, 299 

Red plates from EtOH. M.p. 147-5. Spar, 
sol. cold EtOH, C 6 H 6 , AcOH, PhN0 2 ; more 
sol. in these when hot. Cone. H 2 S0 4 > 
yellow sol. 

Ulmann, Ann., 1911, 380, 317. 

2-Anilinoanthraquinone . 

Yellowish-red needles from chlorobenzene. 
M.p. 234-6. Cone. H 2 S0 4 > greenish-yellow 
sol. > bluish- violet on warming. 

Badische, D.R.P. 288,464, ( J. Soc. Chem. 
Ind., 1916, 35, 355). 

p-Anilinoazobenzene . 

See Benzeneazodiphenylamine. 

AnilinobenztMazole . 

See under 2-Aminobenzthiazole. 

1-Anilinobutyric Acid 

CH 3 -CH 2 -9H-COOH 

NH-C 6 H 5 

C 10 H 13 2 N MW, 179 

M.p. 141. Sol. EtOH, Et 2 0. Spar. sol. cold 
H 2 0. Eeduces NH 3 .AgN0 3 . A = 3-1 x 10~ 5 
at 25. 

M ester: C 12 H 17 2 N. MW, 207. Cryst. 
M.p. 26. B.p. 278 d . 

Amide : C 10 H 14 ON 2 . MW, 178. Plates from 
H 2 0, prisms from EtOH. M.p. 123. 
#*^Ze:CioH 12 N a . MW,160. Needles. M.p. 39. 
Anilide : needles from EtOH. M.p. 92. 
TX-Acetyl : prisms from C 6 H 6 . M.p. 118. 
Bischoff, Ber., 1897, 30, 2305, 2313. 



NH-C 6 H 5 
C 10 H 13 2 N MW, 179 

Needles. M.p. 128. Sol. EtOH, Et 9 0. Spar, 
sol. cold H 2 0. 

B,(COOH) 2 : m.p. 137-9. 

Anilide: m.p. 93. BJICl: leaflets from 
EtOH. M.p. 206-7. 

Autenrieth, Pretzell, Ber., 1903, 36, 1266. 

3~Anilino-j>-cresoL 

See 5-Hydroxy-3-methyldiphenylamine. 
2-Anilinocrotonic Acid (Acetoacetic acid fk 
anil) 



NH-C 6 H 5 
or 



C n H 13 2 N. MW, 
M.p. " 



MW, 177 
191. Prisms 




MW, 205. Decomp. 
aniline + aceto- 

MW, 158. Needles from 



C 10 H n 2 N 

Me ester : 
from MeOH. 

Et ester : C 12 H 15 
at 240. Acids or 
acetic ethyl ester. 

Nitrile: C 10 H 10 N 2 . 
EtOH. M.p. 115. 

Knorr, Ann., 1886, 236, 73. 
Meyer, Chem. Zentr., 1908, II, 591. 
Conrad, Simpach, Ber., 1888, 21, 1968. 

Anilinodiacetic Acid. 

See JV*-Phenyliminodiacetic Acid. 

a-Anilinodiphenylmethane . 

See under a-Aminodiphenylmethane. 

2-Anilinoethyl Alcohol. 

See p-Hydroxyethylaniline. 

Anilinoguanidine 



MW, 150 



NH 



C 7 H 10 N 4 

Very unstable. 

B,HCl : needles. M.p. 226 decomp. 

B,HBr : needles. M.p. 210. 

B,HN0 3 : needles. M.p. 178. 

Acetyl deriv. : m.p. 195. 

Picrate : orange needles. M.p. 193. 

Pellizzari, Gazz. chim. ital., 1911, 41, 30. 

1-Anilinoisobutyric Acid 

(Note. There is some doubt in the literature 
as to which is the 1-anilino- and which the 
2-anilino-isobutyric acid) 

(CH 3 ) 2 9-COOH 
NHC 6 H 5 

179 



Needles from hot H 2 0. M.p. 184-5. Sol. 
EtOH, Et 2 0. Insol. ligroin. Sublimes. k = 
1-0 X 10- 6 at 25. 



2-Anilin.oisobutyric Acid 



176 



1-Anilinopropionic Acid 



Amide: C 10 H 14 ON 2 . MW, 178. Needles. 
M p. 136. Sol. EtOH, Et 2 } hot H 2 0. 

Nitrile : C 10 H 12 N 2 . MW, 160. Needles from 
EtOH, prisms from pet. ether. M.p. 93-4 . 
Sol. EtOH, Et 2 0, C 6 H 6 . 

Anilide : tablets from EtOH. M.p. 155 . 
Mulder, Eec. trav. chim., 1907, 26, 180. 

2-Anilinoisobutyric Acid 

(See note under 1-Anilinoisobutyric Acid, 
above) 



C 10 H 13 2 N MW, 179 

Prisms from CHC1 3 . M.p. 142 decomp. Sol 
hot H 2 0. Spar. sol. CS 2 . Insol. ligroin. k = 
3-6 x 10- 5 at 25. Dist. > isopropylaniline. 

Anilide : prisms from EtOH.Aq. M.p. 122. 
Bischoff, Mintz, Ber., 1892, 25, 2326. 

l-AniHnoisovaleric Acid (N-Phenylvaline) 
(CH 3 ) 2 CH*9H-COOH 

NHC 6 H 5 
C n H 15 2 N MW, 193 

Leaflets from H 2 0. M.p. 135. Sol. to 0-7% 
in boiling H 2 0. Sol. EtOH, Et 2 0, AcOH, 
CHCL. Insol. ligroin. Reduces NH 3 .AgN0 3 . 

Et ester: C^H^O^. MW, 221. B.p. 275- 
80. 

Amide : C n H 16 ON 2 . MW, 192. M.p. 102-3. 
Sol. EtOH, Et 2 0, C 6 H 6 . Spar. sol. ligroin. 

Nitrile: C U H 14 N 2 . MW, 174. Needles from 
CH 6 -Egroin. Sol. EtOH, Et 2 0, C 6 H 6 . 

Anilide : m.p. 105-6. 

Bischofi, Ber., 1897, 30, 2303. 



Anilinomalonic Acid 






C 9 H 9 4 N MW, 195 

Needles from EtOH-ligroin. M.p. 119 de- 
comp. > phenylglycine + C0 2 . Sol. EtOH, 
Me 2 CO, AcOH, hot H 2 0. Spar. sol. Et 2 0, C 6 H 6 . 

DiJf e ester : C U H 13 4 N. MW,223. M.p. 68. 

Di-Et ester : C 13 H 17 4 N. MW, 251. Cryst. 
from EtOH or ligroin. M.p. 45. 

Diamide: C 9 H 1:L 2 N 3 . MW, 193. Prisms. 
M.p. 156. 

Anilide : needles from H 2 0. M.p. 157 de- 
comp. 

Di-anilide : prisms. M.p. 162 (plates from 
AcOH, m.p. 246-7). 

Conrad, Reinbach, Ber., 1902, 35, 1813. 

1 ~AniHno-2-methylanthraquinone 

See under l-Amino-2-methylanthraquinone. 
1-Anilmo-l-methylsuccinic Acid (Anil- 
inopyrotartaric acid) 

C 6 H 5 NH'9(CH 3 )-COOHa 

CH 2 -COOH(i 
CL^OJST MW, 223 



Prisms + 1H 2 0. M.p. 111, anhyd. 171. 
Sol. EtOH, hot H 2 0. Prac. insol. Me 2 CO, Et 2 O, 
C 6 H 6 . Reduces NH 3 .AgNO 3 and Fehling's wlien 
hot. 

x-Amide-$-ffi ester : C 13 H 18 3 N 2 . MW, 250. 
Plates. M.p. 109. Sol. H 2 0, EtOH, C 6 H 6 , 
CHC1 3 . Insol. ligroin. 

Imide: a-anih^o-a-methylsuccinimide. Prisms. 
M.p. 167. Sol. EtOH, C 6 Hg, CHC1 3 . Spar, 
sol. H 2 0, Et 2 0. Acetyl deriv. : m.p. 235. 
Benzoyl deriv. : m.p. 190. 

Reissert, Ber., 1888, 21, 1362. 
Schroeter, Kirnberger, Ber., 1902, 35, 

2078. 

7-Anilino-2-naplitbLol . 

See under 7-Amino-2-naphthol. 
AnilinonapMhol-sulpliomc Acid. 
See Phenylaminonaphthol-sulphomc Acid. 
2-Anilinonaplithoquinoaie . 
See under 2-Amino-l : 4-naphthoquinone. 
1-Anilinop^.mitic Acid. 
See under 1-Aminopalmitic Acid. 
Anilinophenol . 
See Hydroxydiphenylamine. 
a-Anilinophenylacetic Acid (&-P~henyl- 
phenylglycine) 

C S H 5 -9H-COOH 
NHC 6 H 5 



C 14 H 13 2 N 



MW>227 



dl-. 

Leaflets from EtOH. M.p. 173-5 (183). 
Sol. EtOH. Spar. sol. Et 2 0, C 6 H 6 . Insol. H 2 0, 
ligroin. 

ffl ester: C 16 H 17 2 lSr. MW, 255. Needles 
from ligroin. M.p. 89-90. B.p. 325-30. 

Nitrile : C 14 H 12 N 2 . MW, 208. Prisms from 
pet. ether, needles from EtOH. M.p. 85. 

Z-. 

M.p. 188. [a] D - 117-9 in Me 2 CO; - 111-7 
in EtOH; 106-8 in AcOEt. [a] 5461 
143-5 in Me 2 CO. 

McKenzie, Bate, J. Chem. Soc., 1915, 107, 
1681. 



1 -Anilinopropionic 

alanine) 



Acid 



NHC 6 H 5 
C 9 H n 2 N MW, 165 

Leaflets from H 2 0. M.p. 162. Sol. EtOH. 
Spar. sol. Et 2 0, C 6 H 6 , CHCL. Sublimes, k 
2-2 x 10- B at 25. 

Et ester : C^H^N. MW, 193. B.p. 272. 
D2S 1-060. 

Amide: C 9 H 12 ON 2 . MW, 164. M.p. 144. 
Sol. EtOH, EtjO, C 6 He, CHC1 3 . 

Nitrile : C 9 H 10 N 2 . MW, 146. Leaflets from 
EtOH, Et 2 or C 6 H 6 . M.p. 92. Sol. CHC1 3 , 
hot H 2 0. 

Anilide : needles from EtOH. M.p. 127. 



2-Anilinopropionic Acid 

N-Acetyl : prisms from H 2 O, leaflets from 
C 6 H 6 . M.p. 143. 

Nastvogel, Ber., 1890, 23, 2010. 



177 Anisaldeliyde 

1-Anilinovaleric Acid (N-Phenylnorvaline) 

CH 3 -CH 2 -CH 2 -CH-COOH 



2-Anilinopropionic Acid (N-Phenyl-$- 
alanine) 

C 6 H 5 -NH-CH 2 -CH 2 -COOH 
C^OgN MW, 165 

Leaflets from CHCl 3 -ligroin. M.p. 60. In- 
sol. ligroin. k = 4-0 x 10~ 6 at 25. 

Et ester: C n H 15 2 N. MW, 193. Yellow 
oil. B.p. 175/18 mm. 

Anilide : leaflets from EtOH. M.p. 92-3. 
Autenrieth, Pretzell, Ber., 1903, 36, 1262. 

3-Anilino-w-propyl Alcohol. 

See y-Hydroxypropylaniline. 
a-Anilinopropylbenzene . 
See under 1-Ph.enylpropylamine. 
2-Anilinopyridine (a-Anilinopyridine, 

phenyl-2-pyridylamine) 




C n H 10 N 2 



MW, 170 



Leaflets. M.p. 108. Sol. EtOH, Et 2 O, C 6 H 6 . 
Spar. sol. pet. ether. Volatile in steam. 

B,HAuCL: red leaflets from EtOH. M.p. 
149. 

B 2 ,H 2 PtCl Q : red needles. M.p. 202. 

Mefhiodide : needles from H 2 O. M.p. 176-9 
decomp. 

Picrate : m.p. 222. 

Fischer, Ber., 1899, 32, 1297. 



2-Anilinoquinoline 

phenyl-2-quinolylamine) 



(a.~AnilinoqmnoUne, 




1NH-C 6 H 5 



C 15 H 12 N 2 MW, 220 

Glittering leaflets from EtOH. M.p. 98. 
MetJiochlpride : cryst. + 2H 2 0. M.p. 99. 
Mefhiodide : yellow cryst. M.p. 118-19. 

Friedlander, Weinberg, Ber., 1885, 18, 
1532. 

Anilinosalicylic Acid. 

See Hydroxydiphenylamine-carboxylic Acid. 
Anilinosuccinanil (N-Phenylaspartic anil) 



MW, 266 
Spar. sol. 



C 6 H 6 -NH-CH~ 
C 16 H 14 2 N 2 

Needles. M.p. 211. Sol. AcOH. 
cold EtOH. Insol. H a O. 

Hell, Poliakow, Ber., 1892, 25, 651. 

Diet, of Org. Comp. I. 



MW, 193 

Cryst. from EtOH.Aq. M.p. 147-8. Insol. 
H.O. 

'Amide : C U H 16 ON 2 . MW, 192. Cryst. from 
Et 2 0-pet. ether. M.p. 99. 

Nitrite : C u H u N a . MW, 174. Leaflets from 
pet. ether. M.p. 51. 

Miller, Ploehl, Eampini, Ber., 1892, 25, 
2038. 

Anil-pyruvic Acid. 

See under Pyruvic Acid. 

Aniluvitonic Acid. 

See Quinaldine-4-carboxylic Acid. 

Anisacetone. 

See Anisylacetone. 

Anisal-. 

See Anisylidene-. 

Anisaldehyde (p-MetJioxybenzaldehyde) 

CHO 



)CH 3 

C 8 H 8 2 MW, 136 

M.p. 0. B.p. 248, 199-200 /210 mm., 134- 
5/12 mm., 1 11-14 /4 mm. Misc. EtOH, Et 2 0. 
T>\ s 1-1191. Volatile in steam. Heat of comb. 
C p 967-3 CaL, C v 966-7 Cal. Oxidises readily to 
anisic acid. KOH > anisyl alcohol + anisic 
acid. HN0 3 + H 2 S0 4 > 3-nitro and 3 : 5- 
dinitro derivs. PC1 5 > anisylidene chloride. 



m.p. 



> amsoni. Aniline >~ anisylidene- 
aniline. Used in perfumery under the name 
Aub^pine. 

ax&i-Oxime : oc-anisaldoxime. Two forms, 
(i) Leaflets. M.p. 45. (ii) Needles. M.p. 65. 
Latter sol. EtOH, Et 2 0, C 6 H 6 . 

8jn.-0xime : (3-anisaldoxime. Needles from 
C 6 H 6 . M.p. 133. Less sol. than a-form. 

Di-Me-acetal : b.p. 253. D 15 1-079. 

Cyanhydrin : see under 4-Hydroxymandelic 
Acid. 

Semicarbazone : needles from EtOH, 
209. Prisms from Me 2 CO, m.p. 168. 

Phenylsemicarbazone : needles from EtOH. 
M.p. 175-7. 

Hydrazone : yellow leaflets. M.p. 167. 

Phenylhydrazone : needles from EtOH. M.p. 
120-1. 

4c-Nitrophenylhydrazone : m.p. 161. 

2 : 4:-DinitropJienylhydrazone : red leaflets from 
xylene. M.p. 254. 

4c-Bromophenylhydrazone : brown leaflets from 
EtOH. M.p. 146-7. 

o-Tolylhydrazone : flakes from EtOH. M.p. 
94. 

12 



Anisamide 



178 



p-Anisidine 



m-Tolylhydrazone : cryst. powder from EtOH. 
M.p. 111. 

p-Tolylhydrazone : yellow leaflets from EtOH. 
M.p. 136. 

Anil : prisms from EtOH. M.p. 60-2. 

p-Bromo-anil : needles from CC1 4 . M.p. 120. 

Tiemann, Herzfeld. Ber. 9 1877, 10, 63. 
Hinkel, Ayling, Morgan, /. Chem. Soc., 

1932, 2795. 
Niedzielski, Nord, J. Am. Chem. Soc., 

1941, 63, 1462. 

Anisamide. 

See under Anisic Acid. 

Anisamine (p-Methoxybenzylamine, anisyl- 
amine) 

CH 2 NH 2 




C 8 H 1]L ON MW, 137 

B.p. 236-7, 122-4/14 mm. Sol. H 2 0, EtOH, 
Et 2 0. Absorbs C0 2 from the air. 

B,HCli prisms. M.p. 240-1. 

,HI : m.p. 183-4. 

,C 6 H 5 COOH : m.p. 135. 

JS 2r ByWZ e : golden leaflets. M.p. 210. 

TS-Acetyl : acetanisamine, anisylacetamide. 
Needles. M.p. 96. 

Tiffeneau, Bull. soc. Mm., 1911, 9, 819. 
Ingold, Shoppee, J. Chem. $oc., 1929, 
1202. 

Anise Ketone. 

See Anisylacetone. 

Anisic Acid (p-Methoxybenzoic acid) 

COOH 




C 8 H 8 3 " MW, 152 

Needles or prisms. M.p. 184. B.p. 275-80. 
Sol. 2500 parts H 2 at 18. Mod. sol. hot H 2 0. 
Sol. EtOH, Et 2 0. Heat of comb. C p 895 CaL, 
C v 894 CaL, k = 3-2 x 10- 5 at 25. Cone. HI 
> p-hydroxybenzoic acid. CaO > anisole. 

Me ester : C 9 H 10 3 . MW, 166. Flakes from 
EtOH or Et 2 0. M.p. 48. B.p. 256 

Et ester : C 10 H 12 3 . MW, 180. 
B.p. 263. 

~iiH u 8 . MW, 



M.p. 7-8 



n-Propyl ester 
176/45 mm. 

n-Butyl ester : 
183/40mm. 

Isobutyl ester : 

Isoamyl ester : 
188/30 mm. 

Phenyl ester : 
75-6. 



194. 



C 12 H 16 3 . MW, 208. 



b.p. 170/46 mm. 
~ ~~ " MW, 



C 13 H 18 3 . 



222. 



C 14 H 12 3 . MW, 228. 



B.p. 
B.p. 

S B. P . 
M.p. 



4-Nitrobenzyl ester : C 15 H 13 O 5 N. MW, 287. 
M.p. 132. 

Chloride : anisoyl chloride. C 8 H 7 2 C1. MW, 
170-5. M.p. 22. B.p. 160-4/35 mm., 145 / 
14 mm. 

Anhydride: C 16 H 14 5 . MW, 286. M.p. 99. 
Sol. EtOH, Et 2 0. 

Amide : anisamide. C 8 H 9 O 2 N. MW, 151. 
Needles or tablets from H 2 0. M.p. 163. B.p. 
295. Spar. sol. Et 2 0. 

Nitrite: anisonitrHe. C 8 H 7 ON. MW, 133. 
M.p. 61-2. B.p. 256-7 (240). Sol. EtOH, 
Et 2 0. Mod. sol. hot H 2 0. 
Anilide : leaflets from C 6 H 6 . M.p. 171. 
Anisidide : leaflets from EtOH. M.p. 202. 
p-Tolylhydrazide : needles from EtOH. M.p. 
158. 

Rossel, Ann., 1869, 151, 31. 

Korczynski, Eandrich, Chem. Abstracts, 

1927, 21, 77. 

Sah, Yuin, Chem. Abstracts, 1947, 41, 
5869. 

Anisic Ketone. 

See Anisylacetone. 

o-Anisidine (o-Aminophenol methyl ether, 
o-methoxy aniline, o-aminoanisole) 

OCH 3 



C 7 H 9 ON MW, 123 

M.p. 5. B.p. 225. Volatile in steam. Dl 
1-0978. k = 1-9 X 10- 10 at 15. 

N-Formyl: m.p. 83-5. Sol. EtOH, Et 2 O, 
C 6 H 6 , hot H 2 0. 

N-Acetyl : o-acetanisidide. Pearly cryst. 
M.p.87-8. B.p. 303-5. Sol. hot H 2 0, AcOH. 
100 parts EtOH diss. 55 parts at 21. k = 
1-9 X 10- 10 at 15. 

N-Benzoyl : see under o-Hydroxybenzanilide. 
Vermeulen, Eec. trav. chim., 1906, 25, 20. 
Zuckermann, Chem. Zentr., 1926, 1, 3317. 
Tcherniac, Chem. Abstracts, 1929, 23, 
1908. 

m-Anisidine (m-Aminophenol methyl ether,, 
m-methoxy aniline, m~aminoanisole) . 
B.p. 251. 

N-Formyl : prisms. M.p. 57. 
N-Acetyl : m-acetanisidide. M.p. 81. 
"N-p-Toluenesulphonyl : needles. M.p. 68. 
Picrate : yellow needles. M.p. 169 decomp. 

Beverdin, Luc, Ber., 1914, 47, 1537. 

p-Anisidine (p-Aminophenol methyl ether, 
p-methoxy aniline, p-aminoanisole) . 

Rhombic plates. M.p. 57. B.p. 246. DJ* 
1-071. k = 1-5 X 10- 9 at 25. Heat of comb. 
Op 928 CaL, a 927-3 Cal. 

,(COOJS)t : m.p. 186. 

2 ,(COOB)t : m.p. 199. 



Anisil 



179 



Anisoylacetic Acid 



B } (CH 2 'COOH) 2 : m.p. 125. 

B,C B HsOH: prisms from Et 2 O. M.p. 60. 

N-Formyl : m.p. 81. 

~N-Acetyl : ^-acetanisidide, methacetin. Plates 
from H 2 0. M.p. 130-2. Sol. EtOH. Spar, 
sol. cold H 2 0. Antipyretic and antineuralgic. 

N-Benzoyl : see under ^-HydroxybenzaniHde. 

Blanksma, Eec. tmv. chim., 1909, 28, 107. 
BLorner, Wender, Gazz. chim. ital., 1887, 

17, 493. 

Reverdin, Bucky, Ber., 1906, 39, 2689. 
Schwenk et al, J. Org. Chem., 1944, 9, 1. 

Anisil (pp'-Dimethoxybenzil, 4 : 4' '-dihydroxy- 
dibenzoyl dimethyl ether, 4 : 4' -dimethoxydiphenyl- 
glyoxal) 

CH 3 0<^^CO-CO<^^^ 

C 16 H 14 O 4 MW, 270 

Golden-yellow needles. M.p. 133. Distils 
unchanged. Spar. sol. cold EtOH. Ale. KOH 
> anisilic and anisic acids. 

Monoxime : m.p. 133. Sol. Et 2 O, C 6 H 6 . 

syn.-ZKcmme : cryst. powder. M.p. 217. 
Insol. EtOH, Et 2 0, C 6 H 6 . Diacetyl: prisms. 
M.p. 139. 

anti-jDicmwe : needles from C 6 H 6 . M.p. 
195. Sol. EtOH, AcOH. Diacetyl : m.p. 130. 

Disemicarbazone : leaflets from dil. AcOH. 
M.p. 254-5. 

Dihydrazone : m.p. 118. 

Staudinger, Schlenker, Goldstein, Helv. 

Chim. Acta, 1921, 4, 341. 
Klein, J. Am. Chem. Soc., 1941, 63, 1474. 



C 17 H 18 4 . 



Anisilic Acid 

glycollic acid) 

CH< 




(p : p'-Dimethoxydiphenyl- 



!(OH)-COOH 



C 16 H 165 M^ 288 

Needles from EtOH. M.p. 164. Sol. EtOH. 
Spar. sol. H 2 0. Ox. > 4 : 4'-dimethoxy- 
benzophenone. 

Me ester: C 17 H 18 5 . MW, 302. Cryst. from 
C 6 H 6 -petrol. M.p. 110-11. 

Bosler, Ber., 1881, 14, 327. 

Anisoin (pp'-Dimethoxybenzoin, p-methoxy- 
phenyl-p-methoxybenzoylcarbinol) 



C 16 H 16 4 MW, 272 

Prisms. M.p. 113. Sol. Hot EtOH. Spar, 
sol. Et 2 0, hot H 2 0. Cone. H 2 S0 4 > green 
sol., warm >- yellow, then purple. Ox. > 
anisil. 



MW, 286. Yellow 
M.p. 52-3. Sol. Et a O, 



Cryst. from 



Me ether: 
prisms from CCL. 
Me 2 C0 3 C 6 H 6 . 

Et ether : C 18 H 20 4 . 1VIW, 300. 
EtOH.Aq. M.p. 103-4. 

Acetyl : m.p. 93-5. 

Semicarbazone : prisms from EtOH.Aq. M.p. 
185 (rapid heat.) decomp. 

Eosler, Ber., 1881, 14, 327. 

Anisole (Phenol methyl ether, methyl phenyl 
ether, methoxybenzene) 

C 6 H 5 OCH 3 

C 7 H 8 MW, 108 

M.p. 37-5. B.p. 155. Sol. EtOH, Et 2 0- 
Insol. H 2 0. VII 0-9988. n$ 1-51961. Heat of 
comb. G p 905-5 CaL, C v 904-6 Cal. Mol. b.p. 
elevation, 45-02. Heat at 400 > phenol + 
ethylene. HI at 130 > phenol. 
Picrate : yeUow. M.p. 78-81. 

Hiers, Hager, Organic Syntheses, Collec- 
tive Vol. I, 50. 

Anis ole- o-sulphonamide 
OCH 3 




C 7 H 9 3 NS MW, 187 

Needles from H 2 0. M.p. 171 (169). Sol. 
EtOH, hot H 2 0. 

Shober, Am. Chem. /., 1896, 18, 860. 

Anisole-m-sulphonamide . 

Needles. M.p. 128. 

Shober, Kiefer, Am. Chem. /., 1895, 17, 
456. 

Anisole-p-sulphonamide . 

Needles from H 2 0. M.p. 113 (116). Sol. 
EtOH. Insol. cold H 2 0. 

Shober, Am. Chem. J., 1896, 18, 860. 

Anisole-2 : 4 : 6-tricarboxylic Acid. 

See under Hydroxytrimesic Acid. 
Anisonitrile. 
See under Anisic Acid. 

Anisoylacetic Acid (p-Methoxybenzoylacetic 
acid) 

CH 3 0/~\CO-CH 2 -COOH 

C 10 H 10 4 MW, 194 

M.p. 180 decomp. 

Me ester: C n H J2 4 . MW, 208. Pale yellow 
cryst. M.p. 27-8*. B.p. 190-2/10 mm. Iso- 
nitroso deriv. : m.p. 154. Cu deriv. : green 
cryst. M.p. 248-50. 

Et ester : C 12 Hi 4 4 . MW, 222. Pale yellow 
liq. B.p. 180-90/10-12 mm. with part decomp. 
to anisoyldehydracetic acid (155/4-5 mm.; 
147/2-5 mm.). Sol. EtOH, Et 2 0. Insol. H 2 0. 
^ violet col. Isonitroso deriv. : m.p. 



o-Anisoylbeiizoic Acid ISO 

113-14. Cu deriv. : green cryst. from CHC1 3 - 
EtoH. M.p. 210. 

Wahl, Siiberzweig, Bull. soc. chim., 1912, 

11, 25. 

WaHingford, Homeyer, U.S.P., 2,407,942, 
(Ghem. Abstracts, 1947, 41, 1699). 



o-Anisoylfoenzoic Acid. 

See under 4'-Hydroxybenzophenone-2-carb- 
oxylic Acid. 

Anis oylcarfoinol . 

See under >-Hydroxyphenacyl Alcohol. 

Anisoyl chloride. 

See under Anisic Acid. 

Anis oylgly cine (p-Methoxybenzoylamino~ 
acetic acid, p-methoxyhippuric add, anisuric acid) 



PTT C\s \fY 
UJuL 3 U< >v_/v 



C 10 H n 4 N MW, 209 

Prisms from H 2 0. M.p. 171. Sol. hot H 2 0. 

Insol Et 2 0. Heat of comb. C p and C v 1136 

Gal. 
Et ester: C 12 H 15 4 N. MW, 237, Needles 

from EtOH. M.p. 98-9. * 

Matsuo, J. Biol. Chem., 1918, 35, 292. 

p-Anisoylstyrene . 

See under 4'-Hydroxychalkone, 

Anisuric Acid. 

See Anisoylglycine. 

Anisylacetamide . 

See under Anisamine. 

Anisyl acetate (p-Methoxybenzyl acetate) 



C 10 H 12 3 MW, 180 

B.p. 260-5, 137-9 /12 mm., 115~20/4 mm. 
D 20 1-1014. < 1-515. 

Tiffeneau, Fuhrer, Bull. soc. chim., 1914, 

15, 169. 
Ofuer, Helv. Ghim. Ada, 1935, 18, 951. 

Anisylacetone (Methyl p-methoxybenzyl 
ketone, anisacetone, anisic ketone, anise ketone, 
j)-acetonylani$ole, methyl anisyl ketone. Note. 
This is the commonly accepted trivial name for 
this compound. According to our system of 
nomenclature it is not anisylacetone but p-methoxy- 
phenylacetone) 



C 10 H 12 2 MW, 164 

B.p. 267-9, 142/14 mm., 117-22/5-6 mm. 

Sol. EtOH, Et 2 0. Spar. sol. H 2 0. DJ? 1-0707. 

DJ 8 1-067. < 1-5282. < 1-5253. Spar, volatile 

in steam. Ox. > anisic acid. 

Oxime : two forms, (i) M.p. 78-9. Spar. 

sol. pet. ether, (ii) M.p. 61-2 (63-5). B.p. 

]58-62/6mm. Sol. pet. ether. 



Anisylideneacetophenone 

Semicarbazone : m.p. 178 (182). 

Le Brazidec, Bull. soc. chim., 1922, 31, 255. 
Savitskii, Makhnenko, Chem. Abstracts, 

1941, 35, 4356. 
Doeuvre, Chervet, Compt. rend., 1947, 

224, 660. 
Hoover, Hass, J. Org. Chem., 1947, 12, 

501. 



Anisyl Alcohol 

anisalcohol) 



(p-Methoxybenzyl alcohol, 
CH 3 0/~\CH 2 OH 



C 8 H 10 2 

Needles. 
8 mm. D 
hyde. Ox. 



MW, 138 
127-30 / 



M.p. 24-5. B.p. 259 
1-1129. Heat in air > anisalde- 
> anisaldehyde > anisic acid. 
Esters used in perfumery. 
Me ether : C ? H 12 2 . MW, 152. B.p. 225-6. 
Benzoyl : anisyl benzoate. Prisms or needles. 
M.p. 38. 

Phenylurethane : cryst. from C 6 H 6 . M.p. 
93. 

Carothers, Adams, J. Am. Chem. Soc., 

1924,46, 1675. 
Sosa, Ann. chim., 1940, 14, 5. 

Anisylamine . 

See Anisamine. 

Anisylideneacetone (p-Methoxybenzyliden e- 
acetone, methyl p-methoxystyryl ketone, anisal- 
acetone) 



C U H 12 2 MW, 176 

Leaflets from MeOH, Et 2 0, or AcOEt. M.p. 
73. Sol. C 6 H 6 , AcOH. Sol. HC1 and H 2 S0 4 to 
yellow sols. Bed. > jp-methoxybenzylacet- 
one. HN0 3 + H 9 S0 4 > 3-nitro deriv. Gives 
add. products with HC1, H 3 P0 4 and H 2 S0 3 . 
Oxime : needles from EtOH. M.p. 1 19-20. 

Baeyer, Villager, Ber., 1902, 35, 1191. 
Kohler, Chadwell, Organic Syntheses, 
1930, X, 115. 

Anisylideneacetophenone (p-Methoxychalk~ 
one, phenyl p-methoxystyryl ketone, anisalaceto- 
phenone) 

CH 

c i6 H iA MW, 238 

Yellow needles. M.p. 77-8 (74). B.p, 

187-5-188/19 mm. Sol. Et 2 0, CHCL, hot 

EtOH. Gives add. products with HC1, JlC10 4 , 

and SnCl 4 . 
Picrate: orange needles. M.p. 87. Decomp. 

byH 2 0. ^ * 

Semicarbazone : m.p. 215. 

Pond, Shoffstall, J. Am. Chem. Soc., 1900, 
22, 666. 



Anisylidene chloride 



181 



Anthemol 



Anisylidene chloride (p-Methoxybenzylidene 
chloride, anisal chloride) 



CH 3 0<^ \CHC1 3 

C 8 H 8 OC1 2 MW, 191 

M.p. 20. B.p. 130-2/13 mm. Darkens and 
decomp. on standing. H 2 O or alkalis > 
anisaldehy de . 

Schmidt, Ber., 1908, 41, 2331. 

Anisylidenenitr omethane . 

See under p-Nitro-4-hydroxystyrene. 
1-Anisylidenepropionic Acid. 
See under oc-Methyl-p-coumaric Acid. 
Annotinine 

C 16 H 21 3 N MW, 275 

Alkaloid found in Lycopodium annotinum, 
Linn. Prisms from CHCl 3 -MeOH. M.p. 232. 
Perchlorate : cryst. from H 2 O. M.p. 267. 
Manske, Marion, Can. J. Research, 1943, 
21J5, 92. 

Anol (p-Propenylphenol, $-hydroxy-$-methyl- 
styrene] 

OH 



C 9 H 10 



H:CH-CH 3 

MW, 134 

Leaflets from H 2 0. M.p. 93. B.p. 140/14 
mm. Decomp. on dist. at ord. press, at 250. 
Decomp. on standing in air. Sol. most org. 
solvents. Sol. alkalis. 

Me ether : see Anethole. 

Quelet, Butt. soc. chim., 1929, 45, 268. 

Anolobine 




OH 



Ci 7 H 15 O 3 N MW, 281 

Alkaloid from bark of Asimina tribolba. 
Cryst. from CHCl 3 -MeOH. M.p. 262. [a]f> 7 
-22-5 in CHCL-MeOH. 
Me ether : m.p. 97. [a]U 27-9 in MeOH. 
Di-Me deriv. : B,HCl t m.p. 266 decomp. 
Pier ate : prisms from Me 2 CO-MeOH. M.p. 
226. Methiodide : prisms from MeOH. M.p. 
241. 

Manske, Can. J. Research, 1938, 16, 76. 
Govindachari, Chem. Abstracts, 1941, 35, 

6963. 
Marion, /. Am. Chem. Soc., 1944, 66, 1125. 



Anserine ($-Alanylmethylhistidine} 

H9=9CH 2 9H-COOH 

N N-CH 3 NH 
%/ C 

C 10 H 16 3 N 4 MW 3 240 

Constituent of avian musculature. Needles. 
M.p. 238-9. Sol. H 2 O. Mod. sol. MeOH. 
Spar. sol. EtOH. [ofe 6 + 11-26 in H 2 O. Heat 
with 20% H 2 S0 4 > Z-methylhistidine and 
p-alanine. 

Cu deriv. : C 10 H 16 4 N 4 Cu. M.p. 230-2 de- 
comp. 

B,HNO B : m.p. 216-18 decomp. 

B^PtCl^ : m.p. 215-20 decomp. 

B2HAuCl: m.p. 90-5. 

Et ester : B,H 2 PtCl 6 : m.p. 225-30. 

Monopicrate : m.p. 2058 decomp. 

Linneweh, Linneweh, Zi. physiol. Chem., 

1930, 189, 80. 
Eggleton, Eggleton, Nature, 1932, 130, 

275. 
Ackermann, Timpe, Pollet, Z. physiol. 

Chem., 1929, 183, 1. 

Antabuse. 

See Tetraethylthiuram disulphide. 

Anthanthrene . 

See Dibenz-[cd, jk]-pyrene. 

Anthanthrone 




C 22 H 10 2 MW, 306 

Orange cryst. from PhN0 2 . M.p. 300. 
Mod. sol. hot aniline, hot PhN0 2 . Spar. sol. 
Et 2 0, EtOH, AcOH, C 6 H 6 . Sublimes with part, 
decomp. Green in cone. H 2 S0 4 + AcOH. 

Kalb, Ber. 9 1914, 47, 1724. 
CasseUa, B.P., 280,217, (Chem. Zentr., 
1928, 1, 1102.). 

Anthemene 
C 30 H 62 MW, 422 

Hydrocarbon constituent of Anihemis nobilis, 
Linn. Laminae from Et 2 0. M.p. 64. B.p. 
440. Sol. Et 2 O, CS 2 . Spar. sol. cold EtOH. 
D 16 0-942. 

Klobb, Gamier, Ehrwein, Bull. soc. chim., 
1910, 7, 948. 



Anthemol 



C 10 H 16 



C 10 H 15 OH 



MW, 152 



Aiitlxeraxantbin, 



182 



Anthracene-9-carboxylic Acid 



Alcohol and esters occur in Roman camomile 
oil. Syrupy liq. B.p. 214 slight decomp. 
Dil. HN0 3 > p-toluic and terephthalic acids. 

Acetyl: b.p. 234-6. 

Kobig, Ann., 1879, 195, 92. 

AntheraxantMn 
C4oH 56(58) 3 MW, 584 (586) 

Carotenoid pigment from anthers of Lilium 
tigrinum. Pale yellow leaflets from EtOH. 
M.p. 207. Hypophasic. Prac. insol. pet. ether. 
SbCl 3 in CHC1 3 > blue col. (max. 587 m^). 
Absorption maxima in CS 2 , 512-5, 481, 448 my.; 
in CHC1 3 , 490-5, 460-5, 428 mji. 

Karrer, Oswald, Helv. CJiim. Acta, 1935, 

18, 1303. 
Karrer, Jucker, Helv. Chim. Acta, 1945, 

28, 300. 

Anthorine 
C 22 H 31 2 N MW, 341 

Alkaloid found in Acconitum anihora, Linn. 
Sol. Et 2 0. 
B,HCl: m.p. 335. [] D +24-44. 

Goris, Metin, Compt. rend., 1925, 180, 968. 
Goris, Compt. rend., 1937, 205, 1007. 

Anthracene 




C 14 H 10 MW, 178 

Colourless plates from EtOH. M.p. 216*1. 
B.p. 339-9. 100 parts EtOH dissolve 0-076 
part at 16, 0-83 part at b.p. Sol. to 1-175% in 
Et 2 0, 1-736% in CHC1 3 , 1-478% in CS 2 , 0-444% 
in AcOH, 0-115% in ligroin, 1-296% in C 6 H 6 , all 
at 15. 100 parts toluene dissolve 0-92 part at 
16, 12-94 parts at b.p. Sol. PhN0 2 . Sol. to 
7% in C 6 H 6 at 80, to 1-8% in MeOH at 20, to 
0-8% in Py. Df 1-283. Cryst. and liq. 
anthracene and its sols, exhibit weak violet fluor. 
Heat of comb. C^ 1707-6 Cal. Tribolumin- 
escent. Sp. heat 0-361 (20-210). Vapour 
pressure 0-045 mm./100 , 1-36 mm./150, 18-6 
mm./200, 43-5 mm./220, 99-6 mm./250, 
211 mm./280, 332 mm./300, 503 mm./320. 
Sublimes in vacuo. Cr0 3 , NaC10 3 , V 2 5 > 
anthraquinone. HJST0 3 in AcOH + Ac 2 > 
ws-nitro-, and dinitro-anthracene. Na + EtOH 
> 9 : 10-dihydro deriv. 01 at 100 > 9 : 10- 
dichloro deriv. Er in CS 2 at > 9 : 10-di- 
bromo deriv. Cone. H 2 S0 4 at 100 > 1 : 5- 
and 1 : 8-disulphonic acids. Polymerises to 
dianthracene, best by exposing xylene sol to 
light. 



sym.-Trinitrobenzene add. comp. : red needles. 
M.p. 164. 

Trinitrotoluene add. comp. : red needles. M.p. 
162. 

Picrate : m.p. 138. 

Nanson, Textile Colorist, 1926, 48, 605, 

678, 751 ; 1927, 49, 19, 246, 557, 593. 
Jaeger, Ind. Eng. Chem., 1928, 20, 1330. 

Anthracene-9-aldeliy de . 

See Anthraldehyde. 
Antlir aceneazine . 
See Anthrazine. 

Anthracene-1-carboxylic Acid (Anthra- 
cene- a-carboxylic acid, u-anthroic acid) 

COOH 




C 15 H 10 2 MW, 222 

Yellow needles from AcOH. Yellow prisms 
from EtOH or AcOEt. M.p. 251-2. Mod. sol. 
hot EtOH. Spar. sol. C ? H 6 , CHC1 3 . Insol. H 2 O. 
Sol. alkalis to sols, showing blue fluor. Sublimes. 
CaO > anthracene. 

Me ester: C 16 H 12 2 . MW, 236. Yellow 
plates from AcOH. M.p. 108 (101-2). 

Phenyl ester : C 21 H 14 2 . MW, 298. Yellow. 
M.p. 207-9. 

Amide : C 15 H U ON. MW, 221. Leaflets or 
needles from EtOH. M.p. 260. 

Nitrile : 1-cyanoanthracene. Glassy yellow 
leaflets. M.p. 126. Very sol. EtOH. 

Liebermann, Pleus, Ber., 1904, 37, 648. 
Coulson, J. Chem. Sac., 1930, 133, 1930. 

Anthracene-2-carJboxylic Acid (Anthra- 
cene-$-carboxylic acid, $-anthroic acid). 

Yellow leaflets from EtOH. M.p. 281. Sol. 
EtOH and AcOH but less so than the 1-carb- 
oxylic acid. Spar. sol. Et 2 0, C G H 6 . Insol. 
H 2 0. Sol. alkalis to sols, showing blue fluor. 
Sublimes in leaflets and needles. CaO > 
anthracene. 

M ester: C 17 H H 2 . MW, 250. Leaflets. 
M.p. 134-5. Dist. undecomp. 

Amide : yellow scales from AcOH. Yellow 
needles from EtOH. M.p. 293-5. Spar. sol. 
EtOH. 

Barnett, Cook, Grainger, Ber., 1924, 57, 
1775. 

Anthracene-9-carboxylic Acid (Anthra- 
cene-l^-carboxylic acid, ms-anthracenecarboxylic 
acid, ms-anthroic acid). 

Pale yellow needles from EtOH. M.p. 207 
decomp. (206). Sol. EtOH. Spar, sol hot 
H 2 0. Loses C0 2 at 150-60, or with CaO 



anthracene. 



VA^jj i 

Cr0 9 



anthraquinone. 



Anthracene-1 : 5-dicarboxylic Acid 



183 



Anthrachrysazin 



Me ester : yellow prisms or tablets. M.p. 111. 
Nitrile: 9-(10)-cyanoanthracene. Cryst.ficom 
ligroin. M.p. 170-2. 

Karrer, Zeller, Helv. Chim. Acta, 1919, 2, 

482. 
Dufraisse, Rigandy, Cornvt. rend., 1945, 

221, 625. 

Anthracene-1 : 5-dicarhoxyKc Acid 

COOH 



Anthracene-1 -sulphonic Acid ( Anthracene- 
ct-sulphonic acid) 




Ci 6 H 10 4 MW, 266 

Yellow needles. M.p. above 360. Spar. sol. 
AcOH, hot H 2 0. 

Di-Et ester: C 20 H 18 4 . MW, 322. Pale 
yellow plates from EtOH, AcOH, or CLBL. 
M.p. 185. 

Coulson, /. Chem. Soc., 1930, 1931. 

Anthracene-1 : 9-dicarboxylic Acid. 

Pale yellow cryst. Ox. > anthraquinone- 
1-carboxylic acid. 

Di-Me ester: C 18 H 14 4 . MW, 294. M.p. 
149. 

Anhydride: C 16 H 8 3 . MW, 248. Orange 
cryst. from AcOH. M.p. 289-90. Red in 
cone. H 2 S0 4 . 

Imide: C 16 H 9 2 N. MW, 247. Yellow 
needles from AcOH. M.p. 293-4. Eed in 
cone. H 2 S0 4 with some fluor. 

Kardos, Ber., 1913, 46, 2086. 
Badische, D.R.P., 280,092, (Chem. Ab- 
stracts, 1915, 9, 1396). 

Anthracene-1 : 5-disulphonic Acid 

S0 3 H 




C 14 H 10 6 S 2 MW, 338 

Dichloride: C 14 H 8 4 S 2 C1 2 . MW, 375. Yel- 
low needles from C 6 H 6 . M.p. 249. 

Diamide: C 14 H 12 4 N 2 S 2 . MW, 336. YeUow 
needles. M.p. above 330. 

Dianilide : m.p. 293. 

Lampe, Ber., 1909, 42, 1413. 

Anthracene-1 : 8-disulphonic Acid. 

Dichloride : yellow needles from CJEL. M.p. 
225. 

Diamide : m.p. 333. 
Dianilide : m.p. 224. 

Lampe, Ber., 1909, 42, 1413. 




S0 3 H 



Ci4 H io 3 S MW, 258 

Chloride : C 14 H 9 2 SCL MW, 276-5. Cryst. 

M.p. 90. 

Amide: C^H^^S. MW, 257. Cryst. 

from PhlSr0 2 . M.p. 205. 

Eerrero, Conzetti, Helv. Chim. Acta, 1928, 
11, 1153. 

Anthracene-2-sulphonic Acid (Anthracene- 
fi-sulphonic acid). 

Sol. hot H 2 0. Spar. sol. EtOH. Insol. 
Et 2 0, C 6 H 6 , CHClg. Na salt spar. sol. cold H 2 O. 

Me ester: C 15 H 12 3 S. MW, 272. Yellow 
leaflets. M.p. 157. 

Et ester : C 16 H 14 3 S. MW, 286. M.p. 160. 

Chloride : yellow cryst. from toluene. M.p. 
122. Spar. sol. EtOH, Et 2 0, ligroin. Stable 
to H 2 0. 

Amide: m.p. 261. Sol. PhN0 2 , phenol. 
Insol. EtOH, Et 2 0, AcOH, C 6 H 6 . 

Anilide: leaflets. M.p. 201. 

Phenylhydrazide : m.p. 210. 

Liebermami, Ann., 1882, 212, 57. 
Anthracene-1 : 2 : 4-tricarhoxylic Acid 
COOH 



C 17 H 10 




100H 



MW, 310 

Yellow. Indefinite m.p. Sol. EtOH. Spar, 
sol. C 6 H 6 , petrol. Insol. H 2 0. 

Elbs, J. prakt. Chem., 1890, 41, 129. 

Anthracene-1 : 5 : 9-tricarhoxylic Acid. 

M.p. about 360. 

I.G., D.R.P., 642,717, (Chem. Abstracts, 
1937, 31, 6256). 

Anthrachrysazin (1:3:5: 1-Tetrahydroxy- 
anthraquinone, anthrachrysone) 
CO OH 



OH 



C 14 H 8 6 MW, 272 

Silky yellow needles + 2H 2 0. M.p. above 
360. Sol. AcOH. Mod. sol. EtOH, Me 2 CO. 
Spar. sol. Et 2 0, C 6 H 6 , CHC1 3 , ligroin, CS 2 . 
Insol. H 2 0. Sublimes with part, decomp. 
Zn dust > anthracene. Yellowish-red in cone. 
H 2 S0 4 . 




Anthraclirysone 



184 



Anthragallol 



Di-Me ether : CisH 12 6 . MW, 300. Bronze 
leaflets from aniline. M.p. 280-3. Acetyl 
deriv, : yellow needles from AcOH~Ac 2 0. M.p. 
256. 

Tri-Me ether: C 17 H 14 6 . MW, 314. YeUow 
needles from AcOH. M.p. 225. Acetyl : yel- 
low needles. M.p. 220. 

Tetra-Me ether : C 18 H 16 6 . MW, 328. Gol- 
den prisms from PhN0 2 . M.p. 294. 

Tetra-acetyl : needles. M.p. 253. 

Hirose, Ber., 1912, 45, 2476. 
Hohenemser, Ber., 1902, 35, 2305. 

Antkrachrysone . 

See Anthrachrysazin. 
Anthracoumarin 

CO 



A 





C 16 H 8 3 MW, 248 

Yellow needles from AcOH. M.p. 260. Sol. 
C 6 H 6 , hot AcOH. Sol. hot alkalis with yellow 
col. and green fluor. Spar. sol. EtOH. Sol. 
H 2 S0 4 with green fluor. Sublimes. 

Kostanecki, Ber., 1887, 20, 3141. 

Anthradiamine . 

See Diaminoanthracene. 

1:4:9: 10-Antliradiqiiiaone 

CO 




CO v 
C 14 H 6 4 ~ MW, 238 

YeUow needles from C 6 H 6 ~ligroin. M.p. 211- 
13 decomp. (rapid heat.). Sol. EtOH, Me 2 CO, 
CHC1 3 , C 6 H 6 . Spar. sol. ligroin. Unstable. 
SO 2 > quinizarin. Warm cone. H 2 S0 4 > 
purpurin. 

Dimroth, Schultze, Ann., 1916, 411, 345. 

Anthraflavic Acid (2 : 6-Dihydroxyanthra- 
quinone) 

CO 



H 




iOH 



10 
C 14 H 8 4 MW, 240 

Yellow needles from EtOH. M.p. above 330. 
Spar. sol. EtOH, AcOH. Insol. Et 2 0, C 6 H 6 
CHC1 3 . Sol. cone. H 2 S0 4 > yellow sol. "~ " 
dish-yellow sols, in alkalis. Cone. KOH- 
flavopurpurin. 



Di-Me ether : C ie H 12 4 . MW, 268. YeUow 
needles from C 6 H 6 . M.p. 250. Sol. cone. 
H 2 S0 4 > orange-yeRow sol. 

Di-M ether: C 18 H ]6 4 . MW, 296. YeUow 
needles from EtOH. Sol. cone. H 2 S>0 4 >. red 
sol. 

Diacetyl : cryst. from AcOH. M.p. 228-9. 

Dibenzoyl : needles from AcOH. M.p. 275. 

Schunck, Romer, Ber., 1878, 11, 969. 
M.L.B., D.R.P., 106,505, (Chem. Zentr., 
1900, 1, 741). 

Anthraflavone (2 : 2* ' -Dianthraquinonyleihyl- 
ene, 3:4:3': 4? -diphthaloylstilbene) 

CO CO 




MW, 440 

Golden yellow cryst. from PhNOo. M.p. 
above 360. Spar. sol. C 6 H 6? EtOH" Et0, 
Me 2 CO. Bluish-red in H 2 S0 4 . 

Dibromide : m.p. above 400. 

Hepp, Uhlenhuth, Eomer, Ber., 1913, 46, 

709. 
Ullmann, Klingenberg, ibid., 712. 

Aathragallic Acid. 

See AnthragalloL 

Anthragallol (1 : 2 : 3-Trihydroxyanthraquin- 
one, anthragallic acid) 

CO OH 




C 14 H 8 5 MW, 256 

M.p. 312-3 (310). Sublimes at 290. Sol. 
EtOH, Et 2 0, AcOH. Spar. sol. H 2 0, OHOL, 
CS 2 . Sol. cone. H 2 S0 4 > reddish-brown sol 
Sol. alkalis >- green sols. 

1-Me ether: C 15 H, 5 . MW, 270. Yellow 
rhombic plates + !M.eOH from MeOH. M.p. 
248^50. Diacetyl : m.p. 165-6. %-p-Toluene~ 
sulphonyl : yellow plates from Me CO. M.p, 
289-91. 

2-jSfe ether : m.p. 218-20. l-Acetyl : yellow 
needles from Me 2 CO. M.p. 205-8. $-Acetyl : 
flat orange needles from Me 2 CO. M.p. 167-9-5, 
Diacetyl: yellow needles from MOoCO. M.p, 
152-4. 

3-Jfe ether : red needles from Me 2 CO. M.p. 
242-3. Diacetyl : greenish-yeUow needles. 
M.p. 204-6. 2-Benzoyl : orange needles from 
Me 2 CO. M.p. 221-3. l~Acetyl-%-benzoyl : leaf- 
lets from Me 2 CO. M.p, 195-6. 

l:2JXJfe ether: C 16 H 12 6 - MW, 284. 
Leaflets from EtOH, M.p, 230-2. Acetyl : 
yeUow needles from Me 2 CO. M.p. 177-9. 



Antlirahydroquinone 



185 



1-Antliramine 



1 : 3-Di-lf e ether : yellow needles from EtOH. 
M.p. 212-13. Acetyl : yellow needles from 
EtOH. M.p. 218-20. p-Toluenesulphonyl : 
m.p. 175-7. 

2 : %-Di-Me ether : orange needles from EtOH. 
M.p. 160-2 (166). Acetyl: yellow needles. 
M.p. 168 70. Benzoyl: greenish-yellow needles 
fromMe 2 CO. M.p. 216-18. 

Tri-H e ether : C 17 H 14 O 5 , MW, 298. Green- 
ish-yellow needles from CJEL-petrol. M.p. 
167-9. 

2-Et ether: C 16 H 10 5 . MW, 284. Red 
needles from EtOH. M.p. 175. 

3-Et ether: red needles from EtOH. M.p. 
245. 

2-Acetyl: m.p. 219-20. 

3-Acetyl: m.p. 206-9. 

2 : 3-Diacetyl : m.p. 223-4. 

Triacetyl : yellow needles from AcOH-Ac 2 0. 
M.p. 181-2. 

2-Benzoyl : orange needles from EtOH. M.p. 
241-3. 3-Acetyl : yellow plates from Me 2 CO. 
M.p. 203-6. Diacetyl: yellow needles from 
EtOH-Me 2 CO. M.p. 211-13. 

Dibenzoyl deriv. : yellow leaflets from C e H s . 
M.p. 204-6. 

Tribenzoyl : pale yellow prisms from EtOH- 
C 6 H 6 . M.p. 213-15. 

2 : 3-Di-p-toluenesulphonyl : m.p. 196-8. 
Acetyl : m.p. 212-15. 

Seuberlich, Ber. 9 1877, 10, 39. 

Simon, D.R.P., 119,755, (Chem. Zentr., 

1901, 1, 979). 
Kubota, Perkin, J. Chem. Soc., 1925, 127, 

1889, 
Perkin, J. Chem. Soc., 1929, 1399; 1930, 

292. 



Anthr ahy dr o quinone 

anthracene, anthraquinol) 

OH 



(9 : IQ-Dihydroxy- 




C 14 H 10 2 MW, 210 

Enol form of oxanthranol. Yellowish needles. 
M.p. 180. Sol. EtOH > green fluorescent 
sol. Sol. alkalis -> deep red col. Very un- 
stable in air. Easily oxidised to anthraquinone. 

Me ether : C 15 H 12 2 . MW, 224. M.p. 164. 
Acetyl : cryst. from C 6 H 6 . M.p. 174. Benzoyl : 
yellow leaflets from AcOH. M.p. 224. 

Di-Me ether : "C 16 H 14 2 . MW, 238. Colour- 
less tablets with blue fluor. from C 6 H 6 . M.p. 
202. 

Di-ffl ether : C 18 H 18 2 . MW, 266. Colour- 
less needles with blue fluor. from EtOH. M.p. 
148. 

Diacetyl: needles from AcOH. M.p. 260 
decomp. 



Dibenzoyl : yellow needles from xvlene-CHC! 3 * 
M.p. 292. 

Grandmougin, Ber. t 1906, 39, 3563. 
Meyer, Ann., 1911, 379, 37. 

Antliraldeliy de (A nthracene-$-aldehyde ) 
9HO 




C 15 H 10 MW, 206 

Orange needles from AcOH. M.p. 104-5. 
Decomp. by sunlight. Cr0 3 > anthraquinone. 
Aniline comp. : orange needles from EtOH. 
M.p. 175. 

Oxime: C 15 H U ON. MW 5 221. YeUow 
laminse from EtOH. M.p. 186-7. 

Semicarbazone : yellow micro-laminse from 
EtOH. M.p. 291. 

Azine: brick red. M.p. 296. 
Hydrazone : m.p. 125-6 (108-10). 
Phenylhydrazone : orange needles from EtOH. 
M.p. 207. 

I.G., E.P., 648,069, (Chem. Zentr., 1929, 

I, 2826). 

Hinkel, Ayling, Beynon, J. Chem. Soc., 
1936, 344. 

Anthralin (1:8: 9-Anthratriol, 1:8: 9-in- 
hydrozy anthracene, chrysanthranol, cignolin) 

HO OH OH 



C 14 H 10 O 3 MW, 226 

Yellow plates or needles from ligroin. M.p. 
176-7 (178-80). Sol. EtOH, Me 2 CO, C 6 H 6 . 
Used in dermatitis and other skin diseases. 
Triacetyl : yellow needles. M.p. 209-10. 
Schrobsdorf, Ber. 9 1902, 35, 2930, 
Bayer, D.R.P., 296,091, 305,886, (Chem. 

Zentr., 1917, 1, 351 ; 1918, II, 238). 
Hirose, Ber., 1912, 45, 2480. 



1-Antliramine 

anthracene) 



(a-Anthramine, 1-amino- 




C 14 H U N MW, 193 

Yellow needles from EtOH. M.p. about 130 

(119) (121-5-2-5 ). Sol. EtOH with green fluor. 
N-Formyl : crystals from EtOH. M.p. 193. 
N-Acetyl : green needles from AcOH. M.p. 

198 (213-5-4-5 ). Cr0 3 > 1-acetylaminoan- 

thraquinone. 



2-An.tliranibie 



186 



Anthranilic Acid 



&ym.-Trinitrobenzene add. comp. : black 
needles from EtOH. M.p. 206-7. 

Pisovschi, Ber., 1908, 41, 1434, 
Fierz-David, Blangey, Streit, Helv. Chim. 
Acta, 1946, 29, 1718. 

2-Anthramiae ($-AntJiramine, 2-amino- 
anthracene). 

Yellow leaflets from EtOH. M.p. 238. 
Sol. EtOH with green fluor. Insol. H 2 0. 
Sublimes. 

N-Formyl : yellowish-green cryst. M.p. 242. 
Sol. hot EtOH with blue fluor. 

N-Acetyl: leaflets. M.p. 240. Sol. EtOH 
with blue fluor. 

sym.-Trinitrobenzene add. comp. : black 
needles from EtOH. M.p. 168-5-9. 

I.G., D.E.P., 472,825, (Chem. Abstracts, 

1929, 23, 2987). 
Liebermann, Bollert, Ber., 1882, 15, 852. 

9-Anthramine (ms-Anthramine y 9-amino- 
anthracene, 9~iminoanthracene-dihydride 3 anthrone- 
imide) 

NH 2 



Ant&ranilic Acid (o-Aminobenzoic acid) 
COOH 





C 14 H n N MW, 193 

Golden leaflets from EtOH, brown cryst. 
from C 6 H 6 . M.p. 145-50. Unstable. Sol. 
Et 2 0, CHC1 3 . Sol. EtOH > green fluor. Sol. 
C 6 H 6 > bluish-green fluor. Cr0 3 > anthra- 
quinone. 

yf-Acetyl : needles with blue fluor. from 
EtOH. M.p. 273-4. 

fX-Diacetyl : tables from EtOH. M.p. 159. 
Kaufler, Suchannek, Ber., 1907, 40, 518. 
Mead et al, J. Biol Chem., 1946, 163, 465. 
Singn, Chem. Abstracts, 1943, 37, 3083. 

Anthranil 



C 7 H 5 ON MW, 

B.p. 210-15 part, decomp., 99/13 mm. 
Sol. EtOH and most org. solvents, and cone. 
min. acids. Spar. sol. hot H 2 0. Df 1-1827. 
Tij? 1-5845. Volatile in steam. Gradually 
resinifies on standing. Reduces NH 3 .AgN0 3 . 
Alkalis > anthranilic acid. H > o-amino- 
benzaldehyde. Ac 2 > acetylanthranil. Cl 
> ^V-dichloro deriv., m.p. 77. Hg01 2 > 
mol. comp., m.p. 178. 
Oxime : m.p. 135-6. 
Acetyl deriv, : see Acetylanthranil. 

JSTord, JBer., 1919, 52, 1705. 

Auwers, Ann., 1924, 437, 63. 

Leuchs, Ber., 1925, 58, 1452. 



C 7 H 7 2 N 



MW, 137 



Leaflets. M.p. 144-6. Sol. H 2 0, EtOH, 
Et 2 0. Sublimes. Triboluminescent. Decomp. 
on dist. to C0 2 + aniline. Ic (acid) = 1*07 X 
10- fi at 25; k (base) = 1-4 X 10" at 25. 
NaHg in HC1 -> o-aminobenzyl alcohol 
(hydrochloride). HN0 2 > salicylic acid. 

B,HF: m.p. 217-18. 

BJBGl : needles. M.p. 193-4. 

BiJS^Oi : needles + 2H 2 0. M.p. 188. 

Me ester : see Methyl anthranilate. 

m ester : C 9 H n 2 N. MW, 165. M.p. 13. 
B.p. 266-8, 145-7/15 mm. DJ 1-1174. < 
1-56455. Sol. EtOH with violet fluor. B,HOl : 
needles. M.p. 170 (115-20). Picrate : m.p. 
116. N-Formyl : prisms from ligroin. M.p. 
57. N-CMoroacetyl : cryst. from 95% EtOH. 
M.p. 140. 'N-Benzoyl : needles from EtOH. 
M.p. 98. ~N-Benzenesulphonyl : m.p. 92-5. 
N-y>-Toluenesulphonyl : m.p. 112. 

K-Butyl ester : C n H 15 2 N. MW, 193. B.p. 
182. B,HCl : m.p. 178. 

Isobutyl ester : b.p. 156-7/13 mm. 

Isoamyl ester : C 12 H 17 2 N. MW, 207. B.p. 
169-70 IB mm. 

l-Menthyl ester: C 17 H 25 2 N. MW, 275. M.p. 
62-5-63-5. B.p. 156/0-33 mm. Sol. EtOH 
with violet fluor. B,HOl: cryst. from EtOH- 
HC1. M.p. 150-70. Spar. sol. EtOH with 
violet fluor. 

Phenyl ester: C 13 H 1]L 2 N. MW,213. Needles 
from EtOH. M.p. 70. Sol. EtOH, 
Spar, volatile in steam. 

Phenacyl ester : cryst. from EtOH. 
181-2. 

Amide : see o-Aminobenzamide. 
see 0-Aminobenzonitrile. 
o-aminobenzanilide. C 13 H 
Needles from CJEL. M.p. 
(126). Sol. EtOH, Et 2 0, CHC1 3 , Me 2 CO. 
Mod. sol. H 2 0. Spar. sol. C 6 H 6 . 

o - Toluidide : o - aminobenz - o - tolxiidide. 
C 14 H 14 ON 2 . MW,226. Needles from EtOH.Aq. 
M.p. 104. 

m - Toluidide : o - aminobenz - m - toluidide. 
Needles from C 6 H 6 . M.p. 118. 

p - Toluidide : o - aminobenz - p - toluidide. 
Needles from EtOH.Aq. M.p. 151. 

Hydrazide : prisms from EtOH, needles from 
CHC1 3 . M.p. 121. Sol. hot H 2 0, EtOH. Mod. 
sol. Et 2 0, C 6 H 6 . 

N-Phenyl : see Diphenylamine-2-carboxylic 
Acid. 

N-Tolyl : see MethyldipLenylamine-2-carb- 
oxylic Acid. 



Nitrile : 

Anilide 

MW, 212 



Et 2 0. 

M.p. 



, 12 ON 2 
,p. 131 



Antliram'lmoacetic Acid 



187 



AnthrapheiLorLe 



N-Formyl : needles + iH 2 O. M.p. 169. 
Sol. EtOH, Et 2 0. Spar, sol C 6 H 6 . 

^-Chloroacetyl : needles from EtOH. M.p. 
186-8. 

N-Propionyl : needles from H 2 0. M.p. 117. 

N-Butyryl : prisms from EtOH. M.p. 89. 

N-Isobutyryl : needles from EtOH.Aq. M.p. 

N-Benzoyl : needles from EtOH. M.p. 80-1. 
Sol. EtOH, Et 2 0. 

N-o-Nitrobenzoyl : cryst. from toluene- 
EtOH. M.p. 239. 

N-m-Nitrobenzoyl : prisms from EtOH. M.p. 
233. 

N-p-Nitrobenzoyl : needles from EtOH. M.p. 
235. 

N-Benzenesulphonyl : cryst. from AcOH. 
M.p. 214. 

N~p-Toluene$ulphonyl : cryst. from 80% 
EtOH. M.p. 217. 

Shipley, Calhoun, Chem. Abstracts, 1936, 
30, 391. 

Beall, U.S.P., 1,492,664 (Chem. Abstracts, 
1924, 18, 2009). 

Potter, U.S.P., 1,322,052, (Chem. Ab- 
stracts, 1920, 14, 287). 

Isbell, Henze, J. Am. Ohem. Soc., 1944, 
66, 2096. 

Anthranilinoacetic Acid. 

See Phenylglycine-o-carboxylic Acid. 
Anthranilinodiacetic Acid (o-Carboxy- 
phenyliminodiacetic acid) 

N(CH 2 -COOH) 2 
/\COOH 

C n H n 6 N MW, 253 

Plates or leaflets from H 2 0. M.p. 215. 
Tri-Me ester: C 14 H 17 6 N. MW,295. M.p. 62. 
a-Jf ononitrile : C n H 10 4 :N 2 . MW, 234. 
Cryst. Decomp. at 140. 

vL-Dinitrile : C U H 9 2 N 3 . MW, 215. Prisms 
from MeOH. M.p. 168-71 decomp. 

Badische, D.R.P., 216,748, (Chem. Zentr., 
1910, 1, 308). 

Anthranol (ms-Hydroxyanthracene, Q-anthrol, 
9-hydroxyanthracene) 

OH 




C 14 H 10 MW, 194 

Enol form of anthrone. Pale yellow needles. 
M.p. 120 (rapid heat). Sol. AcOH, hot C 6 H 6 . 
PhN0 2 , alkalis. Slow heat. > anthrone. 
Ox. > anthraquinone. Easily oxidised (e.g., 
with FeClg, Br, etc.). Zn dust > anthracene. 
Glycerol + H 2 S0 4 > benzanthrone. Con- 



denses with ^p-nitrosodimethylaniline. Couples 
with diazo-comps. 

Acetyl ; 9-acetoxyanthracene. Needles from 
EtOH.Aq. M.p. 134. Sols, show blue fluor. 

Backstrom, Beatty, J. Phys. Chem., 1931, 

35, 2530. 
Perkin, B.P., 151,707, (Chem. Abstracts, 

1921, 15, 690). 
Meyer, Ann., 1911, 379, 37. 

Anthranol-carboxylic Acid. 

See 10-Hydroxyanthracene-l-carboxylic Acid 
and 9-Hydroxyanthracene-2-carboxylic Acid. 

Anthranoylantliranilic Acid (o-Amino- 
benzoylanthranilic acid) 



C 14 H 12 3 ISr 2 



^]STH 
IJCOOH 



MW, 256 



Pale yellow needles from EtOH.Aq. M.p. 
203. Mod. sol. Et 2 O. InsoL cold H 2 0, CHC^, 
CS 2 , ligroin. Ethereal sols, show blue fluor. 
Loses C0 9 on prolonged heating. 

N-Acetyl : needles from EtOH. M.p. 226. 
Amide : prisms or leaflets from EtOH. M.p. 
232. 

'N-Tp-Toluenesulphonyl : m.p. 217. 

Me ester : C 15 H 14 3 N 2 . MW, 270. Needles 
from MeOH. M.p. 118-19. Spar. sol. MeOH. 

Et ester: C 16 H 16 3 N 2 . MW, 284. Yellowish 
prisms from EtOH. M.p. 106-5. 

Anhydride : 



^^. MW, 238. M.p. 162. Acetyl : 
m.p. 211-12. 

Mohr, Kohler, J. prah. Chem., 1910, 80, 

521. 

Schroeter, Ber., 1919, 52, 2224. 
Simpson et dl., J. Chem. Soc. y 1945, 646. 



Anthraphenanthrene 




C 26 H 16 " " " MW, 328 

Yellow needles. M.p. 281-2 decomp. 
Cook, /. Chem. Soc,, 1931, 499. 

Anthraphenone (ms-Benzoylanthracene, 
phenyl anthranyl ketone, 9-benzoylanthracene) 

!0-C 6 H 5 



C 21 H 14 




MW,282 



188 



p-Anthrapyridinequinone 



Yellow needles from C 6 H 6 or AcOH. M.p. 
148. Gives fugitive blue col. with H 2 S0 4 . 
OO 3 in AeOH > anthraquinone + benzoic 
acid. H 2 S0 4 in 3iot AcOH > anthracene + 
benzoic acid. Zn + AcOH > 9 : 10-dihydro 
deriv. 

Cook, J. CJiem. See., 1926, 1284. 

Antlirapurpurin (1 : 2 : 7-Trihydroxyanthra- 
quinone, isopurpuriri) 

CO OH 



cc-Anthrapyridine (6 : 1-Benzquinoline, 2:3- 
naphthapyridine, naphthazine, 1-azanthracene) 




C 14 H 8 O 5 MW, 256 

Orange needles from EtOH. M.p. 369. B.p. 
462 part, decomp. Sublimes at 170. Sol. hot 
EtOH, hot AcOH, hot CHCl^ Spar. sol. Et 2 0. 
InsoL C 6 H 6 . Sol. alkalis to violet sols. Heddish- 
brown in cone. H 2 S0 4 . 

1-Jfe ether : C 15 H 10 5 . MW, 270. Orange- 
red needles. M.p. 299-300. 2 : 7-Diacetyl : 
pale yeUow leaflets from EtOH. M.p. 136-7. 
2 : 7 '-Dicarbethoxyl : yellow needles from MeOH. 
M.p. 120-1. 

2-Me ether : orange-red needles from EtOH. 
M.p. 308-9. 7-Acetyl : orange-yellow needles. 
M.p. 207. 1 : 7-Diacetyl : yellow leaflets from 
Py. M.p, 154-5. 

1 : 7-Di-Me ether : C 16 H 12 5 . MW, 284. 
Yellow needles. M.p. 218-19. 2-Acetyl : pale 
yellow needles. M.p. 175-6. 2-Benzoyl : yellow 
leaflets from MeOH. M.p. 201-3. 

2 : 1-Di'Me ether : orange-yellow needles from 
MeOH. M.p. 242-3. 1-Acetyl : pale yeUow 
needles. M.p. 228-30. l-Benzoyl: yellow plates 
from EtOH-AcOH. M.p. 209-11. 

Tri-Me ether: C 17 H 14 5 . MW, 298. Yellow 
needles from EtOH. M.p. 201. Sol. CHC1 
C 6 H 6 . Spar. sol. cold EtOH. 

2-Acetyl : yellow needles from EtOH. M.p. 
296-8. 

2-Benzoyl : yellowplates or prisms from MeOH. 
M.p. 272-3. 1 : 7-Diacetyl ; pale yellow plates 
or leaflets. M.p. 201-3. 

2 : 7-Diacetyl : yellow needles from EtOH- 
AcOH. M.p. 192-3. 

2 : 7 -Dicarbethoxyl : golden-yellow needles 
from EtOH. M.p. 166-7. 

Triacetyl : pale yellow cryst. from AcOH. 
M.p. 223. Mod. sol. AcOH. Spar. sol. EtOH. 

Wedekind, D.R.P., 137,948, (Chem. 

Zentr., 1903, 1, 267). 
JSTolting, Wortmann, Ber., 1906, 39, 642. 
Grandmougin, Compt. rend., 1921, 173, 

1176. 
Perkin, Storey, J, Chem. Soc. 3 1928, 

229. 



3> 




C 13 H d lS[ MW, 179 

Cryst. M.p. 114. B.p. 200-5/14 mm. Sol. 
EtOH, Et 2 O. Less soluble than p-anthrapyr- 
idine. Sols, show marked fluor. Sunlight 
irradiation > a-anthrapyridinequinone. 

B,HC1 : yeUow cryst. from EtOH. M.p. 
196-7. Sinters at 191 (m.p. 142-3). 

B,HI : red. M.p. 171-3. 

Picrate: m.p. 258. Darkens at 229. Spar, 
sol. EtOH. 

Methiodide : yellowish-brown cryst. from H 2 0. 
M.p. 225-6 (219). Sol. EtOH. 

v. Braun, Gruber, Ber., 1922, 55, 1715. 

p-Antlirapyridine (6 : 7-Benzisoquinoline, 
3 : ^-naphthapyridine, 2-azanthracene) 




C 13 H 9 1S[ " " ' MW, 179 

Light reddish leaflets. M.p. 166 (174). Sol. 
most org. solvents. Spar. sol. H 2 0. Sublimes in 
yellow leaflets. Sols, show blue to bluish-green 
fluor. Salts are yellow and their sols, show 
green fluor. Sunlight irradiation > (3-anthra- 
pyridinequinone . 

Philips, Ber., 1895, 28, 1658. 

v. Braun, Nelles, Ber., 1937, 70, 1764. 

$tienne, Robert, Compt. rend., 1946, 223, 
331. 



a-Anthrapyridiuequinone 

quinone, 2 : 3-phthaloylpyridine) 

CO 



(l-Azanthra~ 




C 13 H 7 2 N MW, 209 

Yellowish-brown needles from C C H 6 . M.p. 
280. Weak base. Sublimes. Zn + NH 3 > 
a-anthrapyridine. 

v. Braun, Gruber, Ber., 1922, 55, 1716. 
I.G., B.P., 427,485, (Chem. Abstracts, 

1935, 29, 6076). 
Clemo, Driver, /. Chem. Soc., 1945, 829. 

p-Anthrapyridinequinone (2-Azanthra- 
quinone, 3 : k-phthaloylpyridine) 
CO 





C 13 H 7 2 N MW, 209 



Antlirapyridone 



189 



1 : 4-Antkraquinone 



Yellow needles from C 6 H 6 or CCI 4 . M.p. 
(265-6). Sublimes. Sol. dil. min. acids. C 



179 
Cone. 

H 2 S0 4 > yellow sol. Zn + KE 3 
anthrapyridine . 

Philips, Ber., 1894, 27, 1925. 
Etienne, Robert, Oompt. rend., 1946, 223, 
331. 

Antkrapyiidone . 

See Pyridanthrone. 
Anthraquinol . 
See Anthrahydroquinone. 
a-AnthraqninoliJie (l:2-Pyridinoanthracene, 
2' : 3 '-1 : S-naphthaquinoline) 




C 17 H n N " ~ " MW,229 

Cryst. M.p. 126-5-128. Sol. EtOH, Et 2 0, 
C 6 H 6 . Insol. H 2 O. Ale. sol. shows blue fluor. 
B,HCl: yellow needles. Mod. sol. EtOH, 
hot H 2 O. 

Graebe, Pollak, Ghem.-Ztg. 9 1895, 19, 
1229. 

p-Anthraquinoline (2 : 1-Pyridinoanthracene, 
2' : 3' : 5 : 6-naphthaquinoline) 




C 17 H U N MW, 229 

Plates or leaflets. M.p. 170. B.p. 446. 
Sol. EtOH, Et 2 0, C 6 H 6 . Insol. H 2 0. Sols, 
show intense blue fluor. Sublimes readily. 
Cr0 3 in AcOH > (3-anthraquinolinequinone. 
Salts are yellow and dissolve in EtOH.Aq. with 
green fluor. 

Graebe, Ber., 1884, 17, 170. 

a - Anthraquinolinequinone (a - Anthra- 
quinonequinoline, 1 : 2 - pyridinoanthraquinone, 
1 : S-phthaloylquinoline) 




C 17 H 9 2 N MW, 259 

YeUow needles from EtOH.Aq. M.p. 169. 
Sol. C 6 H 6 , dil. min. acids. Cone. H 2 S0 4 > 
pale yellow sol. Nitration in H 2 S0 4 > mono- 
nitro deriv., m.p. 284. 

M.L.B., D.E.P., 189,234, (Chem. Zentr., 

1908, 1, 76). 

Badische, D.B.P., 218,476, (Chem. Zentr., 
1910, 1, 781). 



p-Antliraqiiinolineqiiijioiie (fi-Anthraqmn- 

onequinoline, 2 : I -pyridinoanthraquinone, 5:6- 
phtha loylquinoline ) 




C 17 H 9 2 N MW, 259 

Yellow needles from C 6 H 6 . M.p. 185. Sol. 
EtOH, Et 2 0, C 6 H 6 . Insol. H 2 0. Sublimes. 
Zn dust > p-anthraquinoline. Mtration in 
H 2 S0 4 > mononitro deriv., m.p. 258. 

Graebe, Ann., 1880, 201, 333. 

Bally, Scholl, Ber., 1911, 44, 1656. 

y-Antliraquinolinequinone (y-Anihraquin- 
onequinoline, 2 : 3 -pyridinoanthraquinone, 6 : 7- 
phthaloylquinoline) 

CO 




CO N 
C 17 H 9 2 N MW, 259 

YeUow needles. M.p. 322. Mtration in 
H 2 S0 4 >- mononitro deriv., m.p. 305. 

Badische, D.R.P., 171,939, (Chem. Zentr., 

1906, II, 573). 
Bally, Scholl, Ber., 1911, 44, 1656. 

1 : 2-Anthraquinone 



V.O 




C 14 H 8 2 MW, 208 

Orange-brown cryst. M.p. 185-90 decomp. 
Mod. sol. EtOH, hot CHC1 3 , hot AcOH. Spar. 
sol. hot H 2 0. Sol. cone. H 2 S0 4 to violet sol. 
Bed. > 1 : 2-dihydroxyanthracene. 

1 - Oxime : 1 - nitroso - 2 - hydroxyanthracene. 
Orange-brown needles. Decomp. at 188. Blue 
in H 2 S0 4 . Bed. > l-ammo-2-hydroxyanthrac- 
ene. Me ether : m.p. 130. Et ether : m.p. 143. 

2 - Oxime : 1 - hydroxy - 2 - nitrosoanthracene. 
Orange-brown needles. Decomp. at 200. Bed- 
dish-violet in H 2 S0 4 . Bed. > l-hydroxy-2- 
aminoanthracene. Me ether : m.p. 134. Et 
ether : m.p. 144. 

Lagodzinski, Ann., 1905, 342, 80. 
1 : 4-Anthraquinone 




C M H 8 2 



MW, 208 



9 : 10-AntliraqTiinone 



190 



Anthraqiiinone-1-carboxylic Acid 



YeUow needles. Blackens at 200-10; m.p. 
218 decomp. 

Oxime : I - hydrosy - 4 - nitrosoanthraeene. 
Brown needles. Darkens at 205; in.p. 233 
decomp. Spar. sol. org. solvents. Blue in 
H 2 S0 4 . 

Pisovschi, Ber., 1908, 41, 1436. 

9 : 10-Antliraqiiinone (Ordinary anthra- 

qulnone) 

CO a 



C 14 H R 






MW, 208 

Yellowish rhombic cryst. M.p. 286. B.p. 
379-81. Sublimes. Sol. hot C 6 H 6 , hot toluene 
(6% at 100), and in PhN0 2 and aniline. Mod. 
sol. EtOH. Spar. sol. Et 2 0. Sol. cone. H 2 S0 4 . 
D 4 1-419-1-438. Heat of comb. C v 1547-9 
Gal., C P 1548-5 Gal. Triboluminescent. Zn dust 
> anthracene. Al + H 2 S0 4 > anthranol. 
Sn + HC1 > anthrone. Na 2 S 2 4 ^ anthra- 
hydroquinone. Not reduced by S0 2 . Alk. 
fusion > benzoic acid. Ox. > phthalic 
acid. Gives no phenylhydrazone and only a 
monoxime. 

Monoxime : pale yellow needles. M.p. 224 
(rapid heat). Me ether : m.p. 147. M ether : 
m.p. 97. 

Philips, Chem. Reviews, 1929, 6, 157 

(Review). 
Underwood, Walsh, Organic Syntheses, 

1936, XVI, 74. 

TLwskii,Chem.Zentr., 1933,1, 125 (Review). 
I.G., D.RP., 598,476, (Chem. Abstracts, 

1934, 28, 5470). 
Selden Co., U.S.P., 1,886,023, (Chem. 

Abstracts, 1933, 27, 1366). 
Harding, Colour Trade Journal, 1921, 9, 

184. 
Fedorov, Semenova, Chem. Abstracts, 

1941, 35, 2138. 
Newman, J. Am. Chem. Soc., 1942, 64, 

2324. 

Houben, Las Anthracen und die Anthra- 
chinone mit den zugehorigen viellcernigen 
Systemen. Ann Arbour, Michigan. 

Anthraquinone-1 -aldehyde 

CO CHO 



Anthraqninone-2-aldeh.y de . 

Yellowish leaflets or needles from AcOH. 
M.p. 188-9. Sol. Py, aniline. Mod. sol. 
Me^CO, AcOH, C 6 H 6 . Spar. sol. EtOH, hot 
Et 2 0, hot ligroin. 

Anil : yellow cryst. from toluene. M.p. 185. 
Oxime : yellow needles. M.p. 238-9. Sol. 
Et 2 0, ligroin. Spar. sol. EtOH, C 6 H 6 . 

Semicarbazone : yellow cryst. from PhNO 2 . 
M.p. 397. Sol. hot PhN0 2 , aniline. InsoL 
EtOH, Et 2 0, C 6 H 6 , ligroin. 

Phenylhydrazone : needles. M.p. 242 . 
p-Nitrophenylhydrazone : leaflets from PhN0 2 . 
M.p. 305-6. 

Azine : pale yellow needles from PhNO 2 . 
M.p. 410. 

Ruggli, Disler, Helv. Chim. Ada, 1927, 

10, 938. 
Ullmann, Klingenberg, Ber., 1913, 46, 

715. 

Jacob, Helv. Chim. Acta, 1921, 4, 782. 
Chem. Fabr. Griesheim-Elektron, D.R.P., 
293,981, (Chem. Abstracts, 1917, 11, 
2580). 
M.L.B., D.R.P., 361,043, (Chem. Zentr., 

1923, II, 481). 

Anthraquinone-1-carboxylic Acid 
CO COOH 




iO 

C 15 H 8 3 MW, 236 

Cryst. from AcOH or C 6 H 6 -EtOH. M.p. 
186-8. 

I.G., B.P., 369,902, (Chem. Abstracts, 

1933, 27, 2159), 
Scholl, Donat, Ber., 1931, 64, 320. 




C 15 H 8 4 MW, 

Pale yellow needles from AcOH. M.p. 293-4. 
Spar. sol. hot H 2 0. Zn + NaOH > blood- 
red col. Zn + NH 3 > anthracene-1-carb- 
oxylic acid. 

Me ester: C^H^O^ MW, 266. Pale yellow 
cryst. from MeOBL M.p. 189. 

Et ester: C 17 H 12 4 . MW, 280. Yellow needles 
from EtOH. M.p. 169. Sol. hot EtOH 

Amide: C 15 H 9 3 N. MW, 251. Pale yellow 
cryst. from EtOH. M.p. 280. Mod. sol. EtOH. 
InsoL cold H 2 0. Sublimes. Very stable towards 
alkalis. 

Nitrile : 1-cyanoanthraquinone. C 16 H 7 2 N. 
MW, 233. YeUow leaflets from AcOH. M.p. 
247 (216-17). 

Anhydride : C 30 H,,0 7 . MW, 486. Pale yel- 
low cryst. from PJxN 2 . 

Anilide: C^H^OgN. MW, 327. Palo yel- 
low cryst. from EtOH. M.p. 288-9. Zn dust- 
dist. > anthracene. 

Graebe, Blumenfeld, Ber., 1897, 30, 1115. 
I.G.,B.P., 369,902, (Chem. Abstracts, 1933,. 

27, 2159). 
Gen. Aniline Works, U.S.P., 1,830,838, 

(Chem. Abstracts, 1932, 26, 737). 
Coulson, J. Chem. Soc., 1930, 1932. 
Hey, Mcholls, Pritchett, J. Chem* 800.9, 
1944, 97. 



Antlirac[U]bioiie-2-carboxylic Acid 



191 Antliraqiiinone-2 : G-dicarboxylic Acid 



Anthraquinone-2-carboxylic Acid. 

Yellow needles from AcOH. M.p. 290-2 
(285-6). Sol.Me 2 CO. Spar. sol. EtOH, AcOH. 
Prac. insol. Et 2 0, C 6 H 6 . Sublimes on careful 
heating. Zn + NH 3 ^ anthracene-2-carb- 
oxylic acid. 

Me ester : m.p. 170. 

Et ester : needles. M.p. 147. Sol. EtOH. 

Amide : needles from AcOH-C 6 H 6 . M.p. 
280. Spar. sol. EtOH, C 6 H 6 . 

Chloride : C 15 H 7 3 CL MW, 270-5. Needles 
from C 6 H 6 . M.p. 147. 

Anilide : m.p. 258-60. 

Liebermann, Glock, Ber., 1884, 17, 888. 
Whitmore, Carnahan, J. Am. Chem. Soc., 

1929, 51, 858. 

I.G., B.P., 314,020, (Chem. Abstracts, 

1930, 24, 1123). 

Barnett, Cook, Grainger, Ber., 1924, 57, 

1779. 
IFinskii, Kazakova, Chem. Abstracts, 

1941, 35, 5487. 

Anthraqtdnone-1 : 2-dicarboxylic Acid 

CO COOH 

hCOOH 




C 16 H 8 6 MW, 296 

Yellowish needles from AcOH. M.p. 270. 
Sol. hot EtOH, AcOH. Insol. Et 2 0, C 6 H 6 . 
Sol. 2200 parts H 2 at 20. Heat at 250-300 
> anhydride. Cone. H 2 S0 4 > yellow sol., 
changing to red. Dist. with lime > anthra- 
quinone. 

Di-Me ester: C 18 H 12 6 . MW, 224. Pale 
yellow needles from AcOEt. M.p. 208. 

Anhydride: C 16 H 6 5 . MW, 278. Yellow 
needles. M.p. 319-21. Sublimes. 

Imide : yellow needles from AcOH. M.p. 
293. 

SchoU, Schwinger, Ber., 1911, 44, 2992. 
Whitmore, Carnahan, J. Am. Chem. Soc., 
1929, 51, 857. 

Anthraquinone-1 : 3-dicarboxylic Acid. 

Pale yellow needles from EtOH . Aq. Decomp. 
at 320-5. Spar. sol. ord. solvents. Zn + NH 3 
> anthracene- 1 : 3-dicarboxylic acid. 

Fieser, Martin, J. Am. Chem. Soc., 1936, 

58, 1445. 
Scholl, Donat, Bottger, Ann., 1934, 512, 

127. 

Anthraquinone-1 : 4-dicarboxylic Acid. 

Yellow cryst. M.p. above 300. Mod. sol. 
EtOH. Spar. sol. Me 2 CO, AcOH. Zn + NH 3 
> anthracene- 1 : 4-dicarboxylic acid. 



Dichloride: C 16 H 6 4 CL>. MW, 333. Pale 
yellow needles from C 6 H 6 . M.p. 203-5. 

Elbs, J. praU. Chem., 1890, 41, 29. 
SchoU, Meyer, Ann., 1934, 512, 117. 

Anthraquinone-1 : 5-dicarboxyHc Acid. 

Needles. Does not melt below 390. 

Di-Me ester: C 18 H 12 6 . MW, 324. Leaflets 
fromMeOH. M.p. 236. 

Di-Et ester: C 20 H 16 6 . MW, 352. Pale yel- 
low needles or prisms from AcOH. M.p. 155. 

Dichloride : C 16 H 6 4 CL>. MW, 333. M.p. 
260-3 decomp. 

Dinitrile : C IQ E 6 0^ 2 . MW, 258. Yellow- 
ish-brown needles from benzyl cyanide. Does 
not melt below 390. Almost insol. ord. sol- 
vents. 

Anhydride : C 16 H 6 5 . MW, 278. Pale yel- 
low. M.p. about 336. Spar. sol. all ord. org. 
solvents. 

Coulson, J. Chem. Soc., 1930, 1932. 
SchoU, Hass, Meyer, Ber., 1929, 62 ? 
109. 

Anth.raquinone-1 : 6-dicarboxylic Acid. 

Eaintly yellow needles from EtOH. M.p. 
336-8. 

Fieser, Martin, J. Am. Chem. Soc., 1936, 
58, 1444. 

Anthraquinone-1 : 7-dicarboxylic Acid. 
Pale yellow cryst. from EtOH. M.p. 346-8. 

Pieser, Martin, J. Am. Chem. Soc. 9 1936, 
58, 1444. 

Anthraqninone-1 : 8-dicarboxylic Acid. 

Dinitrile: C 16 H 6 2 N 2 . MW, 258. Cryst. 
Does not melt below 400. Sol. cone. H 2 S0 4 
with red col. 

I.G., F.P., 624,544, (Chem. Zentr., 1929, 
II, 935). 

Anthraquinone-2 : 3-dicarboxylic Acid 

YeUow needles from AcOH. M.p. 340-2. 
Sol. EtOH. Spar. sol. H 2 0. Zn + NH 3 > 
anthracene-2 : 3-dicarboxyllc acid. 

C 18 H 12 6 . MW, 324. M.p. 



Di-Me ester : 
183-4. 



MW, 295. Brown 



Monoamide : C 16 H 9 5 N". 

leaflets from AcOH. Does not melt below 340. 
Anhydride: C 16 H 6 5 . MW, 278. M.p. 290. 

Whitmore, Carnahan, J. Am. Chem. Soc., 

1929, 51, 859. 
Elbs, J. prakt. Chem., 1890, 41, 8. 

Anthraquinone-2 : 6-dicarboxylic Acid. 

Does not melt below 400. Spar. sol. ord. 
solvents. Heated with KOH for 6 days > 
iso- and tere-phthalic acids. 

Dichloride: C 16 H 6 4 C1 2 . MW, 333. Pale 
yellow needles from C 6 H 6 . M.p. 197-8. Stable 
to water. 



Anthraqiiinone-2 : 7-dicarboxylic Acid 192 Anthraquinone-2 : 6-disulplionic Acid 



Diamide : C 16 H 10 4 N 2 . MW, 294. Needles 
from AcOH. Does not melt below 370. 

Seer, Monatsh., 1911, 32, 163. 

Antkraquinone-2 : 7-dicarboxylic Acid. 

Pale yellow rhombic plates from AcOH. Does 
not melt below 360. 

Bichloride : pale yellow needles from C 6 H 6 . 

Morgan, Coulson, J. Chem. Soc., 1929, 

2211. 
Scholl, Zeigs, Ber., 1934, 67, 1748. 

Anthraquinone dichloride. 

See ras-Dichloroanthrone. 

Anthraquinone-dihy droazine . 

See Indanthrone. 

Antkraquinone-1 : 5-disulphonic Acid 

CO S0 3 H 




'0 

C 14 H 8 8 S 2 MW, 368 

Yellowish cryst. + 4H 2 0. M.p. 310-11 de- 
comp. Sol. H 2 0, EtOH. Anhyd. acid dis- 
solves in 1-5 parts H 2 at 15. Spar. sol. 
Me 2 CO. 

Na salt : + 5H 2 0. Sol. 7 parts H 2 at 
100, 54 parts at 18. 

K salt: sol. 28 parts H 2 at 100, 145 
parts at 18. 

NH salt : sol. 13 parts H 2 at 100, 44 
parts at 18. 

Ca salt : + 3H 2 0. Sol. 108 parts H 2 at 
18 and at 100. 

Dichloride : C 14 H 6 6 S 2 C1 2 . MW, 405. Yellow 
needles from PhN0 2 . M.p. 265-70 decomp. 
Sol. PhN0 2 . Spar. sol. AcOH, chlorobenzene. 

Diamide: C 14 H 10 6 N 2 S2. MW, 366. Does 
not melt below 350. Spar. sol. all solvents. 

Dianilide : reddish-yellow prisms from PhN0 2 . 
M.p. 269-70 decomp. 

Fierz-David, Helv. Chim. Acta, 1927, 10, 

202. 

Lauer, J. praJct. Chem., 1931, 130, 185. 
Rogers, StoweU, U.S.P., 1,721,317, (Chem. 

Abstracts, 1929, 23, 4230). 

Anthraquinone-1 : 6-disulphonic Acid. 

Yellow needles + 5H 2 from HC1, golden 
prisms + 5H 2 from AcOH. M.p. 215-17. 

Na salt : + 3 or 5H 2 0. EasUy sol. H 2 0. 

K salt : + liH 2 0. Sol. 7 parts H 2 at 
100, 95 parts at 18. 

NH^ salt : very sol. H 2 0. 

Ca salt : + 5H 2 0. Sol. 6 parts H 2 at 100, 
65 parts at 18. 

Dichloride : a 4 H 6 6 S 2 Cl 2 . MW, 405. YeUow 
needles from PhN0 2 . M.p. 197-8 decomp. 
Sol. PhN0 2 , chlorobenzene. 



Dianilide : yellow cryst. powder from chloro- 
benzene or anisole. M.p. 227-8 decomp. 

Lauer, J. praM. Chem., 1931, 130, 185. 
Fierz-David, Helv. Chim. Acta, 1927, 10, 

207. 
Wedekind, D.R.P., 202,398, (Chem. 

Zentr., 1908, II, 1476). 

Anthraquinone-I : 7-disulphonic Acid. 

Cryst. + 4H 2 0. Very sol. H 2 0, EtOH. Sol. 
AcOH. Melts in its own H 2 of cryst. at 120. 

Na salt : + 2H 2 0. Very sol. H 2 0. 

K salt : + 2H 2 0. Very sol. H 2 0. 

NH^ salt : + 2H 2 0. Very sol. H 2 0. 

Ca salt : + 6H 2 0. Very sol. H 2 0. 

Dichloride : C 14 H 6 O 6 S 2 C1 2 . MW,405. Brown- 
ish-yellow plates from PhJST0 2 . M.p. 231-2. 

Dianilide : yellow prisms from anisole or 
chlorobenzene. M.p. 237-8. 

Lauer, J. praJct. Chem., 1931, 130, 185. 
Fierz-David, Helv. Chim. Acta, 1927, 10, 

205. 
Wedekind, D.R.P., 202,398, (Chem. 

Zentr., 1908, II, 1476). 

Anthraquinone-1 : 8-disulphonic Acid. 

Cryst. + 5H 2 0. M.p. 293-4 decomp. An- 
hyd. acid sol. 1-5 parts H 2 at 15. Sol. 
EtOH. 

Na salt: + 4H 2 O. Sol. 8 parts H 2 at 
95 parts at 18. 

salt : + 2H 2 0. Sol. 45 parts H at 
565 parts at 18. 

salt: +2H 2 0, Sol. 7 parts H 2 at 
102 parts at 18. 
salt : + 5-pI 2 0. Sol. 
Spar. sol. cold_. 
Dichloride : 
prisms from 
Sol. PhN0 2 . 
sol. AcOH. 
Diamide: C 1A H 1ft ONoSo. MW, 366. Does 



100, 
K 
100, 



100 

Ca 

100. 



C 14 H 6 6 S 2 C1 2 . 
PhN0 2 . M.g 
Mod. sol. 



parts H 2 at 



MW,405. Yellow 
222-3 decomp. 
chlorobenzene. Spar. 



C 14 H 10 6 N 2 S 2 
not melt below 340. Spar, sol most solvents. 

Dianilide : yellow cryst. powder from PhN0 2 
or chlorobenzene. M.p. 237-8 decomp. 

Lauer, J.prakt. Chem., 1931, 130, 185. 
Fierz-David, Helv. Chim. Acta 9 1927, 10, 

205. 
Rogers, StoweU, U.S.P., 1,721,317, (Chem. 

Abstracts, 1929, 23, 4230). 

Anthraquinone-2 : 6-disulphonic Acid. 

Yellowish cryst. + 6H 2 0. Easily sol. H 2 0. 
Sol. EtOH. Insol. Et 2 0, C 6 H.. 

Na salt : yeUow cryst. + 2H 2 0. Sol. to 18% 
in H 2 at 100, 4% at 18. 

K salt : yeUow cryst. Sol. to 8% in H 2 at 
100, 1-5% at 18. 

NH* salt : yellow cryst. Sol. to 31% in H0 
at 100*, 5-5% at 18. 

Ca salt : pale yellow cryst. + SELO. Sol. to 
2-4% in H 2 at 100. 



Anthraguinone-2 : 7-disulplionic Acid 193 



Aiithraqiiinone-2-sulplioiiic Acid 



Dichloride : C^HeOgSaClg. MW, 405. Yellow 
leaflets from chlorobenzene. M.p. 250. 
Dianilide : m.p. 321. 

Lauer, J. prakt. Chem., 1931, 130, 185. 
Kara-David, Helv. Chim. Acta, 1927, 10, 

219 
Thuminler, D.R.P., 214,156, (Clem, 

Zentr., 1909, II, 1396). 

Anthraq^iinone-2 : 7-disulphonic Acid. 

Yellow cryst. Very sol. H 2 0. Sol. EtOH. 
Insol. Et 2 0, C 6 H 6 . 

Na salt : + 4H 2 0. Very sol. H 2 0. 

NH salt : + 1H 2 0. Very sol. H 2 0. 

K salt : + 1H 2 0. Very sol warm H 2 0. 

Ca salt : + 2H 2 O. Sol. to 6% in H 2 O at 
100. 

Dichloride : C 14 H 6 6 S 2 C1 2 . MW, 405. Yellow 
needles from CHC1 3 . M.p. 186. 

Dianilide : m.p. 192. 

Lauer, J. prakt. Chem., 1931, 130, 185. 
Fierz-David, Helv. Chim. Acta, 1927, 10, 
219. 

Anthraquinone-1-mercaptan (a-Mercapto- 
anthraquinone) 

CO SH 




C 14 H 8 2 S 



MW, 240 



Orange-yellow prisms or yellow needles from 
AcOH. M.p. 187. Sol. AcOH. Spar. sol. 
EtOH, C 6 H 6 . Sol. ale. alkalis to violet sols. Sol. 
cone. H 2 S0 4 with red col. changing to yellow. 

S-Me: C 15 H 10 2 S. MW,254. Yellow needles 
from EtOH. M.p. 218. Sol. C 6 H 6 . Mod. sol. 
EtOH. Spar. sol. pet. ether. 

S-Et : C 16 H 12 2 S. MW, 268. YeHow prisms 
from EtOH. M.p. 183. 

S-Vinyl: C 16 H 10 2 S. MW, 266. Brownish- 
red needles from EtOH. M.p. 163. 

Gattermann, Ann., 1912, 393, 113. 
Fries, Schurmann, Ber., 1919, 52, 2170. 
M.L.B., D.KP., 292,457, (Chem. Zentr., 
1916, II, 42). 

Anthraquinone-2-mercaptan ( p- M ercap- 
toanthraquinone) . 

YeUow needles from AcOH. M.p. 206. Spar. 
sol. usual solvents. Sol. alkalis to reddish- violet 
sols. Bed in cone. H 2 S0 4 . 

&-M e : pale yellow needles from EtOH. M.p. 
162. 

S-Et : golden-yellow needles from EtOH. 
M.p. 138. 

S- Vinyl : golden-yellow needles from 
EtOHAq. M.p. 133. 

Diet, of Org. Oomp. I. 



S-Allyl: C 17 H 12 2 S. MW, 280. Yellow 
needles from EtOH. M.p. 126. 

Gattermann, Ann., 1912, 393, 113. 
Pries, Schiirmann, Ber., 1919, 52, 2170. 
M.L.B., D.R.P., 292,457, (Chem. Zentr., 
1916, H, 42). 

Anthraquinone-1-oxaunic Acid. 

See under 1-Aminoanthraquinone. 
Anthraqiiinonequmoline . 
See Anthraquinolinequinone. 
Anthraquinone-1-sulplionic Acid (<x.-Sul- 
phoanthraquinone) 

CO SO^H 



C 14 H 8 5 S 








MW, 288 

Leaflets. M.p. 218. Very sol. H 2 0. Ppd. 
by HC1. Cryst. + 3H 2 from H 2 0. Anhyd. 
cryst. from AcOH. NH 3 > 1-aminoanthra- 
quinone. Ca(OH) 2 under pressure > 1-hydr- 
oxyanthraquinone. NaC10 3 + HC1 > 1- 
chleroanthraquinone . 

Na salt : yellow pearly leaflets + 1H 9 0. Sol. 
to 5% in H 2 at 100. 

K salt : yellow pearly leaflets. Sol. to 3-8% 
in H 2 at 100. 

NH salt : very sol. hot H 2 0. 

Ca salt : + 3H 2 0. Sol. to 1-8% in H 2 at 
100. 

Chloride : C 14 H 7 4 SC1. MW, 306-5. YeUow 
needles from PhN0 2 . M.p. 216-18. Hyd. by 
hot H 2 O. Heat. > 1-chloroanthraquinone. 

Anilide : golden-yellow cryst. M.p. 214. 

Eierz-David, Helv. Chim. Acta, 1927, 10, 

198. 

Lauer, J. prakt. Chem., 1931, 130, 185. 
Schwenk, Waldmann, Z. angew. Chem., 

1932, 45, 17. 
du Pont, U.S.P., 1,881,498, (Chem. Ab- 

stracts, 1933, 27, 515). 

Anthraquinone-2-sulphonic Acid (fi-Sul- 
phoanthraquinone) . 

Leaflets + 3H 2 0. Sol. H 2 O, EtOH. Insol. 
Et 2 0. Ppd. from H 2 by cone. HC1. 

Na salt : + 1H 2 0. Sol. to 21% in H 2 at 
100, 0-8% at 18. Insol. EtOH, Et 2 0. Known 
in commerce as " silver salt." 

K salt: yellow leaflets. Sol. to 12-5% in 
H 2 at 100, 0-9% at 18 



Nl 
at 18 

Ca salt : 
100. 

Me ester : 
M.p. 123. 

Et ester: C 16 H 12 5 S. MW,316. White cryst. 
M.p. 125. 

13 



salt : sol. to 46% in H 2 at 100, 5% 
+ 2H 2 0. Sol. to 0-5% in H 2 at 
C 15 H 10 5 S. MW, 302. Cryst. 



Anthraquinone-1 : 2 : 5 : 6-tetra- 194 

carboxylic Acid 

Chloride: C 14 H 7 4 SC1. MW, 306-5. Pale 
yellow needles from C 6 H 6 or chlorobenzene. 
M.p. 197. Stable to cold H 2 0. 

Amide : C 14 H 9 4 ]SrS. MW, 287. Yellow cryst. 
from AcOH. M.p. 261. 
Anilide : yeHo wish-brown cryst. M.p. 193. 
Fierz-David, Eeh\ Chim. Ada, 1927, 10, 

216. 

Lauer, J. praJct. Chem., 1931, 130, 185. 
Schwenk, Z. angew. Chem., 1931, 44, 912. 
I.G., D.R.P., 576,444, (Chem. Abstracts, 
1933, 27, 3722). 

Anthraquinone-1 :2 :5 : 6-tetracarboxylic 
Acid 

CO COOH 



HOOC! 6 
HOOC 




COOH 



MW, 384 
Does not 



C 18 H 8 10 

Cream coloured needles from H 2 0. 
melt below 360. 

Tetra-Me ester: C 22 H 16 10 . MW,440. Pow- 
der from xylene. M.p. 292-3. Spar. sol. most 
solvents. 

Cook, J. Chem. Soc., 1931, 2531. 

Anthraquinone-1 : 2 : 6 : 7-tetracarboxylic 
Acid. 

Tetra-Me ester : cryst. from C 6 H 6 . M.p. 188- 
90. 

Cook, J. Chem. Soc., 1933, 1595. 

Anthraquinone-1 :2 : 7 : 8-tetracarboxyHc 
Acid. 

Tetra-Me ester : yellow rosettes from xylene. 
M.p. 237-9. 

Cook, J. Chem. Soc., 1933, 1595. 

Anthraquinone-1 :3:5 : 7-tetracarboxylic 
Acid. 

Yellow needles. Does not melt below 300. 
Spar. sol. hot PhN0 2 . Insol. most org. solvents. 
Tetra-chloride ; yellow needles from C 6 H 6 . 
Scholl, Meyer, Keller, Ann., 1934, 513, 
299. 

Anthraquinone-1 :4:5 : 8-tetracarboxylic 
Acid. 

Yellow prisms from AcOH. 
Tetrachloride : colourless leaflets from C 6 H 6 . 
Scholl, Meyer, Keller, Ann., 1934, 513, 
302. 



Anthraquinone - 1 
Acid 




C 17 H 8 8 



; 2 : 3 - tricarboxylic 
COOH 



MW, 340 



Anthrarufin 



Tri-Me ester : C 20 H 14 8 . MW, 382. Cryst. 
from C 6 H 6 -cyclohexane. M.p. 184-5. 
Cook, J. Chem. Soc., 1933, 1595. 

Anthraquinone -1:2:4- tricarboxylic 
Acid. 

Yellow cryst. from EtOH. Does not melt 
below 320. Insol. H 2 O. Zn + NH 3 > an- 
thracene- 1 : 2 : 4-tricarboxylic acid. 



Tri-Et ester : C 23 H 20 8 . MW, 424. Leaflets 
from EtOH.Aq. M.p. 125. 

Elbs, J. praJct. Chem., 1890, 41, 126. 

Anthraquinone -1:2: 5 - tricarboxylic 
Acid. 

Tri-Me ester: cryst. from C 6 H 6 . M.p. 212-13. 
Cook, J. Chem. Soc., 1933, 1595. 

Anthraquinone -1:2 : 6 - tricarboxylic 
Acid. 

Tri-Me ester : cryst. from xylene. M.p. 234. 

Cook, J. Chem. Soc., 1933, 1595. 



Anthraquinone - 1 : 
Acid. 

Tri-Me ester : cryst. from CHCl 3 ~EtOH. 
204. 

Cook, J. Chem. Soc., 1933, 1595. 



7 - tricarboxylic 
M.p. 



6 - tricarboxylic 

below 300. 



Insol. H 2 0. 



Anthraquinone - 1 : 
Acid. 

Yellow leaves. Does not melt 
Spar. sol. most org. solvents. 

Elbs, J. prakt. Chem., 1890, 41, 144. 

Anthrar obin . 

See Deoxy alizarin. 

Anthrarufin (1 : 5-Dihydroxyanthraquinone 

CO OH 



C 14 H 8 4 




HO CO 

MW, 240 

Pale yellow plates from AcOH. M.p. 280. 
Sublimes. Sol. C 6 H 6 , PKNOo. Spar. sol. EtOH, 
AcOH, Et 2 0. Sol. KOH. Prac. insol. carbon- 
ates and NH 3 . Sol. cone. H 2 S0 4 to fluor. 
crimson sol. HN0 3 + H 2 S0 4 > 4 : 8-dinitro 
deriv. 

Di-Me ether: C^JEiaO^ MW, 268, Pale 
yellow needles from EtOH. M.p. 236. Bluish- 
red in cone. H 2 S0 4 . Oxime : brown amorph. 
powder from EtOH.Aq. M.p. 196. 

Et ether: C 16 H 12 4 . MW, 268. Yellow 
needles from EtOH.Aq. M.p. 163-4. Acetyl : 
yellowish leaflets. M.p. 172-3. 

Di-Et ether : C, 8 H 16 4 . MW, 296. Yellow 
needles from EtOH. M.p. 178. 

Diphenyl ether : C 26 Ht 6 4 . MW,392. Yellow 



needles from AcOH or 
most org. solvents, 



M,p. 215, Sol. 



Antlirazine 



195 



Anthroxanaldeliyde 



Diacetyl : yellow needles from AcOH. M.p. 
244. Sol. AcOH. Spar. sol. EtOEL Cone. 
H 2 SO 4 > red sol. > anttLrarufin. 

Schwenk, J. praJct. Chem., 1921, 103, 106. 
National Aniline & Chemical Co., B.P., 

181,673, (Chem. Abstracts, 1922, 16, 

3762). 
Gewerkshaft Mathias Stinnes, D.R.P., 

605,446, (Chem. Abstracts, 1935, 29, 

1100). 



Anthrazine (Anthracene-1 : 2 : 1' : 2'-azine) 




C 28 H 16 N 2 MW, 380 

Yellowish-brown needles from PhN0 2 . M.p. 
390. Sublimes at about 340. Sol. hot PhN0 2 , 
anisole. Spar. sol. CHC1 3 , CC1 4 . Insol. other low 
boiling solvents. Dil. sols, show yellowish-green 
fluor. Sol. cone. H 2 SO 4 , cone. HN0 3 . Insol. 
dil. acids, alkalis. 

B.H^SO^ : brownish-red needles. Hyd. by hot 
H 2 0. 

Pier ate : red needles. Decomp. on warming 
with EtOH or PhN0 2 . 

Scholl, Berblinger, Kiinzel, Ber., 1907, 

40, 933. 
Bayer, D.R.P., 172,684, (J. Chem. Soc., 

1906, 90, 868). 
Schiedt, /. prakt. Chem., 1941, 157, 203. 

Anthroic Acid. 

See Anthracene-carboxylic Acid. 
l-Anthrol (l-Hydroxy anthracene, a-anthrol) 

OH 




C 14 H 10 MW, 194 

Brown leaflets or needles from EtOH or 
AcOH. M.p. 150-3. Sol. org. solvents with 
blue fluor. Sol. alkalis to unstable, green fluor. 
sols. Heat with acetamide > 1-amino- 
anthracene. 

Me ether: C 15 H 12 0. MW, 208. Leaflets. 
M.p. 70. 

Et ether: C^H^O. MW, 222. Needles. 
M.p. 69. Sol. EtOH with blue fluor. 

Acetyl : 1-acetoxyanthracene. Needles from 
EtOH. Turns brown at 80, m.p. 130 decomp. 
Ox. > 1-acetoxyanthraquinone. 

Dienel, Ber., 1905, 38, 2863. 
Fierz-David, Blangey, Streit, Helv. Chim. 
Acta, 1946, 29, 1718. 



2-Aatlirol (2-Hydroxyanthmcene, $-anthrol). 

Brownish leaflets or needles from EtOH.Aq. 
Decomp. at 200. Very sol. EtOH, Et 2 0, 
Me 2 CO. Insol. H 2 0. Sol. KOH, Ba(OH) 2 with 
green fluor. EtOH sol. shows reddish-violet 
fluor. Reduces Ag sols, on warming. Ale. 
FeCl 3 > yellow coL 

Me ether : m.p. 175-8. 

Et ether : needles from EtOH.Aq. M.p. 145-6. 
Can be distilled. 

Acetyl : 2-acetoxyanthracene. Leaflets from 
C 6 H 6 . M.p. 198. Sol.C 6 H 6 . Spar. sol. AcOH. 
Ox. > 2-aeetoxyanthraquinone. 

Lagodzinski, Ann., 1905, 342, 67. 

9-Anthrol. 

See Anthranol. 

2-Antlirol-l -aldehyde (2-Hydroxy- 1 -alde- 
hyctoanthracene) 

CHO 

H 




C 15 H 10 2 " " ' MW,222 

Light yellowish needles from EtOH. M.p. 

164. Sol. EtOH, NaOH. Spar. sol. cold H 2 0. 

Ethereal sol. shows green fluor. Ale. FeCl^ >- 

olive-brown col. 

Oxime : greenish leaflets from C 6 H 6 . M.p. 

197 decomp. Spar. sol. cold C 6 H 6 . 
Azine : deep red needles. Does not melt 

below 300. Spar. sol. usual solvents. 

Bezdzik, Friedlander, Monatsh., 1909, 30, 
874. 

Anthrol-carboxylic Acid. 

See Hydroxyanthracene-carboxylic Acid. 
Anthrone 

CO 




C 14 H 10 MW, 194 

Keto form of anthranol. Needles from AcOH . 
M.p. 154 (163-70). Sol. hot C 6 H 6 . Ale. sol. 
shows blue fluor. In hot caustic alk. sol. > 
anthranol. Ac 2 > acetylanthranol (ms- 
acetoxyanthracene). Not oxidised by FeClg, 
Br, etc. Does not condense with ^p-nitrosodi- 
methylaniline. Does not couple with diazo 
comps. 

Meyer, Organic Syntheses, Collective 
Vol. I, 52. 

Antliroxanaldehyde 

C-CHO 








C 8 H 5 2 N 



N 



MW, 147 



Antliroxanic Acid 



196 



Antipyraldehyde 



Long, yellowish needles from pet. ether. M.p. 
72*5. Sol. hot H 2 0. Sublimes. Volatile in 
steam. 

Oxinie : needles. M.p. 172-3. 

Bamberger, Ber., 1909, 42, 1707. 
Heller, Ber., 1916, 49, 523. 



Anthroxanic Acid 



OCOOH 




\ 



C 8 H 5 3 N MW, 163 

Needles. M.p. 190 (196 decomp., 197-5). 
Sol. Me 2 CO. Mod. sol. hot H 2 0. Spar. sol. 
AcOH, C 6 H 6 . Insol. cold H 2 0. EeS0 4 + 
NH 3 .Aq. > isatin. 

Brucine salt : prisms + H 2 from MeOH. 
M.p. 210-12 decomp. 

Quinine salt : prismatic needles from MeOH. 
M.p. 198-202 decomp. 

Strychnine salt : prisms + H 2 0. M.p. 210- 
12 decomp. 

Me ester : C 9 H 7 3 N. MW, 177. M.p. 70. 

Et ester: C 10 H 9 3 N. MW, 191. Needles. 
M.p. 64-5. 

Amide: C 8 H 6 2 N 2 . MW, 162. Needles from 
H 2 0. M.p. 211-12. 

HeUer, Ber., 1916, 49, 523. 
Leuchs, Ber., 1925, 58, 1452, 2827. 

Antiarigenin 

(?)HO 




OH 

Suggested structure 
C 23 H 32 7 MW, 420 

Cardiac poison. M.p. 242. [a],, + 42. 
Benzoyl deriv. : m.p. 307. [a] D + 27. 
Semicarbazone : needles from AcOH.Aq. 
Does not melt below 250. 

Tschesche, Haupt, Ber., 1936, 69, 1377. 
Doebel, Schlittler, Eeichstein, Helv. Chim. 
Acta, 1948, 31, 688. 

Antiarin 

The name given to two isomeric glycosides 
isolated from the milk sap of Antiaris toxicaria. 



a-. 



Tablets from H 2 0. M.p. 220-5. 
D-gulomethylose + antiarigenin. 



MW, 566 
Hyd. >- 



Cryst. from H 2 O. M.p. 225. Hyd. > 
rhamnose + antiarigenin. 

Tschesche, Haupt, Ber., 1936, 69, 1378. 
Doebel, Schlittler, Beichstein, Helv. Chim. 
Acta, 1948, 31, 688. 

Antiarol (5-Hydroxy-\ : 2 : 3-trimethoxybenz- 
ene) 



OCH, 



H 



C 9 H 12 4 




CH 3 



MW, 184 

Occurs in Antiaris toxicaria, Lesch. Needles 
from H 2 0. M.p. 148. Sol. EtOH. Spar. sol. 
Et 2 0. Prac. insol. H 2 0. FeCl 3 > yellowish- 
green col. Ox. > 2 : 6-dimethoxy->-benzo- 
quinone. 

Me ether : 1:3:4: 5-tetramethoxybenzene. 
C 10 H 14 4 . MW, 198. Leaflets. M.p. 47. B.p. 
271. Sol. EtOH, Et 2 0, C 6 H 6 . 
Acetyl : prisms from EtOH. M.p. 74. 

Hattori, Acta Phytochimica, 1931, 5, 219. 
Chapman, Perkin, Robinson, J. Ghem. 
Soc., 1927, 3028. 

Antiarose. 

See D-Gulome thy lose. 
Antifebrin. 
See Acetanilide. 
Antimony pentaetayl 

(C 2 H 5 ) 5 Sb 
C 10 H 25 Sb MW, 267 

B.p. 100. 

Buckton, Jahresber. Fortschr. Ghem., 1860, 
374. 

Antimony triethyl. 

See Triethylstibine. 
Antimony trimethyl. 
See Trimethylstibine. 
Antimony triphenyl. 
See Triphenylstibine. 
Antimycin-A 

C 28 H 40 9 N 2 MW, 548 

Antibiotic antifungal compound from a species 
of Streptomyces. M.p. 139-40. [a]?? + 64-8 
(c = 10 in CHC1 3 ). Sol. EtOH. InsoL H 2 0. 
Weakly acidic. 

Dunshee, Leben, Keitt, Strong, </* Am. 
Ghem, Soc., 1949, 71, 2436. 



Antipyraldehyd (l-Phenyl-2 : 3- 
aMehydopyrazolone-5, 4:-aldehydoantipyrine) 



OC 



N-CH 3 
N-CH 



C 12 H 12 2 N 2 



MW, 216 



Antipyrine 



197 



Aphylline 



M.p. 216-17. 

Oxime : syn-, m.p. 228-30 : anti- 9 m.p. 
220-2. 

Phenylhydrazone : syn-, m.p. 253-5 : anti-, 
m.p. 190-2. 

p-Nitrophenylhydrazone : syn-, m.p. 276-80 : 
anti-, m.p. 240-2. 

Semicarbazone : syn-, m.p. 249-51 : anti-, 
204-8. 

Passerini, Losco, Gazz. chim. ital., 1940, 

70, 710. 
Ridi, Gazz. chim. ital., 1941, 71, 95. 

Antipyrine (l-PJienyl~2 : 3-dimethylpyrazo- 
lone-5, phenazone) 



JST-CEU 



C n H 12 ON 2 MW, 188 

Leaflets or scales from Et 2 5 C 6 H 6 or H 2 0. 
M.p. 114. B.p. 319. Sol. to 85% in H 2 0, 
75% in EtOH, 2-5% in Et 2 O. Powerful anti- 
pyretic. Weak base. POC1 3 > chloride, 
C n H 12 N 2 Cl 2 , MW, 243 : m.p. 137. HN0 2 > 
green col. (nitroso-comp.). Acid sol. gives ppt. 
with Mayer's reagent. 

Picrate : yellow needles. M.p. 188. 

Salicylate: Salipyrine. M.p. 92. Sol. 200 
parts cold H 2 0, mod. sol. hot H 2 0. 

Acetylsalicylate : Acetopyrine. M.p. 65. 

Thorns, Schnupp, Ann., 1923, 434, 296. 

Rodionov, Bull. soc. Mm., 1926, 39, 
305. 

Reuter, U.S.P., 2,005,505, (Chem. Ab- 
stracts, 1935, 29, 5130). 

Soc. des usines chim. Rhdne-Poulenc, 
D.R.P., 581,779, (Chem. Abstracts, 1934, 

28, 1366). 

Klebanskii, Lemke, Chem. Abstracts, 1935, 

29, 6891. 

Antrycide (4- Amino-6- [%'-amino-6'-methyl- 
pyrimidyl - 4' - amino] - quinaldine - 1 : 1' - dimetTio 
salts, 4:-amino-6-[2'-amino-l':6'-dimethylpyrimid- 
inium-4:' -amino]-l : 2-dimethylquinolinium salts) 





6n 3 



J 



C 17 H 22 N 6 X 2 MW, 310(X 2 ) 

Antimalarial drug for treatment of animal 
trypanosomiasis. Administered in the form of a 
salt, usually the chloride or methosulphate. 

Di-iodide : in .p. 312-13 decomp. 

Dichloride : m.p. 316-17 decomp. 

Dibromide : m.p. 316 decomp. 



Di-methosulphate : m.p. 265-6. 

Curd, Davey, Nature, 1949, 163, 89; 

Brit. J. Pharmacol., 1950, 5, 25. 
Ainley, Curd, I.C.I., B.P. 634,818, (Chem. 

Abstracts, 1950, 44, 7889). 
Curd, I.C.I., B.P. 634,531. 

Antrypol. 
See Bayer 205. 
Aphrodine. 
See Yohimbine. 
AphylHdene 

CH CH 2 CH 2 
H N CH 2 



H 2 C N CH-CH CH 2 
CH 2 CO CH 2 

Suggested structure 

C 15 H 22 ON 2 MW, 246 

Alkaloid from Anabasis aphylla. Plates from 
pet. ether. M.p. 112-13. [oft 8 +5-57 in 
MeOH. 

B,HCl: cryst. from EtOH M.p. 235-7. 
[<*!> + 30 in H 2 0. 

B,HClOi : prisms from H 2 0. M.p. 212-13. 
[at + 15 in MeOH. 

Methiodide: needles from MeOH. M.p. 223-5. 
[a] D + 9-8 in H 2 0. 

Picrolonate : yellow prisms from EtOH. M.p. 
235-6. 

Orekhov, Chem. Zentr., 1938, 1, 2365. 
Or6khov, Menschikov, Ber., 1932, 65, 234. 
Or^khov, Norkina, Maximova, Ber., 1934, 

67, 1976. 

Orekhov, Norkina, Ber., 1934, 67, 1845. 
Spath et al, Ber., 1942, 75, 805. 



Aphylline 



CH 2 



H 



H 2 C 



,C CEH 



CH 2 CH 9 



H 



CH-CH 

CH 2 CO CH 2 

MW, 248 

Alkaloid from Anabasis aphylla. B.p. 200 /4 
mm. [a]3> + 10-3 in MeOH. 

B,HCl : prisms. M.p. 207-9. [a] D +12-91. 

Methiodide : needles from MeOH. M.p. 212- 
13 decomp. 

Picrolonate : yellow prisms from EtOH. M.p. 
230-1 decomp. 

Or6khov, Chem. Zentr., 1938, 1, 2365. 
Or^khov, MenscMkov, Ber., 1932, 65, 

234; 1931,64,266. 
Spath et al., Ber., 1942, 75, 805. 



Apigenin 



198 



Apione 



Apigenin (5:7: 4' '-Trihydroxyflavone) 
HO CO 

/5\/4\PTT 

J6 Y SH- 11 /srsA 

HOI 7 



24 

Ale. FeCL 



MW, 298. 
7-Acetyl : 



C 15 H 10 5 MW, 270 

Constituent of parsley and celery as glyeoside, 
apiin. Occurs in yellow dahlia. Yellow needles 
from PyAq. M.p. 347-8 (352). Sol. Py. 
Mod. sol. hot EtOH. Insol. H 2 0. Sol. aq. 
carbonates to yellow sols. Cone. H 
yellow sol. with weak greenish fluor. 
> brownish-black col. 

1-M e ether : see Genkwanin. 

4! -Me ether : see Acacetin. 

5 : '-Di-Me ether : C 17 H 14 5 . 
Needles from EtOH.Aq. M.p. 264 
m.p. 204. 

7 : 4'-ZH-Jkfe ether 
Pale yellow needles. M.p! 171-2 
EtOH. Cone. H 2 S0 4 
greenish fluor. Alk. 
one + phloroglucinol. 
EtOH. M.p. 195~6 r 

Tri-Me ether : C 18 H 16 5 . MW, 312. Needles 
from EtOH. M.p. 156. Sol. C 6 H 6 . Cone. 
H 2 S0 4 > pale yellow sol. with green fluor. 

7 : 4'-Di-Et ether : C 19 H 18 5 . MW, 326. Yel- 
low needles. M.p. 163-4. Spar. sol. EtOH. 
5-Acetyl: leaflets from Me 2 CO. M.p. 148-149-5. 



MW, 298. 
, Spar. sol. 
pale yellow sol. with 
> p-hydroxyacetophen- 
5-Acetyl : needles from 



* (199-200). 

MW, 312. 



MW, 354. M.p. 
needles from EtOH. M.p. 
M.p. 210-12. 



Tri-Et ether: C 21 H 22 5 
189-91. 

5:7: 4/ -Triacetyl : 
181-2 (186). 

5:7: 4:'-Tribenzoyl : needles. 
Spar. sol. EtOH. 

Czajkowski, Kostanecki, Tambor, Her., 

1900, 33, 1988. 
Schmid, Waschkau, Monatsh , 1928, 49, 

83. 
Nakano, Ghent. Abstracts, 1932, 26, 4334. 

Apiin 

C 2 6H 28 14 MW, 564 

Apigenin glycoside. Constituent of parsley. 
Needles + 1H 2 0. M.p. 228. Sol. EtOH, hot 
H 2 : pptes from these in gelatinous form. 
Dil. H 2 S0 4 >- apigenin + apiose + glucose. 

Vongerichten, Ann., 1901, 318, 121. 

Apiol (2 : 5-Dimethoxy-3 : 4=-methylenedioxy-l- 
allylbenzene : cf. Dill-apiol) 




Chief constituent of oil of parsley. Needles. 
M.p. 30. B.p. 294, 179 /33 mm. Sol. EtOH, 
Et 2 0. Insol. H 2 0. DJ 1-015. < 4 1-5380. 
Volatile in steam. Ox. ^ apiolic acid. Ale. 
KOH > isoapiol. 

Walmsley, Quart. J. Pharm. PharmacoL, 
1929,1, 388 ; Chemist and Druggist, 1928, 
109, 127 ; Pharm. J., 1928, 121, 89. 

Baker, Savage, J. Chem. Soc., 1938, 1602. 

Apiolaldehyde (Apiolic aldehyde, 2 : S-di- 
methoxy*& : 4-methylenedioxybenzaldehyde : cf. 
Dill-apiolaldehyde) 

CHO 



CHoO 




C 10 H 10 5 MW, 210 

Needles from EtOH. M.p. 102. B.p. 315. 
Sol. EtOH, Et 2 0, C 6 H 6 , AcOH, CS 2 . Spar. sol. 
pet. ether. Cone. H 2 S0 4 ^yellow sol. > 
olive-green on warming. Gives bisulphite comp. 
Ox. >- apiolic acid. 

Oxime: needles from EtOH. M.p. 161. 
Sol. Et 2 0, AcOH, AcOEt, hot EtOH. Acetyl : 
prisms from EtOH. M.p. 128-9. 

p-Nitrophenylhydrazone : orange-red. M.p. 
228-9. 

Fabinyi, Sz4ki, Ber., 1917, 50, 1335. 

Apiolic Acid (2 : 5-Dimethoxy-3 : ^-methyl- 
enedioxybenzoic acid : cf. Dill-apiolic Acid) 

COOH 



CH 3 Ol 



C 10 H 10 6 " MW 5 226 

Needles from H 2 0. M.p. 175. Sol. Et 2 0, 
hot EtOH, hot AcOH, C 6 H 6 , AcOEt. Spar. sol. 
hot H 2 0, insol. cold, k = 8-0 x 10" 6 at 25. 
Dil. H 2 S0 4 at 130-40 > apione. 

Jfe ester : U H 12 6 . MW,240. Needles from 
H 2 0. M.p. 71-2* Sol BtjO, EtOH, AcOH. 
Spar. sol. hot H 2 0. 

Nitrile : 0^0^. MW, 207. Cryst. from 
EtOHAq. M.p. 135-5. Sol. ord. org. solvents. 
Insol. H 2 0. 

Baker, Savage, J, Chem. Soc,, 1938, 1606. 
Oiamioian, Silber, Ber., 1888, 21, 1623. 

Apione (1 : &-Dimethoxy-2 : $-methylenedioxt/~ 
benzene) 

OCH 




MW, 222 C 9 H 10 4 



MW, 182 



Apionic Acid 



199 



Apocafieine 



Needles from EtOH.Aq. M.p. 79. Sol. 
Et 2 O 9 AcOH, AcOEt, hot EtOH. Insol. H 2 O. 
Volatile in steam. 

Baker, Savage, J. Chem. Soc., 1938, 1605. 
Ciamician, Silber, Ber., 1888, 21, 1630. 

Apionic Acid (Tetrahydroxyisovaleric acid] 



C 5 H 10 6 MW, 166 

Colourless syrupy liq. HI + P > isovaleric 
acid. 

Ca salt : cryst. + 2H 2 0. [ag, - 1-34 in H 2 0. 
Phenylhydrazide : m.p. 127. 

Vongerichten, Ann., 1902, 321, 78. 
Schmidt, Ann., 1930, 483, 12L 

Apionol (1:2:3:4- Tetrahydroxybemene, 
phenetetrol) 



OH 
A 

UOH 

OH 



CO 



or 



H< 
HC 



:q 9HOH 



CHOH 



O 



C 6 H 6 4 



MW, 142 

Pale pink needles from AcOEt. M.p. 161. 
Sol. 400 parts C 6 H 6 . Sol. H 2 0, EtOH, Et 2 0, 
AcOH. FeCl 3 > blue col. 

1 : 2-Di-Jf e ether : C 8 H 10 4 . MW, 170. B.p. 
283. 3 : 4-Diacetyl : cryst. from pet. ether. 
M.p. 85. 

1 : 4-Di-Me ether : m.p. 106. B.p. 298. 
Sol. EtOH, Et 2 0, C 6 H 6 , hot H 2 0, alkalis. 
2 : 3-Diacetyl : cryst. from EtOH. M.p. 144. 

Tetra-Me ether : C 10 H 14 4 . MW, 198. Prisms 
from ligroin. M.p. 89. Sol. EtOH, Et 2 0, 
Me CO, C 6 H 6 . Volatile in steam. 

fetra-acetyl : cryst. from EtOH. M.p. 142 
(136, 139). Sol. Et 2 0. 

Tetrabenzoyl : m.p. 191-2. 

Einhorn, Cobliner, Pfeiffer, Ber. } 1904, 

37, 119. 
Terry, Milas, J. Am. Chem. Soc., 1926, 

48, 2647. 
Wessely, Lechner, Monatsh., 1932, 60, 

160. 

Apiose (Tetrahydroxyisovakraldehyde) 

HOH 2 C> C(OH) ' CH(OH) ' CHO 
C 5 H 10 5 MW, 150 

Clear pale yellow syrup. [a]|> 5 + 5-6 in H 2 0. 
Br > apionic acid. 

p-Bromophenylosazone : m.p. 211-12. 

Benzylphenylhydrazone : cryst. from CHC1 3 . 
M.p. 187-8. Sol. Py, hot EtOH. Mod. sol. 



H*OOC->C 6 H 5 



CHCL, AcOEt. Spar. sol. Et 9 0, CCL, ligroin. 
Ms ~ 94-0 in Py. 

Schmidt, Ann., 1930, 483, 115. 

Vongerichten, Ann., 1902, 321, 74. 

Hudson, Advances in Carbohydrate 
Chemistry, 1949, 4, 57. 

Aplotaxene. 

See Heptadecatetraene. 

Apoatropine (Tropine atropic ester, atrop- 
amine) 

CH 2 - CH - CH 2 
| CH 3 -N 
CH 2 ^3 

C 17 H 21 2 N JVIW, 271 

In belladonna root. Prisms from CHCL. 
M.p. 60-2. Very sol. EtOH, Et 2 0, CHC1 3 . 
C 6 H 6 , CS 2 . Mod. sol. ligroin, isoamyl ale. 
Spar. sol. H 2 0. Optically inactive. Has no 
mydriatic action. Cone. HC1 at 130 >- 
tropine, isatropic and atropic acids. Ba(OH) 2 
at 100 > tropine + atropic acid. 

B,HCl : leaflets. M.p. 237-9. Mod. sol. hot 
H 2 0. Spar. sol. EtOH, Me 2 CO. Insol. Et 2 0. 

"B,HBr : leaflets. M.p. 248. 

B,HAuGl : yeUow needles from H 2 0. M.p. 
112. 

Picrate : yellow needles. M.p. 166-8. Spar. 
sol. cold H 2 0. 

Hesse, Ann., 1893, 277, 292. 

Apocadalene (2-Methyl-8-isopropylnaphthal- 
ene) 

(CH 3 ) 2 CH 




C 14 H 16 MW, 184 

B.p. 282, 139-41/12 mm. DJ 0-9833. < 
1-5884. 

Picrate : orange-yellow needles from EtOH. 
M.p. 102. 

Styphnate : yellow needles from EtOH. M.p. 
166 (163-4). 

Barnett, Sanders, /. Chem. Soc., 1933, 

437. 
B/uzicka, Mingazzini, Helv. Chim. Acta, 

1922, 5, 710. 

Apocafieine (1 : 7-Dimethylcaffolide) 

CH 3 -N 90 

CO-O-C N-CH 3 

yO 

(30 NH 
C 7 H 7 5 N 3 MW, 213 

Cryst. from H 2 0. M.p. 154. Sol. EtOH, 
MeOH, AcOH, Me 2 CO. Spar. sol. cold H 2 0, 
Et 2 0, CHClg, C 6 H 6 , Prac. insol. CS 2 , CC1 4 , 
ligroin. Boiling H 2 >- caffuric acid. 

Biltz, Ber. : 1910, 43, 1618. 



Apocampliane 



200 



Apocinchene 



Apocamphane (a-JFenchocamphorane) 
CH 2 yH CH 2 



j CH 3 -9-CH 3 
CH 2 CH~ 



-CHo 



MW, 124 



MW, 186 



C 9 H 16 

M.p. 86. B.p. 148/755 mm. 

Komppa, Hasselstrom, Ann., 1932, 496, 
164. 

Apocamplioric Acid (Camphopyric acid) 

CH 2 yH CO OH 
i nTT .rxmr 

1 ^- / -"-3 V 3 

CH 2 CH COOH 
C 9 H 14 4 

Exists in two stereoisomeric forms. 

(I) Cis : 

Cryst. from H 2 0, m.p. 204 (209). Optically 
inactive. InsoLtJHClg. k = 3-5 X l(Kat 18. 

Anhydride: C 9 H 12 3 . MW, 168. Needles 
from EtOH, prisms from CHCL-pet. ether. 
M.p. 178 (174-5). Sol. EtOH, CHC1 3 . Spar. 
sol. Et 2 0. Sublimes. Volatile in steam. 

Bichloride : C 9 H 12 2 C1 2 . MW, 223. Colour- 
lessliq. B.p. 125-30/13 mm. Hyd.byhotH 2 0. 

Mono-anilide : m.p. 212. 

(II) Trans: 

Plates from H 2 0. M.p. 190-1. 
The cis-trans mixture (mesoapocamphoric 
acid, mesocamphopyric acid) has m.p. 163-70. 
Cryst. from H 2 0. 

Wallach, Ann., 1908, 362, 184. 
Komppa, Ann., 1909, 368, 151. 
Nametkin, Alexandroff, Ann., 1928, 467, 
191. 

p-Apo-2-carotenal 

C(CH 3 ) 



C 30 H 



-[CH:CH-C:CH] 2 CH 




From oxidation of (3-carotene. 
from MeOH. M.p. 139. 

Oxime: violet prisms. M.p. 180. 
Semicarbazone: m.p. 212. 

Karrer, Solmssen, Helv. Chim. 
1937, 20, 682, 1020. 

p-Apo-4-carotenal 

H 2 C C(CH 3 ) 2 

" 



C 25 H 34 



MW, 416 

Violet plates 



Acta. 9 



OHC-9-CH-CH 
CH 3 

MW, 350 



From oxidation of (3-carotene. Not obtained 
in cryst. form. 

Oxime: rhombic plates from MeOH. M.p. 
165. 

/Semicarbazone: carmine red powder from 
EtOH. M.p. 217 decomp. 

Karrer, Solmssen, Helv. Chim. Acta y 1937, 
20, 688, 1020. 

Apocholic Acid 
OH 



!H-[CH 2 ] 2 -COOH 



HO' 




MW, 390 



n 



M.p. 166-8 (176-7). [a] 2 D +49-87 
EtOH. Forms addition compounds. 

CH^COOH add. comp.: prisms from AcOH. 
M.p. 170-1. [a]! +45-35 in EtOH. 

C 6 H 6 add. comp. : needles. M.p. 174-5. 

Me ester: prisms + IMeOH, m.p. 83-4; 
solvent free, 88-90. 

Hydrazide: m.p. 191-2. [a]? +35-6 in 
EtOH. 

Devor, Marlow, J. Am. Chem. Soc., 1946, 

68, 2101. 

Barton, /. Chem. Soc., 1946, 1116. 
Boedecker, Ber., 1920, 53, 1852. 



Apocinchene 



CH-CH 




C 19 H 19 ON MW, 277 

Cinchona alkaloid obtained from cinchene 
with HBr. Cryst. from. EtOH. M.p. 209-10. 
Sol. acids and alkalis. 

B,HBr : needles. M.p. 256. 

Me ether: C 20 H 21 ON. MW,29L Oil. Picrate: 
m.p. 200 decomp. 

Et ether: C 2JL H 23 ON. MW,305. Prisms from 
EtOH.Aq. Mip. 70-1. Picrate : m.p. 179-80 
decomp. 

Acetyl : cryst. from ligroin. M,p. 118-19. 

Kenner, Statham, Jones, J. Chem. Soc, 9 

1935, 299. 
Comstock, Koenigs, Ber., 1885, 18, 2381. 



Apocinclionine 



201 



Apogossypolic Add 



Apocinchoniae (Allocinchonine) 
N 9 H 

ELC GEL 05 




i 



CICH-CEL 



!H(OH) CH CH 2 CH 2 

JSF 



C 19 H 22 ON 2 



MW, 294 

Prisms from EtOH. M.p. 219 (216). Sol. 
26 parts EtOH at 20. Mod. sol. hot EtOH. 
Spar. sol. Et 2 } CHCL, C 6 H 6 , Hgroin. Insol. 
H 2 0. [a]* +167-4 in EtC~~ ~ 
H 2 SO 4 > apocinchordcin. 

B,HCl: needles + 2H 2 0. 
H 2 0. 

B,HBr : needles + 1H 2 0. 



Heated with 
Hi? + 139 in 



. [a]J? +126 in 
H 2 0. 

0-Acetyl : plates from ligroin. M.p. 92-4. 
Sol. EtOH, Et 2 0, CHOj, C 6 H 6 . [a]i 6 + 71-4 
in EtOH. 

Q-Benzoyl : needles from Et 2 0. M.p. 118-19. 
B,HCl : cryst. + 2H 2 from 50% EtOH. M.p. 
223. 

Hesse, Ann., 1880, 205, 330. 

v. Peesis, Monatsh., 1902, 23, 444. 

L6ger, Compt. rend., 1918, 166, 76, 255. 



Apocodeine 

methyl ether) 



$- Apocodeine, apomorphine 3- 




C 18 H 19 2 N MW, 281 

Cryst. + lEtOH from EtOH. M.p. 104-5- 
106*5. Loses EtOH at 78 /2 mm. M.p. (sol- 
vent-free) 122-5-124-5. [ogf - 90 in EtOH. 

JS,HCl : cryst. from EtOH-Et 2 0. Softens at 
140, deeomp. at 260-3. [og? 43-3 in H 2 0. 

Folkers, J. Am. Chem. 8oc., 1936, 58, 
1814. 



Apoconchinine . 

See Apoquinidine. 

Apoconquinine . 

See Apoquinidine. 

Apocrocetin. 

See Hexadecaheptaene-dioic Acid. 

Apocupreine. 

See Apoquinine. 

Apocynamarin (Cyanotoxin, cymarigeniri) 

MW, 386 



Occurs in rhizomes of Apocynum androsaemi- 
folium, Linn. Cryst. from MeOH. M.p. 170-5 



deeomp. Product of hyd. of cymarin by cold 
HCL Bitter taste. Reducing agent. 
Benzoate : m.p. 230. 

Moore, J. Chem. Sac., 1909, 95, 734. 
Windaus, Hermanns, Ber., 1915, 48, 979. 
Searle, Journal American Inst. Homeo- 
pathy, 1931, 25, 460 (Review). 

Apocynin. 

See Acetovanillone. 

Ap of enchene ( 1 -Mefhyl-4z-isopropylcydopent- 
ene) 

HgC * C CH 2 

|| >CH-CH(CH 3 ) 2 
HC CH 2 
C 9 H 16 MW, 124 

B.p. 142-3. D 21 0-7945. n$ 1-4403. [!> 
+ 66-2. 

Hydrochloride : b.p. 60/8 mm. Di 8 0-9275. 
[a] p + 1-24. 

Hydrobromide : b.p. 83/13 mm. 

Nitrosochloride : cryst. from CHCL. M.p. 
115. [ag? - 272 in CHC1 3 . 

WaUach, Ann., 1911, 379, 185 ; 1909, 369, 
83, 95. 

Apogossypol 




Degradation product of gossypol. Unstable. 
Darkens in air. 

Hexa-Me ether: ppt. from C 6 H 6 with MeOH. 
M.p. 259. 

Hexa-Et ether: ppt. from C 6 H 6 with MeOH. 
M.p. 176-80. 

Hexa-acetyl: m.p. 291. 

Tetra-benzoyl: almost colourless cryst. from 
MeOH-C 6 H 6 . M.p. 314-16. 

Clark, J. Biol. Chem., 1928, 78, 159. 
Adams, Butterbaugh, J. Am. Chem. Soc., 
1938, 60, 2174, 2193. 

Apogossypolic Acid (4 : 5-Dimethoxy-3-iso- 
propylphthalic acid) 

CH(CH 3 ) 2 



CH 3 Ok v /COOH 

C 13 H 16 6 MW, 270 

Degradation product of gossypol. Cryst. 

from C 6 H 6 . M.p. 162-5. 
Di-Me ester: m.p. 45-6-5. 
Anhydride: sublimes. M.p. 93-4. 

Adams, Butterbaugh, J. Am. Chem. Soc., 
1938,60,2174,2191. 



Apoharmine 



202 



Apoquinidine 



CH 



Apoharmine 



HC C N 

~>CH 3 

MW, 132 

Prisms from C 6 H 6 . M.p. 186. Very sol. 
MeOH, EtOH, CHC1 3 . Mod. sol. H 2 0. Spar, 
sol. Et 2 0, C 6 H 6 . H 2 S0 4 + trace formaldehyde 
> green fluor. Basic. Sulphonation > 
sulphonic acid, m.p. above 280. 

B,HCl : needles -f H 2 from MeOH. Aq. De- 
comp. at 220. 

B,HAuCL : pale yellow needles from H 2 0. 
M.p. 250. 

Picrate : yellow needles. M.p. 247. 

N-Jfe: C 9 H 10 N 2 . MW, 146. Needles + 
2H 2 0. M.p. 64, anhyd. 183. 

Lawson, Perkin, Robinson, J. Chem. Soc., 

1924, 125, 626. 
Hasenfratz, Ann. Chim., 1927, 7, 151. 



Apomorphine 




C 17 H 17 2 N " MW, 267 

Cryst. from air-free Et 2 with 1 mol. Et 2 0, 
which it loses at 100. White when pure. 
Turns green in moist air. Sol. EtOH, Et 2 0, 
CHC1 3 , C 6 H 6 . Slightly sol. H 2 0. Sol. alkalis : 
sols, turn brown in air. Has no narcotic pro- 
perties. Powerful emetic. 

B,HCl : grey cryst. Spar. sol. H 2 0, EtOH. 
[a]t> 6 30-5 in H 2 0. Turns green in air. 

3 -Me ether : see Apocodeine. 

Di-Me ether: C 19 H 21 2 N. MW,295. Yellow 
viscous mass. B.p. 195-205 in cathode ray 
vacuum, [a]? 148 in EtOH. BJRI : pale 
yellow cryst. from H 2 0. M.p. 220. Sol. hot 
H 2 0. [aft 8 49 in EtOH. Methiodide: needles 
from EtOH. M.p. 195. [aft 1 48 in EtOH. 
Benzoyl deriv. : m.p. 165-5. 

: Q-Diacetyl : needles from AcOEt-pet. 
ether. M.p. 129. Sol. most org. solvents. 
Spar. sol. pet. ether. Insol. H 2 0. [a] D 47-2 
inAc 2 0. B,HCl: [a] D - 67-26 in H 2 0. Meth- 
iodide : m.p. 233. 

Triacetyl deriv . : m.p. 137. Optically inactive, 

: Q-Dibenzoyl : prisms from EtOH. M.p. 
156-8. Sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . Spar, 
sol. ligroin. Insol. H 2 0. [a]g + 43 in CHCL. 
Methiodide: needles. M.p. 229-30 corr. Mod. 



sol. EtOH, AcOH. Spar. sol. H 2 0. Insol. Et 2 0, 
C 6 H 6 , ligroin. 

Tribenzoyl deriv. : needles. M.p. 217-18. 
Optically inactive. 

Acetyl-dibenzoyl deriv. : m.p. 156-8. 
Methobromide : C 18 H 20 2 NBr. MW, 362. 
Needles from MeOH. M.p. 180. Sol. H 2 O, 
EtOH. Insol. Et 2 0. 

Gotland, Haworth, Virden, Callow, J. 

Chem. Soc., 1929, 1666. 
Spath, Hromatka, Ber., 1929, 62, 325. 
Avenarius, Pschorr, Bear., 1929, 62, 321. 
Chemnitius, Pharm. Zentralhalle, 1929, 

70, 101. 

Oparina, Karasina, Smirnov, Chem. Ab- 
stracts, 1935, 29, 1940. 
Bick, Nature, 1952, 169, 755. 
Pschorr, D.R.P. 158,620, (Chem. Zentr., 

1905, 1, 703). 

Kiedel, D.R.P. 167,879, (Chem. Zentr., 
1906, 1, 1067). 

Aponucidine 
C 15 H 22 ON 2 MW, 246 

Degradation product of brucidine. M.p. 122- 
3. [a]|? -84 in H 2 0. 

B,3H 2 : square plates from moist ether. 

N-Acetyl: prisms from H 2 0. M.p. 262 
decomp. 

Dipicrate: m.p. 196-8. 

Leuchs, Overberg, Ber., 1931, 64, 1007; 
1938, 71, 1525. 

Apophyllenic Acid (C inchomeronic N -methyl- 
betaine) 

COOH COO- 



H 3 C- 



or 



H 3 C< 



C 8 H 7 4 N MW, 181 

Needles or prisms + H 2 from H 2 0. M.p. 
219, anhyd. 242 decomp. Spar. sol. H 2 0. 
Insol. EtOH, Et 2 0. Aq. sol. reacts strongly 
acid. Dry dist. ^ pyridine. Sn + HC1 > 
hexahydro--ZV"-methylcinchomeronic acid. Ba 
salt sol. H 2 0. 

Me ester : C 9 H 9 4 N". MW, 195. Prisms from 
MeOH. Decomp. at 218. Sol. H 2 0, warm 
EtOH. Insol. Et 2 0. 

M ester: G^EL^OJS. MW, 209. Needles 
from EtOH. Decomp. at 205. 

B 2J H 2 PtCl Q : yeUow cryst. + H 2 0. M.p. 235 
decomp. 

Mumra, Gottschaldt, Her., 1922, 55, 2075. 
Kirpal, Reiter, Arm., 1923, 433, 112. 

Apoquinidine (Apoconguinine 3 apoconchinine) 
C 19 H 22 2 N 2 MW ? 310 



Apocpinine 



203 



Acpaaticine 



Prisms -f !Me 2 CO from Me 2 CO. Loses Me^CO 
at 140, m.p. 178-80 decomp" Needles or short 
prisms + lEtOH from EtOH. Loses EtOH at 
160, m.p. 185-90 decomp. [a]? -f 253-9 or 
+ 181-8 in EtOH. For base dried at 160, 
[<x]i 5 + 291-4 or 208-6. 

B.HGI : plates or prisms + lEtOH from 
EtOH. M.p. 183-5 decomp. [a]J? + 156-3 in 
HoO or + 177 for EtOH-free salt. Also forms 
needles + 2H 2 from H 2 0. M.p. 238-40 de- 
comp. [og? + 178-3 in H 2 0. 

B,2HBr: needles + H 2 6 from H 2 0. M.p. 
280 decomp. [a]J? + 192-5 in K>0. Spar. 
sol. EtOH. 

B^H^SO^: needles + 2EtOH from EtOH. 
M.p. 257-8 decomp. Cryst. + H 2 O from H 0. 
M.p. 260. [ a ]i? + 242-4. Spar. sol. H 2 0. - 

B,2HCl,ZnCl 2 : needles from 5% HC1. M.p. 
290 decomp. [<x]i? + 175-3 in H 2 0. 

Me ether : C^H^O^. MW, 324. Needles 
from Et 2 0, prisms from EtOH. M.p. 185 
(180-1). [a]i 5 -f 278-8. BjaCl : cryst. -f 
H 2 O from H or 96% EtOH. M.p. 267. 
[ofi? + 174-7! B$HBr : prisms from EtOH. 
M.p. anhyd. 210-15. [oc]3> 5 + 186-3 in H 2 0. 

Henry, Solomon, Gibbs, J. Chem. Soc. 

1935, 969. 

See also Thron, Dirscherl, Ann., 1935, 
515, 252. 

Apoqninine (Apocupreine) 
19 H 22 2 N 2 MW, 310 

By heating quinine with acids. Exists in 
two forms (geometrical isomers ?). 

a-. 

Prisms from Et 2 0. Decomp. at 184. Sol. 
MeOH, EtOH. Mod. sol. Et 2 0, Me 2 CO, CHC1 3 , 
C 6 H 6 , CS 2 , hot H 2 0. Prac. insol. cold H 2 O. 
Sol. caustic alkalis, [a]g 214-8 in EtOH. 

B,HCl : needles from EtOH.Aq. M.p. 272-5 
decomp. Sol. EtOH.Aq. Spar. sol. H 2 O, EtOH. 
[a]i? -163-8. 

B,2HCl: cryst. from EtOH. M.p. 261 de- 
comp. [a]f> -233 in H 2 0. 

JS,# 2 #0 4 : plates from H 2 0. M.p. 203-8 
decomp. Spar. sol. H 2 0, MeOH. [a] 224 
inH 2 0. 

P- 

M.p. 180-90 decomp. [a] D 194 in EtOH. 

B,HCl: [a] D -145inH 2 0. 

B,2HCl: [a] D -206 in H 2 0. 

B^SO^: [a] D -208. 

Unclassified : 

B,HBr : needles from EtOH.Aq. M.p. 284 
decomp. 

B,2HBr : cryst. from EtOH. M.p. 255 de- 
comp. [a]J> 5 - 180-9. 

Sesquioxalate : pale yellow needles from EtOH. 
M.p. 224-5-226 decomp. Spar. sol. H 2 0, EtOH. 
[a]g> - 193-6 in H 2 O. 

Me ether : C 20 H240 2 N 2 . MW, 324. Needles 



from C 6 H 6 . M.p. 183-5. [ajjf -201-2 in 
EtOH. B,HOl : needles from EtOH-Me 2 CO- 
Et 2 0. M.p. 249-51 decomp. Sol. H 0, EtOH. 
Spar. sol. Me 2 CO. [a]J 5 - 196, 

Et ether : ethylapoquinine. C 21 H 26 OoN 2 . MW, 
338. Oryst. from C 6 H 6 . M.p. 195-7. [a]i 5 
199-7 in EtOH. B : HCl: needles from Me 2 CO. 
M.p. 247-50 decomp. [aft 5 191-7. 

Henry, Solomon, /. Chem. Soc., 1934, 

1923. 
Cretcher, et al. y J. Am. Chem. Soc., 1935, 

57, 1083; 1942,64,1162. 

AporpMne 




C 17 H 17 N MW, 235 

Sjaithetic alkaloid regarded as the parent of 
the phenanthrene-isoquinoline series. Eroehde's 
reagent > green. Mandelin*s reagent > 
bluish-red col. " Exhaustive methylation" > 
1-vinylphenanthrene + !N"(CH 3 )3. 

B,HCl : decomp. above 250. 

B,HI : decomp. at 260. 

B,HBr : decomp. at 230. 

B,HNO Z : decomp. at 200-210. 

Gadamer, Oberlin, Schoeler, Arch. Pharm., 
1925, 263, 81. 

Apoxanthoxyletin (7 ~Hydroxy-5-methoxy-Q- 
aldehydocoumarin ) 

CH 3 






C 1]L H 8 5 MW, 220 

Ozonolysis product of xanthoxyletin. Needles 
from EtOH. M.p. 217-18. Spar. sol. EtOH, 
AcOH, C 6 H 6 . Sol. hot EtOH. Insol. petrol, 
NaHC0 3 .Aq. Yellow sol. in NaOH.Aq, Bed 
col. with FeCl 3 . Eed with KE s -AgNO 3 and 
Fehling's. 

Phenylhydrazone : needles from EtOH. M.p. 
251 decomp. 

Bell, Eobertson, Subramaniam, J. Chem. 
Soc., 1936,627; 1937,286. 

Acpiaticine 
C 18 H 25 5 N MW, 335 

Alkaloid of marsh ragwort (Senecio aquaticus). 
Octahedra. M.p. 220 decomp. [a]i? 83. 
Toxic. 



Araban 204 

Picrate : cryst. from MeOH. M.p. 182. 
Evans, Evans, Nature, 1949, 164, 30. 



Arab an 
(C 5 H 8 4 ) n MW, (132) n 

Obtained from peanuts, citrus and apples* 
Hydrolysis gives L-arabinose. [a]^ 1 160 in 
H 2 0. Sol. H 2 0. Insol. Me 2 CO, Et 2 0, EtOH. 

Acetyl deriv.: [a]g> 90 in Me 2 CO. Sol. 
Me 2 CO, hot MeOH, hot EtOH. Insol. petrol, 
H 2 0. 

Hirst, Jones, J. Chem. Soc., 1938, 502; 
1939, 452, 454, 1865. 

Arabinal (Ribal) 

fitt 

9H 

H90H 
H90H 



Arabinose 




CH 2 - 



C 5 H 8 3 

d-. 
M.p. 83. 

Diacetyl : 

I. 



MW, 116 



[a] 2 D +181-2. 
m.p. 99-100. [a]?? +262-8. 



M.p. ca. 90. [aft 9 



202-8 in H 2 0. 
m.p. 127-9. 



Gakhokidze, J. Gen. Chem. U.S.S.K., 

1945, 15, 539. 

Meisenheimer, Jung, Ber., 1927, 60, 1462. 
Gehrke, Aichner, Ber., 1927, 60, 918. 

Arabinamine (Tetrahydroxy-n-amylamine, 
arabinosamine) 

HOCH 2 -[CHOH] 3 -CH 2 NH 2 
C 5 H 13 4 N MW, 151 

Cryst. M.p. 98-9. Sol. H 2 0. Mod. sol. 
EtOH. [a]i fi -4-58 in H 2 0. Sweet taste. 
Absorbs C0 2 . HI > w-amylamine. 

B,HCl: leaflets. M.p. 137-8. Mod. sol. 
H 2 0. Spar. sol. EtOH. 

B,HI : leaflets. M.p. 190-1. 

B 2 ,(COOH)z : needles. M.p. 190. Sol. H 2 0. 
Spar. sol. EtOH. [a]J? 13-5 in H 2 0. 

Picrate : m.p. 144-5 decomp. 

Roux, Compt. rend., 1903, 136, 1079. 

Arabinosamine . 
See Arabinamine. 
Arabinose 

HO CH, 

H i 5 z |' OH 
OH 

Pyranose (I) 




!/>3 



HO-EUC OH 

" 6 H OH 

Furanose (II) 



H 



H OH 

HOCH 2 -9 9 9-CHO 
OH OH H 

Aldehyde (III) 



MW, 150 



M.p. 155-5-56-5 



C 5 H 10 5 

I. Pyranose Form. 

d-. 

Cryst. from MeOH.Aq. 
j>|> - 108 in H 2 0. 

Mefhylglycoside : b.p. 165-68/14 mm., 117- 
18/0-1 mm. [aff - 15-4 in H 2 0. 

2-Me ether: C 6 H 12 5 . MW, 164 Syrup. 
[a]J - 102 in H 2 0. 

2 : 4-Di-Me ether : C 7 H 14 5 . MW, 178. B.p. 
140 (bath temp.)/0-09 mm. n% 1-4800. [a]i 7 
30-8 in H 2 0. Anil : plates from EhOH. 
M.p. 142-3. 

Tetm-acetyl: m.p. 99-100. [a]| -44-2 . 

Oxime : plates from EtOH.Aq. M.p. 136- 
7. [a]l> - 84 > - 13-5. 

Phenylosazone : yellow needles from Py.Aq. 
M.p. 162-3 (171-2). [ag> -60-7 in Py-EtOH. 

Benzylphenylhydrazone : m.p. 173. 

2 : ^DinitropTienylosazone : red rhombs from 
Py. M.p. 259 decomp. 

Hockett, Maynard, J. Am. Chem. Soc., 

1939,61,2111. 
Hockett, Hudson, J. Am. Chem. Soc., 

1934, 56, 1632. 
Neuberg, Collatz, Chem. Abstracts, 1937, 

31, 2586. 
Hockett, Millman, J, Am. Chem. Soc., 

1941, 63, 2587. 

Wiggins, J. Chem. Soc., 1946, 13. 
Reichstein, U.S.P., 2,389,325, (Chem. 

Abstracts, 1946, 40, 1974). 
Hirst, Jones, J. Soc. Dyers Colourists, 

1947, 63, 249. 
1-. 

Cryst. from EtOH.Aq. M.p. 158. |a]J? 8 o 
+ 185 > + 108 in H 2 0. Red. > I 
arabitol. Ox. > Z-arabonic acid. HC1 - > 
furfural. Reduces Eehling's. 



Methylglycoside : C 6 H 12 



Form: m.p. 165-6. 
2:3: &-Tri-Me ether : 



164. 



5 . MW, 

+246 in H 2 0. 
cryst. from pet. other. 



M.p. 44-6. B.p. 124/14 mm. 

H 2 0. $-Form : prisms from AcOEt. 

115-17. [aB + 73 in H 2 0. 3~Me ether 

about 200 (bath temp.)/0-001 mm. 

[aJJ 1 +46 in H 2 0. 2 : 3-Di-lfe ether : b.p. 

115-20 (bath temp.)/0-001 mm. <' 8 14522. 

[a]g +14 in H 2 0. 2 : 3 : 4-rn-Jfe ether: 

needles. M.p. 46-8. B.p. 123 /24 mm. [a] B 



[a]?? + 251 in 
M.p. 
: b.p. 
ri$ 14710. 



Arabinose 



205 



Arabinose 



1-4850. [x]f? -4- 96 



+ 46 in H 2 0. 2:3: 4-Triacetyl : m.p. 85. 
[a]ff + 182 in CHCig, 

3-J/e ether : syrup. 

in H 2 O. Phenylosazone : yellow needles from 
EtOH.Aq. M.p. 163. 

2 : 3-Di-Me ether : syrup, ni 7 14650. [a]*? 
4. 86 - > + 107 in H O. Ami : cryst. from 
Me 2 CO-pet. ether. M.p. - 139. 

2:3: k-Triacetyl : phenylosazone : needles from 
EtOH.Aq. M.p. 114. [a& 6 + 5 in CHC1 3 . 

Tetra-acetyl : <x-Form : cryst. from Et0 or 
H 2 0. M.p. 94-6. [ag + 45 in CHC. p- 
Form : cryst. from H 2 0. M.p. 86 
+ 147 in CHC1 3 . 

Tetra-propionyl : m.p. 80 



mm. [<xg? +116 



M.p. 86. ' [a] 
B.p. 200/0-001 
M.p. 



2:3: 4-Tribenzoyl : cryst. from MeOH. 
162-3. [og> + 236 in CHC1 3 . 

Tetra-benzoyl : a-Form : cryst. from MeOH. 
M.p. 160-61. [og? +112-5 in CHC1 3 . p- 
Form : cryst. from MeOH. M.p. 173-4. [a]? 
+ 325 in CHCLj. 

Tetra-p-bromobenzoyl : &-Form : sinters at 
205. M.p. 210. [afi + 383 in CHC1 3 . p- 
Form : sinters at 118. M.p. 125. [a]! 1 
+ 147 in CHC1 3 . 

Oxime : m.p. 139. 

Semicarbazone : m.p. 163 decomp. 

Phenylosazone: m.p. 164-6 (171-2). [a]? 
+51, [ag? +60-5 in Py-EtOH. 

p-Bromophenylosazone : sinters at 175. M.p. 
180-85 corr. 

o-Tolylosazone : m.p. 133. 

p-Tolylosazone : m.p. 176-7. 

p-Bromophenylhydrazone : m.p. 155. 

o-Nitrophenylhydrazone : reddish-yellow cryst. 
from EtOH. M.p. 185. 

m-Nitrophenylhydrazone : reddish-yellow cryst. 
M.p. 184. 

f-Nitrophenylhydrazone : 
+ 14-9. 

m-Tolylhydrazone : needles from 50% EtOH. 
M.p. 157. 

p-Tolylhydrazone : m.p. 160. 

1 : 2-Monoacetone deriv. : + 0*5H 2 0. 
SO . [ a g + 129 in H 2 O. 

1:2-3: 4:-Diacetone deriv. : m.p. 42-3. 

CaCl 2 deriv. : a,~Form : m.p. 112-15. [a]| 
+ 36-4 > 47-6 in H 2 0. 

Levene, Compton, /. Biol. Chem., 1936, 
116, 189. 

Carrington, Haworth, ffirst, J. CTiem. 
Soc., 1934, 1653. 

Purdie, Eose, J. Chem. 8oc., 1906, 89, 
1204. 

Hirst, Robinson, /. Chem. Soc., 1925, 127, 
358. 

Smith, J. Chem. 8oc. 9 1939, 753. 

Hirst, Jones, J. Chem. Soc., 1938, 504. 

Anderson, Sands, Organic Syntheses, Col- 
lective Vol. I, 60. 



m.p. 186-5-188 



M.p. 



Wolfrom, Christman, J. Am. Chem. Soc., 

1936.58, 41. 
Hirst, Jones, Woods, /. Chem. Soc., 1947 

1048. 

dl- (presumably pyranose form, I). 

Prisms from EtOH. M.p. 161-2. 

Phenylosazone : yellow needles from H 2 
M.p. 169-70 corr. 

p-Bromophenylosazone : yellow cryst. from 
EtOH. M.p. 200-202. 

Methylphenylosazone : needles from C 6 H R 
Softens at 171. M.p. 175 corr. 

p~Bromophenylhydrazone : needles from HoO 
M.p. 160. 

Ruff, er., 1899, 32, 554. 

II. Furanose IForm. 
1-. 

Methylglycoside : mixture of the two forms 
B.p. 173-5 /0-15 mm. n 1-4880. [a] D - 47 
in H 2 0. a.-Form : hygroscopic cryst. from 
Et 2 0. [a]| - 125 in H 2 0. 2:3: 5-JVi-Jlfe 
ether : b.p. 85-7 /0-3 mm. %, 1-4355. Fal n 
- 56 in H 2 0. 

Uthylglycoside : C 7 H 14 5 . MW, 178. Cryst. 
from AcOEt. M.p. 48-9. [a]^ - 116 in 
H 2 0. 

2:3: 5-Tri-Me ether : b.p. 97-9 /0-18 mm 
nj 1-4400. [a]|? - 36 in H 2 0. 

1 : 2-Monoacetone deriv. : cryst. from EtOH 
M.p. 117-18. [agf - 29 in H 2 0. 

d-. 

Methylglycoside : en-Form : prisms from 
AcOEt or Et 2 0. M.p. 65-7. [a] D + 123 in 
H 2 0. 2:3: 5-Tri-Me ether : b.p. 135/15 mm. 
< 1-4350. [afe 5 + 80 in H 2 0. 

2:3: 5-Tri-Me ether : b.p. 95/0-05 mm. < 
1-4490. [a]i* + 40 in MeOH. 

Montgomery, Hudson, J. Am. Chem. 8oc., 

1937, 59, 992. 

Green, Pacsu, J. Am. Chem. 8oc., 1938, 

60, 2056. 
Haworth, Peat, Whetstone, J. Chem. 8oc., 

1938, 1975. 

Baker, Haworth, J. Chem. Soc., 1925, 
127, 365. 

III. Aldehydo Form, 
d-. 

Di-Me acetal : prisms from MeOH. M.p. 
122. [a]| -18-5 in H 2 0. Tetra-acetyl : 
prisms from Et 2 0-pet. ether. M.p. 80. rain 
+ 22 in CHC1 3 . 

Tetra-Me ether: b.p. 85/0-01 mm. ratf 
1-4340. [aft 7 + 16-6 in H 2 0. 

Hexa-acetyl: (-CH(OAo) 2 ). Needles from 
EtOH.Aq. M.p. 89-5. [a]ff + 28 in CHC1 3 . 

2 : 3-4 : 5-Diacetone deriv. : b.p. 8Q/0-03 mm. 
Jf 1-4421. [a]i 7 -14-4 in CHC1 3 . 

1-. 

Tetra-acetyl : needles from Me 2 CO-EtOH- 
pet. ether. M.p. 113-15. [a]? 58 in 



Arabitol 



206 



Arabonic Acid 



CHClg. Oxime : m.p. 137-9. [a]| 2 5-2 in 
CHC1 3 . Semicarbazone : m.p. 184-7. 

Hexa-acetyl : cryst. from EtOH.Aq, M.p. 
89-5. [aft - 27 in CHCij. 

Montgomery, Hann, Hudson, J. ^Lm. 

Chem. Soc., 1937, 59, 1124. 
Wolfrorn, Newlin, J. ^Lm. CJiem. Soc., 

1930, 52, 3619. 
Wiggins, J. <7Aem. tfoc., 1946, 13. 



Arabitol 



? H OH 

HOCH 2 -C 9 6-CH 2 OH 
OH OH H 



C 5 H 12 5 



MW, 152 



Cryst. M.p. 102. Very sol. H 2 0. Sol. 46 
parts 90% EtOH at 12. Sweet taste. Heat of 
comb. Q v 611-7 Gal., G P 612-0 Cal. Does not 
reduce Fehling's. 

Penta-acetyl : m.p. 76. 

Di-isopropylidene deriv. : b.p. 145-52/23mm. 

d-. 

Pound in lichens and the fungus Ustilago 
virens. Prisms. M.p. 103. Very sol. H 2 0. 
Sol. 48 parts 90% EtOH at 12. [og> + 7-7 in 
saturated borax sol. Sweet taste. 

Penta-acetyl : prisms from MeOH.Aq. M.p. 
74-5 corr. [og? + 37-2 in CHC1 3 . 

1: 3-Benzylidene : m.p. 152. 

2 : 3-Benzylidene : m.p. 81-3. 

dl-. 

Prisms from 90% EtOH. M.p. 105-6. Sol. 
66 parts of 90% EtOH at 12. 

Penta-acetyl : cryst. from MeOH. M.p. 96- 
96-5. 

Buff, Ber., 1899, 32, 555. 
Asahina, Yanagita, Ber., 1934, 67, 799. 
Lespieau, Compt. rend., 1936, 203, 145. 
Baphael, J. CJiem. Soc., 1949, 544. 

Araboflavin (9-(l'-Arabityl)-isoalloxazine) 




Ci 5 H 16 6 N 4 MW, 348 

d-. 

M.p. 296. 

Tetra-acetyl : m.p. 260. 

Z-. 

M.p. 296-5 (from H 2 0). [a] D -108 10 
in 0-05-y-NaOH, -4 2 in H 2 0. 
Tetra-acetyl : m.p. 260. 

dl-. 

M.p. 296. 



Tetra-acetyl : m.p. 274. 

Kuhn, Weygand, Ber., 1935, 68, 1001. 
Karrer, Schopp, Benz, Pfaehler, Ber., 
1935, 68, 216. 

Arabo-kydroxyglutaric Acid. 

See Trihydroxyglutaric Acid. 
Araboketuronic Acid 

C 5 H 8 6 MW, 164 

Z-. 

Brudne salt diJiydrate : C 28 H 38 12 ISr 2 . M.p. 
160-1 from H 2 0-EtOH. Naphthoresoroinol 
^ pink col. Probably identical with brucine 
cZ-xyloke turonate . 

Crews, Hart, Everett, J". Am. Ckem. Soc. y 
1940, 62, 491. 

Arabonic Acid 

H H OH 

HOCH 2 C C COOH 
OH OH H 



C 5 H 10 6 



MW, 166 



Sytup. Heat on water-bath > lactone. 

Ginchonine salt : needles from EtOH. M.p. 
178-80. [oc|> + 120-3 in H 2 0. 

Quinine salt : cryst. from EtOH. M.p. 
172-3. [oc]J> - 106-2 in H 2 0. 

Brucine salt : plates from EtOH.Aq. M.p. 
167-70. [ag> - 26-33 in H 2 0. 

Strychnine salt : needles from EtOH. De- 
comp. at 167-70. [ag 26-08 in H 2 0. 

Triacetyl deriv. : needles or prisms from 
C 6 H 6 . M.p. 127. Sol. EtOH, Me 2 CO, CHC1 3 . 
Mod. sol. H 2 0. Spar. sol. Et 2 0, CJBL, pet. 
ether. [ag> 7 + 27-23 in EtOH. 

Tetra-acetyl deriv. : m.p. 135-6. 

Lactone : C 5 H 8 5 . MW, 148. Needles from 
Me a CO. M.p. 98-9. []? +73-7 in H 2 0. 
Dibenzoyl deriv. : m.p. 200. Tribenzoul : in.p. 
120. 

Z-. 

Cryst. from MeOH or EtOH. M.p. about 
118-19. [a] - 10-02 ^ - 7-11 > 
41-6. Readily forms the lactone. 

Lactone : needles from Me 2 CO. M.p. 98-100". 
[a]? 73-9 in H 2 0. Triacetyl : cryst. from 
C 6 H 6 -pet. ether. M.p. 52-4. Sol. EtOH, 
Me 2 CO, CHC1 3 . Spar. sol. Et 2 0. Almost insol 
H 2 0. [a]*?' 6 - 60-5 in C 6 H 6 . Dibenzoyl deriv. : 
m.p. 200. [aR~ 37-65 in Me 2 C(X Tribenwyl: 
m.p. 120. [aS - 24 in Me 2 CO, - 28-2 in 

Ctr z ? 

s^-e- 

Triacetyl deriv. : m.p. 127. [ali? 27-23 in 
EtOH. 

Me ester : C 6 K 2 6 . MW, 180. Cryst. from 
MeOH. M.p. 148 s (rapid heat). [a]J 6-30 
in H 2 0. Tetra-acetyl : m.p. 130. 

Et ester ; C 7 H 14 6 . MW, 194. M.p. 126-5 . 
Tetra-acetyl : m.p. 68. 



Araciiidic Acid 



207 



Arbutin 



Amide : C 5 H 11 5 N. MW, 165. Cryst. from 
MeOH or 90% EtOH. M.p. 136. Very sol. 
H 2 O. Mod. sol. MeOH. Spar. sol. EtOH 
[a + 38-4 in H 2 0. 

Nitrile: C 5 H 9 4 N. MW, 147. Tetra- 
acetyl ; cryst. from H 2 0. M.p. 117-18. Sol. 
EtOH, Et 2 O. Spar. sol. H 2 0. 

Anilide : m.p. 204. [og? + 68-1 in H 2 O. 

o-Toluidide : m.p. 172. fog + 56-5inH 2 0. 

m-Toluidide : m.p. 186. [a]g + 67-7 in 
H 2 0. 

p-Toluidide : m.p. 200. [<x] + 68-2 in H 2 0. 

Hydrazide : cryst. M.p. 138-9. Sol. H 2 0. 
Insol. EtOH. [a]? + 51*9 in H 2 O. 

Phenylhydrazide : m.p. 215. [a!? 16*1 in 
H 2 0. 

"K salt : m.p. about 220 decomp. [a]| +5-2 
in H 2 O. 

dl-. 

Mod. sol. H 2 0. 

Lactone: needles from Me 2 CO. M.p. 115-16. 
Very sol. H 2 O, EtOH. 

Tetra-acetyl deriv. : m.p. 141-3. 

Kiliani, Ber., 1925, 58, 2344. 
Hasenfratz, Compt. rend., 1927, 184, 210. 
Rehorst, Ber., 1930, 63, 2288. 
Brackenburg, Upson, J. Am. Chem. Soc., 

1933, 55, 2512. 
Weidenhagen, CJiem. Abstracts, 1936, 30, 

3411 
Spengler, Pfafenstiel, D.R.P., 620,248, 

(Chem. Abstracts, 1936, 30, 736). 

Arachidic Acid. 

See ?i-Eicosanic Acid. 

Arachidic Alcohol. 

See Eicosyl Alcohol. 

Arachidonic Acid (Eicosane-tetraenoic acid) 

CH 3 -[CH 2 ] 4 '[CH:CH-CH 2 VCH:CH-[CH 2 ] 3 -COOH 

Suggested structure 

MW, 304 



Ararobinol 



CO OH 



Present in brain tissue, liver lipides and 
suprarenal glands. M.p. 49-5. n 20 1-4824. 
Essential for maintenance of normal health of 
the rat. 

Me ester: b.p. 194-6/0-6-0-8 mm., 200- 
5/l-2 mm. DJ 0-9168. < 1-4875. 

Dolby, Nunn, Smedley-Maclean, Bio- 

chem. J., 1940, 34, 1422. 
Shinowara, Brown, /. Bid. Chem., 1940, 

134, 331. 

Brown, J. Biol Chem., 1928, 80, 455. 
Wesson, J. Biol Chem., 1924, 60, 183. 
Mowry, Brode, Brown, J. Biol. Chem., 

1942, 142, 671, 679. 
Baudart, Bull. soc. chim., 1942, 9, 919. 
Arcus, Smedley-Maclean, Biochem. J., 

1943,37,1. 

Aralen. 

See Chloroquine. 




HO CO OH 

6 MW, 478 

Constituent of some Goa powders and con- 
tained in extracted chrysarobin. Yellow cryst. 
Darkens at 218. M.p. 224. Sol. AcOH and 
10% KOH. Unstable in sol., developing colour 
and fluor. In H 2 S0 4 orange changing to blue, 
then through green, to grey. Cr0 3 > chryso- 
plianic acid. 

Eder, Hauser, Arch. Pharm., 1925, 263, 
321, 436, (J. Chem. Soc., 1925, 128, I, 
948, 1160). 



Arasaponin A 
C 30 H 52 10 MW, 572 

Occurs in the Chinese drug san-ch'i, Aralia 
bipinnatifida. Arnorph. M.p. 195-210. [a] D 
+23. Dil. H 2 S0 4 > arasapogenin A + 
glucose + 2 other cryst. products. Yields a 
hepta-acetyl derivative with Ac 2 0. 

Chou, Chu, Chinese Journal of Physiology, 
1937, 12, 59. 

Arasaponin B 

C 23 H 38 10 MW, 474 

Occurs in the Chinese drug san-ch'i, Aralia 
bipinnatifida. Amorph. M.p. 190-200. [oc] D 
+8. EtOH-HCl > arasapogenin B + glucose. 

Chou, Chu, Chinese Journal of Physiology, 
1937,12,59; 1941,16, 139. 

Arbutin (Hydroquinone-glucose) 
0-C 6 H n O 5 



C 12 H 16 7 MW, 272 

Glucoside in pear leaves, etc. Needles + 
1H 2 from H 2 0. Extracted product usually 
contaminated with methylarbutin (see below). 
M.p. 142-3 ; melts again at 187 (m.p. anhyd.). 
Synthetic arbutin has m.p. 163-4 and again 
199-200. Sol. H 2 0, EtOH, Et 2 0. [a]* 
60-34 in H 2 0. Hyd. > glucose + hydro- 
quinone. FeCl 3 > blue col. 

Me ether : methylarbutin. C^HioO,. MW, 
286. Cryst. + 1H 2 0. M.p. 158-60"; again at 



Arcaine 



208 



Arecaidine 



175. Tetra-acetyl deriv. : cryst. from EtOH.Aq. 
M.p. 95-6. 

Penta-Me ether: C 17 H 26 7 . MW, 342. 
Needles from EtOH.Aq. M.p. 75-5. Very sol. 
Me 2 CO, Et 2 0. Sol. EtOH, CHC1 3 , C 6 H 6 . Spar. 
sol. H 2 0. [a]J? 48-2 in EtOH. 

Tetra-acetyl deriv. : m.p. 136. 

Penta-acetyl : needles from EtOH. M.p. 146. 
[ag - 28-18 in Me 2 CO. 

Benzoyl deriv. : m.p. 184*5. 

Macbeth, MacELay, J. Chem. Soc., 1923, 

123, 717. 
Robertson, Waters, J. Chem. Soc., 1930, 

2732. 
SMshido, Chem. Abstracts, 1936, 30, 7119. 

Arcaine (1 : 4c-Diguanidinobutane) 



C 6 H 16 N 6 



NH NH 

MW, 172 

Occurs in the marine bivalve Area noae. 
Lowers blood sugar of warm-blooded animals. 
Not hyd. by arginase of guinea-pig liver. 

B,H^SO^ : needles. Decomp. at 291. 

B$HAuCl: needles. M.p. 170-5. Spar, 
sol. 

B,H 2 PtCl 6 : m.p. 222. Spar. sol. H 2 0. 

Picrate : needles or fine powder. Decomp. 
at 251-4. 

Picrolonate : powder. Decomp. at 303. 

Kutscher, Ackermann, Z. physioL Chem.> 

1931,199, 277; 203, 132. 
Sugino, Sjirai, Aoydgi, Chem. Abstracts, 

1947, 41, 4455. 

Arctigenic Acid (l-Hydroxymefhoxybenzyl-2- 
dimethoxybenzyl-3-hydroxybutyric acid) 

CH 3 



BD 



CH-COOH 



CH 3 0<("~\-CH 2 -CH-CH a OH 



C 21 H 26 7 MW, 390 

M.p. 131. 

Ar.-Me ether : m.p. 97-8. 

Omaki, J. PTwurm. Soc. Japan, 1935, 55, 
816. 

J-Arctigenin 



HO/~\-CH 2 -CH CO 



CH 3 0^~V-CH 2 -CH 



From seeds of burdock (Arctium lappa). 
Plates from MeOH-Et 2 O. M.p. 102. Spar. 
sol. Et 2 0, ligroin. Eeduces NH 3 -AgN0 3 . 

Me ether : needles from MeOH. M.p. 125-7. 

Acetyl : needles from AcOEt. M.p. 52-60. 

Haworth, Kelly, J. Chem. Soc., 1936, 998. 
Shinoda, J. Pharm. Soc. Japan, 1929, 49, 

565, 1165; Chem. Abstracts, 1930, 24, 

1387; 1929,23,4707. 

Arctiin 

CH 3 

C 6 H U 5 '0<(^>CH 2 -CH CO 

X>H 2 O 



C 27 H 34 O n -H 2 MW, 552 

Constituent of the seeds of Arctium lappa, 
Linn. M.p. 111-12. [a]if -38-8 in EtOH. 
Beduces Fehling's. Hyd. >- arctigenin >- 
arctigenic acid. Acts as a sympathomimetic 
drug. 

Shinoda, Kawagawe, J. Pharm. Soc. 

Japan, 1929, 49, 565. 
Omaki, J. Pharm. Soc. Japan, 1935, 55, 

816. 

Arctose 

(C 6 H 10 5 ) X MW, (182), 

Occurs in roots of Arctium lappa. Needles 
from EtOELAq. M.p. 178. [aft 1 41-02 in 
H 2 0. Very sol. H 2 0. Spar. sol. EtOH. Does 
not reduce Fehling's. Hyd. > fructose. Cry- 
oscopic MW, 1702. 

Acetyl deriv. : cryst. from AcOH-MeOH. 
M.p. 108. [ajjf - 3648 in CHC1 3 . 

Murakami, Acta Phytochimica (Japan), 
1949, 15, 107; Chem. Abstracts, 1949, 
43, 8451. 

Arecaidine (N-Methyl- 
acid, N-methylguvacine, arecaine) 

CH 



C 7 H n 2 N 



MW, 372 



N-CH 3 

MW, 141 
Alkaloid of areca nuts. Plates + 1H 2 from 

EtOH.Aq. M.p. 223-4 decomp., anhyd. 232. 

Sol. H 2 0. Insol. most org. solvents. Dil. aq. 

sol, reacts neutral, cone, as weak acid. 
B,HCl : needles. M.p, 262-3 (rapid heat), 

(250-5-252-0 ). 
B,HBr: cryst. from MeOH. M.p. 248-9 

(197 decomp.). 



Arecaine 



209 



Aiicine 



l : prisms from dil. HC1. M.p. 200. 
' yellow cryst. M.p. 234-5 de- 
comp. 

Methochloride : plates from H 2 O. M.p. 256-8. 
Methopicrate : leaflets. M.p. 224-5. 
Me ester : see Arecoline. 

Hess, Leibbrandt, Ber., 1918, 51, 806. 

Ereudenberg, ibid., 976. 

Merck, D.R.P., 485,139, (Chem. Abstracts, 

1930, 24, 919). 
Ugryumov, Chem. Abstracts, 1941, 35, 

3644. 
Dankova et al., Chem. Abstracts. 1943, 37, 

381. 

Arecaine. 

See Arecaidine. 

Arecoline (N - Methyl - A 3 - tetrahydronicotinic 
acid methyl ester, methyl ester of arecaidine) 

C 8 H 13 O 2 N MW, 155 

B.p. 209 (220), 94/17 mm, (105/12 mm.), 
74/7 mm. Sol. H 2 O, EtOH, Et 2 O, CHCL. DJg 
1-0504. *S 1-4860. Volatile in steam. 

B,HCl: needles. M.p. 157-8. Sol. H 2 O, 
EtOH. 

B 9 HBr : prisms from EtOH. M.p. 170, 
(172) (177-4-7-9). Sol. H 2 O, hot EtOH. 

B 2 ,HftCl Q : orange-red plates. M.p. 176. 

Methiodide : prisms. M.p. 173-4. Very sol. 
H 2 O, hot EtOH. Spar. sol. MeOH, Me 2 CO. 
Insol. Et 2 O. 

Hess, Leibbrandt, Ber., 1918, 51, 806. 

Freudenberg, ibid., 976. 

Chemnitius, J. praJct. Chem., 1927, 117, 

147. 
Merck, D.R.P., 485,139, (Chem. Abstracts, 

1930, 24, 919). 
Ugryumov, Chem,. Abstracts, 1941, 35, 

3644. 

Mannich, Ber., 1942, 75, 1480. 
Dankova et al., Chem. Abstracts, 1943, 37, 

381. 

Arecolone (l$-Methyl-AP-piperid-3-yl methyl 
ketone) 

CH 



Areolatin 

See 1:5:6: 7-Tetrahydroxy-2-methylanthra- 
quinone. 

ArgJBme (l-Amino-4-gtianidino-iL-valeric acid) 



C 8 H 18 ON MW, 139 

B.p. 97/10 mm. 
B,HCl: m.p. 204. 
B,HBr : m.p. 223. 

Semicarbazone : m.p. 219 decomp. B,HCl : 
m.p. 233. 

Albers, Kallischnigg, Schmidt, Ber., 1944, 

77, 617. 
Wohl, Prill, Ami., 1924, 440, 139. 

Diet, of Org. Ck>mp. I. 



C 6 H 14 2 N 4 



MW, 174 



Constituent of seeds and shoots of pine, fir, 
acacia, arachis, etc., and present in many 
proteins. Plates or prisms. M.p. 207 decomp. 
SoL H 2 0. Spar. sol. EtOH, |Vg? + 11-37. 

B,HCl: sinters at 218. M.p. 235 (222) 
decomp. [a]| + 12-12 in H 2 O. 

B,HNO* : cryst. + |H 2 O. M.p. 126. SoL 
H 2* MS + 9-31 in H 2 O. Hygroscopic. 

B,2HNO 3 : m.p. 145 decomp. (150). 

Me ester: C 7 H 16 O 2 N 4 . MW, 188. Syrup. 
B,2HCl : needles or prisms from EtOH-Et 2 O. 
M.p. 195 decomp. Very sol. H 2 O. SoL EtOH, 
MeOH. Spar. sol. other solvents. 

Dibenzoyl deriv. : leaflets from EtOH. M.p. 
235 decomp. B,HCl : m.p. 218. 

Picrate : m.p. 217 decomp. 

Dipicrate : m.p. 190 decomp. 

Picrolonate : yellow needles from HO. M.p. 
231. 

BJSCl: needles. M.p. 215. 
B,HNO 3 : needles. M.p. 183. 
B,2HNO Z : m.p. 151 decomp. 
B 2 ,H 2 SO^: m.p. 213. 
Picrate : needles from H 2 O. M.p. 205. 
Picrolonate : yellow needles. M.p. 231. 

dl-. 

B,HNOz : plates. M.p. 230. 
B,2HNO 3 : m.p. 151. SoL H 2 O. 
Picrate : prisms from H 2 O. M.p. 200-1. 
Picrolonate : yellow needles. M.p. 248. 
Dipicrate : decomp. at 196. 
Dibenzoyl deriv. : plates + H 2 O from EtOH. 
M.p. 176, anhyd. 230. 

Vickery, Leavenworth, J. Biol. Chem., 

1927, 75, 115. 

Cox, J. Biol. Chem., 1928, 78, 475. 
Felix, Dirr, Z. physiol. Chem., 1928, 176, 

29. 
Cox, King, Berg, J. Biol. Chem., 1929, 81, 

755. 

Argol. 

See under Tartaric Acid. 
Aribine. 
See Harman. 
Aricine (Cusconine) 

C23H 26 O 4 N 2 MW, 394 

Constituent of Cusco bark. Prisms from dil. 
EtOH. M.p. 188-9. SoL 100 parts EtOH at 
15, 11 parts at 78. SoL 33 parts Et 2 O at 15. 

14 



AristolocMne 



210 



Aromadendrene 



Sol. CHa 3 . Insol. HgO. [at 58-18 In 
EtOH, - 92-5 in Et/X 
BJSCl : [ak 14-5 in EtOH. 

Moissan, Landrin, CompL rend., 1890, 

110, 469. 
Hamet, CompL rend., 1945, 221, 307. 

AristoIocMne 
C 32 H 22 13 N 2 MW, 642 

Constituent of seeds of Aristolochia clematitis, 
roots of Aristolochia rotunda, and Aristolochia 
India L. Orange-yellow cryst. from MeOH. 
M.p. 215 decomp. Sol. hot H 2 O, EtOH, Et 2 0. 
Insol. C 6 H 6 , pet. ether. Sol. alkalis, repptd by 
C0 2 . Sol. 2^304 to dark green sol 

Dawson, Pharm. J. y 1927, 119, 396. 
Ryo, Ber. ges. Physiol. exptl. PharmakoL, 

1927, 40, 462. 

Kjishnaswamy, Manjunath, Rao, J. In- 
dian Chem. Soc., 1935, 12, 476. 

Arjunetin 
C^Hi/VHjO MW, 232 

Occurs in the bark of Terminalia arjuna, 
Bedd. M.p. 215. Contains a lactone ring. 

Agarwal, Dutt, Proceedings of the National 
Academy of Science of India, 1936, 6, 
305. 

Arlitan. 
See Sorbitan. 
Armepavine 




MW, 313 

Alkaloid of Papaver armeniacum. Needles 
+ 1H 2 from Me 2 CO-Et 2 0. M.p. about 100 ; 
solidifies and remelts at 148-9. Sol. EtOH, 
CHCI 3 . Mod. sol. Et 2 0. Insol. H 2 0. 

B,HCl: needles from EtOH-Et 2 0. M.p. 
151-2. 

Oxalate : cryst. from EtOH. M.p. 211-12. 

Methiodide : m.p. 199-200. 

Me ether : C 20 H 25 3 ]SL MW, 327. M.p. 63- 
4. []j> 84-5 in CHCL. Methiodide : m.p. 
335-6. 

Junusov, Konovalova, Orekhov, J. Gen. 

Chem., U.S.SM., 1940, 10, 641. 
Konowalowa, Yunussoff, Orechoff, Ber., 

1935, 68, 2161. 



Arnidanediol 



MW.444 



M.p. 232. 

Diacetyl deriv. : m.p. 215 (210). 

Dieterle, Schreiber, Arch. Pharm., 1941, 

279, 312. 

Zimmermann, Helv. Chim. Acta, 1943, 26, 
642. 

Amidenaldiol 

C 30 H 48 3 MW, 456 

Diacetyl deriv. : m.p. 230-2. 

Dieterle, Schreiber, Arch. Pharm., 1941, 
279, 312. 

Araaidenediol (Arnidiol) 

C 30 H 50 2 MW, 442 

Occurs in Taraxacum officinale, Linn., Arnica 
montana, Linn., and other plants. M.p. 257 
(from Et 2 or EtOH-AcOEt). [a]J? +78-2. 
Dehydrogenation ^ arnidenolone . Cr O 3 > 
arnidenedione. O 3 > H'CHO. 

Diacetyl deriv. : m.p. 75 (from AcOH), 189 
(193) (from EtOH or Me 2 CO). [a] D + 80. 
H 2 -PtO 2 -AcOH > diacetylarnidonediol. Se0 2 
> diacetylarnidenaldiol. 
Dibenzoyl deriv. : m.p. 230. 

Dieterle, Engelhard, Arch. Pharm., 1940, 

278, 225. 
Zimmermann, Helv. Chim. Acta, 1941, 

24,393; 1943,26,642. 
Jeger, Lardelli, Helv. Chim. Acta, 1947, 

30, 1020. 

Lardelli, Kriisi, Jeger, Buzicka, Helv. 
Chim. Acta, 1948, 31, 1815. 

Arnidenedione 

C 30 H 46 O 2 MW, 438 

M.p. 182. 
Di-oxime : m.p. 253-4. 

Zimmermann, Helv. Chim. Acta, 1943, 26, 
642. 

Arnidenolone 

C 30 H 48 2 MW, 440 

M.p. 241-3. 

ip-Nitrophenylhydrazone : orange-red prisms. 
M.p. 268. 

Dieterle, Engelhard, Arch. Pharm., 1940> 
278, 225. 

Arnidiol. 

See Arnidenediol. 
Aromadendrene 



>CH-CH(CH 3 ) 2 



MW, 204 




Suggested structure 



Aromadendrol 



211 



Arsenic diethyl 



Sesquiterpene occuring in various eucalyptus 
oils. B.p. 260~5/760 mm., 121-2/10 " mm. 
B 19 0-9249. n% 1-4993. H 2 >- dihydro- 
aromadendrene. O 3 > aromadendrone. 

Briggs, Short, /. Chem. Soc., 1928, 2524. 
Radcliffe, Short, J. Chem. Soc., 1938, 

1200. 
Nares, Perrottet, Helv. Chim. Acta, 1940, 

23, 912. 

Treibs, Barchet, Ann., 1950, 566, 89. 
Birch, Annual Reports on the Progress of 

Chemistry, London, 1950, XLVIE, 196. 




Suggested structure 
C 14 H 24 MW, 208 

Long needles. M.p. 54-9. B.p. 139-40/10 
mm. 

Radcliffe, Short, J. Chem. Soc., 1938, 

1200. 
Birch, Annual Reports on the Progress of 

Chemistry, London, 1950, XLVn, 196. 

Aromadendrone 
CH 




CH S 

Suggested structure 
C 14 H 22 MW, 206 

M.p. 85 (from MeOH). [<x]J? 70 +5-42 in 
EtOH. 

Oxime : m.p. 103. 

Semicarbazones : u,-form : hexagonal plates 
from MeOH. M.p. 190 decomp. $-form: 
hexagonal plates from MeOH. M.p. 202 
decomp. 

p~Nitrophenylhydrazone : needles from ligroin. 
M.p. 131. 

Benzylidene deriv. : m.p. 66 (from MeOH). 
B.p. 182-97 /! mm. 

Radcliffe, Short, J. Chem. Soc., 1938, 

1200. 

Treibs, Barchet, Ann., 1950, 566, 89. 
Birch, Annual Reports on the Progress of 

Chemistry, London, 1950, XLVTE, 196. 



Aromadeadrylamine 

CH 









H 2 C N | / 



CHg 

Suggested structure 



1 25 L 



MW, 207 
> aroma- 



B,(COOH)z : m.p. 164-5*. Mel 
dendryltrimethylammoniuin iodide. 

Radcliffe, Short, /. Chem. Soc., 1938, 

1200. 
Birch, Amuwal Reports on the Progress of 

Chemistry, London, 1950, XLVII, 196. 

Aromoline 

C 32 H 24 2 (OH) 2 (OCH 3 ) 2 (N-CH 3 ) 2 
Cs 6 H 38 O e N 2 MW, 594 

Cryst. + 1CHC1 3 from chloroform. M.p. 

174-5. [a]g + 327. 

Bick, Whalley, Chem. Abstracts, 1949, 43, 
6787. 

Arsacetin. 

See under Arsanilic Acid. 

Arsacridine. 

See Phenarsazine. 

Arsanilic Acid (p-Aminophenylarsonic acid, 

p-aminophenylarsinic acid) 

OIAs(OH) 2 




C 6 H 8 3 NAs MW, 217 

Needles. M.p. 232. Sol. Et 2 0. Span sol. 
EtOH, AcOH. Insol. Me 2 CO, CHClg, C e H 6 . 
Sol. alk. carbonates. Diazotises and couples. 
Reduce >- p - aminophenylarsinic oxide, 
NH 2 -C 6 H 4 -AsO. Sn + HC1 ^ ^'-diamino- 
arsenobenzene. Na salt + KI + H 2 S0 4 ^ p- 
iodoatiiline. The Na salt is the drug Atoxyl and 
the JV-acetyl deriv. of this is Arsacetin. 

N-Chloroacetyl : plates from H 2 0. M.p. 285 
decomp. Sol. hot EtOH, Mod. sol. hot H 2 0, 
AcOH. 

Lewis, Cheetham, Organic Syntheses, Col- 

lective Vol. I, 63. 
Poulenc Freres, D.R.P., 468,757, (Chem. 

Abstracts, 1929, 23, 849). 

Arsanthrene. 

See Phenarsine. 
Arsenic diethyl 

tetraethyl) 



(Ethyl caeodyl, diarsenic 



C 8 H 20 As 2 



MW, 266 



Arsenic dimethyl 



212 



Artemisoi 



B.p. 185-90. Sol, EtOtL Et 2 0. InsoL 
H 2 0. Spontaneously inflammable. Reduces 
Ag and Hg sols. Ox. > diethylarsinic acid, 
C 2 H 5 ) 2 AsO*OH. 

^Landolt, Ann,, 1854, 89, 319. 

Arsenic dimethyl. 

See CacodyL 
Arsenic triacetate 



C 6 H s 6 As MW, 252 

Needles. M.p. 82. B.p. 165~-70/31 mm. 
Sol. CHC1 3 , AcOEt. Spar. sol. CeH 6 , CC1 4 . 
Insol. CS 2 , pet. ether. Decomp. by dist. at ord. 
press. H 2 > As 2 3 + CH 3 COOH. 

Pictet, Bon, Bull. sac. chim., 1905, S3, 
1141. 

Arsenic triet&yl. 

See Triethylarsine. 

Arsenic trimethyL 

See Trimethylarsine. 

Arsenic triphenyl. 

See Triphenylarsine. 

Arsenoacetic Acid (Diarsenoacetic acid) 



268 

Yellow needles. Decomp. about 205. Does 
not melt below 260. Sol. Py., alkalis, alk. 
carbonates. 

Palmer, Organic Syntheses, Collective 
Vol. I, 66. 

Arsenobenzene 



C 12 H 10 As 2 MW,304 

Needles from chlorobenzene. M.p. 212. Sol. 
CHCLj, C 6 H 6 , CS 2 . Spar. sol. EtOH. InsoL 
H 2 0,Et 2 O. Sols.resinify. Heat >triphenyl- 
arsine + As. Adds C^. 

Micbaelis, Schafer, Ber., 1913, 46, 1742. 
Palmer, Scott, /. Am. Chem. Soc., 1928, 

50, 536. 
Lyon, Mann, /. GTiem. Soc., 1945, 30. 



p - Arsenophenol 

benzene) 



C 12 H 10 2 As 2 



(4:4'- Dihy&roxyarseno - 



MW, 336 



Arsenoetliane. 

See Ethylarsenioiis oxide. 
o-Arsenotoluene (2 : 2'-Dimethylarsenobenz- 
ene) 

CH 3 H 3 C 

-AsIAs- 



Yellowish-brown powder. Decomp. above 
200 with darkening. Sol. EtOH, Et 2 O, Me 2 CO, 
and alkalis. 

Hochst, Chem. Zentr., 1909, I, 964. 

Bart, Chem. Zentr., 1914, 1, 1039. 



',332 
A Cryk from C 6 H 6 . M.p. 205-8. 

Palmer, Adams, J. Am. Chem. Soc., 1922, 
44, 1372. 

m-Arsenotoluene (3 : 3'-Dimethylar8enobenz- 
ene). 

Amorph. powder. M.p. 106. Sol. CS 2 , hot 
cymene. Insol. EtOH, Et 2 0, AcOH, C 6 H 6 , pet. 
ether. 

Michaelis, Ann., 1902, 320, 327. 

2>-Arsenotoluene (4 : 4' -Dimethylarsenobenz- 
ene). 

Plates from C 6 H 6 . M.p. 202. (Cryst. from 
CHC1 3 , m.p. 184). 

Michaelis, Ann., 1902, 320, 301. 
Michaelis, Schafer, Ber., 1913, 46, 1742. 
Lyon, Mann, J. Chem. Soc., 1945, 30. 

Arsinobenzene. 

See Phenylarsine. 

Arsphenamine . 

See Salvarsan. 

Artabotrine. 

See Isocorydine. 

Artemisin (Hydroxysantonin) 

HC 



yj-xg 

HC CHa 
HC C CH 
OC C C-0: 



2 

OH 



CH 



^ 

CH 3 CO 



MW, 262 



1518 4 

Occurs with santonin in seeds of Artemisia 
maritima,Lwn. Cryst. M.p. 203. Sol. EtOH. 
Spar. sol. H 2 0. [a] D - 84-3 in EtOH. 

Acetyl : pale yellow cryst. M.p. 200. [a]j> 
52-6. Oxime : m.p. 188-9. Phenylhydraz- 
one : m.p. 145. 

Oxime : needles from MeOH. M.p. 233-4. 

Desmotropicform : m.p. 236. [a] D 84-16. 

Smith, Smith, Pharm. J., 1927, 119, 688, 

701. 
Tettweiler, Engel, Wedekind, Ann., 1932, 

492, 105. 

Artemisoi. 

See jp-Menthanol-9. 



Arterenol 



213 



Ascaiidoi 



Arterenol (a-3 : ^-Trikydroxy-^-ami no-ethyl- 
benzene, a - aminometkyl -3:4- dihydroxyplienyl- 
carbinol) 



OH 



HC) CH 



MW, 169 

Colourless eryst. M.p. 191 decomp. Spar. 
sol. H 2 O. Very spar. sol. EtOH, Et 2 O. Sym- 
pathomimetic drag. 

B,HCl : tan col. cryst. M.p. 141 deeomp. 
Sol. H 2 0. Spar. sol. EtOEL Intense green 
col. with FeCl 3 . 

Oxalate : m.p. 175. Very sol. H 2 0. 
Hochst, D.R.P. 157,300. 
Zernick, Ghem. Zentr., 1909, 1, 1185. 
Beyer, Physiol Rev., 1946, 26, 169. 

Asaronaldehy de . 

See Asarylaldehyde. 

Asarone (2:4: 5-Trimethoxy-l-propenylbenz- 
ene) 

CHICH-CHg 



C 12 H 16 3 



OCH 



MW, 208 

Constituent of roots of Asarum europceum, 
Linn., and of calmus oil. Monoclinic cryst. 
M.p. 67 (62). B.p. 296. Sol. EtOH, Et 2 O, 
AcOH, CHCLj, CC1 4 . Mod. sol. boiling H 2 O. 
D 11 1-091. < 1-5719. Heat of comb. C* 1575-2 
CaL, C y 1576-7 Cal. Sublimes with part, de- 
comp. Ox. > asarylaldehyde >- asarylic 
acid. 

Dibromide : m.p. 86. Unstable. 

Pier ate : brownish-black needles. M.p. 82. 

Gattermann, Eggers, JBer., 1899, 32, 290. 
Bert, Gompt. rend., 1941, 213, 873. 

Asaronic Acid. 

See Asarylic Acid. 

Asarylaldehyde (2:4: 5-Trimethoxybenz- 
aldehyde, asaronaldehyde) 

CHO 

/NOCH, 
CH 3 olj 

OCH 3 
C 10 H 12 4 MW, 196 

Needles from CHC1 3 . M.p. 114. Sol. hot 
H 2 O, Et 2 0, C 6 H 6 , ligroin. Sublimes. Sol. 
NaHS0 3 . 

Di-Et acetal : cryst. from EtOH. M.p. 101 -5. 
Sol. EtOH. 

Oxime : yellowish leaflets from H 2 0. M.p. 
138. B,HCl : golden-yellow prisms. M.p. 159. 

Semicarbazone : needles from EtOH. M.p. 
205-6. 



Semioxamazone : pale yellow needles from 
H 2 O. M.p. 249-50 decomp. Insol. EtOH. 
Phenylhydrazone : m.p. 120-1. 
p-Nitrophenylhydrazone : red needles from 
EtOH. M.p. 234. Insol. H 2 O. 

v. Alphen, Eec. trav. chim., 1927, 46, 193. 
Gattermann, Eggers, Ber., 1899, 32, 289. 



Asarylic Acid 

add, asaronic acid) 



(2:4: 5-Trimet~hoxybenzoic 

COOH 
)CH 3 




CH 3 0! 



CioH^Og MW, 212 

Needles from C 6 H 6 ~pet. ether. M.p. 144. 
B.p. 300. Sol. hot H 2 0, EtOH, C 6 H 6 , pet. 
ether. 

Me ester : C^H^O,. MW,226. Yellow crvst. 
M.p.97-5. 

Et ester: C 12 H 16 5 . MW,240. Yellow cryst. 
M.p. 72. 

Isoamyl ester : C 15 E 22 O 5 . MW, 282. Yellow 
oil. B.p. 140/0-2 mm. 
Bornyl ester : m.p. 73. 
Phenyl ester : m.p. 119. 
Chloride: C 10 H lt O 4 CL MW } 230-5. Cryst. 
M.p. 115-16. 

Nitrile: C 10 H n 3 N. MW, 193. Needles from 
EtOH. M.p. 112-14. Sol. EtOH, AcOH, C R H 6 . 
Insol. H 2 O, pet. ether. 

Amide : C 10 H 13 4 N. MW,211. M.p. 184-5. 
Anilide : m.p. 154-5. 

Bargellini, Madesani, Gazz. chim. itaL } 

1931, 61, 688. 
Haraszti, Chem. Abstracts, 1931, 25, 

5154. 
Luff, Perkin, Eobinson, /. Chem. Soc., 

1910, 97, 1131. 
Fabinyi, Szeki, Ber., 1906, 39, 3680. 

Ascaridol 

C-CH 3 

\ 

T_r r^ f\ C^~Cf 
1 2 O U Oil 

C-CH(CH 3 ) 2 
C 10 H 16 2 MW, 168 

Chief constituent of oil of Chenopodium. M.p. 
2-5. B.p. 115/15 mm., 83 /5 mm. D|? 0-9985, 
7^ 1-4769. Formic acid >#-cymene. Explodes 
on decomposition with HC1, H 2 S0 4 , HN0 3 or 
H 3 P0 4 . Heated to 150 gives ascaridol glycol 
anhydride which with steam > ascaridol glycol. 
Anthelmintic. 

Glycol: C 10 H 18 3 . MW, 186. Two forms. 
(a-.) M.p. 62-5-64. B.p. 271-2, 135-6/15 
mm. DlSl -0981. < 1-4796. (p-.) Cryst. + 
H 2 O from CHC1 3 -H 2 O. M.p. anhyd. 103-5. 



AscorMc Acid 



214 



jp-Asebotin 



Dil, H 2 SO 4 > thymol. Benzoate : prisms from 
EtOH. M.p. 136-7. Dibenzoate: needles from 
EtOH. M.p. 1 17. Hyd. > a-form of glycol. 

Paget, Analyst, 1926, 51, 170. 
Schimmel, Chem. Zentr., 1908, I, 1839. 
Nelson, J, Am. Chem. Sac., 1911, 33, 

1408. 
leaves, Parfums de France, 1935, 13, 4 

(JReview). 
Schenck, Zlegler, Naturwiss., 1945, 32, 

157, (Chem. Abstracts, 1946, 40, 2132). 



Ascorbic Acid 

CH 2 OH 

CH(OH> 




/ 



M CO 

c=c 



HO 



H 



C 6 H 8 6 

dl-. 

M.p. 168-9. 



MW, 176 



M.p. 190 (187-9) decomp. [a]g - 48, [a]^ 3 
48-3 in MeOH, [a]f? 23;8 in H 2 0. Shows 
no marked antiscorbutic action. 

I-. (Z-Xyloascorbic acid). 

Natural ascorbic acid (Vitamin C). Occurs 
in adrenal cortex, paprika, oranges, cabbages, 
etc. M.p. 190, (187-9) decomp. [a]J? + 49, 
[ag? + 48 in MeOH, [a]g +23-0 in H 2 O. 12% 
HC1 >* furfural. Reduces cold Fehling's. 
No col. with SchifPs reagent. Violet col. 
with neutral FeCl^, Reduces AgNO 3 and neutral 
KMn0 4 . Decolourises Br.Aq. and I.Aq. Acid 
KMn0 4 > Z-threonic acid. Possesses powerful 
antiscorbutic properties. 

Di-phenylhydrazone : red needles. M.p. 187 
deeomp. 

Di-p-nitrophenylhydrazone : cryst. from EtOH. 
M.p. 262 decomp. 

Di-p-bromophenylhydrazone : m.p. 170 de- 
comp. 

Di-2 : 4:-dinitrophenylhydrazone : brownish-red 
needles. M.p. 282 decomp. 

Ault, Baird, Carrington, Haworth, Her- 

bert, Hirst, Percival, Smith, Stacey, 

J. Chem. Soc., 1933, 1419. 
Reichstein, Griissner, Oppenauer, Helv. 

Chim. Acta } 1933, 16, 1019. 
Reichstein, Griissner, Helv. Chim. Acta, 

1934, 17, 311. 
Banga, Szent-Gyorgyi, Biochem. J., 1934, 

28, 1625. 
Reichstein, Swiss P., 180,810, (Chem. 

Abstracts, 1936, 30, 8533); U.S.P., 

2,056,126, (Chem. Abstracts, 1936, 30, 

8247). 



Hirst, Fortschritte der Chemie Organischer 

Naturstoffe (Springer, Wien), 1939. 2, 

132. 
Haworth, Hirst, Ergebnisse der Vitamin- 

und Hormonforschung (Akademische 

Verlag. Leipzig), 1939, 2, 160. 
King, White, U.S.P., 2,318,500, (Chem. 

Abstracts, 1943, 37, 6096). 
Borisoglebskii, Chem. Abstracts, 1944, 38, 

2789. 

Isbell, Chem. Abstracts, 1945, 39, 277. 
Goth, Zeitschrift fur Vitaminforschung, 

1943, 14, 103. 



Ascosterol 




CH(CH 3 ) 2 
C 28 H 46 O MW, 398 

Minor constituent of yeast fat. M.p. 146-7 
from MeOH. [a]ff +45-1 in CHC1 3 . H 2 /Pt0 2 
> dihydroascosterol. 

Benzoyl: m.p. 135-6 from Me 9 CO. [a]! 1 
+41-1. 

Acetyl: m.p. 152-3 from Me 2 CO-MeOH. 
[a]g +21-5 in CHC1 3 . 

Wieland, Kanaoka, Ann., 1937, 530, 146. 
Barton, J. Chem. Soc., 1946, 813. 

Asebogenin (Phloretin 4 f -methyl Ether] 




C 16 H 16 5 MW, 288 

M.p. 168. KOH >- phloroglucinol mono- 
methyl ether + phloracetic acid. 

4 : 2' : V-Triacetyl : m.p. 66-7 (76-5). Sol. 
EtOH, Me 2 CO, AcOEt. 

4 : 2'-Di-Me ether : see phloretin 4:2': 4'- 
trimethyl ether, under Phloretin. 

Zemplen, Mester, Ber., 1942, 75, 1298. 
Tamura, J. Chem. Soc. Japan, 1936, 57, 
1141. 

jp-Asebotin (Phloridzin ^-methyl ether) 



HO^O-C^Os 

IB' s'j 

v*' 

3H 3 



10 



MW, 450 



Asiatic Acid 



215 



AspartMone 



Occurs in the leaves of Andromeda japonica, 
Thunb. M.p. 148. [] -46-2 in EtOH. 
Bil. HC1 > asebogenin. FeCl 3 > reddish- 
brown col. 

4 : fy'-Di-Me ether : see phioridzin trimethyl 
ether, under Phioridzin. 

Zemplen, Mester, Ber., 1942, 75, 1298. 
Tamura, J. CJiem. Sac. Japan, 1936, 57, 
1141. 

Asiatic Acid 
C3<>H 48 5 MW, 488 

Triterpene acid formed by hydrolysis of 
asiatieoside, a glycoside present in CenteUa 
asiatica. Needles. M.p. 300-305. Sublimes at 
230-60/0-1 mm. 

Me ester: C 31 H 50 5 . MW, 502. Exists in 
two forms, (i) Cryst. from EtOH. M.p. 160- 
70. Resolidifies at 180 giving form (ii). 
Cryst. from C 6 H 6 . M.p. 225. Hot HC1 > 
(i). 

Diacetyl deriv. : cryst. M.p. 168-70. [a]J? 
+ 35-2 in CHC1 3 . 

Polonsky, Compt. rend., 1949, 228, 1450; 
1950, 230, 485, 1784; 1951, 232, 1878; 
233, 93, 671; Butt. soc. chim., 1952, 
649. 

Asiatieoside 

C^HggO^ MW, 1104 

Occurs in leaves and stems of Centella asiatica. 
M.p. 230-3. Hyd. > ^-glucose + Z-rham- 
nose + asiatic acid. 

Boiteau, Buzas, Lederer, Polonsky, Butt. 
soc. chim., 1949, 31, 46. 

Asparacemic Acid. 

See ^-Aspartic Acid. 

cc-Asparagine (61-x-Asparagine, aspartic acid 
K-monoamide, dl-a-aminosiiccinamic acid) 

9H 2 -COOH p 
H 2 N-CH-CONH 2 a 

C 4 H 8 3 N 2 MW, 132 

Cryst. + 1H 2 O. Decomp. at 213-15 with- 
out melting. Sol. hot H 2 O. Insol. EtOH, 
Et 2 0. D} 5 1-454. Eeactsacid. 
N-a-Benzoyl : m.p. 190-1 decomp. 
'N-u-Benzenesulphonyl : m.p. 174-5. 

Piutti, Gazz. chim. itaL, 1888, 18, 463. 
Wesley Cocker, J. Chem. Soc., 1940, 62, 

1489. 
Vickery, Pucher, Deuber, /. Biol. Chem., 

1945, 45, 142. 

p-Asparagine (Asparagine, aspartic acid p- 
monoamide] 



d-. 

Rhombic cryst. 
- 5-41. 



H 2 O. M.p. 234*5. [xgf 



Ordinary asparagine. Constituent of aspara- 
gus, beetroot, peas, beans, etc. Rhombic hemi- 
hedral cryst. -f- 1H 2 0. M.p. 234-6 (rapid heat), 
226-7 decomp., heated slowly in sealed tube. 
Sol. 3-2% in H*0 at 30, more in hot. InsoL 
EtOH. BJ 5 1-543. [a]? - 5-42 in HgO. Trl- 
boluminescent. Reacts acid, k (acid) = 0-88 X 
10- 9 at 18, 1-3 X 10~ at 25. Jc (base) = 1-5 x 
10~ 12 at 25, 1-9 X 10' 11 at 60. HN0 2 ^ 
^-malic acid. 

N-Chloroacetyl : needles from H 2 0. M.p. 
148-9. [a]? + 4-71 in KOH. 

yt-0tycyl : needles from EtOH.Aq. M.p. 216 
decomp. Very sol. H 2 0. Spar. sol. EtOH. Acid 
to litmus. Cu salts >- reddish- violet col. 

N-a-Bromopropiatiyl : m.p. 158-9 decomp. 
[a]? 6*60 in H 2 O. 

N-Senzoyl: needles. M.p. 189. [aj? +18-9 
(1-057 gm. in 448 c.c. ^/NaOH and 5-56 c.c. 



^Aniaoyl : needles from Et 2 0. M.p. 190-1. 
[aft + 15-11 in KOH. 

N-m-Nitrobenzoyl : cryst. from H 2 O. M.p. 
176. [aft* + 12*55 in KOH. 

N-p-Nitrobenzoyl : prismatic needles. M.p. 
178. [aft + 10-96 in KOH. 

N-p-Toluenesulphonyl : needles. M.p, 175. 
[aft + 6-83 in KOH. 

Bergmann, Zervas, Salzmann, Ber., 1933, 

66, 1288. 
Berlingozzi, Gazz. chim. ital., 1927, 57, 

814. 

Piutti, Chem. Abstracts, 1925, 19, 3285. 
Steward, Thompson, Nature, 1952, 169, 

739. 

Asparaginic Acid. 

See Aspartic Acid, 

Asparaginimide . 

See under Aspartic Acid. 

Asparthione ($-Aspartykysteinylglycine) 



H 2 N-CH-COOH 
C 9 H 15 6 N 3 S 



MW, 293 



C 4 H 8 O 3 N 2 



H 2 N-CH-COOH a 



MW, 132 



Amorph. [aft 5 -29-0 in H 2 0. Forms cryst. 
Cu salt. Can replace glutathione as co-enzyme 
for glyoxylase. 

a-Benzyl-N-carbobenzoxy-S-benzyl : m.p. 153 
(from CHCl 3 -AcOEt). 

N-Carbobenzoxy-S-benzyl : m.p. 168-70 (from 
EtOH). 

Miller, Behrens, du Vigneaud, J. Biol. 
Chem. 3 1941, 140, 411. 



*f-Aspartic Acid 



216 



dfl-Aspartic Acid 



f-Aspartic Acid (d-Asparaginic add, d- 
(tmin-osuccinic acid) 



EysX3E-COOH a 

C 4 H 7 4 ^ irW > 133 

Cryst. (>]? - 25-5 in HCLAq. Sol. hot 
H,O,dil. HCL Insol. EtOH, 



Amide : see d-fr-lj- _ - 

TS-Benseayl : cryst. M.p. 184-5. [># - 37-4 
in KOH. 

Fischer, Ber., 1899, 32, 2463. 

I-Aspartic Acid (l-Asparaginic acid, l-amino- 
succinic acid). 

Constituent of young sugar cane and sugar 
beet molasses. Leaflets. M.p. 271 (rapid heat, 
in sealed tube). Sol. hot HgO, dil. HCL Insol. 
EtOH. Dg 1-6613. [ag +4-36 in H 2 0, 

1-86 at 90. Dextrorotatory in acid sol., 
isevorotatory in alk. sol. k (acid) = 13-5 X 10~ 5 
at 25. k (base) = 1-20 X 1<H 2 at 25. H]ST0 2 
> Z-malic acid. 

Brucine salt : prisms + 5H 2 from H 2 0, 
needles from MeOH-AcOEt. M.p. 100, an- 
hyd. decomp. at 200. Sol. MeOH. Mod. sol. 
EtOH, Insol. Me 2 CO. [off - 28-4 in H 2 0. 

Strychnine salt: needles. M.p. 252 5 de- 
comp. Very sol. H 2 0. Insol. EtOH. [*g 

28-3 in H 2 0. 

p-lfe ester": C 5 H 9 4 N. 
M.p. 181 decomp. Sol. 
Insol. Et 2 0. 

Di-Me ester : C 6 I 
119-20/15 mm. 

$-Et ester : C 6 H r 
from EtOH. M.p. 
sol. EtOH. Insol. 
M.p. 199-200. 

Di-Et ester: C 8 H 15 4 N. MW, 189. B.p. 
130/13 mm. D 20 1-085. [aff 9-93. Msc. 
with EtOH, Et 2 O, C 6 H 6 . Sol. H 2 0, ligroin. 
B,HCl: needles. Decomp. at 95. N-Chloroacetyl: 
needles from pet. ether. M.p. 46-7. 

$-Propyl ester : C 7 H 13 4 N. MW, 175. Leaf- 
lets. M.p. 200. SoLHjO. 

$-Isopropyl ester: needles from H 2 0. 



MW, 147. Cryst. 
H 2 0, boiling EtOH. 



. MW, 161. B.p. 

MW, 161. Leaflets 
\ Sol. H 2 0. Mod. 
Et 2 0. B,HCl : needles. 



,0 A N. 



210. Sol. H.O. Insol. Et 2 0. 



MW, 189. 



M.p. 

Cryst. 



$-Butyl ester : C 8 H 15 4 lSr. 
M.p. 198. Sol. hot H 2 0. 

$-Isobutyl ester: cryst. M.p. 197-8. Sol. 
hot H 2 0. 

^Isoamyl ester: C 9 H 17 4 N. MW,203. Cryst. 
M.p. 195-6. Sol. hot H 2 O. 

^Allyl ester: C 7 H U 4 N. MW, 173. Yellow 
needles. M.p. 194-5*. Sol. H 3 O. 

fi-Amide : see Z-p-Asparagine." 

Diamide: C 4 H 9 2 N 3 . MW,131. Cryst. M.p. 
131. Very sol. H 9 0, MeOH. Spar. sol. EtOH. 



Insol. Et 2 0> 
red col. 



CJBL. Alk. Cu salts - 



violet- 



Hydrazide: needles + H 2 O from EtOH.Aq. 
M.p. 174. Reduces AgN0 3 .XH 3 in cold, 
Fehling's on long heating. 

Dihydrazide: cryst. from EtOH. Aq. M.p. 135 
decomp. Very sol. H 2 0. 

~N-Chloroacetyl : cryst. powder from AcOEt. 
Mp about 142. Very sol. H 2 0, EtOH. Insoi. 
Et 2 0, pet. ether. [*& + 4-21^ in H 2 0. 

"N-Glycyl : cr} r st. powder + H 2 O. Loses i 2 O 
at 105 in vac. M.p. 207 decomp. Sol. H 2 O. 
Insol EtOH. [B? + 11-1 in H 2 0. Strongly 
acid in aq. sol. Heat with CuO > deep bine col. 
TS-Bewoyl: m.p. 171-3. Wf? +37 (0*91 
gm. in 7-67 c.c. NjN&OR and 2-37 c.c. H 2 O). 

Piutti, Magli, &azz. chim. Hal., 1906, 

36, II, 742. 

Fischer, Koenigs, Ber., 1904, 37, 4599. 
Freudenberg, JSToe, Ber., 1925, 58, 2399. 
Sumiki, Chem. Abstracts, 1929, 23, 2531. 

dl-Aspartic Acid (dk-Asparagimc acid, aspar- 
acemic acid). 

Monoclinic prisms. M.p. 338-9. Sol. 209 
parts of H 2 at 15. Insol. EtOH, Et 2 O. 

jQia-5 [[.5532 

-m ester: G^B-^Q^. MW, 161. Plates. 
M.p. 165 decomp. Sol. H 2 0. Spar. sol. EtOH. 

$-Et ester : leaflets or needles from EtOH.Aq. 
M.p. 200 decomp. Sol. H 2 O. Spar. sol. EtOH. 
B,EGl : m.p. 178-80 decomp. 

Di-Me ester: C 6 H n 4 N. MW, 161. 2T- 
Propionyl: needles. M.p. 46-8. B.p. 150 / 
1-5 mm. Sol. H 2 O, EtOH, Et 2 O, Me 2 CO, AcOH. 
< 1-4592. 

Di-Et ester : C 8 H 15 4 N. MW, 189. B.p. 
150-4/25 mm., l30-5/13-5 mm. Sol. H 2 0, 
EtOH, BtgO, C 6 H 6 . N-Acetyl: b.p. 180/15 
mm., 124/l-2 mm. N-Benzoyl: m.p. 165-6 
(on cryst. from boiling water this falls to 158). 
~N-J3enzenesulphonyl : m.p. 181-2. 

a- Amide : see a-Asparagine. 

Imide : asparaginimide. C 4 H 6 2 N 2 (or 
C 8 H 12 4 N 4 ). MW, 114 (228). Needles. M.p. 
275 decomp. Prac. insol. H 2 0. Insol. EtOH, 
Et 2 0. 

TS-Benzoyl : cryst. + 1H 2 from H 2 0. M.p. 
119, anhyd. 174 (164). 

TX-Carbamyl : m.p. 178-80. 

Ephedrine salt : m.p. 207 decomp. 

Wegscheider, Frankl, Monateh., 1906, 27, 

488. 

Fischer, Ber., 1899, 32, 2461. 
Fischer, Koenigs, Ber., 1904, 37, 4603. 
Pachlopnlk, Chem. Abstracts, 1926, 20, 

1386. 

Dunn, Fox, J, Biol Chem., 1933, 101, 493. 
Keimatsu, Kato, Chem. Abstracts, 1930, 

24, 70. 
Bergmann, Kann, Miekeley, Ann., 1926, 

449, 142. 
Klostermanu, Painter, /. Am. Chem. Soc., 

1947, 69, 1674. 



Aspergillic Acid 
AspergilHc Acid 

H fiK 

CH,-CH 2 -9H-C. 



2IT 



/CIO 



>H 



(CH 3 ) 2 CH-CH 2 -c v /c:o 



(ii) 



2 MW, 224 

Antibiotic from Asp&rgiUus fiavus. Pale yel- 
low rods. M.p. 97-9. [a] + 13. pK a 5-95. 
Sol. most org. solvents. Insol. H 2 O. FeCl 3 
> red col. AcOH + P -f I > deoxy- 
aspergillic acid. 

Ag salt : colourless plates from EtOH. De- 
comp. at 190. 

Cu salt : green leaflets. M.p. 198-9. 
Phenylhydrazine salt : m.p. 99-5. 
B,ECl : m.p. 182 decomp. 
3 : 5-Dinitrobenzoyl : (i) m.p. 166-8 ; 
m.p. 123. 

Methiodide : cryst. + Mel. M.p. 169. 

Butcher, /. Biol. Chem., 1947, 171, 321, 

341. 
Dunn, Gallagher, Newbold, Spring, J. 

Chem. Soc., 1949, SuppL, 126. 
Dunn, Newbold, Spring, ibid., Suppl., 
131. 

Aspemloside 

C^H^O!! MW, 404 

Glycoside occurring in Galium aparine, Ritbia 
tinctorum, and Daphniphyllum macropodum. 
Needles from EtOH. M.p . 125-7. [a] Jf 204 
in H 2 O. HCl-AcOH in presence of Cu > clear 
bright blue sol. 

Octa-acetyl : m.p. 153. Sol. EtOH, MeOH, 
AcOEt. 

Herissey, Bull. soc. chim. biol., 1925, 7, 

1009. 
Trim, Hill, Biochem. J., 1952, 50, 310. 

Asphodelin. 

Polysaccharide from Asphodelus Jcnollen, con- 
taining at least seven hexose units. M.p. 210. 
Very sol. H 2 0. Sol. EtOH. [a]f? 30-9 in 
H 2 O. 

Acetyl deriv. : [a]f 16-6. 
Methyl deriv. : brown viscous syrup, [a]?? 
33-3 in C 6 H 6 . Hyd. > mixture of methyl- 
ated hexoses. 

Schlubach, Lendzian, Ann., 1937, 532, 

191. 

Colin, Neyron, Bull. soc. chim., 1931, 49, 
1542. 



Aspidin (Aspidine) 

H 3 C CH 3 



Aspidospermine 



CO-C 3 H 7 



.W i| OHH0 ll 



C 25 H 32 8 MW, 460 

Occurs in rhizomes of Dryopteris spinulosa 
and Dr. austriaca. Pale yellow cryst. from 
EtOH. M.p. 125. 

Diacetyl deriv. : needles and prisms from 
MeOH. M.p. 108. 

Anilide : cryst. from EtOH. M.p. 132. 
Hausmann, Chem. Zentr., 1899, II, 919. 
Boehm, Ann., 1903, 329, 321. 
Carlsson, Backstrom, SvensJc. Farm. 
Tids., 1943, 47, 33. 

Aspidinol (Z-Methyl-^-butyrylphloroglwinol 
1-methyl ether, 3 : 5-dihydroxy-l-methoxy-2-methyl- 
4-butyrylbenzene, 2 : $-dihydroxy-%-methyl~4:- 
methoxyphenyl n-propyl ketone) 

OCH 3 




)0-CH 2 *CH 2 -CH 3 
C 12 H 16 4 MW, 224 

Constituent of male fern. Yellow needles or 
plates from C 6 H 6 . M.p. 156-61. Sol. EtOH. 
Et 2 O, CHClg, Me 2 CO. Spar. sol. C 6 H 6 , hot H 2 0, 
Sol. cone, alkalis. 

Dibenzoyl : prisms from EtOH. M.p. 108-9 C . 

Karrer, Widmer, Helv. Chim. Acta, 1920. 
3 392 

Fumarola, B.P., 256,758, (Chem. Ab- 
stracts, 1927, 21, 3105). 

Aspidospermine 



CH 3 




OCH 3 



CO-CH 3 



, MW, 354 

Alkaloid firom bark of Aspidosperma que- 
bracho, Schlecht. Identical with vallesnie from 
Vallesia glabra and Vattesia dichotoma. Needles 
from EtOH. M.p. 208. Sol. CHC1 3 , C 6 H 6 . 
Mod. sol. EtOH. Spar. sol. H 2 0. Colourless 



n cone. 



[a]Jf - 100-2 in EtOH. 



Ewins, J. Chem. Soc., 1914, 105, 2738. 
Meld, J. Chem. Soc., 1924, 125, 1444. 
Deulofeu, deLanghe, Labriola, Marquez, 

Chem. Abstracts, 1938, 32, 2135. 
Witkop, J.Am. Chem. Soc., 1948, 70, 3712. 
Openshaw, Smith, Experientia, 1948, 4, 

428. 



Aspirin 



218 



Atisine 



Aspirin. 

See Acetylsalicylic Acid. 
Astacene (Astacin, 4:5:4': o r -tetraketo-$- 
caroten-e) 



Jx 

H 2 9 ig C 

OC? 



H:CH-C:CH*CH:CH-C:CH-CH 



H 3 C X/ CH 3 
C 



CH 3 



CH 3 



OC C*CH 3 

CO 

4 MW, 592 

Bluish-red needles from Py. M.p. 243. Sol. 
AeOEt, CHC1 3 , C 6 H 6 , Py, dioxan. Spar. sol. 
MeOH, Et 2 5 pet. ether, CS 2 . Insol. H 2 0, 
NaOH. Absorption maximum at 500 mjz in Py. 
Eorms dioxime. 

Karrer, Loewe, Hiibner, Helv. Chim. Ada, 

1935, 18, 96. 

Kuhn, Lederer, Ber., 1933, 66, 488. 
See also references under Astaxanthin 
below. 

Astaxanthin (5 : o'-DihydroxyA : 4:'-diketo-$- 
carotene) 



y\ 

H 2V 9~~ CH:CH*C:CH-OH:CH-C:CH-CH 

HOHC C-CH 3 
CO 



C 



Asterm. 

See Chrysanthemin. 

Asterubin 




CH 3 



CH, 



MW 3 596 



HOHC C-CH 3 

CO 
C40H 52 4 

In form of esters or chromoproteins in crusta- 
ceans, etc. Violet plates with metallic lustre 
from PyAq. M.p. 215-6 decomp. In absence 
of air gives blue sol. in alkalis. Alkalis + 
>- astacene. 
Diacetyl : blue-black needles from PyAq. C 22 H 31 2 N or C 22 H 33 2 N 

M.p. 203-5. ^ 

Hydrogen palmitate : m.p. 115. 
Dipalmityl : violet-red needles from Pv~ 
MeOH. M.p. 72. 

Kuhn, Sorensen, Ber. y 1938, 71, 1879. 
Kuhn, Stene, Sorensen, Ber., 1939, 72, 
1688. 



K\ T :C-NH-CH 2 -CH 2 -S0 3 H 
C 5 H 13 3 N 3 S MW, 195 

Isolated from starfish. Needles from 
MeOH.Aq. M.p. 272-3 decomp. Neutral 
reaction. KMn0 4 > guanidine. 

Ackermann, Z. physioL Chem., 1935, 232, 

206. 
Ackermann, Miiller, ibid., 235, 233. 

AtebiiH (Acricfiine, acriquine, mepacriTie, 
guinacrine) 

2s T H-CH(CH 3 ).[CH 2 ] 3 -N(C 2 H 5 ) 3 
yv 
CH, 

Jci 

MW, 3995 

YeUow oil. [aji 7 197 in EtOH. 
B,2HCl: yeUow needles from EtOH-Et 2 O. 
M.p. 244-5 decomp. [a] 1 ^ - 379 in H 2 0. 

d-. 

YeUowoil. [a]J? + 205 in EtOH. 
B,2HCl: yellow needles from EtOH-Et 2 0. 
M.p. 244-5 decomp. [a& + 388 in H 2 0. 

(B-. 

M.p. 86-8. Spar. sol. Me 2 CO. Insol. dry 
Et 2 0. 

B,2HCl : cryst. from H 2 0. M.p. 248-50. 

MethanesulphoTiate : m.p. 143-5. 

Antimalarial drug administered in the form 
of salts. 

Knunyantz et al., Chem. Abstracts, 1934, 

28, 2126, 4837. 
Mietzsch, Mauss, Angew. Chem., 1934, 47, 

633. 

I.Q., B.P. 363,392, (U.S.P. 2,113,357). 
Poulenc, B.P. 452,805, (U.S.P. 2,092,114). 
I.C.I., B.P. 544,846. 
Sherndahl, Chemical Engineering News, 

1943, 21, 1154. 
Brown, Hammick, J. Chem. Soc., 1948, 

99. 

Atisine (Anthorine) 

MW, 341 (343) 

Alkaloid from Aconitum heterophyllum, Wall. 
M.p. 57*60. Sol. EtOH, Et 2 0. MeOH/NaOH 
-> dihydroatisine. H 2 /Pt0 2 ^ tetrahydro- 
atisine. Se > 1-methylphenanthrene + (?) 
1 -methyl-6-ethylphenanthrene. 

B,HCl : m.p. 340 (311-12). [a] D +26-9. 

B,HI: m.p. 295. 



Atlantone 



219 



Atrolactinic Add 



Diacetyl : hydrochloride, m.p. 241-3 decomp. 

Jacobs, Craig, J. Biol. Chem., 1942, 143, 

589. 

Lawson, Toffs, J. Chem. Soc., 1937, 1640. 
Govis, Compt. rend., 1937, 205, 1007. 

Atlantone 
CH 3 -C CH 9 CH 3 -C CH 2 

^\/^\ /\/\ 

TT/" 1 mr r^TJ TT r* o VITT 

JLly yJa. yljLo 2 iy L/ Y ^ 

OC H 2 C^ ^C-CH 3 OC H 2 C C-CH 3 

pH CH x- CH CH p. 

C C 



Atranoiin 



CEL 



15 H 22 MW,218 

Present in a mixture, b.p. 120-1/1 mm., con- 
taining a- and (3-atlantones and sesquiterpene 
alcohols, in oil from Cedrus atlantica, Manet, and 
C. deodar a, Loud. 

St. Pfau, Plattner, Helv. Chim. Acta > 
1934, 17, 129. 

Atophan. 

See 2-Phenylquinoline-4-carboxyHc Acid. 

Atoquinol. 

See under 2-Phenylquinoline-4-carboxylic Acid. 

Atoxyl. 

See under Arsanilic Acid. 

Atractylol. 

See Eudesmol. 

Atranol (p-Orsellinaldehyde, y-orcylaldehyde, 
3 : 5-dihydroxy-p-toluic aldehyde, 4:-methyl~y- 
resorcylic aldehyde) 




C 8 H 8 3 

o o O 



O 



MW, 152 

Yellow needles from H 2 0. M.p. 124. Takes 
up |H 2 from air ^hydrate, m.p. 118-19. 
Sol. "alkalis and alkali carbonates with yellow 
col. Slightly volatile in steam. FeClg > 
olive-green col. in dil. ale. sol. 

Di-Me ether : C 10 H 12 3 . MW, 180. Needles 
from pet. ether. M.p. 90-1. 

Mono-acetyl deriv. : needles from EtOH.Aq. 
M.p. 75-75-5. 

Triacetyl deriv. : m.p. 140-2. 

Oxime: cryst. from C 6 H 6 . M.p. 194-5 
decomp. 

Semicarbazone : cryst. from EtOH. M.p. 
273-5. 

Anil : brownish-red needles from EtOH.Aq. 
M.p. 207-9. 

St. Pfau, Helv. Chim. Acta, 1934, 17, 
1327: 1926,9,661. 



GH 3 



^ CO-OCH 3 



CH 3 
C 19 H 18 8 MW, 374 

Obtained from lichens. Prisms from CHCL. 
M.p. 196-7 (187-8). Sol. hot CHC1 3 . Sol. 
alkalis to yellow sols. 

Di-Me ether : C 21 H 22 8 . MW, 402. Prisms 
from AcOEt-ligroin. "M.p. 136. Ale. FeCij 
>- light brown col. 

Tri-Me ether : C^H^Og. MW, 416. Prisms 
from MeOH. M.p. 123. 

Curd, Robertson, Stephenson, J. Chem. 

Soc., 1933, 130. 
St. Pfau, Helv. Chim. Acta, 1926, 9, 650. 

Atrogly eerie Acid. 

See 1-Phenylglyceric Acid. 

Atrolactic Acid. 

See Atrolactinic Acid. 

Atrolactinic Acid (l-Phenyl-lactic acid, 1- 
phenyl-I-hydroxypr<ypionic acid, x-hydroxyhydra- 
tropic acid, &-methylmandelic acid, atrolactic acid) 

HOv 



C 9 H 10 3 MW, 166 

d-. 

Prisms from H 9 0. M.p. 116-17. Sol. 20 
parts H 2 at 18^ [a]i 65 +37-7 in EtOH. 

Quinine salt : needles from EtOH. M.p. 
about 216 decomp. 

l-Menthyl ester : liq. B.p. 154-5 /0-03 mm. 
WJ? 5 - 58-8 in EtOH. 

Z-. 

Needles from C 6 H 6 . M.p. 115-16. Sol. EtOH, 
Me 2 CO,hotC 6 H 6 . Mod. sol. BUG. [a]? 8 - 37-7 
in EtOH. 

m ester : C U H 14 O 8 . MW, 194. B.p. 127/12 
mm. Df 1-097. [a]i 3 - 26-7. 

l-Menthyl ester : m.p. 55-5-56. [ofo 102-7 
in CHC1 3 . 

Amide: C 9 H n 2 N. MW, 165. Rhombic 
plates from C 6 H 6 . M.p. 62-5-63*5. [a] D + 12-6 
in EtOH. 

dl-. 

Needles or prisms + iH 2 from H 2 0. M.p. 
68. Loses H 2 of cryst. at 85-90 : m.p. 
anhyd. 94. Sol. H 2 0. Misc. H 2 all pro- 
portions at 100. Boiling HC1 > atropic acid. 
Br at > 1-bromohydratropic acid. 

Et ester: b.p. 259, 129-30/13 mm. Df 
1-100. ng 1-50997. 

l-Menthyl ester : b.p. 190-2/10-ll mm. [a] D 
- 67-5 in CHCV 

Amide : leaflets from dichloroethylene. M.p. 
101-2. Sol. H 2 0. 



Atromentln 



220 



Atroxindole 



Et ether : C U H 14 3 . MW, 194. Cryst. from 
ligroin. M.p. 60-2. Sol. Et 2 0. Mod. sol. hot 



McKenzie, Clough, /. Chem. Sac., 1910, 
97, 1018; 1912, 101, 393 (Nate). 

Wren, Wright, J. Chem. Sac., 1921, 119, 
798. 



Atromentin 



H 




H0 4^- 



C 18 H 12 6 MW, 324 

Colouring matter from the fungus PaxiUus 
atromentosus. 

4':4"-DiVafe eftsr : C2oH 16 O 6 . MW, 352. 
Bronze plates from toluene. M.p. 297-8. 

Tetra-Me ether : C^H^Og. MW, 380. Red 
cryst. from EtOH. M.p." 199. 
*Tetra-acetyl : cryst. from AcOH. M.p. 242. 
Shildneck, Adams, J. Am. Chem. Soc., 

1931, 53, 2378. 
Kogl, Becker, Detzel, Voss, Ann., 1928, 

465, 211. 
Kogl, Becker, Voss, Wirth, ibid., 243. 

Atromentinic Acid ($$' -Dihydroxypulvinic 
acid) 




C 18 H 12 7 MW, 340 

Bed needles + 1H 2 from H 2 0. M.p. 332. 
Anhyd. at 100 > yellow needles which take 
up 1H 2 in air > red needles. 

Et ester: C 20 H 16 7 . MW, 368. Orange 
cryst. from EtOH. M.p. 346. 

Tri-Me ether : yellow leaflets from AcOH. 
M.p. 170. 

Tetra-Me deriv. : yellow needles from 
AcOH.Aq. M.p. 168. 

Lactone : yellow leaflets from AcOH. M.p. 
346 decomp. 

Kogl, Becker, Voss, Wirth, Ann., 1928, 

465, 253. 

Asano, Huziwara, J. Pharm. Soc. Japan, 
1939, 59, 284. 

Atropamine. 

See Apoatropine. 

Atropic Acid (l-Phenylacrylic acid) 

C 6 H 5 -f}-COOH 

GEL 

C 9 H 8 2 MW, 148 

Cryst. from H 2 or EtOH. M.p. 106-7. 
B.p. 267 part, decomp., 202-4 /75 mm. Sol. 
Et 2 0, C 6 H 6 , CS 2 . Mod. sol. EtOH. Spar. sol. 
cold H 2 0. Volatile in steam. Heat of comb. 
1044 Cal k = 1-43 X 10" 4 at 25. Cr0 3 > 



benzoic acid CO 2 . NaHg > hydratropic 
acid. KOH fusion > phenylacetic + formic 
acids. Cone. HC1 > 2-chlorohydratropic acid. 
Dry HBr at > 1-bromohydratropic acid. 
Fuming HBr at 100 > 2-bromohydratropic 
acid. Br > dibromohydratropic acid. HOC1 
> chlorotropic acid. 

Et ester : C U H 12 2 . MW, 176. B.p. 124 / 
16mm. DI 6 1-0508. 7^1-52605. 

Amide: C 9 H 9 ON. MW, 147. Cryst. from 
H 2 0. M.p. 121-2. Spar. sol. H 2 0. 

Chloride : C 9 H 7 OC1. MW, 166-5. B.p.87-8 / 
0*35 mm. 

Anilide : m.p. 134. 

McKenzie, Wood, /. Chem. Sac., 1919, 

115, 834. 

I.C.I., B.P., 446,908, (Chem. Abstracts, 
1936, 30, 6763). 

Atropine (Tr opine ester of tropic acid, dl- 
Jiyoscyamine) 



0-CO-CH 




M.p. anhyd. 194 



C 17 H 23 3 N MW, 289 

In Atropa belladonna, Datura stramonium, etc. 
Probably formed by racemisation of Z-hyoscy- 
amine during extraction. Cryst. M.p. 118 
(114-15). Sol. to 68% in EtOH at 25, to 
6% in Et 2 at 25, to 64% in CHC1 3 at 25. 
Spar. sol. H 2 0. Insol. pet. ether. Optically 
inactive. Strong base. Used in medicine as a 
mydriatic. 

B,HBr : m.p. 163-4. 
B 2 ,HoSO* : cryst. + H 2 0. 
Sol. H 2 0, EtOH. 
B 2 ,(COOH) : m.p. 198. 

~~ m.p. 137-9. 

m.p. 197-200. 
Picrate : m.p. 175-6. 
Styphnate : m.p. 180. 

Duilius, Chem.-Ztg., 1930, 54, 182. 
Chemnitius, J. praJct. Chem., 1927. 116, 

276. 
BarrowcHff, Tutin, /. Chem. Soc., 1909, 

95, 1966. 
Zalay, Chem. Abstracts, 1941, 35, 8204. 

Atropine oxide. 

See Genatropine. 
Atroscine. 
See Hyoscine. 

Atroxindole (Z-Methyloxindole, o-amino- 
hydratropic lactam) 




C 9 H 9 ON MW, 147 

Exists in two modifications. ] . Cryst. from 

C 6 H 6 , m.p. 123. 2. Needles from H 2 0, m.p. 



Aiibepine 



221 



Aureusin 



1 13 C . Sol. EtOH, EtgO. Spar. sol. H 2 O. Very 

spar, volatile in steam. Distils undecomp. in 
small quantities. Aq. sol. reacts neutral. 
Reduces NH 3 .AgX0 3 , hot Fehling's. 
N- Me : see 1 : 3-Dimethyloxindole. 

Brunner, Monatsh., 1897, 18, 533. 

Aixbepine. 

See Anisaldehyde. 

Aucubine 

OR 

H/CH CH 2 




R: 



: CH 2 

OH 

glucose residue 



15 H 22 9 ~ MW, 346 

Glucoside from Plantago lanceolata, Linn., 
AuvuJba japonica, Thunb., etc. Cryst. + 1H 2 O 
from EtOH.Aq. M.p. 181. [a]! 1 171-4 in 
H 2 O. 

Hexa-acetyl deriv. : m.p. 128. [a]g 154-9 
in CHC1 3 . 

Bergmann, Michalis, JBer. s 1927, 60, 935. 
Kariyone, Kondo, Chem. Abstracts, 1929, 

23, 393. 
Karrer, Schmidt, Helv. Chim. Acta., 1946, 

29, 525. 
Trim, Hill, Biochem. /., 1952, 50, 310. 



Aurapten 




O 

Oi 5 H 16 4 MW, 260 

Occurs in orange peel oil. M.p. 98. B.p. 
140-50/0-02 mm. Sol. C 6 H 6 , CHC1 3 , Et 2 O, 
AcOH, AcOEt, dioxan. Pd/H 2 > dihydro- 
auraptene. NaOMe >- cis-auraptenic acid. 
Heat in solution >- iraw^-atu-aptenic acid. 



AcOH/H 2 SO 4 



isoaurapten. 



Cr0 



3 



OxaHc acid 
acetone + 



aurapten hydrate. 
ostholic acid. 

Bohme, Pietsch, Arch. Pharm., 1938, 276, 

482. 
Bohme, Schneider, Ber., 1939, 72, 780. 

Auraptenic Acid 

/\CH:CH-COOH 



C 15 H 18 S 



_ M.p 151 5 . Hi? + 2 s in EtOH. Pfc/H 2 > 
dihydroattrapt enic acid . Ac 2 O > acetyl deriv. 
of trans- form. 

Trans-. 

M.p. 204. [>]f? +90-4 in EtOH. Pt/H 2 
> dihydroauraptenic acid. 
Jfe esfer : m.p. 99. 
Acetyl : m.p. 180. 

Bohme, Schneider, Arch. Pharm., 1941, 
279, 213. 

Aureomycia. 
C 22 H 23 O 8 ISr 2 Cl MW, 478-5 

Antibiotic produced by Streptamyces aureo- 
faciens. M.p. 168-9. [a]! 3 275-0 in MeOH. 
Sol. to 0-5-0*6% in H 2 O at 25. Very sol. 
cellosolve, dioxan. Spar. sol. MeOH, EtOH, 
butanol, Me 2 GO, AcOEt, C 6 H 6 . Insol. Et 2 0, 
pet. ether. Very sol. in aq. sols, of pH above 
8-5. Used in undulant fever, pneumonia, 
sinusitis and bacterial endocarditis. 

B,HCl : decomp. above 210. [og? 24-0 in 
H 2 O. 

Stephens et al. } J. Am. Ghem. Soc., 1952, 

74, 4976. 
Waller et al, ibid., 4978. 



OH 




MW, 286 

Aglucone from yellow Antirrhinum majus. 
Deep yellow cryst. + 1H 2 from MeOH.Aq. 
Melts and resolidifies at 270. Decomp. at 295. 
10% NaOH or cone. H2SO 4 > orange-red col. 
FeClg > brown col. 

Tetra-Me ether: C 19 H 16 O 6 . MW, 342. 
Greenish-yellow needles from MeOH.Aq. M.p. 
169-72. Cone. H 2 SO 4 > dark red col. 

Tetra-acetyl : yellow needles from pet. ether. 
M.p. 184^5. 

Seikel, Geissman, J. Am. CUem. Soc. t 
1950, 72, 5725. 



Aureusin 



OH 



or 
CO 



H CX:: 

L.O.-O 



OH 



MW, 278 



MW,448 



Anrofosarin 



222 



Avenacein. 



Pigment of Antirrhinum majus. 

Hepta-acetyl : colourless needles from AcOEt. 
M.p. 264-5-265-5 . 10% ISfaOH, slowly > 
red sol. Cone. H 2 S0 4 - > orange-red col. 

Seikel, Geissman, J. Am. Chem. Soc. 9 
1950, 72, 5725. 

Aurofasarin 
QsoHMOa MW, 572 

Occurs in Fusarium culmorum, Socc. M.p. 
above 360. Contains two -OCH 3 groups. 

H 2 ^ tetrahydroaurofusarin. 
Benzoyl deriv. : m.p. 212-15. 

Animate : m.p. 205. 

Ashley, Hobbs, Raistrick, Biockem. J., 
1937, 31, 385. 



Atiroglaucin 




C 19 H 22 3 MW, 298 

Occurs in the AspergiUus colouring matters. 
Orange-red pigment. M.p. 153. Pd/H > 
octahydroauroglaucin and decahydroauro- 
glaucin. FeCl 3 > red col. 
Me ether : yellowish-brown. M.p. 100. 
Oxime : yellowish-green cryst. M.p. 117 
decomp. 

2 : 4-Dinitrophenylhydrazone : brick red. M.p. 
223-4. 

Phenyluretkane : pale yellow cryst. M.p. 
161. 

Raistrick, Robinson, Todd, J. Chem. Soc., 

1937, 80. 
Cruickshank, Raistrick, Robinson, J. 

Chem.Soc., 1938,2056. 
Quilico, Panizzi, Mugnani, Gazz. chim. 
ital., 1949, 79, 89. 



H 3 C CH 




!:CH-CH:CH-C:CH-CH: 



Probable structure 

C 40 H 56 4 MW, 600 

Carotenoid pigment from Viola tricolor. Long 

bright yellow needles from EtOH. M.p. 203. 

^ 382, 403, 428 m^ (in EtOH) ; 423, 454 m^ 

(in CS 2 ). 
Monohydrate : m.p. 191-2. 

Karrer, Jucker, Helv. Chim. Acta, 1945, 

28, 300. 
Karrer, Ruthschmann, Helv. Chim. Acta, 

1942, 25, 1624. 



Australene, 

See a-Pinene. 

Auxenolonic Acid. 

See Auxin B. 

Auxentiiolic Acid. 

See Auxin A. 

Auxin A (Auxentriolic acid) 



CH 3 -CH,-CH-9H-C-CHOH-CH,-[CHOH] 2 -COOH 



CH 3 -CH,-9H-CH-CH 
"CH 3 

Suggested structure 
C 18 H 32 5 MW, 328 

Plant growth hormone. Isolated from human 
urine and yeast. Hexagonal cryst. from EtOH- 
ligroin. M.p. 196. Mod. sol. MeOH, EtOH, 
AcOEt. Spar. sol. Et 2 0, H 2 0. Insol. pet. 
ether, C 6 H 6 . [a]| 3-19 in EtOH. Readily 
decomp. by alkalis. 

Lactone : C 18 
from Me 2 CO.Aq. 
pet. ether, C 6 H 6 . 

Me ester : C 1fl l 
Et 2 0. M.p. 



-p-Phenylphenacyl ester : C 32 H A , 



Cryst. from 
MW, 522. 



MW, 310. Needles 
173. Spar. sol. H 2 0> 
- 3-44. 
MW, 342. 

[off - 3-77. 

" ~~-ZB 
Cryst. from EtOH.Aq. M.p. 166. 

Tri-m-dinitrobenzoyl : cryst. from 
M.p. 168. 

Kogl et al, Z. physiol. Chem., 1934, 227, 
51; 1934, 225, 215; 1933, 216, 31; 
1933, 214, 241 ; 1935, 235, 201. 

Auxin B (Auxenolonic acid) 



EtOEL 



CH 3 -CH 2 -CH-9H C-CHOH-CH,-CO-CH 2 -COOH 



CH 3 -CH 2 -9H-CH CH 
CH 3 

Suggested structure 

C 18 H3o0 4 MW, 310> 

Plant growth hormone. Isolated from various- 
grain oils and from urine. Cryst. from EtOH- 
ligroin. M.p. 183. [oft - 2-8. 

p-Phenylphenacyl ester : needles from EtOH. 
Aq. M.p. 174. 

Semicarbazone : prisms from MeOH.Aq. M.p. 
176. 

Kogl, Erxleben, Z. physiol. Chem., 1934,. 

227, 51. 
Kogl, Erxleben, Haagen-Smit, Z. physiol. 

Chem., 1934, 225, 215. 

Avenacein 
C 26 H M 7 N 2 MW, 484 

Antibiotic of Fusaria avenaceum. Tetrahedra 
from MeOH.Aq. M.p. 139. [oft? - 101 2" 



Avertin 



223 



Azsdrixi 



(c = 1 in EtOH). HCi > D-a-hydroxyiso- 
valeric acid + N-methyl-Z-valine hydrochloride. 

Cook, Cox, Farmer, J. CJiem. Soc. 9 1949, 
1022. 

Avertin. 

See 2 : 2 : 2-Tribromoethyl Alcohol. 

Axerophtliene 

HgC GJcij. Y s V ^3 

\<^ ,,CH-CH:C-CH:CH-CH:C-CH 2 -CH 3 




Probable structure 

C^Hgo MW, 270 

Purified by mol. distillation. Thick yellow 
oil. SbCl 3 > violet-blue col. (^^ 577 mp). 
Shows slight vitamin A type activity. 

Karrer, Benz. Helv. Chim. Ada, 1948, 81, 
1049. 

Axerophthol. 

See Vitamin-A. 
Ayapin (6 : 7-Methylenedioxycoumarin) 

CH 



TT 




C 10 H 6 4 



MW, 190 



Present in leaves ofEupatorium ayapana Vent. 
Cryst. from MeOEL M.p. 231-2 (evacuated 
tube). 

Spath, Bose, Schlager, Ber. } 1937, 70, 702. 

Ayfivin. 

See Bacitracin. 

l-Azabicyclo-[5 : 3 : 0]-decane 



N - CH 2 
C U H 21 N 

B.p. 111~12/18 mm. ri$ 14930. 
Picrate : m.p. 139-40. 
Picrolonate : m.p. 186-7. 



Methiodide: m.p. 243-4. 

Leonard, Goode, J. Am. CJiem. Soc., 1950, 
72 ? 5404. 

l-Azabicydo-[5 : 4 : 0]-liendecane 



C 10 H 19 N 



N - CH 2 

MW, 153 

B.p. 90/16 mm. g 14872. 
Picrate: cry st. from EtOH. M.p. 161-2. 
Picrolonate : cryst. from EtOH. M.p. 213 
decomp. 

Leonard, Goode, /. Am. Ckem. Soc., 1950^ 
72,5404. 

Azabicyclo-[2 : 2 : l]-lieptane 



, 97 



B.p. 130/755 mm. Se > 
m.p. 320 decomp. Slightly 



C 6 H n lS T 

M.p. 78-9 
y-picoline. 

Methiodide 
hygroscopic. 

Chloraurate : yeUow. M.p. 280 decomp. 
Picrate : m.p. 285 decomp. 
Picrolonate : pale yellow. M.p. 255. 

Clemo, Prelog, J. CTiem. Soc. y 1938, 400. 
Prelog, Cerkovnikov, Ustricev, Ann., 
1938, 535, 37. 

6-Azacholantlirene 



H,9 I 

H 2 C N C m 

C 9 H 17 N MW, 139 

B.p. 71 73-5/14 mm. < 1-4822. 
Picrate: m.p. 214-15. 
Picrolonate : m.p. 191-2. 
Methiodide : m.p. 279-80. 

Leonard, Goode, J. Am. CJiem. Soc., 
1950, 72, 5404. 

l-Azabicyclo-[5 : 5 : 0]-dodecane 



167 




M.p. 187-8. 

Picrate : M.p. 222-4 decomp. 

Postovski, Lundin, J. Gen. 
U.S.S.R., 1940, 10, 71. 



255 



CJiem. 




C 27 H 38 4 



MW, 426 



Pigment of the Eschobedia class. Orange-red 
isms from Me 2 CO-toluene. M.p. 213-14. 



prisms 



Azaiadole 



224 



[*] 



~ 5 *& i n EtOH. Absorption bands in 
CHCLj, 458, 428 znji, in CS 8 , 476, 445, 419 mj*. 
Ethereal sol. -f- HCI > deep violet acid layer. 
If e ester: methykzafrin. CggH^O* MW, 
440. Orange leaflets from MeOH. M.p. 193. 
[*]g - 73 in EtOH. 

Eoihn, Deutsch, Ber., 1933, 66, 883. 

Azaindole. 

See Pyrrolopyridine. 
Azantlira cene , 
See Anthrapyridine. 
Azanthraqtunone . 
tiee a-Anthrapyridinequinone. 
Azap&enaiitliFene * 
See Benzquinoline and Phenanthridine. 
Azelaic Acid (n-Heptane-l : l~dica,rboxylic 
acid, lepargylic acid) 

HOOC-CH 2 -[CH 2 ] 5 -CH 2 COOH 

cys 16 o 4 " ~ MW, iss 

Needles or leaflets. M.p. 106-5. B.p. 287 / 
100 mm., 265/50 mm., 237/15 mm., 226/10 
mm. Distils at ord. pressure above 360 with 
partial anhydrisation. Non-volatile in steam. 
Sol. to 2-2% in H 2 at 65. Sol. EtOH. Spar. 
sol. Et 2 O. D 1-0287. n 1-42808. Heat of 
comb. C, 11404 Cal. k (first) = 2-88 X 10~ B 
at 25; k (second) = 2-8 X 10" 6 at 25. 

Di-Me ester: C^H^O^. MW, 216. B.p. 
140-l/9 mm. Df 1-0082. < 1-43669. 

Et ester ; C l:L H^O^ MW, 216. M.p. 28-9. 
B.p. 178-9/5-5 mm. 

Vi-m ester : C 13 H M 4 . MW, 244. B.p. 291, 
148/7-5 mm. Df 0-97294. v$ 1-43509. 

Diphenyl ester-. CgiH^O,. MW 3 340, 
Needles. M.p. 49. Sol. Et 2 0, C 6 H 6 . 

Diphenacyl ester : m.p. 69-7. 

Di-$-bromophenacyl ester : m.p. 130-6. 

Dinttrile:* C^N,. MW, 150, B.p. 195/ 



20 mm., 183/11 mm., 159-60/3 mm. 
1-4426. Sol. EtOH, Et 2 0, C 6 H 6 . Insol. H 2 0. 

Dichloride: C 9 H 14 2 C1 2 . MW, 225. B.p. 
166/18 mm. 

Monoamide: CgH.^0^. MW, 187. Needles. 
M.p. 93-5. 

Diamide: C 9 H 18 02N 2 . MW, 186. Prisms. 
M.p. 175. 

Anhydride : m.p. 53-5. 

Monoanilide : m.p. 107-8. 

Dianilide : m.p. 186-7. Prac. insol. H 2 0, 
Et 2 0, C 6 H 6 . 

Di-o-toluidide : m.p. 164. 

Di-p-toluidide : m.p. 191. 

Di-p-bromoanilide : m.p. 215. 

Carmichael, J. Chem. Soc., 1922, 121, 

2545. 
Griin, Wittka, Chem. Abstracts, 1926, 20, 

301. 
Fourneau, Sabetay, Bull. soc. chim., 1929, 

45, 834. 



RiecJbe, D.R.P., 565,158, (Ohem. Abstracts, 

1933, 27 ; 1008). 
Hill, McEwen, Organic Syntheses, 1933, 

XIII, 4. 
Mowry, Ringwald, J. Am. Chem. Soct, 

1950, 72, 4439. 



(1'Formylcaprylic 
7 -a Idehydocapr ylic 



C 9 H 16 3 



Azelaic Semi-aldehyde 
acid, 7-aldehijdo-octoic acid, 
acid) 

OHC-[CH 2 ] 7 -COOH 

MW, 172 

M.p. 57-63 (70). B.p. 181-2/15 mm. Sol. 
common org. solvents. Insol. H 2 0. 

Me ester : C 10 H 18 3 . MW, 186. B.p. 111- 
12/3 mm. (I40-5/15 mm.). Df 0-9704. <> 
1-4384. Semicarbazone: m.p. 104-5 (107). 2:4- 
Dinitrophenylhydrazone : m.p. 678. Di-Me 
acetal : C 12 H 24 4 . MW, 232. B.p. 148-50/14 
mm. Df 0-9379. ng 1-4312. Trimeride: cryst. 
from pet. ether. M.p. 34-6. 

Et ester: Q^n^O^ MW, 200. B.p. 158- 
68/14 mm., 100-2/l mm. Di-Et acetal : b.p. 
158-60/14 mm. 2 : ^-Dinitrophenylhydrazone : 
m.p. 63-4. 

Semicarbazone : m.p. 163 (166-5). 

%-Nitrophenylhydrazone : m.p. 114-15. 

2 : 4:-Dinitrophenylhydrazone : m.p. 120. 

Trimeride : cryst. from Me 2 CO. M.p. 112-13. 

Fischer, Dull, Ertel, Ber., 1932, 65, 1471. 
Noller, Adams, J. Am. Chem. Soc., 1926, 

48, 1074. 

Helferich, Schafer, Ber., 1924, 57, 1911. 
HaUer, Brochet, Compt. rend., 1910, 150, 

496. 

Azelaone (Cyclo-octanone) 



CH 2 -CH 2 -CH 2 -CH 2 
C 8 H 14 MW, 126 

M.p. 28. B.p. 195-7, 91/23 mm., 73/12 
mm. D 20 0-9581. < 14694. Gives bisulphite 
compound. Cr0 3 in H 2 S0 4 >- suberic acid. 

Semicarbazone : m.p. 167-8. 

Oxime : m.p. 36-7. 

Buzicka, Brugger, Helv. Chim. Acta, 

1926, 9, 339. 
Kuzicka, Kobelt, Hafliger, Prelog, Edv. 

Chim. Acta, 1949, 32, 544. 

Azetidine . 

See Trimethyleneimine. 
Azetidinone. 
See p-Propiolactam. 

Azibenzil (Phenylbenzoyldiazomethane, phenyl- 
benzoylazimethylene) 

CeHg^-CO-CeHg C 6 H 6 -C-CO-C 6 H 5 

or A 

NSN 



C 14 H 10 ON 2 



MW, 222 



Azidoacetic Acid 



225 



1-Azidoisovaleric Acid 



Red cryst. from Et. 2 O. M.p. 63 decomp. 
Explodes on rapid heating above m.p. HC1 -> 
desyl chloride (monochlorodeoxybenzoin). 

Curtius, Ber., 1889, 22, 2162, 
Schroeter, Ber., 1909, 42, 3356. 

Azidoacetic Acid (Triazoacetic acid) 



C 2 H 3 2 N 3 

Cryst. M.p. about 16 



MW, 101 
B.p. 116/12 mm., 



92/3 mm. Sol. H 2 O. B 3S 1-354. Explodes 
on heating. 

Et ester : C 4 H 7 2 N 3 . MW, 129. B.p. 75/21 
mm.,45/2mm. B|J 1-127. < 1-43487. 

Chloride : azidoacetyl chloride. C 2 H 2 ON 3 CL 
MW, 119-5. B.p. 50/20 mm., 43-4/14 mm. 
Decomp. by H 2 0. 

Amide : azidoacetamide. C 2 H 4 ON 4 . MW, 
100. Needles from C 6 H 6 . M.p. 58. Sol. H 2 0, 
EtOH. Explodes on heating. 

Forster, Miiller, J. Chem. Soc., 1909, 95, 

200. 
Curtius, Bockmuhl, Ber. 9 1912, 45, 1035. 

o - Azidobenzaldeliyde (o - Triazobenzalde - 
hyde, o-aldehydophenyl azide) 

CHO 




C 7 H 5 ON 3 ' MW, 147 

Plates from EtOH or pet. ether. M.p. 37-8 
Sol. EtOH, Et 2 0, C 6 H 6 , hot pet. ether. 



Heat 



KMnO, 



C 6 H 



anthramlic acid. 
M.p. 103. 



with H 2 O > anthranH + N. 
azidobenzoic acid. NaOH 

Oxime : needles from 
Spar, volatile in steam. 

PTienylhydrazone : m.p. 1012. 

Bamberger, Bemuth, Ber., 1901, 34, 1314. 

p - Azidobenzaldehy de (p - Triazobenzalde - 
hyde, p-aldehydophenyl azide). 

Colourless liq. Turns brown in air. 

syn.-Oxime : yellowish needles from C 6 H 6 . 
M.p. 142 decomp. Sol. most solvents. Vola- 
tile in steam. Barkens in light. 

&nti~0xime : plates from EtOH.Aq. M.p. 
98. Sol. most solvents. Spar. sol. pet. ether. 
Volatile in steam. Turns dark brown in light. 

Phenylkydrazone : m.p. 190. 

Forster, Judd, /. Chem. JSoc., 1910, 97, 
254. 

Azidobenzene. 

See Phenyl azide. 

1-Azidobutyric Acid (1-Triazobutyric acid) 

CH 3 -CH 2 -9H-COOH 



Yellow oil. [oc] D - 63-3 in Et 2 0. 

Et ester: C 6 H 13L 2 N 3 . MW, 157. B.p. 63, 6 
mm. [aS 1 48-1 in Et 2 0. 

Amide : C 4 H 8 ON 4 . MW, 128. Needles from 
C 6 H 6 . M.p. 59. [x] D -f 47-1 in Me 2 CO, 

dl-. 

Needles. M.p. 24. B.p. 81/0-2 mm. Bg 
1-1519. 

Et ester : b.p. 64/7 mm. Big 1-038. Volatile 
in steam. 

Amide : needles from C 6 H 6 -pet. ether. 
M.p. 38-9. Sol. HO, EtOH. Spar. sol. C 6 H 6 , 
pet. ether. 

Forster, MiiUer, J. CUm. Soc., 1909, 96, 
191. 

3-Azidobutyric Acid (Z-Triazobiutyric acid) 



C 4 H 7 2 N 3 MW, 129 

B.p. 135 II 1 mm. Sol. EtOH, Et 2 0. Spar. 
sol. H 2 O. 

Et ester : C 6 H n 2 N 3 . MW, 157. B.p. 102- 
4/22 mm. Misc. with EtOH, Et 2 0, C 6 H 6 . 
Spar. sol. H 2 O. Bf 7 1-0590. n^ 1-44271. 

Curtius, Guilini, Ber., 1912, 45, 1047. 
Azidoethyl Alcoliol (2-Triazoeihyl alcoTiol) 



C 2 H 5 ON 3 MW, 87 

B.p. 73 /20 mm., 60 /8 mm. Misc with H 2 0. 
D|t 1-149. v$S 1-45778. SnCl 2 + HC1 > 
2-aminoethyl alcohol. 

Forster, Fierz, J. Chem. Soc., 1908, 93, 
1867. 

1-Azidoisobutyric Acid (l-Triazoisobutyric 
acid) 



C 4 H 7 2 N 3 MW, 129 

Needles. M.p. 31. B.p. 75/0-2 mm. BJ| 
1-1433. Volatile in steam. 

Et ester: C 6 H n 2 N 3 . MW, 157. B.p. 71/16 
mm., 52-3 /7 mm. B* 1-0344. 

Amide : C 4 H 8 ON 4 . MW, 128. Plates. M.p. 
93-4. Sol. EtOH, warm C 6 H 6 . Spar. sol. H 2 0. 

Forster, Miiller, J. Chem. Soc., 1909, 95, 
191. 

1-Azidoisovaleric Acid (l-Triazoisovaleric 
acid) 



C 4 H 7 2 N 3 

Diet, of Org. Comp. I. 



C 5 H 9 O 2 N 3 MW, 143 

B.p. 82/0-l mm. B1 3 3 1-0638. 

Et ester : C 7 H 13 2 N 3 . MW, 171. B.p. 82/16 



MW, 129 mm., 68 /8 mm. 



1-0295. 



15 



AzidometliaiLe 



226 



Azofoenzene~4-caxboxylic Acid 



Amide : C 5 H 10 OX 4 . MW, 142. Xeedlesfrom 

M.p. 78-9. Sol. EtOH, warm C 6 H 6 . 

Eorster, Muller, /. C%?w. Soc., 1909, 95, 
191. 



C 6 H 6 



Azidometliane . 
See Methyl azide. 
AzidonapJitlialene . 
See Naphthyl azide. 

1-Azidopropionic Acid (1-Triazopropionic 
acid) 



MW, 115 



C 3 H 5 2 lSr 3 

Z-. 

Oil. Dg 1-229. [*gf 28-9 in 



mm. Dg 1-063. [a]f 18-5 in Et 2 0. 

Amide; OH 6 ON 4 . MW, 114. Needles from 
C 6 H 6 . M.p.85 S . [a] B + 49-1 in H 2 0. 

dl-. 

B.p. 121-5/20 mm., 97-S/3 mm. Explodes 
on heating. 

m ester : b.p. 70/16 mm., 46/2 mm. Dg 
1 -065. w? 1 -42857. Volatile in steam. 

Amide : plates from C 6 H 6 . M.p. 80. 

Forster, Fierz, /. Chem. Soc., 1908, 93, 
1859. 

2-Azidopropionic Acid (2-Triazopropionic 
acid) 



C 3 H 5 2 N 3 

Et ester: ( 
mm. Dg 1-087. 
steam. 

Forster, Fierz, J. Chem. Soc., 1908, 93, 
669. 



MW, 115 

MW, 143. B.p. 62/5 
rig 1-43833. Volatile in 



Azidotoluene. 

See Tolyl azide. 

Azimethylene . 

See Diazomethane. 

Azimidol. 

See under Benztriazole. 

Aziminobenzene . 

See Benztriazole. 

Aziminotoluene . 

See Methylbenztriazole. 

Azirane. 

See Ethyleneimine. 

Aziridine. 

See Ethyleneimine. 

Azo aniline. 

See Diaminoazobenzene. 

Azoanisole. 

See under Dihydroxyazobenzene. 

Azobenzaldehy de . 

See Dialdehydoazobeuzene. 



Azobenzene (Benzeneazobenzene, azobenzide) 

C 12 H 10 N 2 MW, 182 

Trans : 

Orange-red rhombic cryst. M.p. 68. B.p. 
293, deep red vapour. Sol. EtOH, Et 2 0, 
AcOH, ligroin. Spar. sol. H 2 0. Sol. cone. 
H 2 S0 4 -with, suiphonation. Heat of comb. C v 
1555-0 Cal. Aik. red. ^ hydrazobenzene. 
Zn -f AcOH > aniline. Sn + HC1 > 
benzidine. Cr0 3 in AcOH >- azoxybenzene. 
Salts are unstable. 

Henke, Brown, /. Phys. Chem., 1922, 26, 

631. 
Opolonick, Ind. Eng. Chem., 1935, 27, 

1045. 

Alekseevskii, Golbrakht, Russ. P., 32,499, 
(Chem. Abstracts, 1934, 28, 3425). 

Cis : 

Orange-red plates from pet. ether. M.p. 71. 
Slowly converted to trans form at ord. temps. 
Cook, J. Chem. Soc., 1938, 876. 
Cook, Jones, J. Chem. Soc., 1939, 1309. 
Hartley, J. Chem. Soc., 1938, 633 ; Nature, 
1937, 140, 281. 

Azobenzene-2-carboxylic Acid (Benzene- 
azo-O'benzoic acid) 

900H 



C 13 H 10 2 N 2 



Dark red cryst. from EtOH. 



MW, 226 

M.p. 95 (92). 
Heat - 
> hydrazo- 



Eed cryst. 
sol. ligroin. 



Sol. EtOH, Et 2 0, C 6 H 6 , AcOH. 
azobenzene + CO 2 . Zn + AcOH 
benzene-2-carboxylic acid. 

Me ester: C 14 H 12 2 lSr 2 . MW,240. 
M.p. 56. Sol. EtOH, Et 2 O. Less 
D 4 1-1486. 7$ .8 1-6179. 

Et ester : C 15 H 14 2 N 2 . MW, 254. Eed liq. 
B.p. 206~10/12 mm. D 20 1-1195. w5? 08 1-6126. 

Propyl ester : Ci 6 H 16 2 N 2 . MW, 268. B.p. 
210-45/10 mm. D ao 1-1158. ^? 08 1-6037. 
Dnval, Bull. soc. chim., 1912, 11, 18. 
Jacobson, Ann., 1909, 367, 327. 

Azobenzene-3-carboxylic Acid (Benzene- 
azo-m-benzoic, acid). 

Orange leaflets from EtOH. M.p. 170-P 
(167). Sol. Et 2 O, CHC1 3 , AcOEt, C 6 H 6 . Mod. 
sol. hot H 2 0. Spar. sol. ligroin. 

Me ester : yellow leaflets from MeOH. M.p. 
58. Sol. EtOH, Et 2 0, CHCij, C 6 H 6 , CS 2 . 

Amide : C, 3 H n ON 3 . MW, 225. Orange leaf- 
lets from EtOH. M.p. 198-9. Spar. sol. cold 
EtOH. 

Jacobson, Ann., 1909, 367, 329. 



Azobenzene-4-carboxylic 

azo-p-benzoic acid). 



Acid (Benzene- 



Azobenzene-2 : 2 / -dicarboxyHc Acid 



22T 



Azobenzene-4 : 4'-disulplioziic Acid 



Red leaflets with golden lustre from EtOH. 
M.p. 241. Sol. Et 2 O, CHC1 S , warm C 6 H 6 , 
AcOH. Spar. sol. iigroin, CS 2 . 

Me ester : C 14 H 12 2 N 2 . MW, 240. Orange- 
red leaflets from MeOH. M.p. 123-4. Sol 
EtOH, Et 2 0, CHCls, C 6 H 6 , OS*. 

M ester : C 15 B. M 0<$ 2 . MW, 254. Orange- 
red needles from EtOH. M.p. 86-7. Very sol. 
EtOH 3 Et 2 0, CHCLj, C 6 H 6 , CS 2 . Sol. ligroin, 
AcOH. 

Propyl ester : C 16 H 16 2 N 2 . MW, 268. Bed 
cryst. from ligroin. M.p. 64. Sol. org. solvents. 

Amide : C 13 H n Ol!s[ 3 . MW, 225. Red leaf- 
lets. M.p. 224-5. Insol. cold EtOH. 

Nitrile : 4-cyanoazobenzene. C 13 H 9 N 3 . MW, 
207. Brown needles from C 6 H 6 . M.p. 120-1. 
Sol. Et 2 0, C 6 H 6 , warm EtOH. 

Jacobson, Steinbrenck, Ann., 1898, 303, 

385. 

Mentha, Heumann, Ber., 1886, 19, 3022. 
Anspon, Organic Syntheses, 1945, XXV, 

86. 



Azobenzene -2:2'- dicarboxylic 

(o : o'-Azobenzoic acid) 

900H COOH 




Acid 



Ci 4 H 10 4 N 2 MW, 270 

Dark yeUow needles from EtOH. M.p. 245. 
Sol. hot EtOH. Spar. sol. hot H 2 0. Insol. 
C 6 H 6 . 

Di-Me ester : C J6 H 14 4 N 2 . MW, 298. Red 
needles from MeOH. M.p. 101. Sol. usual 
solvents. 

Di-Et ester : C 18 H 18 4 ]Sr 2 . MW, 326. Light 
red leaflets from EtOH. M.p. 85. Sol. usual 
solvents. 

Jfowoamidte:C 14 H 11 O a N 8 . MW,269. Reddish 
brown cryst. from AcOEt. M.p. 215 decomp. 
Sol. hot AcOEt, EtOH. Spar. sol. Et 2 0, ligroin. 

Diamide: C 14 H 12 2 1S[ 4 . MW, 268. Reddish 
brown cryst. from AcOH. M.p. about 294 
decomp. 

Bamberger, Ber., 1906, 39, 4269. 

Azobenzene-2 : 3'-dicarboxylic Acid (o : m'- 

Azobenzoic acid). 

Red needles from AcOH. M.p. 237 decomp. 
Spar. sol. EtOH, Et 2 0, Me 2 CO. Prac. insol. 
C 6 H 6 , ligroin. Zn + AcOH > hydrazobenz- 
ene-2 : 3'-dicarboxylic acid. Sn + HC1 > benz- 
idine-dicarboxylic acid. 

Paal, Eritzweiler, Ber., 1892, 25, 3590. 

Azobenzene -3:3'- dicarboxylic Acid 

(m : m'-Azobenzoic acid). 

YeUow needles from AcOH. M.p. 340 de- 
comp. Sol. 413 parts boiling 88% EtOH. 
Prac. insol. H 2 0, Et 2 0. 

Di-Me ester: C 16 H 14 4 N 2 . MW S 298. Golden 



leaflets from AcOH. M.p. 163. Sol. hot AcOH, 
Me 2 CO, C 6 H 6 . Mod. sol. EtOH, Et 2 O, CHC1 3 . 

Di-Et ester: C 18 H 18 4 X 2 . MW,326. Golden 
needles from EtOH. Jfp. 109. Sol. usual 
solvents. 

Maier, Ber,, 1901, 34, 4132. 

Meyer, Dahlem, Ann., 1903, 326, 331. 

Azobenzene - 4 : 4' - dicarboxylic Acid 
(p : p'~Azobenzoic acid). 

Red needles from AcOH. Decomp. at 330. 
Insol. H 2 O, EtOH, Et 2 0. Stable to HCL 

Di-Me ester : red needles from AcOH. M.p. 
242. Sol. hot C 6 H 6 , AcOH, Me 9 CO, CHClg. 
Spar. sol. EtOH, Et 2 O, Hgroin. 

Di-Et ester : orange-red needles or leaflets 
from EtOH. M.p. 145-8. 

DicUoride : C 14 H 8 2 N 2 a 2 . MW, 307. Red 
needles from C 6 H 6 . M.p. 144-5. 
Maier, Ber. t 1901, 34, 4132. 
Meyer, Dahlem, Ann., 1903, 326, 331. 



Azobenzene - 3 : 3 7 - disulphonic 

(in : m'-Disulphoazobenzene) 




Acid 



C 12 H 10 6 lSr 2 S 2 MW, 342 

YeUow leaflets + 5H 2 0. Sol. H 2 0, EtOH, 
Et 2 O. Sn + HC1 > metanilic acid. 

Dt-^^fer:C 16 H 18 6 N 2 S 2 . MW,398. Golden- 
yellow needles from Et 2 O. M.p. 100. Sol. 
EtOH, Et 2 0. 

Diamide: C 12 H 12 4 1S[ 4 S 2 . MW, 340. YeUow 
needles from EtOH. M.p! 305. Spar. sol. org. 
solvents. 

DicUoride : C 12 H 8 4 N 2 C1 2 S 2 . MW, 379. Red 
needles from Et 2 0. M.p. 166. 

Mahrenholtz, Gilbert, Ann., 1880, 202, 
331. 

Azobenzene - 3 : 4' - disulphonic Acid 

(m : p'-Disul$>hoazobenzene). 

Syrup. 

Diamide : yeUowish needles from EtOH. M.p. 
288. Spar. sol. H 2 0. 

Dichloride : red needles from Et 2 or CS 2 . 
M.p. 123-5. 

Limpricht, Ber., 1881, 14, 1359. 

Azobenzene-4 : 4 / -disulplionic Acid (p : p'- 

Disulphoazobenzene) . 

Red needles from H 2 with 2, 3 or 5 mols. 
H 2 O. M.p. anhyd. 169 decomp. Deli- 
quescent. SnCl 2 + HC1 > sulpharolic acid. 

Diamide : orange cryst. from EtOH. Begins 
to decomp. at about 250. Sol. hot EtOH. 
Insol. Et 2 0, CHC1 3 , C 6 H 6 . 

Dichloride : red leaflets from C 6 H 6 . M.p. 222 
(170). Stable to H 2 0. 

Laar, Ber., 1881, 14, 1928. 
Janovsky, Monatsh., 1882, 3, 240. 



Azobenzene-4-snlp!ioiiic Acid 



228 



AzometJaane 



Azobenzene-4-snlplioiiic Acid (p-Sulpho- 
azobenzene) 



262 



j?-Azodiplieziyl 



H 2 0. 

Spar. 



C 12 H 10 S X 2 S M 

Orange-red leaflets - 1 - 3H 2 from 

M.p. 127. Sol. 17 parts H 9 at 10. 

sol. EtOH, Et 2 0. 

Chloride: C 12 H,0,>KC1S. MW, 280-5. Orange 

needles from Et^O. TiLp. 82. Insol. cold H 2 0. 
Amide: C 12 H n 2 N 3 S. MW, 261. Orange 

powder from boiling" EtOH. Spar. sol. boiling 

EtOH. Insol, H 2 0. 

Janovsky, Monatsh., 1881, 2, 221. 
Griess, Ann., 1864, 131, 89. 

Azobenzide. 

See Azobenzene. 

Azobenzoic Acid. 

See Azobenzene-dicarboxylic Acid. 

jp-Azocumene (4 : 4' -Di-isopropylazobenzene) 



MW, 266 

Pale yellow leaflets from EtOH. M.p. 107-5. 
Sol. 50 parts EtOH at 19 and 5 parts Et 2 
at 16. 

Pospjechow, J. Euss. Phys.-Chem. Soc., 
1886, 18, 52. 

Azo-vy-cumene (2 : 4 : 5 : 2 ' : 4' : 5'-H examefhyl- 
azobenzene) 

CH 3 H 3 0_ 



TT /i TTTT 

C 18 H 22 N 2 3 3 MW,266 

Brick-red cryst. from AcOH. M.p. 173-4 
(171-2). Sol. C 6 H 6 . Spar. sol. EtOH, Et 2 0. 
Sol. H 2 S0 4 to deep red sol. 

Meigen, Nottebohm, Ber., 1906, 39, 744. 
Vorlander, Meyer, Ann., 1902, 320, 128. 

Azodicarbanilide. 

See under Azoformic Acid. 
Azodicarbonamide . 
See under Azoformic Acid. 
Azodicarboxylic Acid. 
See Azoformic Acid. 
o-Azodiphenyl 




5 

MW, 334 

Reddish-purple needles from EtOH. M.p. 



144-5. 



Friebel, E/assow, J. praJct. Chem., 1901, 
63, 464. 



, MW, 334 

Orange-red plates from C 6 H 6 . M.p. 249-50. 
Sol. Et 2 0. Insol. EtOH, AcOH. Zn + KOH 
>- ^-hydrazodiplienyL 

Bandrowski, Prokopeczko, Chem. Zentr., 

1904, 1, 1491. 

Bell, Kenyon, Robinson, J". Chem. Soc., 
1926, 1239. 

Azof ormamide . 

See uTider Azoformic Acid. 

Azof ormanilide . 

See under Azoformic Acid. 

Azoformic Acid (Azodicarboxylic acid) 

HOOONIN-COOH 
C 2 H 3 4 N 2 MW, 118 

K salt deflagrates at 100, and is decomp. by 
H 2 0, giving K 2 C0 3 , C0 2 , hydrazine and nitrogen. 
The Ba salt is also decomp. by H 2 0. 

Di-Me ester: C 4 H 6 4 N 2 . MW, 146. OH. 
B.p. 96/25 mm. 

Di-Et ester : C 6 H 10 4 N 2 . MW, 174. Yellow 
oil. B.p. 106/13 mm. 

Diamide : azodicarbonamide, azoformamide. 
C 2 H 4 2 N 4 . MW, 116. Orange cryst. Sol. hot 
H 2 0. Heat at 180 ^ cyanuric acid + NH 3 . 

Dianilide : azodicarbanilide, azoformardlide. 
C 14 H 12 2 N 4 . MW, 268. Red needles from 
Me 2 CO. M.p. 183. Sol. EtOH, Et 2 0, AcOH. 
Prac. insol. H 2 0. 

Thiele, Ann., 1892, 270, 42. 

Diels, Eritzsche, Ber., 1911, 44, 3018. 

Azoisobutyric Acid 

HOOC-C(CH 3 ) 2 -N:N-C(CH 3 ) 2 -COOH 
C 8 H 14 4 N 2 MW, 202 

Di-Me ester : C 10 H 18 4 N 
M.p. 33. Heat at 80 
Me ester + nitrogen. 

Di-Et ester: C 12 H 22 4 N 2 . MW, 258. Liq. 
D? 0-9884. 

Diamide: C 8 H 16 2 N 4 (+ 2H 2 O). MW, 200. 
M.p. (hydrate) 95 decomp. Anhyd. decomp. 
at 104. 

Dinitrile: C 8 H 12 N 4 . MW, 164. Prisms. M.p. 
106, decomp. to tetramethylsuccinic nitrile + 
nitrogen. Sol. EtOH, Et 2 0. 

Thiele, Heuser, Ann., 1896, 290, 1. 



2 . MW, 230. Cryst. 
> tetramethylsuccinic 



Azomethane 



MW, 58 



C 2 H 6 N 2 

E.p. - 78. B.p. 1-5. Sol. H 2 and most 
org. solvents. DJ 5 0*744. Red. > dimethyl- 
hydrazine. Explodes readily. 

Ramsperger, J. Am. Chem. Soc., 1927, 
49, 912. 



1 : 1'-Azonaplitlialene 229 

1 : I'-Azonaphthalene (xx-Azonaphihalene) 



Azoxybenzene-2 : 2 / -dicarboxyiic Acid 




CsH 14 N 2 MW, 282 

Reddish needles from AcOH. M.p. 190. 
Sublimes. Sol. C 6 H 6> hot AcOH. Spar, sol." 
EtOH. Sol. cone. H 2 S0 4 to blue sol. Zn 
dust -~ XaOH > 1 : l'~hydrazonaphthalene. 

Wacker, Ann., 1901, 317, 384. 

Bryd, Chem. Abstracts, .1928, 22, 2372. 

1 : 2'-Azonaplitiialene (afi-Azonapkthalene). 
Brown leaflets from AcOH. M.p. 136. Sol. 

AcOH. Mod. sol. EtOH. Sol. cone. H>S0 4 to 
violet sol. 

Nietzki, Gottig, Ber. } 1887, 20, 612. 

2 : 2 / -Azonaplitlialeiie ($$-Azonaphthakne). 
Red leaflets from C 6 H 6 . M.p. 208. Sublimes. 

Sol. C 6 H 6? CHC1 3 . Spar. sol. MeOH, EtOH, 
Et 2 0. Sol. cone. H 2 S0 4 to red sol. Zn + 
AcOH > 2 : 2'-hydrazonaphthalene. 

Meisenheimer, Witte, Ber., 1903, 36, 4159. 

Bryd, Chem. Abstracts, 1928, 22, 2372. 

Azonaphthol. 

See Dihydroxyazonaphthalene. 

Azophenetole. 

See under Dihydroxyazobenzene. 

Azophenine (Dianilino-p-benzoquinone dianil) 



N-C 6 H 5 



/\NH- 

NHJ 



Red plates from toluene. 



C 6 H 5 



MW, 440 
M.p. 240. Sol. 



aniline, C 6 H 6 , toluene. Insol. EtOH, Et 2 5 
alkalis. Blackens in cone. HC1. 

Goldschmidt, Wurzschmidt, Ber., 1922, 
55, 3220. 

Azophenol. 

See Dihydroxyazobenzene. 

2 : 2 / -Azoquinoline (a-Azoquinoline) 




Red leaflets. M.p. 230-1 



MW, 284 
Sol. hot EtOH, 



min. acids. Sublimes. Zn + AcOH ^ 2 : 2'- 
hydrazoquinoline. Zn + HC1 > 2-amino- 
quinoline. 

Marckwald, Meyer, Ber., 1900, 33, 1894. 



Orange-red needles from EtOH or C 6 H 6 . 
M.p. 248. Sol. dil. acids with yellowish-red col. 

Knueppel, Ann., 1900, 310 9 75, 84. 

Azoresorufin. 

See Resorufin. 

Azotoluene. 

See Dimethylazobenzene. 

Azoxyacetanilide . 

See under Diaminoazoxybenzene. 

Azoxyaniline . 

See Diaminoazoxybenzene. 

Azoxyanisole . 

See under Dihydroxyazoxybenzene. 

Azoxybenzaldeiiyde . 

See Dialdehydoazoxybenzene. 

Azoxybenzene (Azoxybenzide) 




C 12 H 10 ON 2 



MW, 198 



Bright yellow needles. M.p. 36. Sol. EtOH, 
Et 2 0. Insol. H 2 0. Decomp. on dist., giving 
azobenzene and aniline. Dist. with Fe > 
azobenzene. Zn or Fe + NaOH ^ azobenz- 
ene ^ hydrazobenzene. Zn + AcOH > 
aniline. Cone. H 2 S0 4 > 4-hydroxyazobenzene. 

Bigelow, Palmer, Organic Syntheses, 1931, 

"VT 1 

XI, 16. 

Kerns, Chem. Abstracts, 1932, 26, 4759. 
Opolonick, Ind. Eng. Chem., 1935, 27, 

1045. 
Deutsche Gold- und Silber-Scheideanstalt 

v. Roessler, D.R.P., 486,598, (Ghem. 

Abstracts, 1930, 24, 1389). 



Azoxybenzene-2 : 2 / -dicarboxylic 

(o-Azoxybenzoic acid) 



COOH COOH 



Acid 




C U H 10 5 N 2 MW, 286 

Yellowish plates or prisms from EtOH. M.p. 
254-5 (246). Very sol. Py. Sol. hot EtOH, 
AcOH, Me 2 CO. Spar. sol. H 2 O, Et 2 0. Almost 
insol. CHClg, C 6 H 6 , ligroin. 

Di-Me ester: C 16 H 14 5 K 9 . MW,314. Prisms 
or needles from MeOH. - M.p. 116-17. Sol. 
most org. solvents. 

Di-Et ester: C 18 H 18 5 N 2 . MW,342. YeUow 
needles from EtOH. M.p. 81-2 (77). Sol. 
usual solvents. 

Dinitrile: C 14 H 8 ON 4 . MW, 248. Needles 
from EtOH. M.p. 194-5. Sol. amyl ale. 



Azoxybenzene-3 : 3'~dicarboxyMc Acid 230 



Azoxytolnidine 



Mod. sol. hot EtOH, AcOH. Spar. sol. EUO, 
Me 2 C0 3 C 6 H 6 , AcOEt. 

Ekecrantz, AHqvist, Ber. } 1908, 41, 878. 
Heller, J. prakt. Chern., 1908, 77, 164. 
Pinnow, Midler, Ber., 1895, 28, 157. 

Azoxybenzene-3 : S'-dicarboxylic Acid 
(m-Azoxybenzoic acid). 

Needles or leaflets from AcOH. M.p. 320 3 
decomp. Sol. EtOH, Et 0. Insol. H 0. 

Di-He ester: C 16 H 14 5 X 2 . MW, 314." Orange 
needles from AcOH, pale yellowish leaflets from 
MeOH. M.p. 134. Sol not AcOH. Spar. sol. 
hot EtOH. 

Di-Et ester: G 18 H 18 5 N 2 . MW,342. Yellow 
needles from EtOH. M.p. 78. Sol. usual 
solvents. 

jDicMor^e:C 14 H 8 O 3 XoCl 2 . MW,323. Needles. 
M.p. 120-121*5. Sol C 6 H 6 . 

Schultz, Ann., 1879, 196, 18. 
Carre, Compt. rend., 1905, 141, 594. 
Meyer, Dahlem, Ann., 1903, 326, 342. 
Uspenski, J. Buss. Phys.-Chem. Soc., 
1891, 23, 92. 

Azoxybenzene-4 : 4'-dicarboxylic Acid 

(p-Azoxybenzoic acid). 

Yellow amorph. powder. Decomp. about 
240. Insol. usual solvents. 

Di-Me ester : yellowish needles from AcOH. 
M.p. 207. Sol. hot C 6 H 6 , AcOH, Me CO. 
Spar. sol. EtOH, Et 2 0, ligroin. 

Di-Et ester : yellow needles from EtOH. 
M.p. 115, to anisotropic liq. 

Dipropyl ester : m.p. 103. 

Di-isopropyl ester : m.p. 96. 

Dibutyl ester : m.p. 105. 

Di-isoamyl ester : m.p. 122. 

Diallyl ester : m.p. 88-9. 

Dibenzyl ester : m.p. 147. 

Meyer, Dahlem, Ann., 1903, 326, 334. 
Vorlander, Ber., 1906, 39, 805. 

Azoxybenzene-3 : S^disulpnonic Acid 
H0 3 S S0 3 H 



C 12 H 10 7 N 2 S 2 







MW,358 



YeUow needles. M.p. 126. -Very sol. H 2 0, 
EtOH, Et 2 0. Decomp. above m.p. NaHg 
azobenzene-3 : S'-disulphonic acid. 



DiMoride : C 12 H 8 5 N 2 C1 2 S 2 . MW, 395. YeUow 
cryst. from toluene. M.p. 138. Sol. Et 2 0, 
C H 

*pfamide : C 12 H 12 5 N 4 S 2 . MW, 356. YeUow 
prisms. M.p. 273. Spar. sol. hot H 2 0. 

Brunnemann, Ann., 1880, 202, 340. 



Azoxybenzide. 

See Azoxybenzene. 

Azoxybenzoic Acid. 

See Azoxybenzene-dicarboxylic Acid. 

o-Azoxydipbenyl 



N:N 

i 
o 








Cj^EjLgONg MW, 350 

YeUow cryst. from He 9 CO. M.p. 157-8. 
Sol. EtOH, Et 2 0, AcOH, "CHC1 3 , C 6 H 6 , pet. 
ether. 

Friebel, Bassow, J. prakt. Chem., 1901, 
63, 458. 

p-Azoxydiphenyl 



-N:N- 

+ 
o 

C 24 H 18 ON 2 MW, 350 

Orange-red plates from AcOH. M.p. 212. 
Sol. C 6 H 6 , Et 2 0. Spar. sol. AcOH. Insol. 
EtOH. 

BeU, Kenyon, Robinson, J. CJiem. Soc., 
1926, 1245. 

Azo-xylene. 

See Tetramethylazobenzene. 
1 : 1'-Azoxynaphthalene 




C 20 H 14 ON 2 MW, 298 

YeUow or reddish cryst. from EtOH. M.p. 
127. Sol. cone. H 2 S0 4 to violet sol. > blue 
on standing. 

Wacker, Ann., 1901, 317, 379. 

2 : 2 / ~Azoxynaphthalene. 

SmaU yeUow needles from Et 2 0. M.p. 167-8 
to deep red liq. Sol. CHC1 3 , C 6 H 6 , hot AcOH. 
Spar. sol. MeOH, EtOH, Et 2 0. Zn + alkali 
> 2 : 2'-azonaphthalene. 

Meisenheimer, Witte, Ber., 1903, 36, 4163. 

Azoxypbenetole . 

See under Dihydroxyazoxybenzene. 

Azoxyphenol. 

See Dihydroxyazoxybenzene. 

Azoxytoluene. 

See Dimethylazoxybenzene. 

Azoxytoluidine . 

See Diaminoazoxytoluene. 



Azulene 



231 



Azntauc Acid. 



Azulene (Bicyclo-\Q.Z.D\~deca-l : 3 : 5 : 7 : 9- 
pentaene) 



C 10 H 8 ' MW, 128 

Occurs in camomile and other essential oils. 
Greenish-black cryst. M.p. 98-5-99. Heat at 
270 > naphthalene. 

Picrate : m.p. 120 decomp. Greenish-blue 
sol. in EtOH. 

Trinitrobenzene add. comp. : m.p. 167. 
Trinitrotoluene add. comp. : m.p. 95-5-100. 
Plattner, St. Pfau, Helv. CMm. Ada, 

1937, 20, 224. 
Hiiter, Chem. Zentr., 1943, I, 686 

(Review). 
Plattner, Heilbronner, Weber, Helv. 

CMm. Acta, 1952, 35, 1036. 
Heilbronner, Simonetta, ibid., 1049. 
Gordon, Chem. Reviews, 1952, 50, 127 
(Bibl.). 

Azulene-5-carboxylic Acid 



C n H 8 2 



OOH 



Violet cryst. M.p. 206-7. 

Me ester: C 12 H 10 O 2 . MW S 186. Violet 
platelets. M.p. 40-1. Trinitrobenzene add. 
comp. : m.p. 122. 



Et ester : CH 12 9 , 



200. Violet-blue 



MW, 172 



13 
cryst. M.p. 30-1 

Trinitrobenzene add. comp. : m.p. 152-3. 
8-BenzyWbiouronium salt : m.p. 164. 

Plattner et al., Helv. CMm. Acta, 1951, 
34, 971. 

Aznlene-6-carboxylic Acid. 

Green needles. M.p. 225-7 decomp. 
Me ester : C 12 H 10 O 2 . MW, 186. M.p. 126. 
Trinitrobenzene add. comp. : m.p. 113. 

Plattner et al. 3 Helv. CMm. Acta, 1951, 34, 
971. 

Azulmic Acid 
C 4 H 5 ON 5 MW, 139 

Brown solid formed by decomp. of aq. sols. 
of cyanogen. Spar. sol. H 2 0, giving violet 
fluor. Sols, in KOH or H 2 S0 4 fluoresce green. 

Bohart, U.S.P., 1,464,802, (Chem. Ab- 
stracts, 1923, 17, 3259). 



Bacitracin 



232 



]3aikia.in 



Bacitracia (Ayfivin). 

Antibiotic polypeptide elaborated by Bacillus 
licheniformis. Consists of three components, 
bacitracins A, B and C, of which A and C have 

similar antibiotic activities and B one third of 
that of A and C. 

Newton, Abraham. Biochem. /., 1950, 47, 

257. 
Sharp, Arriagada, Newton, Abraham, 

Brit. J. Exptl. Path., 1949, 30, 444. 

Badische Acid. 

See 2-NaphthyIamine-8-sulphonie Acid. 
Bseckeol (Methylphloroisobutyrophenone 

dimethyl ether] 

CBL 



C 33 H 18 4 



CH 3 0/\OH 

I JCO-CH(CH 3 ) 2 

OCH 3 



MW,238 



Phenol occurring in the essential oils of 
various species of Myrtaceae, especially Bceckea 
crenulata and Darmnia grandifiora. Pale yellow 
needles from MeOE. M.p. 103-4. Sol. hot 
EtOH, Et 2 0, GHC1 3 , C 6 H 6 , alkaHs. Spar. sol. 
ligroin. Sublimes. FeCI 3 >- bluish-black col. 
H 2 2 ^isobutyric acid. NaOEt at 200 
> methylphloroglucinol di-Me ether. 

Acetyl : dimorphous. (i) Prisms from 
MeOH.Aq. M.p. 73. Heat at 75 > (ii) 
Needles from MeOH.Aq. M.p. 79-80. 

Penfold, Morrison, J. Proc. Roy. Soc. 
N.8. Wales, 1922, 56, 87, (Chem. Ab- 
stracts, 1923, 17, 1006). 

Penfold, Simonsen, J. Proc. Roy. Soc. 
N.8. Wales, 1938, 71,291, (Chem. Zentr., 
1938, II, 2258). 

Ramage, Stowe, J. Chem. Soc., 1940, 426. 

Hems, Todd, ibid., 1208. 

Baicalein (5:6: 1-Trihydroxyflawne) 
HO CO 




c i5 H io5 MW, 270 

Occurs in roots of Scutellaria baicalensis. 
Yellow prisms from EtOH. M.p. 264-5 de- 
comp. Sol. EtOH, MeOH, Et 2 0, Me 2 CO, 
AcOEt, hot AcOH. Spar. sol. CHC1 3 , PhN0 2 . 
Ale. FeCl 3 > greenish-brown col. Cone. 
H 2 S0 4 > yellow sol. 

6:7-Di-Jfe ether : C 17 H U 5 . MW, 298. 



Ale. sol. with trace FeCl 3 >> red col. >- 
greenish with excess FeCl 3 . 

Tri-Me ether: C 18 H 16 5 . MW, 312. Yel- 
lowish needles from EtOH. M.p. 165-6. 
Cone. H 2 S0 4 > yellow col. 

Diacetyl deriv. : yellowish needles from 
AcOH.Aq. M.p. 198-200. Sol. EtOH. FeCl 3 
> red col. 

Triacetyl : needles from EtOH. M.p. 190-2. 
Sol. hot AcOH. Less sol. EtOH. 

Shibata, Iwata, Nakamura, Acta Phyto- 

chim., 1923, I> 109, 
Bargellini, Gazz. chim. ital., 1919, 49, ii, 

47. 

Baicalin 
C^H^On MW, 446 

Found in roots of Scutellaria baicalensis. 
Yellow cryst. M.p. 223. Hyd. > baicalein 
+ glucuronic acid. 
Tetra-acetyl : prisms. M.p. 256-7. 
Tetrabenzoyl : m.p. 229-30. 

Shibata et al., Acta Phytochim., 1923, 1, 

105, (Chem. Abstracts, 1923, 17, 3506) ; 

1930, 5, 117, (Chem. Abstracts, 1931, 25, 

1528). 
Charaux, Rabate, J. pharm. chim., 1941, 

1, 404, (Chem. Abstracts, 1944, 38, 1848). 

Baikiain (I - 1:2:3:6- Tetrahydropyr - 
idine-2-carboxylic acid) 



cOOH 



H 



C 6 H 9 2 N 



MW, 127 



Yellowish needles from MeOH. M.p. 155-6. 



Amino-acid present in Baikiaea plurijuga. 
Prisms from MeOH. M.p. 274 decomp. [a]f> 
-201 -6 in H 2 0. Very sol. H 2 0. Spar. sol. 
EtOH. Insol. Me 2 CO, AcOEt, Et 2 0, C 6 H 6 . 
Zn dust > a-picoline. H >* Z-pipecolinic 
acid. Ninhydrin > yellow-brown col. 

Me ester: C 7 H U 2 N. MW, 141. B.p. 110- 
12/15 mm. B,HCl: prisms from MeOH- 
Me 2 CO. M.p. 164. Benzoyl: oil. B.p. 140- 
45 (bath temp.)/0-l mm. Turns brown in air. 

B,HCl : prisms from MeOH or EtOH. M.p. 
264. Ml? -90-1 in H 2 0. 

Pier ate : needles or plates from H,>0. M.p. 
172-3. 

Benzoyl : prisms from AcOEt, needles from 
Et 2 and H 2 0. M.p. 178-9. [a] 2 D 91-9. 

King, King, Warwick, J. Chem. Soc., 
1950, 3590. 



B.A.L. 



233 



Barisatic Acid 



B.A.L. 

See 1 : 2-DithioglyceroL 

B.A.L.-Intrav. 

See under 1 : 2-DithioglyceroL 

Balsamlnasteroi 

CsjH^O MW, 380 

Unsaturated sterol found in balsam seeds. 

Needles from Me 2 CO or EU3. M.p. 1604. 

[ a ]> +7-66. 
Acetyl : m.p. 170-1. 

Tutiya, J. Chem. Soc. Japan, 1940, 61, 
717, (Chem. Abstracts, 1942, 36, 7337). 

Banisterine. 
See Harmine. 
Baptifoline 

C^EaoOaNg MW, 260 

Alkaloid of Baptisia perfoliata, Linn., B. Br. 

and B. minor, Lehm. M.p. 210. [a]g 147-7 

(c = 0-325 in BtOH). 
B 9 2HCK>4 : m.p. 289-5. JV& 6 -89-05 (c = 

1415 in HgO). 
Picrate : cryst. + MeOH. M.p. 145, then 

again at 256. 

Marion, Turcotte, /. Am. Chem. Soc. 3 
1948, 70, 3253. 

vy-Baptigenetiii (2 : k-Dihydroxy-S' : 4'- 

methylenedioxydeoxybenzoin) 



(TT 
2 



C 15 H 12 5 MW, 272 

Hydrolysis product of ^-baptigenin. M.p. 
151. 

Me ether : C 16 H 14 5 . MW, 286. M.p. 145. 

Di-Me ether: C 17 H 16 5 . MW, 300. B.p. 
200-20/0-01 mm. 

Et ether : C 17 H 16 5 . MW, 300. M.p. 129. 

Oxime : m.p. 206 decomp. 

Spath, Schmidt, Monatsh., 1929, 53-54, 
454. 

y-Baptigenin (1-Hydroxy '-3-[3' : 4:'-methylene- 
dioxyphenyl} - chromone ) 

CO 






C 16 H 10 5 MW, 282 

Found naturally in root of Baptisia species 

as the glycoside ^-baptisin. M.p. 296-8. Spar. 

sol. most solvents. Sublimes in vacuo. Hyd. 

> 0-baptigenetin + H-COOE. 
Acetyl deriv. : m.p. 173 
Et ether : C 18 H 14 5 . MW, 310. M.p. 172. 

Spath, Schmidt, Monatsh., 1929, 53-54, 
454. 




MW, 590 

Cryst. + SELjO. M.p. 148-50, resolidifies at 
180-210 and "melts again at 249-51. [a] B 
98- 1 . H 2 S0 4 > yellowish-brown col. chang- 
ing to orange-red. Hyd. >- ^-baptigenin -f 
?-glueose + rhamnose. 

Spath, Schmidt, Monatsh., 1929, 53-54, 
454. 

Baptitoxine. 

See Cytisine. 
Barbaloin 



HO 




HO OH 3 

Suggested structure 

16 H 18 7 (C 21 H 24 9 ) MW, 322 (420) 

Found in Barbados aloes. Yellow needles 
from EtOH. M.p. 146-8 (150). Easily sol. 
H 2 O, EtOH. Spar. sol. Et 2 0. [a] D 8-3 in 
EtOH.Aq.; 10-4 in AcOEt. Dist. with 
Zn -> methylanthracene. Ale HC1 > aloe- 
emodin + d-arabinose. 

Acetyl deriv. : cryst. from pet. ether. M.p. 
95-6 (92). Ox. >rhein acetate + aloe- 
emodin acetate. 

Me ether : prisms from EtOH. M.p. 177-9. 
M546i -12-05 in CHC1 3 . 

Jowett, Potter, /. Chem. Soc., 1905, 87, 

878. 
Robinson, Simonsen, /. Chem. Soc., 1909, 

95, 1085. 
Leger, Ann. chim., 1916, 6, 318; 1917, 8, 

265. 
Gibson, Simonsen, /. Chem. Soc., 1930, 

553. 
Cahn, Simonsen, J. Chem. Soc., 1932, 

2573. 

Leger, Bull. soc. chim., 1936, [5], 3, 435. 
Gardner, Joseph, J. Am. Pharm. Assocn., 

1937, 26, 794. 

Owen, Simonsen, J. Am. CTiem. Soc. f 
1942, 64, 2516. 

Barbatic Acid (Barbatinic acid) 
CH 3 




Barbatinic Acid 



234 



Bassic Acid 



needles from AcOH. 



Prisms from 



MW, 388. Cubes from 



Occurs in majority of lichens of genus Usnea 
and in Alectorm ockroleum. Cryst. from CJE 6 . 
M.p. 191 (186). InsoL BLjO. Hyd. > 
rlmonic acid and p-orcinol. FeC! 3 > violet 
col. 

Mono-acetijl deriv. : 
M.p. 172, 

Me ester: CgJff^O-. HW,374. 
MeOH. M.p. 176* 

Et ester : C 21 H 94 O 
G 6 H 6 . H.p. 189: 

St. Pfau, Helv. Chim. Acta, 1928, 11, 

864 (BibL). 

Robertson, Stephenson, J. Chem. Soc., 
1932, 1678. 

Barbatinic Acid. 

See Barbatic Acid. 

Barbatol (3 : 5-DihydroxyA-atdeJiydobenzyl 
alcohol, 2 : ft-dihydroxy-^^ydroxymethyl-benzalde- 
hyde, ^-Jiydroxymethyl-y-resorcylic aldehyde) 

CH 2 OH 

HO( loH 

OHO 
C 8 H 8 4 MW, 168 

Brownish-yellow prisms from H 2 0. M.p. 
186-9 decomp. 

Oxime : cryst. from H 2 0. M.p. 195-8. 
Tetra-acetyl : needles. M.p. 116. 

Ph&nylhydrazone : yellow needles from AcOH. 
M.p. 183-4 decomp. 

Anil : orange needles + 1H 2 from 20% 
EtOH. M.p. 184-5. 

Schopf, Heuek, Duntze, Ann., 1931, 491, 
240. 

Barbatol-carboxylic Acid (2 : ^-Dihydroxy- 
6-hydroxymethyl-3-aldehydobenzoic acid) 
CH 2 OH 

/\COOH 
HOl JOH 



HO 

C 9 H 8 6 MW, 212 

Cryst. from H 2 0. M.p. 243-4 decomp. 
Sol. hot EtOH, Me 2 CO, H 2 0. Spar. sol. Et 2 O. 
Suominen, Ohem. Abstracts, 1940, 34, 400. 

BarbatoHc Acid 
GH a 

/V-CO 0-/\CH 2 OH 
HOl JOH OHd JCOOH 

CELO OH 



, 390 
Constituent of Usnea barbata. Needles from 

AcOH. M.p. 205-7. Sol. alkalis. Spar. sol. 

most org. solvents. 

Me ester : C 19 H 16 10 . MW, 404. M.p. 193. 



Dioxime : m.p. 207-9. Diacetyl : m.p. 196-9. 
Dibenzoyl : m.p. 183-5. 

Schopf, Heuck, Duntze, Ann., 1931, 491, 

231. 

Suominen, Brit. Chem. Abstracts, 1939, 
A II, 549. 

Barbital. 

See Veronal. 
Barbitone. 
See Veronal. 
Barbituric Acid (Malonylurea) 

e 



3 NH CO ^ 

C 4 H 4 O 3 lSr 2 MW, 128 

Prisms + 2H 2 from H 2 0. Decomp. on 
heating. Sol. hot H 2 0. k = 0'98 X 10" 4 at 25. 
KOH > K malonate + urea (K 2 C0 3 and NH 3 ). 
HZN"0 9 > violuric acid. Forms metallic salts. 
Has hypnotic action. 

Wood, Anderson, /. Chem. Soc., 1909, 

95, 979. 
Chem. Fabr. Schering, D.Er.P., 171,294, 

(Chem. Zentr., 1906, II, 387). 
Bornwater, Eec. trav. chim., 1915, 35, 128. 

Basseol 



MW, 426 

Diethenoid tetracyclic triterpene alcohol iso- 
lated from unsaponlfiable portion of shea nut 
fat and shea cambium. Needles from EtOH.Aq. 
M.p. 109-5. Sol. Et 2 0, CHC1 3 , C 6 H 6 . Mod. 
sol. EtOH, AcOEt. [oc] D 11-9 in CHC1 3 . 
AcOH-H 2 S0 4 > yellow > brown > red 
col. with marked green fluorescence. Bed. > 
dihydro-deriv. 3 > H-CHO. Se > 



C 18 H 18 or C 17 H 16 hydrocarbon. 

Acetyl : clusters of needles from EtOH or 
AcOEt. M.p. 141. Mi 8 ' 5 +23 in CHClg. 
Cyclised to p-amyrin acetate by a variety of 
reagents. 

Benzoyl : plates from C 6 H 6 -EtOH. M.p. 
130. 

Heilbron, Moffet, Spring, /, Chem. Soc. } 

1934, 1583. 
Beynon, Heilbron, Spring, J. Ch&m. Soc., 

1937, 989 ; Nature, 1938, 142, 434. 
Picard, Sharpies, Spring, Chemistry and 

Industry, 1939, 58, 58. 
Heilbron, Jones, Robins, J. Chem. Soc. 9 
1949, 444. 

Bassic Acid 
C3oH 46 5 MW, 486 

Sapogenin isolated from the seeds of most 
Sapotaceae. Cryst. from MeOH. M.p. 319-24. 
[a] D + 72 in Py. 

Me ester : two forms, (a-). Cryst. from C 6 H e . 
M.p. 214-5. [a] D +64. (p.). Cryst. from 
MeOH or EtOH. M.p. 220. [a] D + 55-5. 



Batyl Alcohol 



235 



Behsaone 



Triacetyl-^-ester : m.p. 148-9. Acetonyl~$- 
ester : prisms from Me 2 CO. M.p. 205-6. 

Triacetyl : yellow powder from MeOH. M.p. 
117. 

Heywood, Kon, J. Chem. Soc., 1940, 713. 

Batyl Alcohol (l-Octadecyl 2 : %-dihydroxy- 
propyl ether, glycerol 1-octadecyl ether) 



Degradation product of curine. 

Di-Me ether : plates from Ac OH. M.p. 198- 



C^H^Og MW, 344 

Constituent of many shark and ray liver oils. 
Colourless cryst. M.p. 70-1. Hi" > octa- 
decyl iodide. 

Phenylurethane : m.p. 98. 
Anthraquinone-2-carboxylate : m.p. 79-80. 
Bis-p-nitrobenzoate : yellow cryst. M.p. 65- 
6: +2MeOH, m.p. 53-4. 

Davies, Heilbron, Jones, J. Chem. Soc., 

1933, 165. 

Heilbron, Owens, /. Chem. Soc., 1928, 942. 
Nakamiya, Bull Inst. Phys. Chem. Re- 
search (Tokyo), 1938, 17, 837. 
Baer, Fischer, J. Am. Chem. Soc., 1945, 
67, 2031. 

Bayer 205 (Antrypol, Fourneau 309, Germ- 
anin, Moranyl, Naganol, Suramin, fiexa-No, salt of 
3 : 3'-ureidodi-[8(3-benzamido~p~toluido)-l : 3 : 5- 
naphthalenetrisulphonic acid]) 

Na0 3 S 





NH-CO-NH 

MW, 1428 

Greyish-white powder. Very sol. HgO. In- 
sol. EtOH. Strong trypanocidal action. 

Fourneau, Tr6fouel, Trefouel, VaUee, 
Compt. rend., 1924, 178, 675. 



B.B.C. 

See a-Bromobenzyl cyanide. 
Bebeerilene 




OCH 3 



,CH 



MW, 532 



9. Cold cone. HJ30 d 



red col. 



9. 



Di-Et ether : plates from AcOH. M.p. 168- 



Eong, J. Chem. Soc., 1935, 1381; 1939, 
1157; 1948,265. 



Bebeeiine. 

See Curine. 

Behenic Acid (u-Docosanic acid, n-docosoic 
acid) 

CH 3 -CH 2 -[CH 2 ] 18 -CH 2 -COOH 

C^H^Og MW, 340 

Occurs in Lophira cdata kernel fat, Carnauba 
wax, Mimusops elengi seed oil. M.p. 81-2. 

Me ester : C^H^O,,. MW, 354. M.p. 54. 

Et ester: C24H 48 2 . A1W, 368. M.p. 50. 
B.p. 240-2/10 mm., 185/0-2 mm. 

Chloride: C^H^OCL MW, 358-5. Colour- 
less flakes. M.p. 73-5 (40^. 

Amide : C 22 H 45 ON. MW, 339. M.p. 111. 

Anilide : C 28 H 49 OJSL MW, 415. M.p. 101-2. 

Levene, Taylor, J. Biol. Chem., 1924, 59, 

905. 

Bleyberg, Uhich, Ber., 1931, 64, 2504. 
Morgan, Holmes, J. Soc. Chem. Ind., 

1925, 44, 491T. 

Behenolic Acid 

CH 3 -CH 2 -[CH 2 ] 6 -C:C-[CH 2 ] 10 -CH 2 -COOH 
C^^Og MW, 336 

Constituent of rape oil. Needles. M.p. 57-5. 
Me ester: C^H^. MW, 350. M.p. 22. 
Et ester : C^H^Oa. MW, 364. M.p. 15-16. 
Chloride: C 22 H 39 OC1. MW, 354-5. M.p. 29- 

30. 

Amide: C 22 H 41 ON. MW, 335. M.p. 90, 
Anilide: m.p. 73. 

Bhattacharya, Saletore, Simonsen, J. 

Chem. Soc., 1928, 2678. 
Holt, Ber., 1892, 25, 964. 
Hofmann-La Eoche, D.E.P., 243,582, 
(Chem. Zentr., 1912, I, 695). 

BehenonaphttLone (Heneicosyl 2-naphthyl 
ketone) 

C 10 H 7 -CO-[CH 2 ] 20 -CH 3 

C 32 H 50 MW,450 

Cryst. from Me 2 CO or pet. ether. M.p. 67-9. 

Mikeska, Cohen, /. Org. Chem., 1941, 9, 

787. 



Behenone (22-Tritetracontanone) 

CH 3 -[CH 2 ] 20 -CO-[CH 2 ] 20 -CH 3 



, 618 



Behenophenone 



236 



2 : 3-BenzacricLbae 



M.p. 96-05-96-30 (92). Spar. sol. org. 
solvents. 

Griin, Ulbrich, Krezil, Zt. angew Chem., 

1926, 39, 423. 

Becker, Strating, Rec. trav. cJiim., 1940, 
59, 933, 

Be&enopiienone (n-Heneicosyl pJienyl ketone, 
docosanophenone } 

C 6 H 5 -COtCH 2 ] 20 "CH 3 

C 28 H 48 MW, 400 

Cryst. from Me 2 CO. M.p. 73-6. 

Mikeska, Cohen, J. Org. Gkem., 1941, 6, 
788. 

Belienoxylic Acid (12 : 13-DiJcetobeJiemc 
acid) 

CH 3 -[CH 2 ] 7 -CO-CO-[CH 2 ] 10 -CH 2 -COOH 
C22H 40 4 " MW, 368 

Yellow plates from EtOH. M.p. 95. Sol. 
Et 2 0, C 6 Hg. Spar. sol. ligroin. Insol. H 2 0. 

Me ester: C^H^. MW, 382. Yellow 
leaflets from EtOH. M.p. 63-3-5. 

Monoxime : needles from EtOH. M.p. 85-6. 

Dioxime : needles from EtOH. M.p. 144-5. 

Hausskneeht, Ann., 1887, 143, 46. 
Spieckermann, Bar., 1896, 29, 810. 

Behenyl Alcohol. 

See Docosyl Alcohol. 

Belmacamdin (Belmacamgenin glucoside) 
C 22 H 22 13 MW, 494 

Found in root of Belmacamda sinensis. 
Colourless cryst. from EtOH. M.p. above 
300. Ale. HC1 > glucose + belmacamgenin. 
Me 2 S0 4 > 7 : 5'-dLmethylmgenin. 

Wang, Hu, J. Clem. Soc., 1944, 307. 

Belmacamgenin (Irigenol monomethyl ether, 
pentahydroxy-meihoxyisoflavone ) 

C 16 H 12 8 MW, 332 

Yellow needles from EtOH.Aq. M.p. 227. 

Me 2 SO 4 > penta-Me ether identical with tri- 

Me ether of irigenin. 

Acetyl : cryst. from EtOH. M.p. 184-5. 
Wang, Hu, J. GUm. JSoc., 1944, 307. 

BeniMnol. 

See under Myrtenol. 

Benihiol. 

See under Myrtanol. 

Benzaceanthrylene 




Cryst. from EtOH. M.p. 122--3 ^cprr. 
Greenish yellow fluor. No carcinogenic activity. 
sym.-Trinitrobenzene add. comp. : orange 
needles from EtOH. M.p. 162*5-163 corr. 

Picrate : dark red needles from EtOH. 
M.p. 141-5-142 corr. 

Fieser, Cason, J. Am. CJiem. Soc.< 1939, 
61, 1740; 1940,62,1293. 

1 :2-Benzacenaphtliene. 

See Fluoranthene. 

3 : 4-BenzacenapMIieneqTiinone. 

See Aceanthrenequinone. 
Benzacephenanthrylene 




MW,252 



Needles from C 6 H 6 . M.p. 167 
Tobler, Holbro, Sutter, 



Kern, 
(Mm. Ada, 1941, 24, 100E. 



Helv. 



1 : 2-Benzacridine (tx.-CJirysidine, a-naphth- 
acridine) 




C 17 H U N MW, 229 

Needles from EtOH.Aq. M.p. 108. Sol. 
common org. solvents. Base and salts show 
blue or green fluor. in sol. Salts hyd. by H 2 0. 

B,HCl : yellow needles. M.p. 244 decomp. 

B,HNO S : yellow leaflets. M.p. 188-9 de- 
comp. 

Ohloroaurate : m.p. 228. 

Ghloroplatinate : yellow needles from dil. HCL 
Decomp. at 255. 

Picrate : yellow needles from PhNO 2 . M.p. 
240. 

MetModide : orange-yellow needles from 
EtOH. M.p. 262-3. 

UUmann, Ann., 1907, 355, 349. 

v. Braun, Wolff, Ber., 1922, 55, 3680. 

2 : 3-Benzacridine 



C 17 H U N 




N 



MW, 240 



MW, 229 

Prisms from CHC1 3 . M.p. 225-6. Sol. cone. 
H 2 S0 4 with violet col. Salts sol. EtOH with 
red col. and greenish-blue fluor. 

Schopf, Ber., 1894, 27, 2843. 



3 : 4-Benzacridine 



237 Benzaldeliyde-2 : 6-dicarboxyIIc Acid 



3 : 4-Benzacridine 

acndine) 




C 17 H n ]Sr MW, 229 

Needles from EtOH.Aq. M.p. 132. Sol. 
common org. solvents with blue fluor. Sol. 
cone. H 2 SO 4 with yellow col. and green fluor. 

B,HCl : yellow needles. M.p. about 220. 

B,HN0 3 : yeUow needles. M.p. 217 decomp. 

Ghloroaumte : m.p. 245 decomp. 

B 2 ,H 2 PtCl 6 ,2H 2 p : yellow needles from dil. 
HC1. M.p. 245 decomp. 

Picrate : yellow needles from PKSSF0 2 . M.p. 
260 decomp. 

Methiodide : orange-yellow needles. M.p. 
264. 

Ullmann, Ann., 1907, 355, 351. 

1 : 2-Benzacridone 
CO 




MW, 245 

Yellow needles from Py. M.p. 365-6. Spar. 
sol. EtOH, AcOH, C 6 H 6 . Insol. Et 2 0, ligroin. 
Green fluor. in Py. Blue fluor. in cone. H 2 S0 4 . 
Ullmann, Ann., 1907, 355, 349. 
Kramer, D.R.P., 590,579, (Chem. Zentr., 
1934, II, 3846). 

2 : 3-Benzacridone 
CO 




C 17 H l:l ON MW, 245 

YeUow leaflets from EtOH. M.p. 304-5. 

Spar. sol. common org. solvents with yellow col. 

and green fluor. S&1. cone. H 2 S0 4 with red col. 
N-jK: C 19 H 15 ON. MW,273. Yellow needles 

from EtOH. M.p. 174-5. 
^-Benzyl: C^H^ON. MW, 235. Yellow 

needles from EtOH. M.p. 188-9. 

Schopff, Ber., 1893, 26, 2590. 
3 : 4-Benzacridone 



CO 




YeUow needles from Py. M.p. 383. Spar, 
sol EtOH with blue fluor. Sol. cone. H 2 S0 4 
with bluish -green fluor. 

Ullmann, Ann., 1907, 355, 351. 
Kramer, D.B.P., 590,579, (Chem. Zentr., 
1934, II, 3846). 

Benzal-. 

See Benzylidene-. 

Benzaldehyde 



C 7 H 6 



MW, 106 



F.p. 55-6 to 56-9. M.p. 26. B.p. 
179/751 mm., 62/10 mm. Sol. 300 parts 
H^O. Misc. with EtOH, Et 2 0. Di 5 1-0504. Vola- 
tile in steam. Forms bisulphite comp. Reduces 
NH 3 .AgM) 3 but not Fehling's. NaHg > 
benzyl alcohol. Easily ox. to benzoic acid. 



PCL 



benzylidene chloride. Condenses 



C 17 H U ON 



MW, 245 



with primary amines yielding Schiff bases : e.g., 
aniline ^ benzylideneaniHne. NH 3 > 
hydrobenzamide. KCN ^benzoin. NaOH 
> benzyl alcohol + benzoic acid. 

Oxime : see Benzaldoxime. 

Di-Et acetal: b.p. 217-21. Df 0-97875. 
< 14843. 

Semicarbazone : m.p. 222 (rapid heat., 
233-5). 

TMosemicarbazone : benzylidenethiosemi- 
carbazide. M.p. 160. Sol. hot EtOH. 

PJienylsemicarbazone : m.p. 180-1. 

Cyarihydrin : mandelonitrile. See under 
Mandelic Acid. 

Hydrazone : see Benzylidenehydrazine. 

MetJiylhydrazone : see Methylbenzylidenehydr- 
azine. 

Phenylhydrazone : two isomers. M.p. 157-8 
and 154-5. 

p-Nitrophenylhydrazone : two isomers. Stable, 
m.p. 261-2. Less stable, m.p. 234-6. 

2 : 4-DinitropJienylhydrazone : m.p. 237. 

Methylphenylhydrazone : see Methylphenyl- 
benzylidenehydrazine. 

Holloway, Erase, Ind. Eng. Chem., 1933, 

25, 497. 
Hinkel, Ayling, Morgan, J. Chem. Soc., 

1932, 2793. 
du Pont, U.S.P., 1,989,700, (Chem. 

Abstracts, 1935, 29, 1834). 
Evdokimov, Chem. Abstracts, 1930, 24, 

2737. 
Kakutani, Yamaguchi, CTiem. Abstracts, 

1929, 23, 3217. 

Benzaldehyde-carboxylic Acid. 
See Aldehydobenzoic Acid. 
Benzaldehyde-2 : 6-dicarboxylic Acid. 

See 2-Aldehydoisophthalic Acid. 



Benzaldehyde-o-sulplioiiic Acid 



238 



Benzanilide 



Benzaldehyde-o-siilplioinc Acid (o-Sul- 
phobenzaldehyde) 

CHO 



C 7 H 6 4 S ' MW, 186 

Sol. H 2 0. 

Me ester : C 8 H 8 4 S. MW, 200. M.p. 62-5. 
CMoride: C 7 H 5 3 C1S. MW, 204-5. M.p. 
114-15. 

Goideberger, Monatsh., 1916, 37, 125. 

Benzalde&yde-m-siilphoidc Acid (m-Sul- 

pJwbenzaHehyde) . 

Cryst. HN0 3 > m-sulphobenzoic acid. 
KOBE fusion > m-hydroxybenzoic acid. 

Wallach, Wiisten, Ber., 1883, 16, 150. 

BenzaMehyde^-sulpKonie Acid (p-Sul- 

pJiobenzaldehyde) . 

Cone. KOELAq. at 220-40 > benzole and 
#-hydroxybenzoic acids. 

Amide: C 7 H 7 3 NS. MW, 185. Plates or 
needles from H 2 0. M.p. 122-4. Sol. H 2 O, 
EtOH, Me^CO. Spar. sol. Et 2 0. Hydrazone : 
plates and needles from 80% EtOH. M.p. 
288-90. Semicarbazone : prisms from H^O. 
M.p. 250-1. PJienylhydrazone : m.p. 244-5 
decomp. 

Dakin, BwcJiem. J., 1917, 11, 93. 

Beitlinger, Z. EleJctrochem., 1914, 20, 268. 

B enzaldoxime 



N-OH HO'IST 

a-Form /f-Form _ 

C 7 H 7 ON MW, 121 

Exists in two stereoisomeric forms (see above 

formulae). 
a-Form : 
Stable. M.p. 35. B,p. 118-19/10 mm. 

Sol. EtOH, Et 2 0, C 6 H 6 . Spax. sol. H 2 O. Df 

1-110. 0-Me : b.p. 190-2. 

p-Form : 

Needles from Et 2 0. M.p. 130. Df 1-145. 
Labile. Gradually inverts to a-form : more 
rapidly on heating or by diL acids. Bed. >- 
benzylhydroxylamine. 0-Me : b.p. 79/ll mm. 

Auwers, Ottens, Ber., 1924, 57, 446. 
Wuyts, Koeck, Butt. soc. chim. Belg., 
1932, 41, 197. 



Benzamarone 



)-CO-C 6 H 5 



C 35 H 28 2 MW, 480 

M.p. 218-19. Spar. sol. cold C 6 H 6 . Ale. 
NaOH > amaric acid. 

Klingemann, Ber., 1893, 26, 818. 



Benzamide 



7 H 7 ON 



G 6 H 5 -CONH 2 



MW, 121 



jti^ fctULU -O-g U.CAJLVJ5. 

C 6 H 5 -C(ONa):NH). 
M.p. 116. 



H 2 0. 



Cryst. in plates from H 2 0. M.p. 130. B.p. 
288. Sol. EtOH, hot H 2 0, hot C 6 H 6 . Spar. 
sol. Et 2 0. D 4 1-341. Heat of comb. C c 851-9 
CaL, C p 852-3 Cal. Distils with part, decomp. to 
benzonitrile. Forms Na, K, Ag_and Hg derivs. 
(e.g. C 6 H 5 *CO'NHNa 
P 2 5 > benzonitrile. 

N-CMoro : cryst. from 
Insol. EtOH 3 C 6 H 6 . 
N-Bromo : m.p. 130-3 
~N~Benzoyl : see Dibenzamide. 
IS-Dibenzoyl : see Tribenzamide. 

Fischer, Dilthey, Ber., 1902, 35, 855, 
I.G., D.B.P., 584,142, (Chem. Abstracts, 

1934, 28, 174). 
Kao, Ma, /. Chem. Soc., 1930, 2788. 

Benzamidine 



Sol. Et 2 O, AcOH. 



C 7 H 8 N 2 MW, 120 

Cryst. M.p. 75-80. Sol. H 2 O, EtOH. Spar, 
sol. Et 2 0. 

B,HCl,2H<>p : m.p. 72, anhyd. 169. 

B^HJPtGl^ : m.p. 209-10 decomp. 

B,CH Z 'COOH : m.p. 229 decomp. 

B,CH Z CI'COOH : m.p. 185 decomp. 

B.GHCl^GOOH : m.p. 194 decomp. 

B,CCL-COOH : m.p. 127 decomp. 

B,C 6 H 5 *COOH : m.p. 230 decomp. 

Salicylate : m.p. 202. 

Picrate : orange. M.p. 230. 

Toluene--p-sulphonate : m.p. 195. 

Crayen, Ber., 1891, 24, 386. 

Partridge, Short, J. Ckem. Soc. } 1947, 390. 

B enzamidoxime 



C 7 H 8 OK 2 MW, 

M.p. 80. Sol. EtOH, Et 2 0, CHC1 3 , C 6 H 6 . 

HN0 2 > benzamide. 
Q-Acetyl : m.p. 96. 
Q-Benzoyl : m.p. 140. 

Krug, Ber., 1885, 18, 1053. 

Benzanilide (Benzoylaniline) 

C 6 H 5 -CO-NH-C 6 H 5 
C 13 H n ON MW, 197 

Leaflets. M.p. 163. B.p. 117-9/10 mm. 
Distils undecomp. Spar. sol. Et 2 0. Sol. 24-5 



parts EtOH at 30. PC1 5 



chloroimide, 



C 6 H 5 CCi:]Sr-C e H 5) m.p, 39-^0, b.p. 310 

N-CMoro: colourless cryst. M.p. 78-80. 
Sol. EtOH, Et 2 0, ligroin. 



Benzanisidicle 



239 



Benzantkrone 



N-Bromo : yellowish cryst. M.p. 99. Sol. 
CHC1 3 , C 6 H 6 . 

Schmidt, B.P., 252, 460, (Chem. Abstracts, 

1927, 21, 2273). 
I.G., D.RR, 633,083, (Chem. Abstracts, 

1936, 30, 7582). 

Webb, Organic Syntheses, Collective Vol. 
1,75. 

Benzanisidide. 

See under Hydroxybenzanilide. 

1 : 2-Benzantliracene (Naphthanthracene, 

2 : 3-benzphenanthrene) 




C 18 H 12 " " ~ MW,228 

Leaflets from EtOH-AcOH. M.p. 158-9 
(141). Sublimes. Sols, fiuor. intense yellowish- 
green. 
Picrate : red needles. M.p. 133. 

Barnett, Matthews, Chem. News, 1925, 
130, 339, (Chem. Zentr., 1925, II, 562). 
Gabriel, Colman, Ber., 1900, 33, 447. 
Graebe, Ann., 1905, 340, 258. 

2 : 3-Benzantliracene (NapMhacene) 




MW, 228 

Orange-red leaflets from xylene. M.p. 341 
(335-6, 331). Sublimes. SoL cone. H 2 S0 4 
with greenish col. Insol. C 6 H 6 . 
Clar, Ber., 1932, 65, 517. 
Dziewonski, Ritt, Chem. Abstracts, 1928, 

22, 2561. 
Deichler, Weizmann, Ber., 1903, 36, 552. 

1' : 2 / -Benzanthracene-7-acetaldeliyde 




MW, 270 
M.p. 150-1- 

vermilion 



,-CHO 
C 20 H 14 

Colourless needles from EtOH. 
No growth-inhibitory activity. 

sym.-Trinitrobenzene add. comp : 
needles from EtOH. M.p. 149-50. 

Badger, Cook, J. Chem. Soc., 1940, 409. 

1' : 2'-Benzanthracene-l-acetic Acid 



HOOC-H 2 < 



Leaflets from C 6 H 6 -pet. ether. M.p. 203-6- 
204-6 corr. 

Eieser, Heymann, J. Am. Chem. Soc., 
1941,63,2333. 

1' : 2'-Benzant!iracene-7-acetic Acid. 

Needles from AeOH.Aq. M.p. 270-4. Xo 
growth-inhibitory activity. Na salt : sol. hot 
H 2 0. 

Et ester : m.p. 85. 

Dansi, Ferri, Gazz. chim. itaL, 1939, 69, 

195. 
Badger, Cook, J. Chem. Soc., 1940, 409. 

I 7 : 2 / -BenzantIaracene-8 -acetic Acid. 
Needles from Me 2 CO-C 6 H 6 . M.p. 232-3. 
Me ester : m.p. 116. 

Bachmann, /. Org. Chem., 1938, 3, 434. 

1 : 2-Ben zanthraquinone (Naphthanthra- 
quinone) 

CO 




C 18 H 10 2 MW, 258 

YeUow prisms from AcOH. M.p. 169. 
Very sol. CHCi^, C 6 H 6 , toluene. Sol. Me 2 CO, 
AcOH. Spar. sol. EtOH, Et 2 O. SoL cone. 
H 2 S0 4 with olive-green col. KMn0 4 >~ 
anthraquinone-1 : 2-dicarboxylic acid. 

Heller, Schiilke, Ber., 1908, 41, 3633. 
Groggins, Newton, Ind. Eng. Chem., 1930, 
22, 159. 



2 : 3-Benzanth.raquinone 

quinone) 

CO 



(NapMhacene - 




C 18 H 10 2 MW 3 258 

Yellow needles from PhN0 2 . M.p. 294 
(284-5 from AcOH). Sublimes. Sol. cone. 
H 2 S0 4 with reddish-violet col. Spar. sol. hot 
Me 2 CO, hot C 6 H 6 . Very spar. sol. AcOH. 

Fieser, J. Am. Chem. Soc., 1931, 53, 2336. 
Waldmann, Mathiowetz, Ber., 1931, 64, 
1713. 

Benzanthrone (Mesobenzanthrone) 



C 20 H 14 O 2 





MW, 286 C 17 H 10 O 



!O 



MW,230 



Benzantliroiie-2-carboxyIic Acid 



240 



1 ' 2-Benzaztdene-7-carboxylic Acid 



Yellow needles from xylene or EtOH. M.p. needles from EtOH. M.p. 159-60. Cone. 



170. SoL cone. H 2 S0 4 to orange-red sol. with 
olive-green fluor. ilk. Xa^ 2 4 > dihydro- 
benzanthrone. Alk. fusion > dibenzanthrone 
(violanthrone). 

Note. The following systems of numbering 
of the benzanthrone ring are also in use : 

jCz 1 : 
/8\/e\/i\ 

L ' 10 ' 4 * 

CO 

CasweiL Marshall, U.S.P., 1,626,392, 
(Chem. Abstracts, 1927, 21, 1992). 

SchoU, -47171., 1912, 394, 143. 

I.G., B.R.P., 596,592, (Chem. Abstracts, 
1934, 23, 5082). 

Benzanthrone-2-carboxylic Acid 
COOH 





C 18 H 10 3 MW, 274 

YeUowneedlesfromPhN0 2 . M.p. 347 (341-2). 
Et ester : yellow needles from EtOH. M,p. 
172-3. 

Amide : G^IS.^0^. MW, 273. Cryst. from 
Ph]S[O 2 . M.p. 306. 

Heilbron, Heslop, Irving, J. Chem. Soc., 

1936, 785. 
Schaarschmidt, Ber., 1917, 50, 300. 

Benzanthrone-3-carboxylic Acid. 

Yellow needles from PhM) 2 . M.p. about 
335. SoL cone. H 2 S0 4 with golden-yellow col. 
and yellow fluor. 

Kranzlein, Vollmann, U.S.P., 1,740,771, 

(Chem. Zentr., 1903, 1, 1539). 
I.G., Swiss P., 136,237, (Chem. Zentr., 
1930, II, 2698.) 

Benzanthrone-4-carboxylic Acid. 

Orange-red cryst. from PhN"0 2 . M.p. 307-8. 
Sol. cone. H 2 S0 4 with red col. Alk. > yellow 
sol. with green fluor. 

I.G., Swiss P., 130,696, (Chem, Zentr., 
1929, II, 218). 

Benzanthrone-11-carboxylic Acid. 

Orange-yellow leaflets from EtOH. M.p. 
273. Sol. cone. H 2 S0 4 with blood-red col. 
Da. alk. > yellow sol. with brilliant yellowish- 
green fluor. Quinoline + Chi bronze > benz- 
anthrone. 

Me ester: C 19 H 12 3 . MW, 288. Yellow 



orange sol. with yellow fluor. 
Rule, Pursell, Barnett, J. Chem. Soc., 
1935, 572, 573. 



Benzanthronequinoline 




C 20 H 11 ON MW, 281 

Yellow needles from toluene. M.p. 251. 

Bally, Ber., 1905, 38, 194. 
Badische, D.R.P., 171,939, (Chem. Zentr., 
1906, II, 573). 

B enzazimidol . 

See 1-Hydroxybenztriazole. 

1 : 2-Benzazulene (Benz-\&\-azulene} 




C 14 H 10 MW, 178 

Blue cryst. from EtOH. M.p. 176. (Dark 
green leaflets from light petroleum. M.p. 225.) 
Sublimes readily. Shows light absorption at 
696-682, 632-613 and 569-556 m^. 

Plattner, Purst, Chopin, Winteler, Helv. 

CMm. Acta, 1948, 31, 502. 
Triebs, Ber., 1948, 81, 38. 

4 : 5-Benzazulene (Benz-[e]-azulene) 




C 14 H 10 MW, 178 

Viscous pale blue oil. Unstable > green 
polymer. 

1:3: 5-Trinitrobenzene add. comp. : brown 
needles. M.p. 160-1. 

2:4: ^-Trinitrotoluene add. comp. : brownish- 
black needles from EtOH. M.p. 120. 

Nunn, Eapson, J. Chem. Soc., 1949, 1051. 

l:2-Benzazulene-7-carboxylic Acid 

,fVr>cooH 

v / \A =a/ 

C 15 H 10 2 MW, 222 

Spar. sol. Et 2 0. 

M ester : C 17 H 14 2 . MW, 250. Dark green 
leaflets. M.p. 176. 

Triebs, Ber ., 1948, 81, 38. 



1 : 2-Benzcarbazole 

1 : 2-Benzcarbazole (x-Benzocarbazale) 



241 



4 : 5-Benzcomnarandioiae 




MW, 217 

Leaflets from EtOH. M.p. 228. Spar, sol, 
EtOH, AcOH. InsoL pet. ether. Sol. cone. 
2^864 with yellow col. Anhyd. oxalic acid >- 
blue col. 

Picrate : red needles from EtOH. M.p. 
185-6. 

l$~Acetyl: needles from EtOH. M.p. 289-90. 
Borsche, Ann., 1908, 359, 79. 
Bucherer, Sonnenburg, J. prdkt. Ohem. 3 

1910, 81, 19. 
Ghigi, Gazz. cMm. ital., 1931, 61, 45. 

2 : 3-Benzcarbazole (^-Benzocarbazole) 




C 16 H n IS[ MW, 217 

Leaflets from toluene. M.p. 332. B.p. 440- 
50, Sublimes. Spar. sol. EtOH, AcOH, C 6 H 6 . 
Sols, show intense blue fluor. Sol. cone. 
with yellow col. 

cetyl : two forms from EtOH. (a) M.p. 
(b) M.p. 121. Interconvertible by cryst. 
Sols, show blue fluor. 

~K-Nitroso : reddish prisms from Et 2 0. 
240. 



1 17 



M.p. 



Graebe, Knecht, Ann., 1880, 202, 16. 
Bucherer, Sonnenburg, J. praJct. Ghern., 
1910, 81, 29. 



3 : 4-Benzcarbazole (y-Benzocarbazole) 




16 H n N 



NH 



MW, 217 
Needles or leaflets from EtOH.Aq. M.p. 135. 

B.p. 447/741 mm. Sol. EtOH, AcOH, C 6 H 6 . 

Spar. sol. Et 2 0, ligroin. Sols, slow blue fluor. 

Sol. cone. H 2 SO 4 with yellowish-brown col. 
N-Acetyl: leaflets from EtOH. M.p. 144 



TS-Benzoyl : needles from AcOH. M.p. 191. 
'N-Nitroso : yellow needles from ligroin. M.p. 
144-5 decomp. (rapid heat.). 

Picrate : red needles from C 6 H 6 . M.p. 174-5 
decomp. 

Bucherer, Sonnenburg, J. prakt. Chem., 

1910, 81, 27. 

Ullmann, Ann., 1904, 332, 101. 
Fuchs, Mszel, Ber., 1927, 60, 213. 

Diet, of O*g. Comp. I. 



5 : S-Benzctfiromone 
1 ^-napJithockromone *' 




13 H 8 2 WW, 196 

Stout pale yellow needles from pet. ether. 
M.p. 103. Sol. EtOH, C 6 H 6 , AcOH. Spar. 
sol. cold pet. ether. The colourless sol. in 
boiling AcOH + 1 drop cone. Ey^ > blue 
fluor. 

Menon, Venkataraman, J. CJt&m. Soc,., 
1931, 2593, 

7 : 8-Benzchromone (a ; fi-NapMiapyrone, 
61 oL-napJithochromone ") 

CO 




C 13 H 8 2 MW, 196 

Needles from EtOH.Aq. M.p. 125. YeHow 

sol. in cone. H 2 SO 4 > intense bluish-green 

fluor. 

ISemicarbazone : m.p. 256 decomp. 

Pfeiffer, Grimmer, Ber., 1917, 50, 922. 

Benzchrysene. 

See Dibenzphenanthrene. 
Benzcinnoline (o-DipJienyleneazine) 




12 H 8 N 2 MW, 180 

Yellow needles from EtOH.Aq. M.p. 156 

(241-3) . Distils above 360. Very sol. AcOH, 

GHC1 3 . Sol. Et 2 0, EtOH, C 6 H 6 . Spar. sol. 

H 2 0, pet. ether. 

Picrate : brown needles. M.p. 194. 

Traube, Ber., 1891, 24, 3081. 

Sandin, Cairns, J. Am. Chem. Soc., 1936, 

58, 2019. 
Slack, Slack, Nature, 1947, 160, 437. 



4:5- Benzcoumarandione 

furandione) 



- Naphtha - 




C 12 H 6 3 



MW, 198 
16 



4 : 5-Benzcoumaran0ne-3 



242 



6 : 7-Benzeoumarone 



Orange-yellow needles from AeOH or C e H 6 . 
M.p. 182 decamp, Sol. EtOH. Spar. sol. 
H 2 0, pot. ether. The blood-red sol. in cone. 
HoSO 4 turns colourless on warming. 

2--4nZ : m.p. 126~7 C . 

2 : 3-Phemzine : m.p. 286-7 \ 

3-Semicarbazone : m.p. 240-1. 

%-Phenylhydrazon& : m.p. 226-7. 

Picrate : m.p. 109. 

Giua, Franciscis, Gazz. chim. ital., 1924, 

54, 509. 

PasserM, ibid., 184. 
Staudinger, Swiss PJS, 92,688, 93,486 y 

(Chem. Abstracts, 1924, 18, 989). 

4:5- Benzconmaranone - 3 (p - Naphtha - 
furanone-%) 




C 12 H 8 2 MW, 184 

Colourless needles from pet. ether, EtOH, or 
AcOH. M.p. 133. Sol. Et 2 0, C 6 H 6 . Sol. 
cone. 2^304 with pale yellow col. Sol. ale. 
NaOH with bluish-red col. HN0 3 > 2-nitro 
deriv., m.p. 190 decomp. 

%--$-Nitrobenzylidene : m.p. 270. 

Dziewonski, Duzyk, Chem. Abstracts, 

1934, 28, 4415. 
Fries, Frellstedt, Ber., 1921, 54, 715. 

6:7- Benzcoumaranone - 3 (a - Naphtha - 
furanone-&) 




G 12 H 8 2 MW, 184 

Pale yellow needles. M.p. 119. Yellow sol. 
in cone. H 2 S0 4 >- green fluor. Fehling's > 
deep purple col. 

2-Benzylidene : m.p. 130. 

Ingham, Stephen, Timpe, J. Chem. 8oc., 
1931, 895. 

3 : 4-Benzcoumarin. 

See under 2'-Hydroxydiphenyl-2-carboxylic 
Acid. 
5 : 6-Benzcoumarin (a : $-Naphthacoumarin) 



C 13 H 8 2 




Bright yellow needles from EtOH.Aq. M.p. 
118. Sol. EtOH, Et 2 0, CHC1 3 , AcOH. Spar. 



sol. hot H 9 



bluish fluor. 



Bey, Rao, Sankaranarayanan, J. Indian 
Chem. Soc., 1932, 9, 71. 

6 : 7-Benzcoumarin (p : fi-Naphthaeoumarin) 

CH 

/YYV 
\/\A o / co 

C 13 H 8 2 MW, 196 

Pale yellowish cryst. from CHCL-pet. ether. 
M.p. 163-4. 

Boehm, Profift, Arch. PJiarm., 1931, 269, 
25, (Chem. Zenlr., 1931, I, 1922). 

7 : 8-Benzcoumarin (j3 : a-NapJifhacoumarin} 

CH 




C 13 H 8 2 " MW, 

Pale yellow needles from EtOH. M.p. 141-2 
(138). Sol. Me 2 CO, CHC1 3 , C 6 H 6 , AcOH. 
Spar. sol. Et 2 0. Insol. H 2 0. Greenish-yellow 
sol. in cone. H 2 S0 4 > blue fluor. 

Dey, Rao, Sankaranarayanan, J. Indian 

Chem. Soc., 1932, 9, 71. 
Bezdzik, Friedlander, Monatsh., 1909, 30, 

280. 
Boehm, Profft, Arch. Pharm., 1931, 269, 

25, (Chem. Zentr., 1931, I, 1922). 

4 : 5-Benzcoumarone ($-Naphthafuran) 




C 12 H 8 MW, 168 

Needles. M.p. 60-1 (65). B.p. 284-6 
(280). Sol. cone. H 2 S0 4 > yeUowish-green 
col., on warming - > pale violet > dirty 
bluish-green > brownish-violet fluor. 
Picrate : red needles. M.p. 141. 

Stoermer, Ann., 1900, 312, 310. 
Boes, Chem. Zentr., 1902, I, 1356. 

6 : 7-Benzcoumarone (v-Naphihafuran) 

'TT 
Jtl 

[TT 
'1 



MW, 196 Cj 2 H 8 




MW, 168. 



Benzdiazole 



243 



BeBzeneazoetliaiie 



Pale yeUow oil. M.p. T. B.p. 282-4 / 
755 mm. D 1 * 1-1504. <rt 1-634. Sol. cone, 
B^SO 4 > yellowish-green col., on wanning 
> blue >- violet fluor. 

Picrate: reddish-yellow needles. M.p. 113. 
Stoermer, Ann., 1900, 312, 310. 
Boes, Chem. Zentr., 1902, 1, 1356. 

Benzdiazole. 

$ee Indazole. 

Benzdiket oliy drindene , 
See a : p-JSFaphthindandione. 
1 : 3-Benzdioxan (Saligenin methylene ether) 
CH 




C 8 H 8 O 2 MW, 136 

M.p. 12-5. B.p. 210-ll /754 mm., 161-2/225 
mm., 100-5-1-5720 mm. Df 4 1-174. n^ 2 1-5478. 
Very sol. most org. solvents. Insol. H 2 O. 

Chattaway, Irving, J. Chem. Soc., 1931, 

2492. 
Baker, /. Chem. Soc., 1931, 1770. 

1 : 4-Benzdioxan (1 : %-Ethylenedioxybenzene, 
catechol ethylene ether) 




C 8 H 8 O 2 ~ MW, 136 

B.p. 212-147757 mm. DJ 1-180, Dgj 1-1831. 
Sol. EtOH, Et 2 O, C 6 H 6 , CHCLj. Insol. H 2 O. 
Vorlander, ^.72,77,., 1894, 280, 205. 
Ghosh, J. Chem. Soc., 1915, 107, 1591. 
Favorski, /. JRuss. Phys. Chem. Soc., 1906, 
38, 741. 



1 : 4-Benzdioxin 












/CH 



MW, 134 
B.p. 1937760 mm., 



C 8 H 6 O 2 

M.p. 20 to 10. 
76713 mm. D 1-204. 

Moureu, Compt. rend., 1899, 128, 559; 

Bull. soc. cUm., 1899, [3], 21, 295. 
Becker, BotheU, Monatsh., 1947, 77, 80. 

Benzdioxole. 

See under Catechol. 

Benzedrine. 

See 2-Phenylisopropylamine. 

Benzene (Benzol, cydohexatriene) 



MW, 78 



Colourless cryst. and liq. M.p. 5-525. B.p. 
80-08 (80-103, 80-12, 80*36, 80-49)/760 mm., 
77-87700 mm., 73-17600 mm., 65/463 mm., 
607394 mm., 507273 mm., 40/184 mm., 30/ 
122 mm., 20/76 mm., 10/46 mm., 0/26 mm. 
100 vols. H 2 O dissolve 0*082 vol. at 22. Misc. 
with EtOH, Et>O, CS 2 , AcOH, Me 2 CO, toluene, 
etc. Benzene "dissolves 0-265% H 2 O at 70, 
0-054% at 15. DS 0-8941, D 1 ^ 0-8787, Df 
0*87896. Tag 1-50141 (1-50110, 1*50108). Sp.heat 
0-397 at 0, 0-4369 at 70. Heat of comb. 
a 781-4 (783-4) CaL, C p 782-3 (784-3) Cal. 
Latent heat of fusion 30-1 cal./gram. Latent 
heat of vap. 105-9 at 10, 94-61 at 80. Mol. 
f.p. depression 50. Mol. b.p. elevation 26. 

For bibliography see Reports of the 

National Benzole Association, 1923 

onwards. 
Ingold, Proc. Roy. Soc., 1938, 169A, 

149. 
Rybicka, Wynne- Jones, J. Chem. Soc., 

1950, 3671. 

Benzeneazoanisole. 

See under Hydroxyazobenzene. 
p-Benzeneazobenzaldeliyde (4-.4 Idehydo- 
azobenzene) 

~^ 



C 13 H 10 ON 2 MW, 210 

Reddish-brown leaflets. M.p. 120-1. Sol. 
EtOH, Et 2 O, C 6 H 6 . Sublimes. 

Oxime : m.p. 143. 

Phenylhydrazone : m.p. 165-6. 

Anil : orange needles from ligroin. M.p. 
125-30. 

Freundler, Compt. rend., 1902, 134, 1359. 

Benzeneazobenzoic Acid. 

See Azobenzene-carboxyHc Acid. 
Benzene azocatechol. 
See 3 : 4-I>ihydroxyazobenzene. 
Benzeneazocresol. 
See Hydro xy-methyl-azobenzene. 
Benzeneazodiphenylamine (p-Anilinoazo- 
benzene) 



C 18 H 15 N 3 MW, 273 

Golden-yellow leaflets. M.p. 82. Sol. 
EtOH, Et 2 O, ligroin. HC1 added to EtOH sol 
pptes. grey hydrochloride. Zn + HC1 > 
j5-aminodiphenylamine. 

Nitroso deriv. : m.p. 119-5. Sol. C 6 H 6 , AcOH. 
Witt, Ber., 1879, 12, 259. 

Benzeneazoethane 



C 8 H 10 N 2 MW, 134 

Yellow oil. B.p. 175-85/760 mm., 88-93 / 

20-25 mm. Volatile in steam. Sol. EtOH, 



Benzeneaasoiiydroqiiiiaoiie 



, C 6 H e , cone. acid. Spar. sol. H 2 O. 
0-9628. tt w 1-53133. Stand with 60% 
or heat with XaOEt > acetaldehyde phenyl- 

hydrazone. Warm dil. acids > C 6 H 5 XH*NH 2 
-h CH a -CHO. 

Fischer, Ehrhard, Ann., 1879, 199, 326. 

Fischer, Ber. 9 1896, 29, 794. 

Bamberger, Pemsel, Ber., 1903, 36, 56. 

BenzeneazoiiydroqTainoiie . 

See 2 : 5-Dihydjoxyazobenzene. 
Benzeneazoiaaethaiie 



244 



4-Benzeneazo-l-napMliylamine 



4-Ben.2eneazo-I -naphihol 

quinone phenylhydrazone) 

OH 



: 4:-NapMho- 




MW, 248 
M.p. 206 decomp. 



, 120 

Yellow oil. B.p. 150/760 mm. Very volatile 
in steam. 

Tafel, Ber., 1885, 18, 1742. 

Baly, Tuck, J. Chem. Soc., 1906, 89, 986. 

Stobbe, Nowack, Ber., 1914, 47, 578. 

l-Benzeneazonaphtiialeiie 



C 17 H 14 ON 2 . 



MW, 262. Brown 
MW, 276. Brown 
MW,339. M.p.l02. 




C 16 B 12 ON 2 

Brownish- violet cryst. 

Sol. hot AcOH, alkalis. Mod. sol. hot EtOH, 
hot C 6 H 6 . Sol. cone. H 2 S0 4 to bluish-violet 
sol. 

Me ether : 
needles. M.p. 83. 

Et ether : C 18 H 16 ON 2 . 
needles. M.p. 99-100. 

Benzyl ether: C 23 H 18 ON 2 

Acetyl : m.p. 128. 

Benzoyl : m.p. 121. 

Witt, Dedichen, Ber., 1897, 30, 2657. 
McPherson, Am. Chem. J., 1899, 22, 376. 

l-Benzeneazo-2-naphthol (1 : 2-Naphtho- 
quinone I- phenylhydrazone) 

N:N-C 8 H 5 

C0 OH 

C 16 H 12 ON 2 MW, 248 

Dark * reddish-yellow leaflets. M.p. 134. 
Sol. Et 2 O, CS 2 , C 6 H 6 , ligroin, cone. HCL Bed- 
dish-violet in cone. H 2 S0 4 . 

Pascal, Normand, Butt. soc. chim., 1913, Me ether : C 17 H 14 ON 2 . MW, 262. Bed 

plates from EtOH. M.p. 62. 

M ether: C 18 H 16 ON 2 . MW, 276. Bed 
(1 : Z-NapWu>- pi ate s from Hgroin. M.p. 79. 

Propyl ether : C 19 H 18 ON" 2 . MW, 290. Bed 
leaflets from EtOH. M.p. 40-1. 

Isopropyl ether : red leaflets from EtOH. 
s M.p. 70. 

Acetyl : m.p. 117. 

Benzoyl : m.p. 125. 

Cu deriv. : brown cryst. M.p. 288. 

Bamberger, Ber., 1920, 53, 2319 
Charrier, Gazz. chim. ital., 1916, 46, 1, 407. 



MW,232 

Bed leaflets. M.p. 70. Sol. EtOH, Et 2 0, 
C 6 H 6 , ligroin. 

Michaelis, Petow, Ber., 1898, 31, 995. 

2-BenzeneazonapIitlialene . 
M.p. 131. 



13, 884. 

2-BenJzeneazo-l-naphthol 

quinone 2-phenylhydrazone) 

OH 
QQ^KVH. 

C 16 H 12 ON 2 MW, 248 

Dark orange-red needles. M.p. 138. Sol. 
hot EtOH, hot AcOH. Sublimes. Sol. H 2 S0 4 
to reddish- violet sol. 

Me ether: C 17 H 14 ON 2 . MW, 262. Orange 
leaflets from EtOH. M.p. 102-3. Cone. 
H 2 S0 4 > ruby-red col. 

Et ether: C 18 H 16 ON 2 . MW, 276. Bed 
needles from EtOH. M.p. 46. Cone. H 2 S0 4 
> red col. 
Acetyl : m.p. 120-1. 

Benzoyl : yellow needles from C 6 H 6 ~ligroin. 
M.p. 191. 

Charrier, ITerreri, Gazz. chim. ital., 1914, 

44, II, 232. 
Charrier, Casale, Gazz. chim. ital., 1914, 

44, 1, 607. 

Auwers, Ber., 1907, 40, 2157, 
Zincke, Bindewald, Ber., 1884, 17, 3030. 



4-Benzeneazo-l-naphthylamine 




C 16 H 13 N 3 " ~ MW,247 

Beddish-violet cryst. M.p. 123. 
B,HCl : m.p. 205. 

m.p. 214-15. 

Thiel, Wulfken, Z. anorg. allgem. Chem., 

1924, 136 T 393. 
Woroshzow, J. praJct. Chem., 1911, 84, 

527. 



1 -Benzeneazo-2-napMIiylamine 



245 



0~Benzenedicazi>amic Acid 



l-Benzeneazo-2-napIitliyIainine 



MW, 247 

Hed plates. M.p. 102-^. Sol. EtOH, AcOH. 
Blue in cone. H 2 SO 4 . 

~N-Acetyl : red needles. M.p. 153. 
N-Benzoyl : red cryst. from AcOH. M.p. 
162-3. 

Ou deriv. : greenish-black cryst. M.p. 174. 
Ni deriv. : green cryst. M.p. 260-5. 

Bamberger, ScMefflin, Ber., 1889, 22, 
1376. 

Benzeneazonitrophenol. 

See 5-Nitro-2-hydroxyazobenzene and 3-Nitro- 
4-hydroxyazobenzene. 

Benzeneazoiiitrosalicylic Acid. 

See 5~Mtro-4-hydroxyazobenzene-3- carboxylic 
Acid. 

Benzeneazonitrotoluene . 

See Mtromethylazobenzene. 

Benzeneazophenetol. 

See under Hydroxyazobenzene. 

Beazeneazophenol. 

See Hydroxyazobenzene. 

Benzene azoresorcinol. 

See 2 : 4-Dihydroxyazobenzene. 

4-Benzeneazosalicylic Acid (Z-Hydroxy-4t- 
carboxyazobenzene) 

COOH 



MW, 242 

Nitrile: C 13 IL Q ON^ MW,223. Reddish yellow 
needles from AcQjNTa.Aq. Me ether : red needles. 
Finger, Wilner, J. praJct. Chem., 1909, 79, 
452. 

5-Benzeneazosalicylic Acid (k-Hydroxy-Z- 
carboxyazobenzene) . 

YeUow needles. M.p. 218. Sol. EtOH, 
Et 2 O. Me 2 CO. Spar. sol. C 6 H 6 , CHC1 3 , hot CS 2 . 

Me etJier: C K H 12 O 3 N 2 . MW, 256. Cryst. 
from EtOH. M.p. 162-5. Me ester: cryst. 
from EtOH. M.p. 63-4. 

Me ester : C 14 Hi 2 O 3 N 2 . MW, 256. Reddish- 
yellow leaflets. M.p. 108. Acetyl deriv. : yellow 
orange needles, m.p. 109. 

Et ester: C 15 H 14 O 3 ISro. MW, 270, Yellow 
cryst. M.p. 101. 

Phenyl ester : C 19 H 14 O 3 ISr 2 . MW, 318. M.p. 
121. Acetyl : m,p. 132. 

Amide : C^HnOaNg. MW, 241. M.p. 235 
(240). 

Anilide : C^H^O^g. MW, 317. M.p. 188-9. 

Acetyl : orange cryst. from EtOH. M.p. 145. 
Limpricht, Ann., 1891, 263, 224. 



Benzeneazotolaene . 
See Methylazobenzene. 
2-Benzeneazo-?n-toluic Acid. 
See 6-Methylazobenzene-2- carboxylic Acid. 
Benzeneazo-xyleaae. 
See Dimethylazobenzene, 
Benzene azo-xylenoi. 
See Hydroxydimethylazobenzene. 
Benzene-d^icetic Acid. 
See Phenylene-diacetic Acid. 
Benzenediazoniuin cMoride (Diazobenzene 
chloride) 

[C 6 H 5 -N:N]^C1- 

C 6 H 5 N 2 C1 M^', 140-5 

Colourless cryst. Sol. EtOH, H 2 O. Insol. 
Et 2 O, C 6 H 6 , ligroin. Decomp. on standing in 
moist air. Explosive. Aq. sol. reacts neutral. 
Strongly dissociated hi H 2 O. Hot H 2 O > 
phenol. Hot EtOH > benzene. 

Hantzsch, Jochem, Ber., 1901, 34, 3338. 

Benzenediazonium nitrate (Diazobenzene 
nitrate) 



167 

Needles. Readily explodes. Sol. H 2 O. Mod. 
sol. EtOH. Insol. Et 2 0, CHC1 3 , C 6 H 6 . Strongly 
dissociated hi H 2 O. Hot H 2 > phenol. 
Bamberger, Ber., 1898, 31, 579. 

Benzenediazonium sulphate (Diazobenzene 
sulphate) 

[C 6 H 5 -N:NrS0 4 H~ 
C 6 H 6 O 4 N 2 S MW, 202 

Colourless prisms. Sol. H 2 0. Insol. Et 2 0. 
Explodes at about 100, Strongly dissociated 
in H 2 O. Hot H 2 ^ phenol. Hot EtOH 
>- benzene. 

Knoevenagel, Ber., 1895, 28, 2049. 
Hodgson, Mahadevan, J. Chem. Soc., 
1947, 325. 

o-Benzenedicarbamic Acid (N : W-Dicarb- 
oxy-o -phenylenediamine ) 

JSTHCOOH 



NHCOOH 



! 8 H 8 4 N 2 MW, 196 

Acid not known hi free state. 
Di-Et ester : needles from EtOH. M.p. 88. 
Di-phenyl ester : needles. M.p. 189-90. 
Di-benzyl ester : plates. M.p. 107. 
Diamide : needles. M.p. 290. 

Lellmann, Ber., 1883, 16, 592. 

Snape, J. Chem. Soc., 1886, 259. 

Ruggli, Dahn, Helv. Chim. Acta, 1944, 
27, 1116. 




wi-Benzenedicarbamic Acid 



246 



Benzene hexacbloride 



m-Benzenedicarbamic Acid (N : X'-Dz- 
ca rboxy-m-phenylenediamine ) . 

Acid not known in free state. 
Di-Et ester : plates from ligroin. M.p. 145. 
Di-phenyl ester : needles. M.p. 163-5 C . 
Di-benzyl ester : cryst. from MeOH. M.p. 
115-16. 

Di-octadecyl ester : m.p. 96. 
Diamide : melts above 300. 

DaYidis, J. prakt. Ghem., 1896, 54, 85. 
Ruggli, Dahn, Hdv. Gkim. Acta, 1944, 27, 

1116. 
Warder, Ber., 1867, 8, 1180. 

p-Benzenedicarbamic Acid (X : ~$'-Dicarb- 
oxy-ip-phenylenedmmine ) . 

Acid not known in free state. 

Di-Et ester : plates. M.p. 196. 

Di-phenyl ester : brown leaflets. M.p. 238-9. 

Di-benzyl ester : plates. M.p. 222-5-253. 

Di-octadecyl ester : m.p. 146. 

Diamide : plates. Decomp. without melting. 

Davidis, J. praU. Chem., 1896, 54, 87. 
Lellmann, Ann., 1883, 221 , 14. 

Benzene-dipropiolic Acid. 

See Phenylene-dipropiolic Acid. 
Benzene-dipropionic Acid. 
See Phenylene-dipropionie Acid. 
Benzene-0-disulphonic Acid 

S0 3 H 




C 6 H 6 6 S 2 MW, 238 

Dichloride: C 6 H 4 4 CLS 2 . MW, 275. M.p. 
143. 

Mono-amide: Et ester, CgHiiOgNSo. MW, 
265. M.p. 190. 

Diamide : C 6 H 4 <^2>N-NH 4 . Imide NH 4 

salt. C 6 H 8 4 N 2 S 2 . MW,236. M.p. 254. 

Dianilide : m.p. 241. 

Anhydride : C 6 H 4 5 S 2 . MW, 220. M.p. 180. 

Imide : C 6 H 5 4 NS 2 . MW, 219. M.p. 186 
(192). 

Phenylimide: C 12 H 9 4 NS 2 . MW, 295. M.p. 
195. 

Hurtley, Smiles, J. Chem. Soc., 1926, 
1821. 

Benzene-an-disulphonic Acid. 

Very deliquescent cryst. + 2JH 2 0. Alkali 
fusion > resorcinol. Na salt cryst. with 
4H 2 0. 

Dichloride : C 6 H 4 4 C1 2 S 2 . MW, 275. Prisms. 
M.p. 63. B.p. 211/20mm. 

Difluoride: C 6 H 4 4 E 2 S 2 . MW, 242. M.p. 
38-9. 



Diamide: C 6 H 8 Q 4 KjS 2 . MW, 236. Needles. 
M.p. 229. 

Heinzelmann, Ann., 1877, 188, 159. 
Soc. des usines chimiques Rhone-Poulenc, 
U.S.P., 1,956,571, (Chem. Abstracts, 
1934, 28, 4071). 

Voluinkin, Chem* Abstracts, 1936, 30, 
7555. 

Benzene-|?-disnlpb.onic Acid. 

Dichloride : C 6 H 4 4 CloS 2 . MW,275. Needles. 
M.p. 131 (139). 

Diamide: C 6 H 8 4 N 2 S 2 . MW, 236. M.p. 
288 

Drushel, Felty, Am. J. Sei., 1917, 43, 57 5 
(Chem. Abstracts, 1917, 11, 581). 

Benzene hexabromide (Hexabromocydo- 
hexane) 

CHBr 



C 6 H 6 Br 6 



Cryst. 
. Ale. 



BrHC CHBr 

CHBr 

MW, 558 

Exists in stereoisomeric forms. 
Trans-foTm, (a). Prisms. 'M.p. 212 
from xylene. Spar. sol. EtOH, Et t 
KOH > 1:2: 4-tribromobenzene. 

Ow-form,(p). M.p. 253. Insol. EtOH, Et 2 O. 
Matthews, J. Chem. Soc., 1898, 73, 243. 
Blair, Ledbury, Wheeler, J. Soc. Chem. 
Ind. t 1924, 43, 289T. 

Benzene-hexacarboxylic Acid. 

See Mellitic Acid. 

Benzene hexacbloride (Hexachlorocydo- 
hexane) 

CHC1 



:9 9HCi 



C 6 H 6 C1 6 



C1H' 

C1HC CHC1 

V 
1HC1 

MW, 291 

Exists in stereoisomeric forms. 
(a) Trans-foim. M.p. 157. B.p. 288 de- 
comp. to 1:2: 4-trichlorobenzene. Mod. sol. 
CHC1 3 , C 6 H 6 . D 20 1-87. Volatile in steam. 

(p) 0^-form. M.p. 310 (297). Spar. sol. 
cold CHC1 3 , cold C 6 H 6 . D 19 1-89. Sublimes at 
m.p. Ale. KOH $- trichlorobenzene. 

(y). Grammexane. Lindane. Needles. M.p. 
112-13. Powerful insecticide. 
(8) Plates. M.p. 129-32. 

van der Linden, Ber., 1912, 45, 231. 
Tei, Komatsu, Mem. Coll. Sci. Kyoto Imp. 

Univ., 1927, 10A, 325. 
Slade, Chemistry and Industry, 1945, 314. 
Marrison, J. Soc. Chem. Ind. } 1949, 68, 192. 
Bastiansen et al., Research, 1949, 2, 248. 



BenzenelLydrazonaplitlialene 



247 



Benzenesulplionlc Acid 



BenzenehydrazonapMhalene . 
See Phenymaphthylhydrazine. 
Benzene-pentacarboxylic Acid 
COOH 

/\COOH 
HOOOJCOOH 

COOH 
CnH 6 10 MW, 298 

Cryst. + 5H 2 O. M.p. 228-30, anhyd. 238. 
Sol. H 2 O, EtOH. Spar. sol. Et 2 O, AcOEt. 
InsoL C 6 H 6 , pet. ether. Heat > di-anhydride. 

Penta-Me ester : C 16 H 16 10 . MW, 368. M.p. 
147-8. 

Fleischer, Retze, Ber., 1923, 56, 228. 
Buzicka, Rudolph, Helv. Chim. Acta, 
1927, 10, 919. 

Benzenepliosphonic Acid 

C 6 H 5 -PO(OH) 2 

C 6 H 7 3 P MW, 158 

Plates from K*O. M.p. 158. Sol. EtOH, 



EtO. InsoL C 



Heat at 250 



C 6 H 6 + 



metaphosphoric acid. 
Di-Me ester : b.p. 247. 
Di-Et ester : b.p. 267, 117-18/l-5 mm. 
Phenyl ester : m.p. 57. 
Di-phenyl ester : needles. M.p. 63*5. 
Anhydride : cryst. from C 6 H 6 . M.p. 100. 
Bichloride : b.p. 258. D 2 1-375. 

Michaelis, Ann., 1876, 181, 305; Ber., 

1879, 12, 564. 
Michaelis, Kohler, Ber., 1876, 9, 521. 

BenzenephosptLonous Acid 

C 6 H 5 -P(OH) 2 

C 6 H 7 O 2 P MW, 142 

Plates. M.p. about 70. Very sol. EtOH. 
Spar. sol. Et 2 O. Oxidised by air. Dist. > 
phenylphosphine + aniline + metaphosphoric 
acid. 

PTienylhydrazine salt : prisms. M.p. 135. 
p-Tolylhydrazine salt : needles. M.p. 148. 
Di-Me ester : b.p. 94-5/13 mm. DJ 1-0972. 
D? 4 1-0732. 

Di-M ester: b.p. 235. D 16 1*032. 
Dipropyl ester : b.p. 137/15 mm. DJ 1-0123. 
Df 0-9925. < 1-4939. 

Di-isopropyl ester : b.p. 121-2/10 mm. DJ 
1-0103. DJ 7 0-9952. < 1-5021. 

DicUoride : b.p. 223, 14Q~-2/57 mm. D 20 
1-319. DJ 1-3428. 

Kohler, Michaelis, Ber., 1877, 10, 810. 
Michaelis, Ananow, Ber. 9 1874, 7, 1688. 
Arbuzov, Razumov, Chem. Abstracts, 
1946,40,3411. 

Benzeneseleninic Acid (Phenylselenious 
acid) 

C 6 H 5 -SeO 2 H 
C 6 H 6 O 2 Se MW, 189 



Plates from H 2 O. M.p. 124-5. Ox. ^ 
benzeneselenonic acid. Bed. > selenophenoi. 
Nitrate : needles. M.p. 112. 

Stoecker, Krafft, Ber., 1906, 39 ? 2197. 
Doughty, Am. Chem. J. 5 1909 ? 41, 326. 
Pyman, J. Chem. Soc., 1919, 167. 

Benzeneselenonic Acid (PJienylselenic acid) 

C 6 H 5 -SeO 3 H 
C 6 H 6 O 3 Se MW, 205 

Xeedles. M.p. 140. Very sol. H 2 O, EtOH. 
InsoL Et 2 O, C 6 H 6 . Bed. >- selenophenoi. 
K salt : + 2H 2 0. Sinters about 50. 

Stoecker, Krafft, Ber., 1906, E9, 2197. 
Doughty, Am. Chem. J., 1909, 41, 326. 
Pyman, J. Chem. JSoc., 1919; 167. 

BenzenesulpMnic Acid 

C 6 H 5 -SO 2 H 
C 6 H 6 O 2 S MW, 142 

Prisms. M.p. 83-4. Decomp. at about 100. 
Sol. hot H 2 O, EtOH, Et 2 O, C 6 H 6 . Spar. sol. 
cold H 2 O. FeCl 3 > orange ppt. 

Anhydride: C 12 H 10 3 S 2 . MW, 266. M.p. 
67. SoL CHC1 35 MeOH, EtOH, C 6 H 6 , Me 2 CO, 
AcOEt. 

Chloride: C 6 H 5 OC1S. MW, 160-5. Colour- 
less plates. M.p. 38. Hyd. by H 2 O. 

Hydrazine salt: A2,NH 2 -NH 2 . MW, 316. 
M.p. 139-^1. 

Diethylamine salt : m.p. 109-10. 
Aniline salt : A 3 C 6 H 5 NH 2 . MW, 235. M.p. 
132 

p~Toluidine salt: A,CH 3 -C 6 H 4 KH 2 . MW, 
249. M.p. 12^5. 

Amide : C 6 H 7 ONS. MW, 141. M.p. 121. 
Dimethylamide : b.p. 90/2-3 mm. 
Anilide : m.p. 112-14. 

Knoevenagel, Kenner, Ber., 1908, 41, 

3318. 
Knoll, D.B.P., 171,789, (Chem. Zentr., 

1906,11,469). 
Braun, Kaiser, Ber., 1923, 56, 549. 

Benzene sulplione. 

See Diphenyl sulphone. 

Benzenesulphonic Acid 
C 6 H 5 -S0 3 H 
C 6 H 6 3 S MW, 158 

Colourless plates + HH 2 O, M.p. 43-4, 
anhyd 65-6 (50-1). Deliquescent. Very sol. 
H 2 O, EtOH. Spar. sol. C 6 H 6 . InsoL Et 2 O, 
CS 2 . ^ = 2 x 10- 1 at 25. Hot cone. H 2 SO 4 
>. benzene. Alkali fusion > phenol. 

Na salt : leaflets + 1H 2 0. M.p. about 450 
decomp. Sol. 1-75 parts H 2 O at 30. 

Phenylhydrazine salt : m.p. 179. 

Me ester : C 7 H 8 O 3 S. MW, 172. B.p,. ISO / 
15mm. Di 7 1-2730. 



Benzene stilplioxide 



248 



7 : 8-Benzflavone 



Et ester : CgH^O^S. MW S 186. B.p. 156/ 
15 mm. Spar, sol H 2 O. Df 1-2192. 

n-Propyl ester : C 9 H 19 OgS. MW, 200. B.p. 
162-3/15 mm. D? 1-1804. 

P&ewifi esfer : C 12 H 10 3 S. MW, 234. M.p. 
34-5, 

Amide: C 6 H 7 OaNS. MW, 157. M.p. 156 

(147-8). Sol. Et" 2 0, hot EtOH. Spar. sol. 
cold H 2 0. Forms metallic derivs. (e.g. 



Anhydride: C^H^O^. MW, 298. M.p. 
92. B.p. 240/10 mm. decomp. 

CJdorMe: C 6 H 5 2 C1S. MW, 176-5. M.p. 
14-5. B.p. 251-2, 177/100 mm., 120/10 mm. 
InsoL H 2 (). Dg 1-3842. Stable to cold H 2 0. 
Zn + H20 4 > thiophenol. 

Fluoride: b.p. 203-4. Df 1-3286. 

Anilide : m.p. 110. 

< . NH . m p 206 o 

m.p. 147. 
: m.p. 110. 

jOi,<({jjLig} 3.1.1 . m.p. 89 . 

A 9 O^HfNH 2 : m.p. 92. 

A,(GJ!K)NH -. m.p. 139. 

" m.p. 120-1. 



Guyot, Chimie et Industrie, 1919, 2, 879. 

Hochstetter, J. Am. Chem. Soc., 1898, 
20, 549. 

Davies, Dick, J. C^em. Soc., 1931, 2104. 

Mazonski, Sucharda, Chem. Abstracts, 
1935, 29, 6218. 

Clarke, Bab cock, Murray, Organic Syn- 
theses, Collective Vol. I, 77. 

Benzene sulphoxide. 

See Diphenyl sulphoxide. 

Benzene-1 : 2 : 3 : 4-tetracarboxylic Acid. 

See Prehnitic Acid. 

Benzene-1 :2 : 3 : 5-tetracarboxylic Acid. 

See Mellophanic Acid. 

Benzene-1 : 2 : 4 : 5-tetracarboxyHc Acid. 

See Pyromellitic Acid. 

BenzenetMosulphonic Acid 

C 6 H 5 -S0 2 -SH 
C 6 H 6 2 S 2 MW, 174 

Free acid unknown. Aq. sols, decomp. $- 
benzenesulphinic acid + S. 
Ag salt : needles. Spar. sol. H 2 0. 
Me ester : C 7 H 8 2 S 2 . MW, 188. Liq. B.p, 

123 /1 mm. 

Gibson, J. Chem. Soc., 1932, 1822. 
Otto, Troeger, Ber., 1891, 24, 491. 

Benzene-1 : 2 : 3-tricarboxyHc Acid. 

See Hemimellitic Acid. 

Benzene-1 : 2 : 4-tricarboxylic Acid. 

See Trimellitic Acid. 

Benzene-1 : 3 : 5-tricar boxy lie Acid. 

See Trimesic Acid. 

Benzene triozonide. 

See Ozobenzene. 



Benzene-1 : 3 : 5-trisulplionic Acid 
S0 3 H 



HO, 




3 H 



C 6 H 6 9 S 3 MW, 318 

Cryst. + 3H 2 0. Decomp. above 100. 

Tri-m ester: C 12 H 18 9 S 3 . MW, 402. Cryst. 
from C 6 H 6 . M.p. 147. 

Trichloride: C 6 H 3 6 C1 3 S 3 . MW, 373-5. 
Needles or leaflets. M.p. 187. PC1 5 at 200 
>- 1:3: 5-trichlorobenzene. 

Trifiuoride : C 6 H 3 6 F 3 S 3 . MW, 324. Cryst. 
from xylene. M.p. 179-81. 

Triamide: C 6 H 9 6 Isr3S 3 . MW, 315. Needles. 
M.p. 310-15. 

Trianilide : m.p. 237. 

Senhofer, Ann., 1874, 174, 243. 
Lamberts, D.E.P., 113,784, (Chem. Zentr., 

1900, II, 883). 
Behrend, Mertelsmann, Ann., 1911, 378, 

361. 
Davies, Dick, J. Chem. Soc., 1931, 2108. 

Benzerythrene (pp' - Diphenyldiphenyl, 

dixenyl, ^-quaterphenyl) 



MW, 306 

Leaflets from C 6 H 6 . M.p. 320. B.p. 428 / 
18 mm. Sol. boiling PhN0 2 , aniline. Spar, 
sol. hot AcOH. Insol. EtOH, Et 2 0, 
ligroin. Sol. 100 parts boiling C 6 H 6 . 

Schmidlin, Ber., 1912, 45, 3179. 
Bowden, J. Chem. Soc., 1931, 1111. 

5 : 6-Benzflavone (a$-Naphthaflavone) 



CO 




!TT 
J 




C 19 H 12 2 MW, 272 

Needles from EtOH. M.p. 164-5. Sol. cone. 
H 2 S0 4 with blue fluor. 

Menon, Venkataraman, J. Chem. Soc., 

1931, 2594. 
Tambor, Plattner, Zach, Helv. Chim. 

Ada, 1926, 9, 463. 

7 : 8-Benzflavone (fa-Naphthaflavone) 
CO 



C 19 H 12 2 




MW, 272 



5 : 6-BenzfLavonoI 



249 



I : 2-BenzfLuoreiione 



Yellow plates from EtOH. M.p. 155 (167). Cryst. from ligroin or AcOH. M.p. 208-9 

Pale yellow sol. in cone. H 2 S0 4 shows weak green (204-6). B.p. 401-2. Sol. ligroin with green- 

fluor. ish fluor. 

Bhuller, Venkataraman, J. Chem. Soc., Koelsch, J. Am. Chem. Soc., 1933, 55, 

1931, 1165. 3887. 

Pfeiffer, Grimmer, Ber., 1917, 50, 925. Barnett, Goodway, Watson, Ber., 1933, 

Buhemann, Ber., 1914, 47, 120. 66, 1891. 

Smith, J. Chem. Soc., 1946, 542. o / T> - 

5 ' 3 : 4-BenzfLnorene 

5 : 6-BenzfLavonol (aj 

CO 




C 19 H 12 3 MW, 288 

YeUow needles from AcOEt. M.p. 147. 
Sol. AcOH. Spar. sol. EtOH. Orange sol. in 
cone. H 2 SO 4 , on dil. with B^O > blue col. 
with green fluor. 

Ingham, Stephen, Timpe, J. Chem. Soc., 
1931, 899. 

7 : 8-BenzfLavonol ($<z-Naphthaflavonol) 
CO 

K>H 

C 6 H 5 

o o 




C 19 H 12 O 3 MW, 288 

Pale greenish leaflets from EtOH. M.p. 210. 
Spar. sol. EtOH, H 2 0. Sol. cone. H 2 S0 4 with 
yellowish-green col. with green fluor. 

Acetyl : leaflets from EtOH. M.p. 194-5. 

Isonitroso deriv. : m.p. 173^. 

Woker, Ber., 1906, 39, 1651. 
1 : 2-Benzfluorene (CJirysofluorene) 




C 17 H 12 v MW, 216 

Cryst. from AcOH. M.p. 189-90 (183-4). 

B.p. 413 (398-400). Sol. Et 2 0, CHC1 3 , hot 

C 6 H 6 . 

Picrate : m.p. 127-5 (124-6). 

Graebe, Ann., 1904, 335, 134. 
Cook, Hewett, J. Chem. /Soc., 1934, 375, 
1737. 



2 : 3-Benzfluorene 




MW, 216 
Plates from EtOH. M.p. 124-5. 
Picrate : red needles from EtOH. M.p. 
130-1. 

Cook et al, J. Chem. Soc., 1935, 1323. 

Benz- [jk] -fluorene . 

See Fhioranthene. 
1 : 2-Benzfluorenol 




C 17 H 12 MW, 232 

Needles or leaflets. M.p. 166-7. Very sol. 
Et 2 0, CHCi^, C 6 H 6 . Spar. sol. ligroin. Sub- 
limes. Sol. cone. H 2 S0 4 with reddish-violet 
coL 

Bamberger, Kranzfeld, Ber., 1885, 18, 
1934. 

2 : 3-Benzfluorenol 




OH 



C 17 H 12 MW, 232 

Plates from ligroin or C 6 H 6 . M.p. 185. 

Very sol. EtOH, Et 2 0, Me 2 CO, CHClg. Sol. 

cone. H 2 S0 4 with violet col. 
Acetyl : needles from pet. ether. M.p. 97. 
Thiele, Wanscheidt, Ann., 1910, 376, 274. 




1 : 2-Benzfluorenone 

chrysoketone) 



C 17 H 10 



(Chrysofluorenone, 




MW,230 

Yellow needles or orange-red prisms. M.p. 
132*5. Sol. common org. solvents. Sol. cone. 
MW, 216 H 2 SO 4 with red col. 



2 : 3-Benzflnorenoiie 



250 



Benzliydrylamine 



Oxime : golden-yellow plates. M.p. 202 
decomp. 

Phenylhydrazone : m.p. 174. 

Graebe, Ann., 1904, 335, 132. 

2 : 3-Benzfiiiorezione 



17 H 10 O 



Benzfuro-[3 ? 2-g]-qiiiiioline 
O N 




O 



MW, 230 

Yellow needles from EtOH. M.p. 152. 
Sol. Et 2 0, C 6 H 6 . 

Owne: yellow needles from EtOH. M.p. 231. 

TMele, Wanscheldt, 4., 1910, 376, 273. 

3 : 4-BenzfluorenoiLe (AUochrysoketone) 




C 17 H 10 MW, 230 

Orange cryst. from toluene. M.p. 161. 
Oxime: cryst. from EtOH. M.p. 215. 
Semicarbazone : yellow needles from dioxan. 
M.p. 235 decomp. 

Phenylhydrazone : yellow cryst. from AcOH. 
M.p. 180. 

Schaarschmidt, Ber., 1916, 49, 1449. 
Cook et al, J. Chem. Soc., 1935, 1323. 

Benzfuran. 

See Coumarone. 

3 : 4-Benzfuranone-2. 

See Phthalide. 

Benzfuril (Benzoyl-a-furoyl, phenyl furyl 
diketone) 

HP ps 

HQ .OCOCOC 6 H 6 



Y 



C 12 H 8 3 MW, 200 

YeUow needles. M.p. 41. Sol. EtOH, Et 2 0. 
Tetrabromide : yellow needles. M.p. 127-8, 
Fischer, Ann., 1882, 211, 229. 

Benzfuro-[2, 3-f]-quinoline 




C 15 H 9 ON ~ " MW,219 

Cryst. from EtOH.Aq. M.p. 168-9. 
B,HCl: yellow. M.p. 216-33. 

Mosettig, Kobioson, /. Am. Ghem. Soc., 

1935, 57, 902. 

Kirkpatrick, Parker, J. Am. Chem. Soc., 
1935, 57, 1123. 




5 / / \ 4 y / 

< 15 H 9 ON MW, 219 

Ciyst. from EtOH.Aq. M.p. 112 (106-7). 
B,HCl : yellow. M.p. 266-85. 

Mosettig, Robinson, J. Am. Chem. Soc., 

1935, 57, 902. 

Kirkpatrick, Parker, J. Am. Chem. Soc., 
1935, 57, 1123. 

Benzhydrazide (Benzoylhydrazine) 



C 7 H 8 01Sr 2 MW, 136 

Plates. M.p. 112-5. If quickly heated, 

boils almost tmdecomp. Mod. sol. H 2 0, EtOH. 

Spar. sol. Et 2 0, CHC1 3 , C 6 H 6 . 

Oxime : needles. M.p. 110 decomp. 

StoUe, J. praJct. Chem., 1904, 69, 145. 

Benzhydrindene . 

See a-Naphthindane. 
Benzhydrindone . 

See a-Naphthindanone. 

Benzhydrol (Diphenylcarbinol, a - hydroxy - 
diphenylmethane} 

C 6 H 5 -CH(OH)-C 6 H 5 
C 13 H 12 MW, 184 

Silky needles. M.p. 69. B.p. 297/748 mm., 
180/20 inm. 1 part dissolves in 2000 parts 
H 2 O at 20. Sol. EtOH, Et 2 0, AcOH, CHCij, 
CC1 4 . Deep red sol. in cold H 2 SO 4 . Ox. > 
benzophenone. 

Acetyl : m.p. 41-2. 

3 : 5-Dinitrobenzoyl : m.p. 142. 

-p-Diphenylurethane : m.p. 197. 

Zechmeister, Rom, Ann., 1929, 468, 117. 
Marvel, Hansen, Organic Syntheses, Col- 
lective Vol. I, 84. 



Benzhydroxamic Acid 






C 7 H 7 2 N MW, 137 

Rhombic tablets. M.p. 125. Sol. 44 parts 
H 2 at 6. Sol. EtOH. Spar. sol. Et 2 0, 
C 6 H 6 . Aq. sol. + FeCl ? > dark red ppt., 
sol. to dark cherry red in excess PeCl 3 . Hyd. 
> NH 2 OH + benzoic acid. 

Benzoyl deriv. : C 6 H 5 -C(:N-0-CO-C 6 H 5 )OH. 
Needles. M.p. 161. Prac. insol. H 2 0. 

Jones, Hurd, J. Am. Chem. Soc., 1921, 

43, 2446. 
Ponzio, Gazz. chim. ital, 1929, 59, 554. 

B enzhy drylamine . 

See a-Aminodiphenylmethane. 



a-BensQiydrylbenzhydrol 



251 



Benzil-suiil 



a-Benzliy drylbenzliy dr ol . 

See 1:1:2: 2-Tetraphenylethyl Alcohol. 
Bens&ydrylbenzoic Acid. 
See Triphenylmethane-carboxylic Acid. 
Benzhydryl bromide. 
See Diphenylmethyi bromide, 
Benzhydryl cnloride. 
See Diphenylmethyl chloride. 
Benzhydrylglycollic Acid. 
See 2 : 2~Diphenyl-lactic Acid. 
Benzhydryl Mercaptan. 
See Thiobenzhydrol. 
Benzliydrylplienol. 
See Hydroxytriphenylmethane. 
Benzhydrylsuccinic Acid. 
See 3 : 3-Diphenylpropane-I : 2-dicarboxyHc 
Acid. 

Benzidine (4 : 4' -Diaminodiphenyl) 



C 12 H 12 N 2 MW, 184 

Exists in three forms, (a). M.p. 125; and 
(b), m.p. 122 are both metastable and are 
deposited from molten benzidine on cooling 
to about 100. The stable form (c), m.p. 128, 
is obtained at temps, nearer the m.p. All three 
forms co-exist indefinitely at ord. temps. B.p. 
400/740 mm. Sol. 2447 parts H 2 O at 12, 
106-5 parts at 100. Sol. EtOH. 

B,2ECl : leaflets, sol. JLf) : ppd. by cone. 
HC1. Boil aq. sol. > ppt. of spar. sol. B,HCL 
B,H^SO^ : scales. Prac. insol. H 2 O, EtOH. 
Monoacetyl: needles from EtOH.Aq. M.p. 
199. Sol. EtOH. Insol. Et 2 O. 
Diacetyl deriv. : m.p, 317. 
Tetra-acetyl : needles from EtOH-C 6 H 6 . M.p. 
214-15. 

Monobenzoyl : m.p. 203-5. 
Dibenzoyl deriv. : needles. M.p. 352. 

Ismailsky, Kolpensky, Z. angew. Chem., 

1926, 39, 507. 
Amiantov, Toporkov, Chem. Zentr., 1932, 

I, 1437. 

Fichter, Chem. Abstracts, 1933, 27, 2886. 
Swann Eesearch Inc., U.S.P., 1,954,469, 

(Chem. Abstracts, 1934, 28, 3744). 
Weygand, Z. ges. Naturwiss., 1937, 2, 
408, (Chem. Zentr., 1937, I, 4095). 

Benzidine-2 : 2'-disulplionic Acid 
S0 3 H 




H 2 N< 

C 12 H 12 6 N 2 S 2 MW, 344 

Prisms. Decomp. without melting. Spar. 

sol. hot H 2 O. Prac. insol EtOH, Et 2 0. 
B,2HCl: prisms + 2H 2 0. M.p. 205. 
d-Diphenyl ester : C^n^O^Sa. MW, 496. 

Leaflets from Me 2 CO-pet. ether. M.p. 222-3. 

rl, +28-0 in: 



l-Diphenyl ester : m.p. 222-3. [a] 5791 24-6 
in Me 2 CO. 

Diamide : C 10 H M 4 N 4 S 2 . MW, 342. Cryst. 
from H 2 0. M.p. 278. Insol. Et^O, CHC1 3 . 
Hydrockloride . m.p. 205. 

Elbs, Wohlfahrt, J. praJcL Chem., 1902, 

66, 558. 
Lesslie, Turner, /. Chem. Soc., 1932, 2025. 

Benzidine-3 : S'-disulplionic Acid. 

Leaflets. Spar, sol. hot H 2 0. Insol. EtOH, 
Et 2 0. 

Griess, Duisberg, Ber,, 1889, 22, 2461. 

Benzil (Dibenzoyl, diphenyl y.$~dilcetone, di- 
phenylglyoocal) 



C 6 H 5 -CO-CO-C 6 H 5 



C 14 H 10 



MW, 210 

Yellow prisms from EtOH. M.p. 95. B.p. 
346-8, 188 /12 mm. Sol. EtOH, Et>0. Insol. 
H 2 0. Na 2 S 2 4 , or SnCl 2 + HC1 > benzoin. 
Ox. $~" benzoic acid. Warm ale. KOH > 
benzilic acid. 

Oximes : see Benzil monoxime and Benzil 
dioxime. 

Mono-semicarbazone : m.p. 174-5 decomp. 
(rapid heat.). 

Di-semicarbazone : leaflets. M.p 243-4 de- 
comp. 

Di-p7ienylsemicarbazone : plates from AcOH. 
M.p. 253 decomp. 

Mono-semioxamazone : prisms from EtOH. 
M.p. 181-2. 

l)i-semioxamazone : m.p. 275-8. 

Mono-hydrazone : cryst. M.p. 151. 

Di-hydrazone : needles from EtOH. M.p. 134. 

Mono-phenylhydrazone : cryst. from EtOH. 
M.p. 134. 

Di-phenylhydrazone : benzil osazone. Needles. 
M.p, 225 (rapid heat.). 

Anil : phenyliminodeoxybenzoin. Yellow 
prisms from EtOH. M.p. 105. 

Biltz, Ann., 1909, 368, 224. 

Hatt, Pilgrim, Hurran, J. Chem. Soc., 
1936, 93. 

Corson, McAllister, J. Am. Chem. Soc., 
1929, 51, 2823. 

Clarke, Dreger, Organic Syntheses, Col- 
lective Vol. I, 80. 

Benzilam. 

See Triphenyloxazole. 

Benzil-anil (Phenyliminodeoxybenzoin) 

C 6 H 5 -CO-f]-C 6 H 5 
N-C 6 H 5 

C 20 H 15 ON MW, 285 

Yellow prisms from EtOH. M.p. 105. Spar, 
sol. cold EtOH. Mod. sol. Et 2 0, C 6 H 6 , Blood 
red sol. in H 2 S0 4 . 

Biltz, Ann., 1909, 368, 224. 



Beiizil-o-carboxylic Acid 



Benzil raonoxime 



Benzil-o-carboxylic Acid 
COOH 



O c - c O 



(I) 



OH 

(II) 



C 15 H 10 4 



MW, 254 



Exists in two modifications : 

(1) Ketoform : yellow cryst. M.p. 143-4. 

(2) Lmtone form : white cryst. M.p. 130. 
Begins to isomerise to (1) at about 66. ELeto 
form more sol. EtOH, CHC1 3 than lactone. 
Alkalis > benzhydrol-dicarboxylic acid. 

Me ester: C lft H 10 4 . MW, 268. Yellow. 
M.p. 117. 

Et ester: C 17 H 14 4 . MW, 282. M.p. 71. 

Chloride: C 15 H 9 3 C1. MW, 272-5. Cryst. 
from CHClg. M.p. 61-3 

Monoxime : m.p. 166. 

Hantzsch, Schwiete, Ber., 1916, 49, 213. 
Schaum, Ann., 1928, 462, 204. 

Benzil-2 : 2 / -dicarboxylic Acid. 

See Diphthalylic Acid. 

Benzil dioxime (Diphenylglyoxime) 

C 6 H 5 -f) frC 6 H 5 . 

HO-N N-OH 

Anti- or a-dioxime 



N-OH HO-N 

Syn* or 5-dioxime 



N-OH N-OH 

A mphi- or y-dioxime 
C 14 H 12 0,N 2 

Three stereoisomers. 



MW 5 240 
See above formulae. 



a- : 

Leaflets. M.p. 238 decomp. Prac. insol. 
EtOH, Et>0, AcOH. Sol. cone. NaOH. 

Q-Me : " C^H^O^. MW, 254. Needles 
from Me 2 CO. M.p. 181-2. Acetyl: plates 
from EtOH. M.p. 107-8. 

O : Q-Di-Me : C 16 H 16 OoN>. MW, 268. Cryst. 
fromMe 2 CO. M.p. 163^ / 

Diacetyl : m.p. 148. 

Dibenzoyl : needles from Me 2 CO-EtOH. M.p. 
220. 

P-: 

M.p. 207 decomp. Sol. EtOH, Et 2 0, AcOH. 
Sol. NH 3 , cone. NaOH. 

0-Me : prisms from AcOH. M.p, 177. 
Acetyl : prisms from EtOH. M.p. 81. Benzoyl : 
prisms from AcOH. M.p. 162, 

: 0-Di-Me : cryst. from EtOH. M.p. 72-3. 

Diacetyl : m.p. 124-5. 

Dibenzoyl : cryst. from EtOH. M.p. 135. 

M.p. 164-5 (163) > p-dioxime. Cryst. 
from EtOH with EtOH of cryst., m.p. 100. 
Insol. ligroin. Sol. cone, alkalis. 

0-Me : needles from CHCl 3 -pet. ether. 



M.p. 172 s . Acetyl : needles from EtOH. M.p. 
80 C . Benzoyl : prisms from AcOH. M.p. 79. 

O : Q-Di-Me : plates from 80% EtOH. M.p. 
59. 

Dibenzoyl : cryst. from EtOH. M.p. 135. 

Meisenheimer. Lamparter, Ber., 1924, 57, 

276. 
Ponzio, Avogadro, Gazz. chim. ital., 1923, 

53, 511. 
Brady, Perry, J. Ohem. Soc., 1925, 127, 

2874. 
Brady, Muers, /. Chem. Soc., 1930, 220. 

Benzilic Acid (Diphenylglycollic acid) 



C 14 H 12 O 3 MW, 228 

Needles. M.p. 150. Sol. EtOH, Et 2 0, hot 
H 2 0. Reddish-violet sol. in cone. H 2 S0 4 . 
Cr0 3 > benzophenone + C0 2 . HI > di- 
phenylacetic acid, k = 9*2 X 10~ 4 at 25. 

Me ether: C 15 H 14 O 3 . MW, 242. Needles 
from AcOH. M.p. 1 1 1-12. 

Et ether : C 16 H 16 3 . MW, 256. Plates from 
Et 2 O. M.p. 114-15. 

Me ester : C 15 H 14 3 . MW, 242. M.p. 74-5. 
B.p. 187/13 mm. Acetyl : m.p. 122. 

" - - MW, 256. M.p. 34. 



Et ester: C 16 H 16 3 . 



B.p. 201/21 mm. Acetyl : m.p. 65 



C 17 H 18 3 . 



MW, 270. 



C 19 H 22 3 . MW, 298. 



C 2 H0 3 . 



2118 



MW, 318. 



B.p. 
B.p. 
M.p. 



Propyl ester: 
220/35 mm. 

Isoamyl ester: 
232/26 mm. 

Benzyl ester: 
756. 

Amide : C 14 H 13 2 N. MW, 227. M.p. 154-5. 

Anilide : C 20 H' 17 2 N. MW, 303. M.p. 175. 

Hydrazide : needles from EtOH.Aq. M.p. 
168-9. 

Acetyl : needles from AcOH. M.p. 98. 
Chloride : b.p. 193-5 /27 mm. Anilide : m.p. 
176. 

Ballard, Dehn, Organic Syntheses, Col- 

lective Vol. I, 82. 
Kao, Ma, J. Chem. Soc. 9 1931, 443. 



Benzil monoxime 

,C 6 H 5 -CO-f)-C 6 H 5 

HO-N 



C 6 H 5 -CO-q-C 6 H s 
N-OH 

a-oxime /3-oxime 

C 14 H n 2 N MW, 225 

Exists in two stereoisomeric forms. See 
above formulae. 

a- : 

Leaflets. M.p. 137-8. Sol. EtOH, Et 2 0, 
CH01 3 , AcOH. Spar. sol. cold C 6 H 6 , ligroin. 
Decomp. at 200 > benzoic acid + benzo- 
nitrile. 

Me ether : m.p. 62-3. 

Benzoyl : m.p. 95-6. 



Benziminazo-[2 , 1 -a]-isoqainoline 



253 



Benzlminoetlier 



M.p. 113-14. Cryst. from C 6 H 6 with |C 6 H 6 , 

m.p. 70 C . Sol. most ord. org. solvents except 
ligroin. 

Me ether : m.p. 64-5. B.p. 220/40 mm. 

Benzoyl : m.p. 138. 

Meisenheimer, Ber., 1921, 54, 3206. 
Brady, Perry, J. Ghem. Soc., 1925, 127, 

2876. 
Brady, Muers, J. Ghem. Soc., 1930, 219. 

Benziminazo - [2, 1 - a] - isoquinoline (Iso- 
\.' : 2' : 1 : 2]benziminazole) 



. 

12 NX 




y 



C 15 H 10 N 2 MW, 218 

Needles from pet. ether. M.p. 129. Becomes 
pink on exposure to light and air. 

9 : ll-Dinitro : golden needles. Melts above 
280. 

Morgan, Stewart, J. Ghem. Soc., 1938, 
1292. 

Benziminazole 




C 7 H 6 N 2 MW, 118 

Plates. M.p. 170. Sol. H 2 O, EtOH. 

^-Acetyl : needles from C 6 H 6 . M.p. 113-14. 
Picrate : yellow cryst. from C 6 H 6 . M.p. 158. 

TS-Propionyl : cryst. from EtOH. M.p. 125, 
Picrate : yellow cryst. from EtOH. M.p. 228. 

N-Benzoyl : needles from EtOH. M.p. 93. 
Picrate : yeUow cryst. from EtOH. M.p. 215. 

Picrate : yellow needles. M.p. 223. 

Phillips, J. Ghem. Soc., 1928, 2393. 
Oddo, Ingraffia, Gazz. chim. ital., 1932, 

62, 1095. 
Wagner, Simons, J. Ghem. Education, 

1936, 13, 265. 

Benziminazolone (o-Phenyleneurea} 

A H 

\A/ co 



NH 



MW, 134 



C 7 H 6 ON 2 

Plates. M.p. 311. 

N : 'N-Dibenzoyl : needles. M.p. 212-13. 
Anil : needles from C 6 H 6 , prisms from 
EtOH. M.p. 190. B.p. 440-50 decomp. 

Heller, /. praJct. Ghem., 1925, 111, 1. 
Mistry, Guha, /. Indian Ghem. Soc., 1930, 
I, 795. 



Benziminazo - [1,2 - ij-plxenantbridine 

(1 : 2 : 10' : W-PJienanthridoA : 5-benz-l : %-di- 
azaline} 



\/ 



C 19 H 12 N 2 



MW, 268 

Needles from EtOH.Aq. M.p. 155. 
10 : 12-Dinitro : deep vellow needles. M.p. 
above 280. 

Morgan, Stewart, J. Ghem. Soc., 1938, 
1292. 

Benziminazo- [2, 1 aj-phtlialazine (2' : 4- 
Anhydro-%'-amino-3-phenylphthalaz-4:-one) 




MW, 219 

Needles from MeOH. M.p. 178. Very sol. 
dil. acids. Insol. aq. alkalis. 

Eowe, Adams, Peters, Gillam, J. Ghem. 
Soc., 1937, 96. 

Benziminazo- [1, 2-a]-qTimoline (Quinvlo- 
[!' : 2' : 1 : 2]-benziminazole t 1 : 2-quinolo-4: : 5- 
benz-l : 3-diazaline) 

A 



C 15 H 10 N 2 MW, 218 

Needles from EtOH.Aq. M.p. 102-3. Be- 
comes yellow on exposure to light and air. 

8 : W-Dinitro : yellow needles from nitro- 
benzene. M.p. above 300. 

10-.A^r0 : yellow needles from toluene. M.p. 
242-3. 

Morgan, Stewart, J. Ghem. Soc., 1938, 
1292 ; 1939, 1057. 

Benzimino ether (Benzimino-ethyl ether) 
r\c* TT 

CTT ,rU xXl - /v - ; 2 I - l -5 
e^s ^^TH 

C 9 H n ON MW. 149 

OH. B.p. 10r/15 mm. k = 11*0 X 10" 9 at 
25. 

N -Benzoyl : m.p. 65. 
B,HCl : m.p. 119-20 decomp. 

Lander, J. Ghem. Soc., 1900, 77, 736. 



2 : 3-Benzindene 



254 



Benzocaine 



2 : S-Benzindene. 
See Pluorene, 

11 - Benzpi]iiideiio - [1, 2 - c] - quinoline 
(1,2(2,1 )'yapktha-3-azafluorene) 

/\/\ 



/\/ -\/X/X/ 

I i , $ 

\/ 

X MW, 267 

Dark yellow. M.p. 223. 

Borsche, Wagner-Roemmieh, Ann., 1940, 

544. 272. 

iS-Benztfjindeno- [l,2-c]-quinoline (1,2 
( 1 ,2 )-Naphtha->%-aza>fluorene ) 




N MW 5 267 

Yellow. M.p. 200. 

Picrate : yellow. M.p. 241 decomp. 

Borsche, Noll, Ann., 1937, 532, 127. 

4 : 5 -BenzisocoTimaranone (2 - Hydroxy- 1 - 
naphthylaceiic lactone, $-naphthafuranone-2) 




C 



12 



H 8 2 



MW, 184 

Leaflets. M.p. 107 (104). Very spar. sol. 
H 2 0. Sol. cone. H2S0 4 >- green fluor. 

I.G., D.B.P., 562,391; B.P., 330,916, 
(Chem. Abstracts, 1933, 27, 735 ; 1930, 
24, 6031). 

Mayer, Schafer, Rosenbach, Chem. Zentr., 
1929, H, 3009. 

6 : 7-Benzisoquinoline. 

See p-Anthrapyridine. 
BenzisotMazole 

H 



C 7 H 5 NS MW, 135 

Cryst. M.p. 37. B.p. 220. Sol. EtOH, 
Et 2 0. Insol. H 2 0. Volatile in steam. Gives 
with AgN0 3 a eomp, (C 7 H 6 NS) 2 .AgN'03, white 
needles from H 2 0. M.p. 105. 

StoUe, JBer., 1925, 58, 2096. 





Benzisoxazolone (Hydroxyanthranil, o-hydr- 
oxylaminobenzoic anhydride) 

JO 
' 

NH 

C 7 H 5 2 N MW, 135 

Colourless needles from C 6 H 6 . M.p. 112 
decomp. Acid reaction. 
TS-Acetyl : needles. M.p. 121. 
IS-Benzoyl : needles from EtOH. M.p. 153-4. 
Bamberger, P^Tnan, Ber., 1909, 42, 2317. 

BenzDaorpholone (o-Aminophenoxyacetic 
lactam, o-aminophenoxyacetic anhydride] 
NH 

9 
yoe, 

C 8 H 7 2 N MW, 149 

Needles or prisms. M.p. 173-5. Sublimes - 
Sol. H 2 0, EtOH, Et 2 0, C 6 H 6 , cone. alkaHs. 
Forms N-Na deriv. 

N-Jfe: GjftOjjN. MW, 163. M.p. 58-9. 
B.p. 156/14 mm. 
N-Acetyl : needles. M.p. 77. 

Jacobs, Heidelberger, J. Am. Chem. Soc.,. 
1917, 39, 2188. 

2 : 3-Benz-6 : 7-naphtha-anthraquinone. 

See 6 : 15-Hexacenedione. 
B enznaphthalide . 
See under Naphthylamine. 
Benzocaine (Ancesthesin, -p-aminobenzoic 
ethyl ester) 

COOC 2 H 5 



NH 2 

MW, 165 

Ehombohedra from Et 2 0. M.p. 92. SoL 
EtOH, min. acids. Sol. 7 parts Et 2 0. Prac. 
insol. H 2 0. Local anaesthetic. 
B,HCl: m.p. 207-8. 
Picrate : m.p. 131. 

TX-Acetyl : m.p. 110 (181). Sol. H 2 0, EtOH, 
Me 2 CO, AcOH. Spar. sol. CHC1 3 . Insol. MeOH, 
Et 2 O. 

N-Chloroacetyl : needles. M.p. 116. 
N-Propionyl : cryst. from EtOH. M.p. 111. 
N-Butyryl : needles from EtOH. M.p. 87. 
N-x-Bromoisovaleryl : m.p. 115. 
TS-Benzoyl : needles from EtOH. ' M.p. 150. 
Sol. Me 2 CO, C 6 H 6 , CHC1 3 , AcOH. Insol. H 2 0. 
N-Phthaloyl : needles from EtOH. M.p. 152. 
Coniglio, Chem. Abstracts, 1931, 25, 1811. 
Tsofin, Kaduchkevich, Chem. Abstracts* 

1934, 28, 5599. 

Adams, Cohen, Organic Syntheses, Col- 
lective Vol. I, 235. 



Benzocateclioi 



255 



Benzoin 



Benzocateclioi. 

See Dihydroxybenzophenone. 
BenzocresoL 

See Hydroxyniethylbenzophenone. 
1:2: 3BenzoditMoi-3-one (2-Dithio- 

benzoyl) 



SO 
C 7 H 4 OS 2 MW, 168 

Pale needles from EtOH.Aq. M.p. 77. 
Red. > H 2 S -}- thiobenzoic acid. 

Smiles, McClelland, J. Chem. Soc., 1922, 
86. 

1:2: 3-BenzoditMol-3-tMone (2 : %-Dithio- 
sulphindene) 



C 7 H 4 S 3 MW, 184 

Bed cryst. from AcOH, C 6 H 6 or EtOH- 
M.p. 98 (94-5). Sol. most org. solvents- 
Insol. cold H 2 0. Py > orange-yellow col- 
Gone. H 2 SO 4 > brownish-yellow col. 

Oxime : yellow. M.p. 210 decomp. 

Hydrazone : orange. M.p. 125. 

Phenylhydrazone : brown. M.p. 106. 

Mannessier, Gazz. chim. ital., 1916, 46, 231. 
McClelland, Warren, Jackson, /. Chem. 
8oc. 9 1929, 1582. 

Benzofuran. 

See Phenyl foryl Ketone. 

Benzoguaiacol. 

See under 3 : 4-Dihydroxybenzophenone. 

Benzohydroquinone. 

See 2 : 5-Dihydroxybenzophenone. 

Benzole Acid 

C 6 H 5 -COOH 
O 7 H 6 2 MW, 122 

White leaflets or needles. M.p. 122. B.p. 
249, 234/500mm., 186/100 mm., 133/10 mm. 
Sublimes at 100. Volatile in steam. 1000 
parts H 2 dissolve 1-8 parts at 4, 2-1 at 10, 
2-7 at 18, 4-2 at 31, 5-5 at 40, 12 at 60, 17-8 
at 70 and 22 at 75. Sol. EtOH to 32% at 
15, 90% EtOH to 294% at 15. 60 parts 
Et 2 dissolve 24 parts at 15. Sol. CHC1 3 , CCL, 
Me 2 CO, MeOH, C 6 H 6 . D} 5 1-2659. wg 1-53974. 
Heat of comb. C* 774-1 CaL, C P 771-7 Cal. 
k = 6-52 x 10- 5 at 25. 

Anhydride : see Benzoic Anhydride. 

Chloride : see Benzoyl chloride. 

Iodide : see Benzoyl iodide. 

Bromide : see Benzoyl bromide. 

Fluoride : see Benzoyl fluoride. 

Amide : see Benzamide. 



Anilide : see BenzaniHde. 

Toluidide : see under Tokddine. 

Xylidide : see under Xylidene. 

Tolyl ester : see under CresoL 

Naphthyl ester : see under Naphthol. 

Menthyl ester : see under Menthol. 

Nitrile : see Benzonitrile. 

Propyl ester: C IQ B I(> 2 . MW, 164. B.p. 
230. Dg 1-0276. 

Isopropyl ester : b.p. 218-19. Sol. EtOH r 
Et 9 0. Insol. H 2 O. Dg 1-0172. 

Butyl ester: C n H 14 Oo. MW, 178. B.p. 
248-9. Dg 1-0111. 

Isobutyl ester : b.p. 241. D^ 1-0035. 

seG.-wtyl ester : d-. B.p. 120/20 mm. Df 
1-0018. Tiff 1-4930. [cc]^ +39-2. Z-. B.p. 
98-9/13 mm. Df 1-002. < 1-5005. [a^ 
- 44-1. (B-. B.p. 235, 115~17/20 mm. Df 
0-9945. < 1-4933. 

Isoamyl ester: C 12 H 16 2 . JVIW, 192. B.p. 
261/746mm. D\*i 0-9925. 

Hexyl ester: C 13 H 18 2 . MW ? 206. B.p. 
272/770mm. 

Octyl ester: C 15 H 22 2 . MW, 234. B.p. 
305-6. Dg 0-9679. 

Cetyl ester : C 23 H 38 2 . MW, 346. M.p. 30. 
Sol. Et 2 0. 

Allyl ester : C IO H 10 2 . MW, 162. B.p. 242 
(230). D 1-0578. 

PJienylefhyl ester : C 6 H 5 CO-OCH 2 -CH 2 -C 6 H 5 . 
c i5 H i4 2 - MW,226. B.p. 189/21 mm. 

Gilman, Kirby, Organic Syntheses, Col- 
lective Vol. I, 355 (Note 10). 
Morton, Le Fevre, Hechenbleikner, J. Am. 

Chem. JSoc. } 1936, 58, 754. 
I.G., U.S.P., 2,005,183, (Chem. Abstracts,. 

1935, 29, 5125). 
Kenyon et al., J. Chem. Soc., 1935, 1080. 

Benzoic Anhydride 

C 6 H 5 CO-0-GOC 6 H 5 
C U H 10 3 MW, 226 

Colourless rhombic prisms. M.p. 42. B.p. 
360. Insol. H a O. Sol. EtOH, Et 2 0. Df 
1-1989. Tig 1-57665. Stable to H 2 O and cold 
alkalis. Hyd. by boiling alk. carbonates and 
caustic alkalis. 

Kaufmann, Luterbacher, Ber., 1909, 42, 

3484. 
Gazopulos, Ohem. Abstracts, 1932, 26^ 

4318. 
I.G., D.R.P., 520,153, (Chem. Abstracts,. 

1931, 25, 2739). 
Monsanto Chem. Co., U.S.P., 1,948,342,, 

(Chem. Abstracts, 1934, 28, 2730). 

Benzoic sulphimide. 

See Saccharin. 

Benzoin (Phenyl aL~hydroxybenzyl Jcetone) 

C 6 H 5 -CH(OH)-CO-C 6 H 5 

14 H 122 



BenzonaplLthezxe 

dl. 

Prisms. M.p. 137 2 . B.p. 344; 768 mm., 
194/12 mm Spar. sol. hot H 2 0, Et 2 0. Sol. 
EtOH. Reduces FehHng's. Cone. HX0 3 > 
benzil. XaHg in EtOH > hydrobenzoin. 
HI at 250 > dibenzyl. 

Me ether: C 15 H 14 2 . 1IW, 226. Needles. 
M.p. 49. Sol. EtOH, EtaO, C 6 H 6 . Oxime: 
needles from EtOH.Aq. M.p. 130-2 C . 

Et ether: C 16 H 16 O a . MW, 240. Needles. 
M.p. 62. Sol. EtOH, EtgO, C 6 H 6 . 

\cetyl : prisms. M.p. 83. Sol. EtOH, Et 2 O. 

Benzoyl : needles from EtOH, prisms from 
Et 9 0. M.p. 125. AAO 

syn-Oxime : (p-oxime). Prisms. M.p. 99 . 

&nti-0xime : (cc-oxime). Prisms. M.p. 151-2 . 

Phenylhydrazone: two forms, a-, needles, 
m.p. 158-9. p-, prisms, m.p. 106. 

Semicarbazone: prisms, m.p. 206 decomp. 

Phenylsemicarbazone : a-, needles from EtOH. 
M.p. 198 decomp. p-, needles from EtOH. 
M.p. 169. 

Hydrazone : prisms from EtOH. M.p. 75. 

2 : 4-Dinitrophenylhydrazone : orange-yellow. 

M.p. 234. 

2 : 4-Dinitrophenylsemicarbazone : m.p. 228 . 

Needles. M.p. 131-132-5. Sol. Me 2 CO, hot 
EtOH, hot MeOH. [a]g -117-5 in Me 2 CO. 

Me ether : m.p. 53-4. MS -88-2 in CHC1 3 . 
[]g 94-3 in EtOH. 

Acetyl : colourless needles. [a]g 217-7 in 
CTTOI 

Oxime: m.p. 164. [B -3-2 in CHC1 3 . 
[ a ]g +4-4 in EtOH. 

d-. 

Needles. M.p. 131-132-5. [a]g +120-5 in 

Me 2 CO. 
Enolform : see a : g-Dihydroxystilbene. 

Adams, Marvel, Organic Syntheses, Col- 
lective Vol. I, 88. 

Buck, Jenkins, J. Am. Chem. Soc., 1929, 
51, 2163. 

Arnold, Fuson, J. Am. Ghem. Soc., 1936, 
58, 1295. 

Corson, Saliani, Organic Syntheses, 1932, 
XII, 1. 

Wren, J. Chem. Soc., 1909, 95, 1597. 

Benton, Voss, McCusker, /. Am. Chem. 
Soc., 1945, 67, 82. 



Benzonaphtlxene (peri-Naphindene) 




Benzoplienone 

Benzonitrile (Phenyl cyanide, cyanobenzene) 

C H N 6 5 Bfw ' 103 

Vp. -13. B.p. 190-7, 174/500 mm., I21 / 
100 mm , 69 /10 mm. Misc. with EtOH, Et 2 O. 
Sol. 100 parts H 2 at 100. D}^ 1-0102. ng 
1-52892. Heat of comb, ft 865-5 Cal. s Gp 865-9 
Cal. Caustic alkalis or hot mod. cone. min. 
> benzoic acid. 
I.G., B.P., 326,149, (Chem. Abstracts, 

1930, 24, 4055). 
Gen. Aniline Works, U.S.P., 1,879,209, 

(Chem. Abstracts, 1933, 27, 997). 
v. Braun, Rudolf, Ber., 1934, 67, 1769. 
Rozhdestvenskii, Zepalova-Mikhailova, 
Chem. Abstracts, 1934, 28, 2698. 

Benzonitrolic Acid (<&-Nitrobenzaldoxime, 
&-nitro-<*-oximinotoluene) 



MW, 166 

M.p. 85. Readily sol. most org. solvents. 
Picrate : red needles. Decomp. at 110. 
Lock, Gergely, Ber., 1944, 77, 461. 



C 7 H 6 3 N 2 MW, 166 

Colourless needles. M.p. 58. Unstable. Sol. 
alkalis to orange sols, with decomp. 

Wieland, Semper, Ber., 1906, 39 3 2522. . 

Benzophenone (Diphenyl ketone) 

C 6 H 5 -CO-C 6 H 5 
C 13 H 10 MW, 182 

Exists in stable and labile modifications. 
Stable form : rhombic prisms, m.p. 49. B.p. 
306. Sol. EtOH, Bt a O, AcOH. Insol. H 2 O. 
DgJ 1-0976. Labile form : monoclinic prisms, 
m.p. 26. Sunlight > benzpinacol. Na + 
EtOH > diphenylmethane. NaHg > 
benzhydrol. Zn + H 2 S0 4 > benzpinacol 
^ a-benzpinacolin > p-benzpinacolin. 

Di-Me acetal : plates from Et a O. M.p. 106-7. 
B.p. 288-90. 

Di-Et acetal: prisms from EtOH. M.p. 
51-2. B.p. 294-5. 

Dipropyl acetal : prisms from pet. ether. 
M.p. 33-4. B.p. 204 /40 mm. 

Di'isobutyl acetal : plates. M.p. 35-7. B.p. 
210 /35 mm. 

Diphenyl acetal : cryst. from EtOH. M.p. 
132. 

Dibenzyl acetal : cryst. from MeOH. M.p. 
104-5 . B .p . 305 /40 mm. 

Oxime : m.p. 144 (140). Sol. Bt a O, Me 2 CO. 
Mod. sol. CHC1 3 , C 6 H 6 . Spar. sol. H 2 0. Me 
ether : plates from pet. ether. M.p. 102. 
Acetyl : cryst. from CHC1 3 . M.p. 55. 

Hydrazone : m.p. 98. B.p. 225~30/55 mm. 
Sol. Bt 2 O, C 6 H 6 . 

Semicarbazone : m.p. 167. 

P?ienylsemicarbazone : m.p. 163-4. 

Phenylhydrazone : needles. M.p. 137. 

"Q-NitropTienylhydrazone : yellow cryst. M.p. 
154_5. Isomer, red cryst. M.p. 144. 

2 : 4:-Dinitrophenylhydrazone : m.p. 238. 



Benzoplienone-4-aldeliyde 



257 



y-Benzopyrone 



o-Ghlorobenzoylhydrazone : m.p. 142. 

p-Ohforobenzoylhydrazone : m.p. 137-9. 

Marvel, Speny, Organic Syntheses, Col- 
lective Vol. I, 89. 

LacJunann, Organic Syntheses, 1930, X, 
10. 

Mackenzie, J. Ghem. Soc., 1896, 69, 987 ; 
1901, 79, 1206. 

Rivkin, Russ. P., 38,634, (Ghem. Abstracts, 
1936, 30, 3446). 

I.G., D.R.P., 633,083, (Ghem. Abstracts, 
1936, 30, 7582). 

Benzoplienone-4-aldeliyde . 
See 4-Benzoylbenzaldehyde. 
Benzophenone-carboxylic Acid. 
See Benzoylbenzoic Acid. 
Benzophenone chloride. 
See aa-Diehlorodiphenylmethane. 
Benzopiienone-2 : 3-dicarboxyKc Acid. 
See 3-Benzoylphthalic Acid. 
Benzophenone-2 : 4-dicarboxyiic Acid. 
See 4-Benzoylisophthalic Acid. 
Benzoplienone-2 : 5-dicarboxylic Acid. 
See Benzoylterephthalic Acid. 
Benzoplienone-2 : 6-dicarboxylic Acid. 
See 2-BenzoyHsophthalic Acid. 
Benzoplienone-2 : 2 / -dicarboxyHc Acid 

900H 900H 



C 15 H 10 5 MW, 270 

M.p. 150-5 decomp. Sol. EtOH, Et 2 0, 
AcOH. Spar. sol. H. 2 O. At 200 > an- 
hydride. 

Di-Me ester : C 17 H 14 5 . MW, 298. Leaflets. 
M.p. 85-6. Sol. EtOH, MeOH. 

Di-Et ester : C 19 H 18 5 . MW, 326. Prisms. 
M.p. 73-4. 

Anhydride: C 15 H 8 4 . MW, 252. Leaflets. 
M.p. 212. Sol. CHC1 3 , C 6 H 6 . Sublimes. 

Imide: C 15 H 9 3 N. MW, 251. Leaflets. 
M.p. 251-2. Sol. EtOH, alkalis. 

Graebe, Juillard, Ann., 1887, 242, 243. 



Benzophenone-2 : 4'-dicarboxylic Acid. 

Needles from H 2 O. M.p. 235. Sol. EtOH, 
hot AcOH. Spar. sol. H 2 0, C 6 H 6 . 

Di-Me ester : Cj,H 14 6 . MW, 298. M.p. 107. 

Dichloride: Ci 5 H 8 3 Cl 2 . MW, 307. M.p. 
102. 

Diamide: C 15 H 12 3 ISro. MW, 268. M.p. 
above 285. 

Limpricht, Ann., 1899, 309, 98. 

Benzophenone-3 : 4 / -dicarboxyMc Acid. 

Needles from EtOH. M.p. 326-7. Insol.H 2 0. 

Lavaux, Ann. chim., 1910, 21, 144. 

Diet, of Org. Oomp. I. 



Benzoplienone-4; : 4'-dicarboxyMc Acid. 

Sublimes below 360 without melting. Mod. 
sol. AcOH. Spar. sol. EtOH, Et 2 0, C 6 H 6 , 
Me 2 CO. 

Di-Me ester: C 17 H 14 5 . MW, 298. M.p. 
224 (231). 

Dichloride : C 15 H 8 3 Cl>. MW,307. M.p. 133. 

Diamide: C 15 H 19 O 3 X 2 . MW, 268. M.p. 
above 300. 

Dinitrih: C 15 H 8 ON 2 . MW, 232. Cryst. 
M.p. 204-5. 

Limpricht, Ann., 1900, 312, 92. 
Staudinger, Clar, Ser., 1911, 44, 1632. 

Benzoph.enoiie-3 : S'-disulplionic Acid 



SOJS 



S0 3 H 



CO 
C 13 H 10 7 S 2 ~ MW, 342 

Dichloride : C 13 H 8 5 Cl2S 2 . MW, 379. M.p. 
137-8. Sol. CHC1 3 . Isomer, m.p. 121-5. 



Diamide : C 13 H 12 5 N 9 S 2 . MW, 340. Needles. 
M.p. 157. Sol. EtOHfMe 2 CO. 
Dianilide : m.p. 177-8. 

Lapworth, J. Ghem. Soc., 1898, 73, 404. 
sulphone 



Benzophenone 

o-dioxide) 



(Thioxanthone 




C 13 H 8 3 S " MW, 244 

Needles or prisms. M.p. 186-7. Sol. EtOH, 
Et 2 0, CHC1 3 . Ale. KOH ^ blue sol. 

Lapworth, J. Ghem. Soc., 1898, 73, 404. 

Graebe, Schultess, Ann., 1891, 263, 10. 

TJlmann, v. Glenck, Ber., 1916, 49, 2509. 

Benzoplienone-2-sulplio:aic Acid 

S0 3 H 



C 13 H 10 O 4 S 



MW, 262 
benzoic + benzene- 



Syrup. KOH fusion - 
sulphonic acids. 

NH^ salt, 1H 2 : m.p. 202. Sol. H 2 O, EtOH. 
Na salt, 4JH 2 : m.p. 60. M.p. anhyd. 236. 
K salt, IH%0 : m.p. 211 (182). 
Ba salt, IH 2 : m.p. anhyd. 197-8. 
Et ester : C 15 H 14 O 4 S. MW, 290. M.p. 126. 
Chloride: C 13 H 9 3 C1S. MW, 280-5. M.p. 
96-7. 

Anilide : m.p. 143-5. 

List, Stein, Ber., 1898, 31, 1663. 
Eemsen, Saunders, Am. Ghem. J., 1895, 
17, 355. 



y-Benzopyrone. 

See Chromone. 



17 



o-Benzoquiiioiie 



258 



Benzoxantliene 



o-Benzoqiiinone (o-Quinone) 

O 



.1 



C 6 H 4 



or 



r V9 (n) 



1IW, 108 

(I). Quinone form. 

Light red prisms. Decomp. at 60-70 or on 
standing. Sol. C 6 H 6 , Et 2 5 Me 2 CO. InsoL pet. 
ether. Non-volatile. Decomp. by H 2 0. S0 2 , 
etc. > catechol. 

Monoxime : see o-Xitrosophenol. 

Dioxime : vellow needles. M.p. 142 de- 
comp. Sol. EtOH, AcOH. 



Mod. sol. Et 2 0. 



Changes 



(II). Peroxide form. 
Colourless prisms, 
rapidly to I. S0 2 > catechol. 

Pfannenstiel, Ber., 1904, 37, 4745. 
Willstatter, MiiHer, Ber., 1908, 41, 2581. 
Kekrmann, Ber., 1911, 44, 2632. 

p-Benzoquinone (Quinone) 




C 6 H 4 2 MW, 108 

Yellow prisms. M.p. 115-7. Sol. EtOH, 
Et 2 0, hot H 2 0, hot ligroin. Cryst. from H 2 
or pet. ether. Sublimes. Volatile in steam. 
Df 1-318. Heat of comb. C P and G v 659-2 Gal. 
S0 2 , H 2 S, HI, etc. > hydroquinone. Forms 
additive comps. with many phenols and 
thiophenols. E.g. with hydroquinone > 
quinhy drone. 

Monoxime : see p-Mtrosophenol. 

Dioxime : pale yellow needles. Decomp. at 
240. Sol. hot H 2 0. 

Mono-semicarbazone : yellow needles. M.p. 
178 decomp. 

Di-semicarbazone : reddish cryst. powder. 
M.p. 241-3 decomp. 

Picrate : m.p. 78-9. 

Underwood, Walsh, Organic Syntheses, 

1936, XVI, 73. 
Palfremann, Knibbs, B.P., 430,572, (Chem. 

Abstracts, 1935, 29, 7834). 
Eastman Kodak Co., U.S.P., 2,043,912, 

(Chem. Abstracts, 1936, 30, 5241). 
Vliet, Organic Syntheses, Collective Vol. I, 

469. 

Benzoqumoneimine Oxime. 

See ^-NitrosoanUine. 

Benzorcin. 

See 4 : 6-Dihydroxy-2-methylbenzophenone. 

Benzoresorcinol. 

See Dihydroxybenzophenone. 



Benzotetronic Acid. 

See 4-Hydroxycoumarin. 

B enzotzichloride ( co - Trichlorotoluene,phenyl- 

chloroform) 



C 7 H 5 d 3 MW, 195*5 

M.p. -5. B.p. 214. B 14 1-380. Sol. 
EtOH, Et 2 0. Insol. H 2 0. H 2 at 150, or 
aq. alkalis > benzoic acid. 

Seldon, Gibbs, B.P., 123,341, (Chem. Ab- 

stracts, 1919, 13, 1478). 
Meyer, Monatsh., 1915, 36, 729. 
Kyrides, U.S.P., 1,345,373, (Ghem. Ab- 
stracts, 1930, 14, 2644). 

BenzotricKloride-carboxylic Acid. 

See 03-Trichlorotoluic Acid. 
Benzotrifluoride (a>-Trifluorotoluene) 

C 6 H 5 *CF 3 
C 7 H 5 F 3 MW, 146 

B.p. 98-9/725 mm. 

Pouterman, Giradet, Helv. Chim. Acta, 
1947, 30, 107. 

3 : 4-BenzotropoIone (3 : k-Benztropolone) 
OH 




U H 8 2 " MW, 172 

Cryst. from cyclohexane. M.p. 85-6. 

Cook, Somerville, Nature, 1949, 163, 410. 
Cook et al. 9 J. Chem. Soc., 1952, 603. 

4 : 5-Benzotropolone (4 : 5-Benztropolone) 
OH 

:o 




MW, 172 

Cryst. from EtOH. M.p. 159-5-160-5 . 
Acetyl: cryst. from AcOEt-hexane. M.p. 
103-4. 

Tarbell, Scott, Kemp, J. Am. 
Soc., 1950, 72, 379. 

Benzoveratrol. 

See under 3 : 4-Dihydroxybenzophenone. 
Benzoxanthene 




C 16 H 10 MW, 218 

Cryst. M.p. 107-4-108. 
1:3: 5-Trinitrobenzene add. comp. : red cryst. 
M.p. 147-8-148-4 . 

Orchin, J. Am. Chem. Soc., 1948, 70, 495. 

Kruber, Ber., 1937, 70, 1556. 



Benzoxazole 



259 



2-Ben.zoylacrylic Acid 



Benzoxazole 




C 7 H 5 ON MW, 119 

Cryst. M.p. 31. B.p. 183. Insol. H 2 0. 

Hot cone. HC1 > o-aminophenoi. 

MetModide : yellowish needles. M.p. 202. 
Bamberger. Ber. 9 1903, 36, 2051. 



Bezuzoxazolone 

lactone) 



(o-Hydroxyplienylcarbamie 



'0 




or 



C 7 H 5 O 2 N MW, 135 

Needles + 1H 9 from hot dil. HC1. M.p. 
97-8, anhyd. 141-2. Sol. EtOH. Mod. sol. 
Et 2 0. Spar. sol. cold H 2 0. 
N-Me : CgH^sN. MW, 149. M.p. 86. 
N-Et : C S H 8 O 2 N. MW,163. M.p. 29. B.p. 
300. 

N-Acetyl : m.p. 95. 
N-Benzoyl : m.p. 173-4. 
Phenylhydrazone : m.p. 280. 

Meyer, J. praU. Chem., 1915, 92, 255. 
Lindemann, Schultheis, Ann., 1927, 451, 
253. 

Benzoylacetaldeliyde ( a-Formylacetophen- 
one, o-aldehydoacetophenone, benzoylvinyl alcohol, 
Tiydroxymethyleneacetophenone, hydroxyvinyl 

pTienyl Jcetone, pJienacyl aldehyde, pJienacyl form- 
aldehyde) 

C 6 H 5 -CO-CH 2 *CHO 

or 

C 6 H 5 *CO-CH:CH-OH 

C 9 H 8 2 MW, 148 

Yellow unstable oil. Resinifies readily. FeC^ 
on EtOH sol. > intense red col. Forms 
stable Na and Cu derivs. Heat in AcOH > 
1:3: 5-tribenzoylbenzene. 

Oxime : benzoylacetaldoxime. Prisms from 
C 6 H 6 . M.p. 86-7. 

Stahler, Ber., 1914, 47, 590. 
Mumm, Miinchmeyer, -Ber., 1910, 43, 
3338. 

BiUow, Sicherer, Ber., 1901, 34, 3891. 
Chelintsev, Dukinin, J. Gen. GJiem. 
U.S.S.H., 1937, 7, 2309. 

Benzoylacetic Acid 

C 6 H 5 -CO-CH 2 -COOH 
C 9 H 8 3 MW, 164 

Needles. M.p. 103-4 decomp. Sol. EtOH, 
Et 2 0. Spar. sol. H 2 0, Hgroin. FeCl 3 on EtOH 
so l. ^ reddish- violet col, Heat alone or with 



dil. H 2 S0 4 > acetophenone. Hot alkalis 
> acetophenone -f benzole acid. 

Di-Et acetal : cryst. M.p. 68 decomp. 

Me ester : C 10 H 10 3 . 11W, 178. B.p. 152 / 
15mm. DJ 1-173. < 1-542. 

Et ester: U H 12 O 3 . MW, 192. B.p. 265- 
70 part, decomp., 147-9/ll mm. D 15 1-1219. 
Volatile in steam. Forms Na and Cu derivs. 
(enol form). Semicarbazom : cryst. from H 2 0. 
M.p. 125 decomp. 

Propyl ester: 10 H 14 3 . MW, 206. B.p. 
l"l!4. 
b.p. 158-8-5/15 mm. 



154-6712 mm. 
Isopropyl ester 
Butyl ester: 



C 13 H 16 3 . MW, 220. B.p. 



B.p. 

M.p. 



C 9 H 7 ON. 
Sol. EtOH, 



169-7071 mm., < T-51BQ.' 

Crotyl ester : b.p. 112-1470-2 mm. 

Isobutyl ester : C 13 H 16 3 . MW, 220. 
160712 mm. 

l-Menthyl ester : needles from EtOH. 
41. [a]| - 56-9 in EtOH. Semicarbazom : 
leaflets from EtOH. M.p. 167. 

Amide: C 9 H<A>N. MW, 163. M.p. 113. 
Sol EtOH, CHCI 3 : 

Nitrite : co-cyanoacetophenone. 
MW, 145. Leaflets. M.p. 80-1. 
Et 2 3 CHC1 3 , C 6 H 6 . 

Anilide : leaflets. M.p. 107-8. 

Meyer, Togel, Ann., 1906, 347, 79. 
Wahl, Doll, Bull soc. chim. t 1913, 13, 277. 
Claisen, Ann., 1896, 291, 67. 
Dorsch, McElvain, J. Am. Chem. Soc. y 

1932, 54, 2962. 
Chi, Lee, Chem. Abstracts, 1935, 29, 467. 

Benzoylacetone (Methyl phenacyl ketone, 
acetylbenzoylmethane, c*-acetylacetophenone) 

C 6 H 5 -CO-CH 2 *CO-CH 3 

MW, 162 

Cryst. M.p. 61. B.p. 261-2, 132714 mm. 
Sol. EtOH. Et 2 O 5 cone, caustic alkalis. Spar, 
sol. cold H 2 0. Volatile in steam. Cone. H 2 S0 4 
>- acetophenone. FeCl 3 > deep red "col. 
Forms metallic derivs. 

Claisen, Ber., 1905, 38, 695. 

B enzoylacetophenone. 
See Dibenzoylmethane. 
2-Benzoylacrylic Acid 

C 6 H 5 -0>CH:CH-COOH 
C 10 H 8 3 MW, 176 

Leaflets + 1H 2 0. M.p. 64, anhyd. 99. 
Sol. EtOH, Et 2 O, hot H 2 0. Hot alkalis > 
acetophenone + glyoxylic acid. Bed. ^ 2- 
benzoylpropionic acid. 

Me ester : C 11 H 10 3 . MW, 190. M.p. 30-2. 
B.p. 185716 mm., 15075 mm. 

Oxime : m.p. 168 decomp. 

Semioarbazone : m.p. 190. 

Hydrazone : cryst. from EtOH. M.p. 185-6. 

Phenylhydrazone : m.p. 197. 



C 10 H 10 2 



B enzoylaminoacetliydrazide 



260 



p-Benzoylbenzoic Acid 



Dibromide : 1 : 2-dibromo-2-benzoy3propionic 

acid. M.p. 148. 

Kozniewski, Marchlewski, Chem. Zentr., 

1906, H, 1189. 
Bogert, Patter, J. Am. CUm. Soc., 1925, 

47, 529. 
Lutz, J. Am. OJiem. Soc., 1930, 52, 3430. 

Benzoylammoacetliydrazide. 
See Hippuryl hydrazide. 
Beaazoylaminoacetic Acid. 
See Hipp uric Acid. 
Benzoyl-o-aminobenzoic Acid. 
See Benzoylanthranilic Acid. 
Beii^oyl^p-amixLobenzoic Acid 
See under p-Aminobenzoic Acid. 
l-Benzoylaniiiio^-a-fiiiylacrylic Acid. 
See FurfurylideneMppuric Acid. 
BenzoylaminoplieiioL 
See Hydroxybenzanilide. 
Benzoylaminoplienylacetic Acid. 
See I-Phenylhippurie Acid. 
B enz oylanisidlno . 
See under Hydrosybenzanilide. 
Benzoylanisole . 
See under Hydroxybenzophenone. 
ms-B enzoylantkracene . 
See Anthraphenone. 

Benzoylanthranil (Anhydro-benzoyl-o- 

aminobenzoic acid) 

nr P TT 

r CH 



MW, 223 

Needles. M.p. 122-3. Sol. EtOH, Et 2 O. 
Insol. H 2 0, ligroin. Insol. cold dil. alkalis. 

Heller, Ber. 9 1920, 53, 731. 
Meyer, Bellmann, J. praJct. Chem., 1886, 
33, 19. 

Benzoylanthramilic Acid (Benzoyl-o-amino- 
benzoic acid) 

COOH 






MW, 241 

Needles. M.p. 181. Sol. EtOH, Et 9 0. In- 
soL H 2 0. 

Me ester : C 15 H 13 3 N. MW, 255. Needles. 
M.p. 100. 

Et ester: C 16 H 15 3 N. MW, 269. Needles 
from EtOH or ligroin. M.p. 98. 

Amide: C 14 H 12 O 2 N 2 . MW, 240. Needles. 
M.p. 218-19. 

Nitrile : C 14 H 10 ON 2 . MW, 222. M.p. 156. 
Anilide : needles. M.p. 279. 
Anhydro-comp. : see Benzoylanthranil. 
Fischer, Ber., 1896, 29, 2063. 
Bell, J. Phys. Chem., 1928, 32, 882. 
Alessandri, Atti. accad. Lincei, 1913, 22, 
II, 229. 



Benzoylani!irac|uinQne . 

See Phenyl anthraquinonyl Ketone. 

Benzoyl azide (Benzazide, benzoylazimide) 

C 7 H 5 OX 3 6 5 " MW, 147 

Colourless plates. M.p. 32. Explodes on 
heating. SoL Bt 2 0. Mod. sol. EtOH. Insol. 
H 2 0. 

Bergel, Zt. angew. Chem , 1927, 40, 974. 

4-Benzoylfoenzaldeiiyde (p-FormylbenzQ- 
phenone, 4-aldehydobenzopJienone, benzophenone- 
4-aldehyde) _ 

\CHO 



C 6 H 5 -CO 

^ MW, 210 

Plates from H 2 0. M.p. 64. Very sol. H 9 0, 
EtOH, Et 2 0, CHClg. Insol. C 6 H 6 , pet. etHer. 
Forms bisulphite comp. 

soc. chim., 1896, 15, 950. 



C 14 H 10 2 



o-Benzoylbenzoic Acid (2-Benzoylbenzoic 
acid, benzophenone-o-carboxylic acid) 

COOH 



C 14 H 10 3 MW, 226 

Needles + 1H 2 from hot H 2 0. M.p. 90. 
M.p. anhyd. 127. Jc = 3-7 X 10~ 4 at 25. 
Cone. H 2 SO 4 > anthraquinone. 

Me ester: C 15 H 12 O 3 . MW, 240. Prisms. 
M.p. 52. B.p. 350-2. 

M ester : C 16 H 14 O 3 . MW, 254. M.p. 58. 

Benzyl ester : C 21 H 16 3 . MW, 316. M.p. 64. 

p-Nitrobenzyl ester : m.p. 100. 

Chloride: C 14 H 9 O 2 C1. MW, 244-5. Prisms. 
M.p. 70. 

Anhydride: C 28 H 18 5 . MW, 434. M.p. 140. 

Amide : C 14 H n 2 N. MW, 225. M.p. 165. 

Rubidge, Qua, J. Am. Chem. Soc., 1914, 

36, 732. 
Stone, Jacobson,U.S.P., 1,656,575, (Chem. 

Abstracts, 1928. 22, 966). 
Calco Chemical Co., U.S.P., 1,942,430, 

(Chem. Abstracts, 1934, 28, 1717). 

m-Benzoylbenzoic Acid (3-Benzoylbenzoic 
acid, benzophenone-m-carboxyhc acid). 

Needles. M.p. 161-2. SoL EtOH, Et 2 0. 
Spar. sol. H 0. Sublimes. 

Me ester :" C 15 H 19 3 . MW, 240. M.p. 62. 
Sol. Et 2 0, hot EtOH. 

Senff, Ann, 1883, 220, 252. 

p-Benzoylbenzoic Acid (4-Benzoylbenzoic 
acid, benzophenone-p-carboxylic acid). 

Plates from EtOH. M.p. 197-200 (226-7). 
Sol. EtOH, Et 2 0, AcOH. Spar. sol. cold H 2 0, 
CHC1 3 ,C 6 H 6 . Sublimes. 

Me ester : C 15 H 12 3 . MW, 240. M.p. 107. 



j>-BenzoyIbenzyl Alcohol 



261 



2~Benzoylcoiunarone 



C-H 6 OBr 



Et ester : C 16 H 14 3 . MW, 254. M.p. 52 C . 
Nilrik : p-cyanobenzophenone. C M H 9 OX. 
MW, 207. M.p. 107-8. Oxime : leaflets. M.p. 
176. 

Bauer, Endres, J. prakt. Ghem., 1913, 87, 

546. 

Wertheim, J. Am. Ghem. Soc., 1933, 55, 
2541. 

fj-Benzoylbenzyl Alcohol. 

See 4-Hydroxymethyl-benzophenone. 
Benzoyl bromide 

C 6 H 5 *COBr 

MW, 185 

Fuming liq. F.p. 24. B.p. 218-19. D 15 
1-570. 

Claisen, Ber., 1881, 14, 2473. 
Staudinger, Anthes, Ber., 1913, 46, 1423. 

4-Benzoylbutyl Alcohol. 

See co-Hydroxyvalerophenone. 

1-Benzoylbutyraldehyde ($-Formylbutyro- 
phenone, $-aldehydobutyrophenone f $-hydroxy- 
methylenebu tyrophenone) 

9HO 

C 6 H 5 -CO-CH-CH 2 -CH 3 
or 

ffHOH 

C 6 H 5 COC-CH 2 -CH 3 

c ii H i22 MW, 176 

Leaflets from EtOH.Aq. M.p. 87-9. B.p. 
260-2 decomp. 

Bishop, Claisen, Sinclair, Ann. 9 1894, 
281, 397. 

1-Benzoylbutyric Acid (Ethyl-benzoylacetic 
acid) 

CH 3 -CH 2 -9H-COOH 

COC 6 H 5 
G ii H i23 MW, 192 

Plates from pet. ether-C 6 H 6 . M.p. 85-7 
decomp. 

Et ester: C 13 H 16 3 . MW, 220. B.p. 168- 
71/19 mm., 118-23/l-5 mm. Insol. cold 
KOH.Aq. Boiling dil. alkali > propyl 
phenyl ketone. Cone. ale. KOH >- benzoic 
and butyric acids. 

- - C 15 H 20 3 . M.W, 248. B.p. 



1-5003. 

MW,191. M.p. 148-9. 
>N. MW, 173. B.p. 134- 



Bwtyl ester : 
116-17 /! mm. 
Amide : CjLjH^ 
Nitrile : ^-^H.^ 
5/3 mm. 

Hope, Perkin, J. Chem. Soc., 1909, 95, 

2047. 

Dorsch, McElvain, J. Am. Chem. Soc. % 
1932, 54, 2962. 



2-Benzoylbutyric Acid 

3 CO-CH 2 



Bhombohedra from hot H 2 0, M.p. 59-60 3 . 
Sol. most org. solvents except pet. ether. 

Semicarbazone : plates from EtOH. M.p. 
177-8. Spar. sol. H 2 0. 

Higginbotham, Lapworth, Simpson, J. 
Chem. Soc. } 1924, 125, 2342. 

3-Benzoylbutyric Acid (Butyrophenone~u>- 
carboxylic acid) 

C 6 H 5 -CO-CH 2 -CH 2 -CH 2 -COOH 
C 131 H 12 3 JfelW, 192 

Plates. M.p. 127. Mod. sol. hot H 2 0. 

Me ester : C^H-^CV MW, 206. M.p. 2. 
B.p. 147-8/8 mm. 2 : 4:-Dinitrophenylhydr- 
azone : red leaflets from CHCL-MeOH. M.p. 
149. 

Et ester : C 13 H 16 3 . MW, 220. B.p. 315. 
Oxime : m.p. 35-6. 

Oxime : m.p. 110. 

Fichter, Bauer, Ber., 1898, 31, 2001. 
Allen, Cressman, J". Am. Chem. Soc., 1933, 

55, 2955. 
Somerville, Allen, Organic Syntheses, 1933, 

XIII, 13 (Note 8). 

Benzoylcarbinol. 

See Phenacyl Alcohol. 

Benzoyl chloride 

C 6 H 5 -COCi 
C 7 H 5 OC1 MW, 140-5 

Colourless, fuming liq. M.p. 1. B.p. 197, 
194/742 mm. D^ 1-2187. rij> 1-55369. Heat 
of comb. Op 784-3 Gal., C, 784-03 CaL Hyd. 
by alkalis and boiling H 2 0. Reacts with 
alcohols, phenols and amines to give benzoyl 
derivs. 

Montanna, J. Am. Chem. Soc., 1927, 49, 

2114. 
Monsanto Chem. Co., U.S.P., 2,006,335, 

(Chem. Abstracts, 1935, 29, 5460). 
Dow Chemical Co., U.S.P., 1,965,556, 

(Chem. Abstracts, 1934, 28, 5474). 

Benzoyl-chlorobenzoic Acid. 

See Chloro-benzoylbenzoic Acid. 
2-Benzoylcoumarone (Phenyl 2,-coumaryl 
ketone) 

/\_TH 

< \ Vfti 

/C-CO-C R H, 



MW, 192 



C 15 H 10 2 MW, 222 

Prisms. M.p. 91. B.p. 360. Sol. EtOH, 
Et 2 0. Red. > benzylcoumarone > benzyl- 
coumaran. 

Oxime : needles. M.p. 125-6. 

Phenylhydrazone: yellow needles. M.p. 128-9. 

Semicarbazone : m.p. 137. 

Stoermer, Chydenius, Schinn, Ber., 1924, 
57, 72. 



S-Benzoyl-^-ciimene 



262 



2-BenzoyMsofoiityric Acid 



5-Benzoyl-^-cunieiie . 

See 2:4: 5-Xrimethylbenzophenone. 

Benzoyl cyanide. " 

See under Benzoylformic Acid. 

Beazoylcyclohexane . 

See Hexahydrobenzoplienone. 

Benzoyl-dimetliylfoeiizoic Acid. 

See Dimethylbenzophenonecarboxylic Acid. 

Benzoyldiplienyi . 

See Phenyibenzophenone. 

Benzoyl disulpMde. 

See Dibenzoyl disuipMde. 

Benzoylethyl Alcohol. 

See Hydroxypropiophenone. 

Benzoylethyiene GlycoL 

See {3 : y-Dihydroxypropiophenone. 

Benzoyl fluoride 



C 7 H 5 OF 



C 6 H 5 *COF 



MW, 124 



Fuming liq. B.p. 154-5 (145). Hyd. by 
hot H 2 0. 

Traube, Krahnier, Ber., 1919, 52, 1296. 
Tseng, Mai, J. Chinese Ghem. Soc., 1936, 
4,22. 

Benzoyliormaldehyde. 

See PhenylglyoxaL 

Benzoylformic Acid (PJienylglyoxylic acid] 



C 8 H 6 3 



C 6 H 5 -CO-COOH 



MW, 150 



Cryst. M.p. 66. B.p. 147-51/12 mm. 
H 2 0. Decomp^ on dist. Cone. H 2 SO 4 
NaHg 



Sol. 



- mandelic acid. 
MW, 164. B.p. 246-8, 
needles from H 2 0. M.p. 



benzoic acid + CO. 

Me ester : C 9 H 8 0< 
137/14 mm. Oxime ; 
138-9. 

Et ester : C 10 H 10 3 . MW, 178. B.p. 256-7, 
156/30 mm., 138/15 mm., 118/5 mm. DJ B 
1-1222. rig 1-51904. Oxime : needles from 
H 2 0. M.p. 112-13. Phenylhydrazone : orange. 
M.p. 156 (rapid heat.). Very slow heat. > 
yellow form at 140, then m.p. 162-3-5 



Propyl ester : 
174/60 mm. 

Isobutyl ester : 
170-4/38 mm. 

d-Amyl ester : 
163/16 mm. 



C n H: i2 3 . MW, 192. 
C 12 H U 3 . MW, 206. 



C 13 H 16 3 . MW, 220. 
1-050. [<x]i 9 -f 4-1. 

Isoamyl ester : b.p. 179-82/40 mm. 

l-Menthyl ester : needles from EtOH. 
73-4. [a]f> - 44-4 in EtOH. 

l-Bornyl ester : prisms from EtOH. 
42-3. [a]g - 26-6 in EtOH. 

Chloride: C 8 H 5 2 C1. MW, 168-5. 
125/9 mm. 

Nitrile : benzoyl cyanide. C 8 H 5 ON. 
131. M.p. 32-3. B.p. 206-8. NH* > 



B.p. 
B.p. 
B.p. 

M.p. 
M.p. 
B.p. 

MW, 

benz- 



amide. Alkalis >~ benzoic acid + formic acid. 
Amide : C 8 H 7 2 N. MW, 149. M.p. 91. 
Oxime : a-isonitrosophenylacetic acid. Two 



forms, a-. Prisms from Et 2 0. 31.p. 127. 
Very unstable, g-. Needles from H 2 O. M.p, 
145^ decomp. Less sol. than a-forni. 

Thiosemicarbazone : pale yellow. M.p. 188- 
9 (corr.). 

2 : 4:-Dinitrophenylhydrazone : yellow. M.p. 
196-7 decomp. (corr.). 

Wislicenus, Schafer, Ber., 190S. 41, 4170. 
Acree, Am. Chem. J., 1913, 50, 389. 
Claisen, Ber., 1879, 12, 729. 
Corson, Dodge, Harris, Hazen, Organic 
Syntheses, Collective Vol. I, 236. 

B enzoylf orznoxime . 

See Isonitrosoacetophenone. 

Benzoylfuran. 

See Phenyl furyl Ketone. 

l-Benzoyl-2-furylethylene . 

See Furforylideneacetophenone. 

Benzoylglycine. 

See Hippuric Acid. 

co-BenzoyHiexaliydrostyrejie . 

See Hexahydrobenzylideneacetophenone. 

Benzoylliydrazine. 

See Benzhydrazide. 

BenzoyUiydrocinnamic Acid. 

See Phenyl benzoylpropionic Acid. 

Benzoyl hydroperoxide. 

See Perbenzoic Acid. 

Benzoyl iodide 



C 7 H 5 OI 



C 6 H 5 -COI 



MW, 232 



Needles. M.p. 3. B.p. 128/20 mm. 

Kishner, Chem. Zentr., 1909, II, 1132. 
Staudinger, Anthes, Ber., 1913, 46, 1423. 

2-Benzoylisobutylene . 

See Seneciophenone. 

1-Benzoylisobutyric Acid (1 : \-Dimethyl- 
benzoylacetic acid) 




C n H 12 3 MW, 192 

Me ester : C lf> H 14 O 3 . MW, 206. B.p. 140- 
2/14 mm. 

M ester: C 13 H 16 3 . MW, 220. B.p. 152 / 
20 mm. Oxime : needles from EtOH. M.p. 
135-6. 

Blaise, Courtot, Bull. soc. chim., 1906, 35, 

599. 
Scheibler, Stein, J. praJct. Chem., 1934, 

139, 105. 

2-Benzoylisobutyric Acid (l-Methyl-2- 
benzoylpropionic acid, 1-phenacylpropionic acid, 
butyrophenone-y-carboxylic acid) 



, 

C 6 H 5 -CO-CH 2 -CH-COOH 



MW, 192 



Benzoyl isocyanate 



263 



2-Benzoyl-l-naphtlioic Acid 



C 8 H 5 2 N 



Xeedies from EtOH.Aq. or C 6 H 6 . M.p. 
140-5. Sublimes. Very sol. MeOH, EtOH 3 
CHCLj. Spar. sol. Et 2 0, C 6 H 6J AcOH. 

Oppenheim, er., 1901, 34, 4228. 

Exollpfeiffer, Schafer, Ber., 1923, 56, 630. 

Benzoyl isocyanate 

c 6 H 5 co-x:c:o 

MW, 147 

Prisms from Et 2 O. M.p. 26. B.p. 202/724 
mm. ? 88-91/20 mm. Polymerises on keeping. 
Billeter, JBer., 1903, 36, 3218. 
Hill, Desnan, J. Am. Chem. Soc. 3 1940, 62, 
1595. 

2-BenzoyHsoplrtlialic Acid (Benzophenone- 

2 : $-dicarboxylic acid) 

COOH 

^ooi? 6 

C 15 H 10 O 5 N MW, 270 

Needles from EtOH.Aq. M.p. 260. SoL 
EtOH, Et 2 0, hot H 2 0. Cone. Hg^ at 145 
>- anthraquinone-1-carboxylic acid. 

Graebe, Leonhardt, Ann., 1896, 290, 232. 
Hayashi, Tsuruoka Morikawa, Nami- 
kawa, Chem. Abstracts, 1936, 30, 5965. 

4-Benzoylisoplitlialic Acid (BenzopJienone- 

2 : 4-dicarboxylic acid) 

COOH 




I IcOOH 
CO-C 6 H 5 



C 15 H 10 5 " ^ MW,270 

Prisms from EtOH.Aq. M.p. 278-80. 

Sublimes. Sol. EtOH, Et 2 0, Spar. sol. hot 

H 2 O, CHC1 3 , toluene. 

Di-Me ester: C 17 H U O 5 . 1MW, 298. Pale 

yellow triclinic cryst. M.p. 119-5-20. 

Di-Et ester: C 19 H 18 5 . MW, 326. M.p. 95. 

Sol. EtA CHC1 3 . 

Zincke, Blatzbecker, Eer., 1876, 9, 1762. 

Benzoylisopropyl Alcohol. 

See y-Hydroxybutyroplienone. 
Benzoyl isothiocyanate 

c 6 H 5 -co-N:c:s 

C g H 5 ONS MW 5 163 

Oil. B.p. 133-7/18 mm., 119/10 mm. D 18 
1-2142. wjf 1-6382. 

Wheeler, Merriam, J. Am. Chem. Soc., 

1901, 23, 285, 298. 

Ambelang, Johnson, J". Am. Chem. Soc., 
1939, 61, 632. 

O-Benzoyl-lactic Acid (\-Benzoylhydroxy- 
propionic acid) 

CH 3 -CH(0-COC 6 H 5 )-COOH 
C 10 H 10 4 MW, 194 



Cryst. M.p. 112. SoL EtOH, Bt 0. Mod. 
sol. hot H 2 0. Hyd. by hot dil. H S0 4 . 

Et ester : C 12 H M 4 . MW. 222. - B.p. 288 

Amide : C 10 fi 11 3 N. ^IW S 193. M.p. 124. 

yitrile: Q^$L g Q^. ^IW, 175. B.p. 269- 
70, 198-200/125 mm, 

a-Naphthalide : C 20 H 17 O 3 N. MW ? 319. 
Needles from EtOH. "M.p. 155. 

$-Naphth&lide : needles from EtOH. M.p. 
177. 

Wislicenus, Ann., 1865, 133, 277. 
Davis, J. Chem. Soc., 1910, 97, 950. 
Aloy, Babant, Bull. soc. chim., 1912, 11, 
393. 

2-Benzoyl-lactic Acid. 

See Phenacylglycollic Acid. 
Benzoylmalonic Acid (Acetophe7ione'<*-di- 

carboxylic acid) 

IOOH 
OH 



I 



C 10 H 8 O 5 lfW 5 208 

Di-Et ester: C 14 H 16 5 . MW,264, Oil. B.p. 
194-5/14 mm., 1S7-90/12 mm. Ale. sol. + 
FeCLj > red col. Zn + AcOH > benzyl- 
malonic acid. Cu deriv. : Cn(C 14 H 15 5 ) 2 . 
Green needles from EtOH.Aq. M.p. 180. 

Me ester-nitrile : C n H 9 3 N. MW, 203. 
Prisms. M.p. 74. 

Et ester-nitrile : C 12 H 11 3 N. MW, 217. 
Prisms. M.p. 41. 

Lund, Ber., 1934, 67, 935. 
Btilow, Hailer, Ber. 3 1902, 35, 934. 

Benzoylmesitylene . 

See 2:4: 6-Trimethylbenzophenone. 

Benzoylmetliylgiinine . 

See Phenacylamine. 

BenzoylnapMlialene . 

See Phenyl naphthyl Ketone. 

2-Benzoyl-l-naphtlioic Acid 



COOH 




C 18 H 12 3 MW,276 

Needles from MeOH. M.p. 141-8-142*8 

(corr.). KOH at 260-80 * 1-naphthoic + 

benzoic acids. 

Me ester: C 19 H 14 3 . MW 5 290. Needles 

from MeOH. M.p. 72-5-73-5. 

ester : cryst. from MeOH. M.p. 156-5. 

Waldman, J. prakt. Ckem., 1931, 131, 71. 
Fieser, Newman, J. Am. Gh&m. Soc., 1936, 
58, 2381. 



4-Benzoyl-l-naphtlioic Acid 



264 



1-Benzoylpropionic Acid 



4-Benzoyl-i-napIitlioic Acid. 
Cryst. from AcOH. M.p. 184. 

I.G., D.R.P., 557.249, (Chem. Zentr., 1932, 

II, 2376) ; 558,471, (Chem. Zentr., 1932, 
II, 2730). 

8-Benzoyl-l-naph.tlioic Acid. 

Needles from AcOH.Aq. M.p. 129-30 (110- 
12 decomp.). Sol. common org. solvents. Sol. 
cone. BF 2 SO 4 with deep yellow col. 

Et ester: OoH 16 3 . MW, 304. Prisms. 
M.p. 166-7. Sol hot C 6 H 6 . 

Chloride: C 18 H n OCi MW, 294-5. M.p. 
125-7. 

Mason, J. Chem. Soc., 1924, 125, 2121. 
Knapp, Monateh., 1936, 67, 336. 

l-Benzoyl-2-napMIioic Acid 
CO-C 6 H 5 
COOH 



MW, 276 

"Cryst. from C 6 H 6 . M.p. 223-5-224-5 (corr.). 
Sol. cone. H 2 SO 4 with green col. KOH fusion 



PCL 



1 : 2-benz- 



2-naphthoic acid. 
anthraquinone. 

Me ester: C 19 H 14 3 . MW, 290. Cryst. from 
MeOH. M.p. 113-14. 

Waldniann, J. prakt. Chem., 1930, 127, 

195. 
Fieser, Newman, J. Am. Chem. Soc* 9 

1936, 58, 2381. 

3-Benzoyl-2-naplitlioic Acid. 

Prisms from CHC1 3 or toluene. M.p. 210. 
Sol. cone. H 2 S0 4 with red col. A1C1 3 > 
2 : 3-benzanthraquinone. 

Me ester : cryst. from MeOH. M.p. 119-20. 
Waldmann, Mathiowetz, Ber., 1931, 64, 
1717. 

6-Benzoyl-2-naplitlioic Acid. 

Yellowish-green needles. M.p. 198. 

Dziewonski, Wodelski, Chem. Abstracts, 
1933, 27, 2145. 



C 8 H 7 O 2 N 



C 6 H 5 -CO-CH,NO 2 

" 



MW, 165 



Needles. M.p. 106. Sol. EtOH, Et 2 0, C 6 H 6 , 
AcOH. Mod. sol. warm H 2 0. 

Oxime : needles from H 2 0. M.p. 96. 

Di-Me-acetal : needles from EtOH. M.p. 
55-6. 

Phenylfvydrazone : yellow needles from EtOH. 
M.p. 105-5-5. 

Wieland, Ann., 1903, 328, 239. 

Fujise, Takeuchi, Kamioka, Tiba, Ber., 

1935, 68, 1275. 
Thiele, Haeckel, Ann., 1902, 325, 10. 



Benzoyl peroxide (Dibenzoyl peroxide) 

C 6 H 5 -CO-0-0-CO-C 6 H 5 

C 14 H 10 4 MW,242 

Prisms. M.p. 103-5 (106-8). Spar. sol. 
H 2 0. Mod. sol. EtOH, C 6 H 6 . Explodes on 
heating. 

Vanino, Herzer, Chem. Abstracts, 1916, 

10, 1252. 

Gambarjan, Ber., 1909, 42, 4008. 
Nencki, Zaleski, Z. physiol. Chem.,, 1899, 

27, 493. 

Benzoyi-plienetidine . 
See under HydroxybenzaniUde. 
BenzoylplLenetoie . 
See under Hydroxybenzophenone. 
BenzoylplieiioL 
See Hydroxybenzophenone. 
3-Benzoylphtlialic Acid (Benzophenone- 
2 : 3-dicarboxylic acid) 

COOH 



JCO-C 6 H 5 

MW, 270 

Plates or needles + 1H 2 0. M.p. 140-1. 
Heated to 145-50 > anhydride. Sol. EtOH, 
hot H 2 0. 

Anhydride : C i5 H 8 4 . MW, 252. M.p. 183. 
Graebe, Blumenfeld, Ber., 1897, 30, 1115. 
Hayashi, Tsuruoka, Morikawa, Nami- 
kawa, Chem. Abstracts, 1936, 30, 5965. 

4-Benzoylphthalic Acid (Benzophenone-3 : 4- 
dicarboxylic acid). 

Shining leaflets from xylene. M.p. 177. 
Heat with Ac 2 > anhydride. M.p. 152. 

Chardonnens, Schlapbach, Helv. Chim. 
Acta, 1946, 29, 1413. 

1-Benzoylpropionaldehyde ($-Formylpro- 
piophenone, I-formylethyl phenyl Jcetone, p- 
hydroxymethylenepropiophenone) 

9HO 

C 6 H 5 -CO-CH-CH 3 
or 



C 6 H 5 -CO-C-CH 3 
C 10 H 10 2 MW, 162 

Needles from EtOH.Aq. M.p. 118-19. B.p. 
155 /25 mm. Sol. MeOH, EtOH, C 6 H 6 , hot 
H 2 0. Spar. sol. Et 2 0, CS 2 . Very spar. sol. 
ligroin. FeCl 3 on EtOH sol. > deep violet ' 
col. 

Eeynolds, Am. Chem. J., 1910, 44, 313. 

1-Benzoylpropionic Acid (Propiophenone- 
fi-carboxylic acid, methylbenzoylacetic acid) 



C 10 H 10 3 



C 6 H 6 -CO-CH-COOH 



MW, 178 



2-Benzoylpropionic Acid 



265 



Benzoyl sulphide 



Cryst. from C 6 H 6 -pet. ether. M.p. 82-3 
decomp. FeCl 3 > brown col. 

Et ester: C 12 H 14 3 . MW, 206. Oil with 
pleasant odour. B.p. 148-150/12 mm., 1 IS- 
IS /! mm. Guderw. : green powder. Decomp. 
at 180. 

Isopropyl ester : b.p. 151-5 /10 mm. 
ieTt.-Butyl ester : b.p. 151-5 III mm. 
Amide : C 10 E 11 2 N'. MW, 177. M.p. 145-6. 
Anilide : prisms from EtOH. M.p. 137-8. 
Spar. sol. H 2 0, Et 2 0. Very sol. EtOH, C 6 H 6 . 

Phenylhydrazone : slightly brownish needles 
from C 6 H 6 . M.p. 100-104. 

Dorsch, McElvain, J. Am. Chem. Soc., 

1932, 54, 2963. 
Rupe, Pieper, Helv. Chim. Acta, 1929, 12, 

644. 

Hope, PerMn, /. Qhem. Soc., 1909, 95, 
2045. 

2-Benzoylpropionie Acid (In enol form, 
3 -hydroxy-%-phenylvinylacetic ac id) 

C 6 H 5 -CO-CH 2 -CH 2 -COOH 

or 

C 6 H 5 -C(OH):OB>CH 2 *COOH 
C 10 H 10 3 MW, 178 

Leaflets. M.p. 116. Sol. EtOH, Et 2 0, 
CHCLj, C 6 H 6 , CS 2J hot H^O. Ox. > benz- 
oic + propionic acids. Jc = 2-2 x 10~ 5 at 25. 

Me ester: C n H 12 3 . MW, 192. M.p. 18- 
20. B.p. 290, 187/30 mm. 

Et ester: C 12 H 14 Oo. MW, 206. M.p. 18- 
19. B.p. 295, 192/33 mm., 163-5/10 mm. 

Attyl ester : b.p. 117-19/0-1 mm. ri$ 1-5243. 

Amide : C^H^O^. MW, 177. Needles 
from H 2 0. M.p. 145-6. 

Nitrile: C 10 H 9 OK MW, 159. B.p. 128-30 / 
3 mm. 

Anilide : m.p. 150 (145). 

Lactone : 

C 6 H 5 -C:CH-CH 2 -CO 

C 10 H 8 2 . MW,160. Leaflets. M.p. 90-1. Sol. 
Et 2 0, AcOH. Mod. sol. EtOH 3 C 6 H 6 . VolatHe 
in steam. Hyd. by alkalis. 

Oxime : labile form, m.p. 95-6 (91). Stable 
form, m.p. 129. 

Semicarbazone : m.p. 181 decomp. 

Komppa, Rohrmann, Ann., 1934, 509, 

259. 
Somerville, Allen, Organic Syntheses, 1933, 

XIII, 12. 
Gabriel, Colman, Ber., 1899, 32, 398. 

Benzoylpropyl Alcohol. 

See p-Hydroxybutyrophenone. 
1-Benzoylpropylene . 
See Crotonophenone. 
Beuzoylprotocatecliiiic Acid. 
See 4 : 5-, and 5 : 6-Dihydroxybenzophenone- 
2-carboxylic Acids. 



Benzoylpyridine. 
See Phenyl pyrldyl Ketone. 
4-Benzoylp3rrogallol . 
See Gallobenzophenone. 
Benzoylpyrrole . 
See Phenyl pyrryl Ketone. 
Benzoylpyruvic Acid (Phenaeylglyoxylic 
acid) 



C 10 H 8 4 



321 

^IW, 192 

Prisms + IH<>0 from EtOH. Aq. M.p. 156-8 
decomp., (161). Sol. EtOH, MeOH. Insol. 
H 2 0, C 6 H 6 . k = 6-5 X 10-* at 25. H 2 S0 4 
> purple-red col. Heat > CO -f C0 2 + 
acetophenone. 

Me ester: C n H 10 4 . ]\IW, 206. Prisms. 
M.p. 59 (62). 

Et ester: C 12 H 12 4 . MW, 220. Prisms from 
pet. ether. M^p. 46. 

Amide: C 10 H 9 3 N. MW, 191. M.p. 138 
decomp. 

l-Oxime : prisms -f- 1H 2 0. M.p. 98-100 de- 
comp. 

3-Semicarbazone : m.p. 170. 

Di-thiosemicarbazone : m.p. 168. 

Mimim, Miinchmeyer, J5er., 1910, 43, 

3335. 
Gault, Funke, Bull. sac. chim., 1927, 41, 

473. 

Benzoylquinoline . 

See Phenyl quinolyl Ketone. 
5-Benzoylsalicylic Acid (k-Hydroxybenzo- 
phenone-3-carboxylic acid) 



COOH 




C 14 H 10 4 ' MW, 242 

Cryst. from EtOH. M.p. 207-10. Sol. 
EtOH, Et 2 0, AcOH. FeCl 3 > violet col. 
Heat with lime > ^-hydroxybenzophenone. 

Me ester: C 15 H 12 4 . MW, 256. Leaflets. 
M.p. 92. 

Et ester: C 16 H X4 4 . MW, 270. M.p. 97. 
Sol. C 6 H 6 . 

Phenyl ester : benzoylsalol. C 20 H 14 4 . MW, 
318. Cryst. from hot EtOH. M.p. 84. Sol. 
Et 2 0. 

Me ether: C 15 H 12 4 . MW, 256. M.p. 156. 

Et ether: C 16 H 14 4 . MW,270. Needles from 
EtOH.Aq. M.p. 109. Et ester : needles from 
ligroin. M.p. 56. 

Limpricht, Ann., 1896, 290, 164. 
Oliverio, Piccaluga, Chem. Zentr., 1933, 
II, 3273. 

Benzoyl sulphide. 

See Dibenzoyl sulphide. 



Benzoylterephtliaiic Acid 



266 



Benzoylterephihalic Acid (Benzophenane- 
2 : 5-dicarboxyIic acid) 

COOH 



MW, 270 
InsoL H 2 0> 



COOH 



Sol. EtOH, Et 2 0. 
C 17 H 14 5 . MW, 298. Needles. 
C 19 H 18 5 . MW, 326. Prisms. 



M.p. 291-2. 
toluene. 

Di-Me ester : 
M.p. 100-1. 

Di-Et ester : 
M.p. 100-1. 

Eibs, Larsen, J. praki. Chem., 1887, 35, 

479. 
v. Braun, Manz, Reinsch, Ann., 1928, 

468, 287. 

BenzoyltMopliene . 

See Phenyl thienyl Eletone. 
BenzoyltMourea (Benzoylihiocarbamide) 

C 6 H 5 -CO-NH-CS-NH 3 
C 8 H 8 ON 2 S MW, 180 

Prisms from EtOH.Aq. M.p. 171. Sol. 
EtOH. Spar. sol. H 2 O. InsoL Et 2 0. 

Pike, Ber., 1873, 6, 755. 



Benzoylurea 

benzoylcarbamide) 



( Benzoylaminoformamide, 

C 6 H 5 -CO-NH-CO-NH 2 
C 8 H 8 OJSF 2 " MW, 164 

Leaflets from EtOH. M.p. 215. Mod. sol. 
hot EtOH, hot H 2 O. InsoL Et 2 0. Heat >- 
benzamide + cyanuric acid. 

Eupe, Ber., 1895, 28, 256. 

Benzoylvanillic Acid. 

See under 4 : 5-Dihydroxybenzophenone-2- 
carboxyKc Acid. 

Benzoylveratric Acid. 

See under 4 : 5-, and 5 : 6-Dihydroxybenzo- 
phenone-2-carboxylic Acids. 

Benzoylvinyl Alcohol. 

See Benzoylacetaldehyde. 

Benzoylxylenol. 

See Hydroxydimethylbenzophenone. 

1 : 2-Benzpentacene (Benzo[ai]pentacene) 




Violet-blue leaflets from PhIST0 2 . 
Cone. H 2 S0 4 > violet > brown col. 



MW, 328 
M.p. 357. 

" 



Benz-plienetidide 
orange-red sol. with yello wish- 



in C 6 H 6 
green fluor. 

Clar, Ber., 1948, 81, 52. 

1 : 2-BenzphenanthFene. 

See Chrysene. 

2 : 3-Benzplienantlirene. 
See 1 : 2-Benzanthracene. 

3 : 4-Benzpls.eiiaiitIirene 




C 18 H 12 



MW, 228 
Has car- 



Needles from EtOH. M.p. 68' 
cinogenic properties. 

Picrate : red needles from EtOH. M.p. 128- 
128-5. 

Hewett, J. Chem. Soc., 1936, 599. 
Newmann, Joshel, J. Am. Chem. Soc., 

1938, 60, 487. 

Bachman, Edgerton, J. Am. Chem. Soc., 
1940, 62, 2972. 

9 : 10-Benzphenantlirene. 

See Triphenylene. 

1 : 2-Benzphenazine (&ng.-Naphthaphenazine) 



1ST 




C 16 H 10 N 2 MW, 230 

Yellow needles. M.p. 142. Dist. undecomp. 

above 360. Sol. EtOH, Et 2 0, AcOH. InsoL 

H 2 0. Sol. cone. H 2 S0 4 with reddish-brown col. 
Ethiodide: C 18 H 15 N 2 I. MW, 386. Black 

needles with violet reflex. M.p. 1 50 decomp. 
N-Oxide: C 16 H 10 01Sr 2 . MW, 246. Green 

cryst. M.p. 182. 

Kehrmann, Mermod, Helv. Chim. Acta, 

1927, 10, 64. 
Fischer, Hepp, Ber., 1897, 30, 393. 

2 : S-Benzplienazine (]m-Naphthaphenazine) 

N 




Sol. 



C 16 H 10 N 2 MW, 230 

Red leaflets from C 6 H 6 . M.p. 233. Sol. 
CHC1 3 , C 6 H 6 , hot AcOH. Spar. sol. EtOH. 
Sol. cone. H 2 S0 4 with yellow col. 

Hinsberg, Ann., 1901, 319, 261. 

Benz-phenetidide . 

See under Hydroxybenzanilide. 



1 : 2-Benzphenoxazine 

1 : 2-Benzplieiioxazi2ie 

NH 




MW, 233 

Yellow cryst. from EtOH containing S0 2 . 
M.p. (sealed tube) 127-8. Sol. EtOH, Et 2 O, 
C 6 H 6 , AcOH. EtOH sol. shows intense green 
fluor. 

Goldstein, Ludwig-Semelic, Helv. Chim. 
Acta, 1919, 2, 660. 

2 : S-Benzplienoxajzine 
NH 



267 Benzpinacolin 

green needles from EtOH-C 6 H 6 . M.p. 132-3. 
Sol. cone. H 2 S0 4 with deep blue col. 

Kehrmann, Christopouios, Ber., 1921, 54, 

653. 

Kehrmann, Ann. t 1902, 322, 47. 
Knoevenagel, J. prali. Ghem. 9 1914, 89, 
14. 

3 : 4-Benzpiie3itliiaziiie 




C le H u ON MW, 233 

Plates from C 6 H 6 -EtOH. M.p. 302. Sol. 

EtOH, C 6 H 6 , AcOH, with bluish- violet fluor. Sol. 

cone. H 2 S0 4 with red col. > bluish- violet on 

heating. 
N-Acetyl : plates. M.p. 151. 

Kehrmann, Neil, Ber., 1914, 47, 3102. 
3 : 4-Benzphenoxazine 

NH 




C 16 H n ON MW, 233 

Yellow solid. M.p. (air exclusion) 107 
decomp. Sol. EtOH, Et 2 0, AcOH, C 6 H 6 . 
Intense green fluor. in EtOH. Sol. cone. ^804 
with pale blue col. > red on dil. Rapidly 
decomp. by light. 

Goldstein, Ludwig-Semelic, Helv. CJiim. 

Acta, 1919, 2, 657. 

Lantz, Wahl, Bull. soc. chim., 1935, 2, 
488. 

1 : 2-Benzphentliiazine 
NH 




C 16 H n NS ~ MW, 249 

Yellow needles from EtOH, toluene or ligroin. 

M.p. 178. Sol C 6 H 6 . Spar. sol. EtOH, AcOH. 

Sols, in C 6 H 6 and EtOH fluor. green. Sol. 

cone. H 2 S0 4 with deep blue col. 
TS-Acetyl : cryst. from C 6 H 6 . M.p. 126. 
N-Jfc: C 17 H 13 NS. MW, 263. Yellowish- 




C 16 H n NS MW, 249 

Yellow leaflets from EtOH. M.p. 137-8. 
Sols, in org. solvents fluor. bluish-green. Sol. 
cone. H 2 S0 4 with deep blue col. Cu powder at 
280 > I : 2-benzcarbazole. 

Kehrmann, Christopouios, Ber., 1921, 54, 

649. 
Kehrmann, Gressly, Misslin, Ann., 1902, 

322, 44. 

Knoevenagel, /. prakt. Chem., 1914, 89, 
14. 

Benzpinacol (Benzpinacone, benzopinacone, 
tetraphenylethylene glycol) 

(C 6 H 5 ) 2 C-OH 

(C 6 H 6 ) 9 OOH 

C 26 H 22 2 " MW, 366 

Prisms. M.p. (capillary tube) 185-6 de- 
comp. ^ benzophenone and benzhydrol. 
Sol. Et 2 0, CHClg, CS 2 . PC1 5 , hot cone. HC1, 
etc. ^ p-benzpinacolin. HI + P at 170 
> tetraphenylethane. 

Diphenyl ether : C 38 H 30 2 . MW, 518. Plates 
~ ~ M.p. about 196. 
Meyer, Wieland, Ber., 1911, 44, 2559. 
Bachmann, Organic Syntheses, 1934, 
XIV, 8. 

Benzpinacolin ( sym . - Tetraphenylethylene 
oxide, benzopinacoline, triphenylbenzoylmethane) 

(a) 



from C 6 H 



C 26 H 20 



or 
(C 6 H 5 ) 3 OCOC 6 H 



65 



MW, 348 



C 6 H 



a-Form. 

Needles. M.p. 204-5. Sol. CHC1 3 , CS 2 , 
Prac. insol. cold EtOH, AcOH. Cr0 3 
in AcOH > benzophenone. 
$-Form. 

Needles. M.p. 181. Sol. CHC1 3 , CS 2 , C 6 H 6 . 
Spar. sol. cold EtOH. Cr0 3 in AcOH > 
triphenylcarbinol + benzoic acid. 

Delacre, Bull. soc. chim., 1909, 5, 1144. 
Bachmann, Organic Syntheses, 1934, 
XIV, 12. 



Benzpyrazole 

Benzpyrazole. 

flea Indazole. 

1 : 2-Benzpyrene 



268 



BenztMazole 



C 20 H 12 MR 7 , 252 

Carcinogenic constituent of coal tars. Pale 
yellow needles from C 6 H 6 -MeOH. M.p. 176*5- 
7*5. B.p. 310-12 C /10 mm. Violet fluor. in 

Picrate : purplish-black needles. M.p. 197-8. 
Cook, Hewett, J. Chem. Soc. s 1933, 398. 

4 : 5-Benzpyrene 




C 20 H 12 ~ MW, 252 

Constituent of coal tars. Non-carcinogenic. 
Prisms from C 6 H 6 . M.p. 178-9. Sublimes at 
250 /3-4 mm. 

Picrate : ruby-red needles from C 6 H e . M.p. 
229-30. 

Cook, Hewett, J. Chem. Soc., 1933, 398. 

y-Benzpyrone. 

See Chromone. 
3 : 4-Benzqiiinoline. 
See Plienantliridine. 

5 : 6-Benzquinoline ($-Naphthaquinoline, 
naphtha-2' : 1' : 2 : 3-pyridine, I-azaphenanthrene) 




MW, 179 

Leaflets from H 2 or pet. ether. M.p. 94. 
B.p. 350/721 mm., 210-15/22 mm. Sol. ord. 
org. solvents. Difficultly volatile in steam. 
Very spar. sol. H 2 0. 

B,H 2 SO : yellow needles. M.p. 90. 

MethocMoride : needles from EtOH-Et 2 O. 
M.p. anhyd. 236. 

Methiodide : yellow needles from H 2 or 
EtOH. M.p. 200-5 decomp. (186). 

Ethobromide : needles from amyl alcohol. 
M.p. 238. 



Ethiodide : yellow needles from H 2 O. M.p. 
206 decomp. 

benzyl chloride quaternary salt : m.p. anhyd. 
196. 

Picrate : yellow prisms from EtOH or C 6 H 6 . 
M.p. 251-2." 

1:3: 5-Trinitrobenzene add. comp. : reddish- 
yellow needles. M.p. 112 corr. 

Bamberger, MiiUer, Ber. 9 1891, 24, 2643. 
Knueppel, Ber., 1896, 29, 708. 
Braun, Gruber, Ber., 1922, 55, 1714. 

6 : 7-Benz<juinoline. 

See a-Anthrapyridine. 

7 : 8-Benz<juinoline (K-Naphthaquinoline, 
naphtha-l' : 2' : 2 : 3-pyridine, k-azaphenanthrene) 




needles from EtOH-Et 2 0. 



MW, 179 

Plates from pet. ether. M.p. 52. B.p. 338 / 
719 mm., 223/47 mm. Sol. ord. org. solvents. 
Volatile in superheated steam. 

B,HCl: yellowish needles. M.p. 213. 

BjH^O^: yellowish prisms from EtOH. M.p. 
213 

i.p. anhyd. 135-7. 

yellow prisms. M.p. 224 de- 
comp. 

Methochloride : 
M.p. 133. 

Methiodide : yellow needles from H 9 or 
EtOH. M.p. 179. 

Methosulphate : C 15 H 14 4 NS. MW, 305. 
Needles from EtOH-Et 2 0. M.p. 162. 

1:3: 5-Trinitrobenzene add. comp. : yellow 
needles from EtOH. M.p. 133-5 (corr.). 

Picrate : m.p. 191-2. 

Stewart, /. Chem. Soc., 1925, 127, 1332. 
Haid, Monatsh., 1906, 27, 318. 
Glaus, Imhoff, J. praJct. Chem., 1898, 57, 
68. 

Benzselenophenone . 

See Selenonaphthene. 

Benzthiazole (Benzothiazole. See Note under 
2-Aminobenzthiazole) 




C 7 H 5 NS MW, 135 

B.p. 223-5. Sol. EtOH, CS 2 . Very spar, 
sol. H 0. Neutral reaction. Volatile in steam. 
B,HCl : m.p. 192. 
B^H^SO^ : m.p. 157-7-5. 
Picrate : m.p. 176. 



269 



1-Benzylacetoacetic Acid 



Methiodide : needles. M.p. 210. 
Efhiodide : prisms. M.p. 138-9. 

Bruni, Levi, Gazz. chim. ital, 1924, 4, 

402. 

Mills, J. Chem. Soc., 1922, 121, 460. 
Kiprianov, Suitnik, Grigor'eva, Chem. 
Abstracts, 1936, 30, 4859. 

BenztMazoliae (Benzothiazoline) 



iEW, 137 



Benztriaziae 



C 7 H 7 NS 

YeUow oil. B.p. 270. 

Claasz, Ber., 1912, 45, 1031. 

Benzthiazolone (Benzothiazolcme) 



CO 



w 



C 7 H 5 ONS MW, 151 

Needles from EtOH. M.p. 128. Sol. cone, 
alkalis and min. acids. 

N-Acetyl : needles from EtOH. Aq. M.p. 50. 
Mills, Whitworth, J. Chem. Soc., 1927, 
2752. 



4 : 5-BenztMoindoxyl 

benzthion aphtkene ) 



(B-Hydroxy-4: : 5- 




C 12 H 8 OS MW, 200 

Needles. M.p. 121. Sol. most org. solvents. 
Volatile in steam. 

Friedlander, Woroshow, Ann., 1912, 388, 
18. 

5 : 6-Benzthioindoxyl (3-Hydroxy-5 : 6- 

benzthionaphthene) . 
Greenish-yellow powder. 

Harley-Mason, Mann, J. Chem. Soc., 1942, 
410. 

6 : 7-Benzthioindoxyl (3-Hydroxy~6 : 7- 
benzthionaphthene) . 

Dark brown cryst. from EtOH.Aq. M.p. 142. 
Readily sol. most org. solvents. 

Friedlander, Woroshow, Ann., 1912, 388, 
18. 

Benzthiophene. 
See Thionaphthene. 
Benzthiopyrone . 
See Thiochromone. 
Benz-toluidide. 
See under Toluidine. 




CTT x" \rw i QI 

yljLEA.^0 jJJLYY, JLO1 

Yellow to orange-red needles from C 6 H 6 . 

M.p. 74-5\ B.p. 235-40 D . Sol. hot Et>0, 
H 2 0, EtOH. 

Bischler, Ber., 1889, 22, 2806. 

Benztriazole (Benzeneazimide, benzotriazole, 
aziminobenzene ) 



C 6 H 5 X 3 



N 



MW, 119 

Needles from C 6 H 6 . M.p. 100. 
l-Hydroxy deriv. : azimidol. M.p. 157. 
1-N-Acetyl : m.p. 51. 
1-N-Benzoyl: needles. M.p. 112. 

Charrier, Beretta, Gazz. chim. itaL, 1921, 
51, II, 267. 

B enztr op olone . 
See Benzotropolone. 
Benzylacetaldehyde . 
See Hydrocinnamaldehyde. 
Benzyl acetate 

CH 3 -CO-OCH 2 -C 6 H 5 
C 9 H 10 2 MW, 150 

Constituent of jasmin, gardenia, and other 
ethereal oils. B.p. 213-5 /756 mm., 93^/10 
mm. D 16 1-057. 1% 1-5232. 

Seelig, J. prakt. Chem., 1889, 39, 162. 
Shapiro, Chem. Abstracts, 1936, 30, 723. 
Givaudan Soc. Anon., Swiss P., 169,040, 
(Chem. Abstracts, 1935, 29, 481). 

Benzylacetic Acid. 

See Hydrocinnamic Acid. 
1-Benzylacetoacetic Acid (a-Acetohydro- 
cinnamic add) 

CH 3 'CO-CH-COOH 
C n H 12 3 MW, 192 

Oil with aromatic odour. B.p. 156-62/13 
mm. Spar. sol. H 2 0. Heat > benzylacetone. 

Me ester : C 12 H 14 3 . MW, 206. B.p. 180- 
82/15 mm. D 17 1-091. Ale. PeCl 3 ^violet 
col. 

Et ester : C 13 H 16 3 . MW, 220. B.p. 283-4 
(276), 157-8/14 mm., 164-5/12 mm. 

Menthyl ester : two forms, (a) M.p. 68. 
[aj? 121-2 in C 6 H 6 . (6) Needles from AcOH- 
EtOH. M.p. 48-51. [a]| - 55-1 in C 6 H 6 . 

Amide: C U H 13 02N. MW, 191. Needles 
from H 2 0. M.p. 150-1. Sol. EtOH. 



co-Benzylacetonaplitlione 



270 



Benzylainine-i-carboxylic Acid 



Xitrile: C n H u OX. 3IW, 173. B.p. 158- 

66/13 mm. Semicarbazone : leaflets from 
EtOE. M.p. 168. P&eTvylhydrazone : m.p. 
112. 
2 : 4:'DinitropJienylJiydrazone : m.p. 71*5. 

Conrad, Bischoff, Ann., 1880, 204, 179. 
Ehriich, Ann., 1877, 187, 12. 
Ceresole, Ber., 1882, 15, 1871, 1875. 

Q-Benzylacetonaplit!ione . 

See Phenylethyl naphthyl Ketone. 

Benzylacetone (Methyl phenyletJiyl Jcetone) 



MW, 148 

B.p. 235, 115/13 mm. Df 0-9849. w 
1-511. Eorms bisulphite comp. Cr0 3 > benz- 
oic and acetic acids and C0 2 . 

Oxime : needles. M.p. 87. 

Semicarbazone : leaflets. M.p. 142. 

2 : 4:-DinitrophenylJiydrazone : scarlet cryst. 
M.p. 131-2. 

Neber, Uber, Ann., 1928, 467, 52. 
Mattar, Hastings, Walker, J. Chem. Soc., 
1930, 2455. 

co-Benzylacetophenone (Phenyl phenylethyl 
ketone} 

C 6 H 5 -CH 2 -CH 2 -CO-C 6 H 5 
C 15 H 14 MW, 210 

Leaflets. M.p. 72-3. Distils above 360, 
Sol. EtOH, Et 2 0. Ox. > benzoic acid + C0 2 . 

Di-Et acetal : b.p. 189/18 mm. Df 1-0425. 
rig 1-5407. 

Oxime : needles from EtOBLAq. M.p. 87. 

Semicarbazone : m.p. 144. 

Perkin, Stenhouse, J. Chem. Soc., 1891, 

59, 1007. 
Adams, Kern, Shriner, Organic Syntheses, 

Collective Vol. I, 95. 

1-Benzylacrylic Acid 

C 6 H 5 -CH 2 -p-COOH 
CH 2 

MW, 162 

Prisms. M.p. 68-9. Sol. most org. solvents. 
Spar. sol. H 2 0. KMn0 4 > benzyl alcohol 
and 1-benzylglvceric acid. 

Et ester : Ci 2 H 14 2 . MW, 190. B.p. 134 / 
15 mm. 

Mannich, Ritsert, Ber., 1924, 57, 1116. 
Simonsen, J. Chem. Soc., 1920, 117, 567. 

2-Benzylacrylic Acid. 

See 3-Phenylcrotonic Acid. 
Benzyl Alcohol (Phenylcarbinol, v-hydroxy- 
toluene} 



C 10 H 10 2 



C 7 H 8 



C 6 H 5 -CH 2 OH 



Constituent of jasmin and other ethereal oils, 
both free and as esters. Colourless liq. B.p. 
205-3, 189/500 mm., 141/100 mm., 93/10 
mm. DJ 1*0579, Dg 1-050. Sol. to 4% in 
H 2 at 17. Sol. EtOH, Et 2 O, Me 2 CO. Heat 
895-3 Cal. ri$ 1-53955. Dil. 



of comb. 

HX0 3 ) 

acid. 
Me ether 
Et ether : 



benzaldehyde. Cr0 3 



benzoic 



see Methyl benzyl Ether. 
see Ethyl benzyl Ether. 
Allyl ether : C 10 H 12 0. MW, 148. B.p. 204-5. 

Meisenheimer, Ber., 1908, 41, 1420. 
Hobart, Pharm. /., 1924, 113, 635. 
Chemische Fabrik Pott, D.E.P., 484,662, 
(Chem. Abstracts, 1930, 24, 1125). 

Benzyl Alcohol carboxylic Acid 

See Hydroxymethyl- benzoic Acid. 
1 -Benzylallene . 
See 4-Phenyl-l : 2-butadiene. 
Benzylamine (<*-Aminotoluene} 



C 6 H 5 -CH 2 NH 2 



MW, 107 



B.p. 185, 90/12 mm. Misc. in all propor- 
tions with H 2 0, EtOH, Et 2 0. D? 0-9826. 
TZ 1-5401. Heat of comb. 0,, 967-6 Cal. Strong 
alkaline reaction. Absorbs C0 2 . k = 2-4 x 
10- 5 at 25. 

B,HCl : m.p. 248 (rapid heat.). Sol. H 2 0. 

B,HBr; m.p. 204. 

B,HI : leaflets. M.p. 162. 

B,H 2 SO*: needles. M.p. 93. 

N-Allyl : CxoHi^N". MW, 147. B.p. 205-8. 

N-p-Toluenesuiphonyl : m.p. 185. 

N-Benzoyl : see Benzylbenzamide. 

Picrate : m.p. 194. 

Erickson, Ber., 1926, 59, 2665. 

Ing, Manske, J. Chem. /Soc., 1926, 2348. 

I.G., U.S.P., 1,873,402, (Chem. Abstracts,. 

1932, 28, 5965). 
Knoll A.-G., U.S.P., 1,926,756, (Chem. 

Abstracts, 1933, 27, 5752). 



Benzylamine-o-carboxylic 
Amino-o-toluic acid) 



00H 



Acid (eo- 




MW, 108 



C 8 H 9 2 N ^ MW, 151 

Cryst. from H 2 0. M.p. 217-20. Heat above 
m.p. > phthalimidine. 

Wegscheider, Glogau, Monatsh., 1903, 

24, 953. 
Gabriel, Landsberger, Ber., 1898, 31, 

2738. 

Benzylamine-m-carboxylic Acid (o>- 
Amino-m-toluic acid). 

Cryst. from H 2 0. M.p. 215-18. 



Benzylamine-p-cariioxylic Acid 



271 



Benzylcarbinol 



Nitrik: C 8 HgX>. MW, 132. Basic oil. 

B,HGl: needles from EtOH. M.p. 221. 

B%,HJPtCl : golden prisms from H^O. M.p. 

240. Picrate : light yellow needles. M.p. 
217 decomp. 

N-Chloroacetyl : needles from EtOH. M.p. 

176. Et ester: needles from EtOH. M.p. 
86-7. 

^-Benzoyl : m.p. 186. 

Reinglass, Ber., 1891, 24, 2419. 
Einhorn, Ann., 1905, 343, 207. 
Ehrlich, Ber., 1901, 34, 3367. 

Benzylamine - p - carb oxyMc Acid ( o> - 

Amino-p-toluic acid). 

Yellow cryst. from H 2 O. Insoi. EtOH, Et 2 0, 
Me 2 CO, C 6 H 6 , ligroin. 

Et ester : b.p. 145-8. BJSOl : m.p. 235-7. 
Nitrik : oil. B,HOl : leaflets from EtOH. 
M.p. 274. B z ,H 2 PtCls : red yellow cryst. 
M.p. 250 decomp. Picrate : needles. M.p. 
218. 

Ehrlich, Ber., 1901, 34, 3368 (Note). 
Gunther, Ber., 1890, 23, 1060. 
Dewing, J. CJiem. Soc., 1946, 466. 

BeE^lamine-p-sulphonic Acid. 
See Homosulphanilic Acid. 
Benzylaminoacetic Acid. 
See Benzylglycine. 
co-Benzylaimnoacetophenone . 
See Benzylphenacylamine. 
Benzylaniline (Phenylbenzylamine) 

C 6 H 5 NH-CH 2 -C 6 H 5 
C^H^N MW, 183 

Prisms. M.p. 37-8. B.p. 306-7, 201-3/37 
mm. Dl?l '0698. <" 8 1-6118. 

B,HCl: m.p. 214-16. 

B,HBr : cryst. from CHClg. Decomp. at 
193 

B 2 ,H z PtCL: yellowish-red leaflets. M.p. 
155. 

p-Toluenesulphonate : m.p. 148-9. 

N - Nitroso : phenylbeiizylnitrosamine. 

C 13 H 12 ON 2 . MW, 212. Yellow needles. M.p. 
58. Sol. EtOH, Et 2 0, ligroin. 

Willson, Wheeler, Organic Syntheses, Col- 
lective Vol. I, 97. 

Benzylanisole . 

See under Hydroxydiphenylmethane. 
Benzylarsinic Acid 

C 6 H 5 -CH 2 <AsO(OH) 2 

C 7 H 9 O 3 As MW, 216 

Needles. M.p. 167. 

Dehn, McGrath, J. Am. CJiem. Soc., 1906, 

28, 347. 
Quick, Adams, J. Am. Ohem. Soc., 1922, 

44, 811. 



Benzyl azide (u-Triazotoluene) 



C 7 H 7 X 3 ' " MW, 133 

B.p. 108/23 mm., 74/ll mm. Insol. H 2 0. 

IBsc. with EtOH, Et 2 0. Volatile in steam. 
D 25 1*0655. n 1-53414. Explodes on strong 
heating. 

Curtius, Ehrhart, Ber., 1922, 55, 1559. 
Benzylbenzaznide (Benzoylbenzylamim) 



C^H^ON MW, 211 

Leaflets. M.p. 105-6. Sol. EtOH, AcOH. 
N-Nitroso : pink cryst. turning green in air. 
M.p. 46-7. 

Beckrnann, Ber., 1904, 37, 4136. 
Blacher, Ber., 1895, 28, 434. 

Benzyl benzoate 

C 6 H 5 -COOCH 2 -C 6 H 5 
C U H 12 2 MW, 212 

Contained in balsam of Peru. Leaflets. M.p. 
21. B.p. 323-4 (316-17). Sol. EtOH, Et 2 0. 
D 18 1*114. rag 1-5681. Spar, volatile in steam. 

Kamm, Kamm, Organic Syntheses, Col- 
lective Vol. I, 99. 

Matheson, B.P., 270,651, (Chem. Ab- 
stracts, 1928, 22, 1597). 

Benzylbenzoic Acid. 

See Diphenylmethane-carboxylic Acid. 

Benzylbenzoylacetic Acid. 

See 2-Phenyl-l-benzoylpropionic Acid. 

Benzylbenzoylcarbinol. 

See p-Hydroxy-y-phenylpropiophenone. 

1-Benzyl-l-benzoylpropionic Acid. 

See 2-Phenyl-l-benzoylisobutyric Acid. 

l-Benzyl-2-benzoylpropionic Acid. 

See 2-Phenyl-2 / -benzoylisobutyric Acid. 

Benzyl borate. 

See Tribenzyl borate. 

Benzyl bromide (<*-Bromotoluene) 

C 6 H 5 -CH 2 Br 
C 7 H 7 Br MW, 171 

Colourless lachrymatory liq. B.p. 198, 127 / 
80 mm. Df 14380. 

Schxamm, Ber., 1885, 18, 608. 
Soc. chim. des usines du Rhone, F.P., 
483,622, (Ohem. Abstracts, 1922, 16,. 

4215). 

Benzyl bromide carboxylic Acid. 

See co-Bromotoluic Acid. 

2-Benzylbutyric Acid. 

See 3-Phenylisovaleric Acid. 

B enzylcarbinol. 

See Phenylethyl Alcohol. 



Benzyl chloride 



979 



Benzyliumaric Acid 



Benzyl chloride (m-Chlorotolnene) 

CTT _/iTT HI 
gJjLe OJDLQVJ'i 

C 7 H 7 C1 MW, 126-5 

M.p. 43 (48). B.p. 179, 106/92 mm., 
99/62 mm., 63/8 mm. DJ 1-1135, D~g 1-1002. 
nS 1-5415. Volatile in steam. Hyd. slowly by 
boiling H 2 to benzyl alcohol. 

Schering-Kahlbaum, D.R.P., 478,084, 

(Chem. Abstracts, 1929, 23, 4228). 
I.C.I., B.P., 334,260, (Chem. Abstracts, 

1931, 25, 973). 

Sors, Chem. Zeit., 1933, 57, 321. 
Nikolyuk, Chem. Abstracts, 1935, 29, 1786. 
Kharasch, Brown, J. Am. Chem. Soc., 
1939, 61, 2142. 

Benzyl cnlorophospMte (Benzyl phospho- 
chloride) 

C 6 H 5 -CH 2 -0-PC1 2 

C 7 H 7 OC1 2 P " " MW, 209 

'B.p. 113-4 C /H mm - D o 1-3243. < 1-5584. 
Razumov, J". Gen. Chem. U.S.S.E., 1944, 
14, 464. 

Benzyl chloropliosplionate. 

See Dibenzyl chlorophosphonate. 
Benzyl cinnamate 

C 6 H 5 -CH:CH-CO-OCH 2 -C 6 H 5 
C 16 H 14 2 MW, 238 

Constituent of storax, tolu and Peru balsams. 
Prisms. M.p. 39. B.p. 195-200 /5 mm. De- 
comp, on dlst. at ord. press, at 350. Mod. 
sol. warm EtOH. 

Kalle, D.R.P., 127,649, (Chem. Zentr., 
1902, 1, 445). 

a-Benzylcinnamic Acid (<^-Benzylidene- 
hydrocinnamic acid) 



C 16 H 14 2 
Needles. 



M.p. 158. 
NaHg- 

Me'ester : C 17 H 16 2 . 
B.p. 200-2/12 mm. 



CHC1 3 , C 6 H 6 



MW, 238 

Mod. sol. EtOH, Et 2 0, 
-> dibenzylacetic acid. 
MW, 252. M.p. 27-8. 



Et ester : C 18 H 18 2 . MW, 266. M.p. 38-9. 
B.p. 227-9/30 mm. Df 1-0831. rag* 1-5885. 

Anhydride : C 32 H 26 3 . MW, 458, M.p. 108-9. 
Spar. sol. EtOH. Prac. insol. Et 2 0. 

Eupe, Ann., 1913, 395, 106. 
Foldi, B.P., 319,273, (Chem. Abstracts, 
1930, 24, 2472). 

p-Benzylcinnamic Acid (2 : 3-Diphenyl- 
crotonic acid) 



Prismatic needles from EtOH. M.p. 169. 
Sol. boiling EtOH. 

Spring, J. Chem. Soc., 1934, 1333. 

5-Benzylcreatinin 

On 



N-C 



C n H 13 ON 3 MW, 203 

Flakes. M.p. 282 decomp. Ba(OH) 2 > 
iV-methylphenyialanine . 

Picrate : yeUow needles from hot H 9 0. M.p. 
206-8. 

Nicolet, Campbell, /. Am. Chem. /Soc., 
1928, 50, 1155. 

Benzyl cyanide (Phenylacetonitrile, &-cyano- 
toluene) 

C 6 H 5 -CH 2 CN 

C 8 H 7 ]S[ MW, 117 

B.p. 234, 107/12 mm. Dg 1-0214. ng 
1-52105. Heat of comb. Q v 1023 Cal. Boil 
with acid or alkali >- phenylacetic acid. 
Red. ^ 2-phenylethylamine. 

Adams, Thai, Organic Syntheses, Collec- 
tive Vol. I, 101. 

Benzyl-dichloroarsine 

C 6 H 5 -CH 2 -AsCl 2 

C 7 H 7 Cl 2 As MW, 237 

B.p. 175/50 mm. Decomp. on standing in 
air. 

Mchaelis, Paetow, Ann., 1886, 233, 91. 



C 16 H 14 2 



CH 2 *C 6 H 5 



MW, 238 



MW,244 

Leaflets. M.p. 85. B.p. 285-6/100 mm. 
Sol. Et 2 0, C 6 H 6 . Mod. sol. EtOH. 

Goldschmiedt, Monatsh., 1881, 2, 433. 
Nenitzescu, Isacesu, lonescu, Ann., 
1931, 491, 211. 

Benzyl disulphide. 
See Dibenzyl disulphide. 
Benzylethylaniline . 
See Ethylbenzylaniline. 
Benzyl-a-ethylbenzyl-amine . 
See a-Ethyldibenzylamine. 
Benzyl fluoride (a-Fluorotoluene) 

C 6 H 5 -CH 2 F 

C 7 H 7 F MW, 110 

Colourless mobile liq. Does not fume in air. 
M.p. -36. B.p. 140, 40/14 mm. Df 
1 -02278. Non-lachrymatory. 

Ingold, J. Chem. Soc., 1928, 2249. 

Benzylfumaric Acid. 

See Phenylmesaconic Acid. 



Benzylglycine 



273 



BenzyHdene-acetylacetone 



Benzylglycine (BenzylamiTioaceiic acid) 



MW, 165 

Needles from H 2 0. M.p. 197-8. 

Hydrochloride : m.p. 226. Sol. H 2 0. 

Et ester : C^H^O^. MW, 193. Decomp. 
on dist. at ord. press. B.p. 165/16 mm. Sol. 
EtOH, Et 2 0, C 6 H 6 . 

?$-Acetyl : m.p. 126-7. 

Scheibler, Baumgarten, Ber., 1922, 55, 

1358. 
Granacher, Wolf, Weidinger, Helv. Ghim. 

Acto, 1928, 11, 1228. 
Mannich, Kuphal, Ber., 1912, 45, 317. 

2-BenzylhydracryHc Acid. 

See 2-Hydroxy-3-phenylbutyric Acid. 
a-Benzylliydratropic Acid. 
See 1 : 2-Diphenylisobutyric Acid. 
BenzyUrydrazine 



2 - Benzyl - 4 - liydrosrymetliyiene - 5- oxaz - 
olone 

HO-CHIC CO 



C 7 H 10 N 2 MW, 122 

B.p. 103/41 mm. Decomp. by heat at ord. 
press. > dibenzyl + N 2 . 

B 9 HCl : leaflets from EtOH. M.p. 111. 
B,2HCl : decomp. at 145. 
'N-Nitroso : m.p. 72. 

Wohl, Oesterlin, Ber., 1900, 33, 2739. 
Hale, Lange, J. Am. Chem. Soc., 1920, 
42, 107. 

BenzyUiydr oqpiinone . 

See 2 : 5-Dihy<&oxydiphenylmethane. 
JV-Benzylhydroxylamine ($-Benzylkydr- 
oxylamine) 



C 7 H 9 OIsr MW, 123 

Cryst. from ligroin. M.p. 57. Mod. sol. 
BUG. Reduces FeHing's. 

B,HCl : m.p. 110. Sol. EtOH. 

'N-Formyl : needles from Et 2 0~ligroin. M.p. 
49-50. 

N-Acetyl : plates. M.p. 124. 

N-Benzoyl : needles from Et 2 0. Ale. FeCl 3 
>- intense red col. 

Nitroso : m.p. 77-8. 

Neubauer, Ann., 1897, 298, 200. 

O-Benzylhydroxylamine (a-Benzylhydr- 
oxylamine) 

C 6 H 5 -CH 2 0-NH 2 
C 7 H 9 ON MW, 123 

B.p. 118-19/30 mm. Volatile in steam. 
Heated at 160 > benzaldoxime benzyl 
ether. 

B,HCl : leaflets. Sublimes at 230-50. Sol. 
warm H 2 O, EtOH. 

p-Aminobenzenesulphonyl : m.p. 130. 

Behrend, Leuchs, Ann., 1890, 257, 207. 

Diet, of Org. Oomp. I. 




C n H 9 O 3 X JVfW, 203 

Xeedles from Me 2 CO-light petroleum. M.p. 
130-2. EeCl 3 > deep blue col. Penicil- 
lamine > benzyl penicillenate 4- benzyl- 
penicillin. 

Me ether: C^H^OsN. ^1W, 217. Cryst. 
M.p. 92-4 (118-19). BJELCl : m.p. 180-2. 

Ut ether: C 13 H 13 3 N. MW, 231. Cryst. 
M.p. 34-6. B.p. 140/0-02 mm. B,HBr : m.p. 
90-115. 

Nasalt: m.p. 238-40. 

Benzylamine salt : cryst. from MeOH-Et>O. 
M.p. 115-16. 

Brown, Cornforth, Hunter, Hinman, 
Carter, Chemistry of Penicillin, 521, 
806, 807, 916. 

Benzylidene- acenaphthenone 




C 10 H 10 



C 19 H 12 v ^ MW, 256 

YeHow needles from EtOH. Aq. M.p. 107. 

Sol. EtOH, Et>0, C 6 H 6 . 
Oxime : m.p. 48. 

Graebe, Jequier, Ann., 1896, 290, 204. 

Benzylideneacetone (Benzalacetone, methyl 
styryl ketone, acetocinnamone) 

C 6 H 5 -CH:CH-CO-CH 3 

MW, 146 

Lustrous plates. M.p. 42. B.p. 260-2, 
151-3/25 mm., 126-8/9 mm. Sol. EtOH, 
Et 2 0, CHC1 3 , C 6 H 6 . Spar. sol. ligroin. J>H 
1-0377. ?^ 59 1-5836. Heat of comb. C p 1258-1 
Gal., Gtf 1256-9 Cal. H 2 S0 4 > orange-red col. 
Oxime : needles. M.p. 116. 
Phenylhydrazone: yellow needles. M.p. 156-7. 
Semicarbazone : m.p. 185 (187). 
p-Nitrophenylhydrazone : m.p. 165-7. 

Drake, Allen, Organic Syntheses, Collec- 
tive Vol. I, 69. 

Grignard, Eluchaire, Ann. chim., 1928, 
9,22. 

Benzylideneacetophenone. 

See Chalkone. 

Benzylidene-acetylacetone (p : $-Diaceto- 
styrene) 

C 6 H 5 -CH:C(COCH 3 ) 2 

C 12 H 12 2 MW, 188 

B.p. 185-8/15 mm. 

Knoevenagel, Ruschhaupt, Ber., 1898, 
31, 1026. 

18 



BenzyMdene-amiiioacetal 
Bexi2yHdeae-ammoacetal 



274 



2-B enzylidenebutane 



C 13 H 19 2 N 1TW, 221 

B.p. 156/12 mm. Heat with HgSC^ > 
isoqulnoline. 

Fischer, Ber., 1893, 26, 467. 

Benzylidene - o - aminobenzyi Alcohol 

(2-Benzylideneaminobenzyl alcohol, o-hydroxy- 
meihylbenzylideneaniline) 

GH 2 OH 



C 14 H 13 ON 



V 



MW, 211 
Leaflets. MLp. 115. Spar. sol. ligroin. 

Paal, Laudenheimer, Ber., 1892, 25, 2970. 

Benzylidene - p - aminobenzyi Alcohol 

(4:-BenzyHdeneaminobenzyl alcohol, p-hydroxy- 
methylbenzylideneaniUne) . 
Leaflets. M.p. 67-8. 

0. Fischer, G. Fischer, Ber., 1895, 28, 

881. 

B enzylideneairdnogiianidine 



C 8 H 30 N 4 MW, 162 

Silvery leaflets. M.p. 178. Sol. EtOH. 

Spar, sol. cold H 2 0, C 6 H 6 . Strong basic pro- 

perties. 

B,HN0 3 : m.p. 158. Spar. sol. cold H 2 0. 
Diacetyl deriv. : m.p. 158-9. 

Thiele, Ann., 1898, 302, 299. 

BenzyKdene-o-amiaophenol (2-Benzyl- 
ideneaminophenol, o-Jiydroxybenzylideneaniline) 

OH 



C 13 H U OK 



u 

MW, 197 

Leaflets. M.p. 89. Sol. Et 2 0, C 6 H 6 . Mod, 
sol. EtOH. 

Acetyl deriv. : m.p. 93-6. Boil with H 2 O 
>> 2V-acetyl-o-aminophenol. 

Et ether : benzylidene-o-phenetidine. 
C 15 H 15 ON. MW,225. B.p. 215-16/20 mm. 

Pictet, Ankersmit, Ann., 1891, 266, 140. 

Benzylidene-p-aminopbenol (^-Benzyl- 
ideneaminophenol, p-hydroxybenzylideneaniline) . 

Leaflets. M.p. 183. Sol. EtOH. 

Me ether : benzylidene-p-anisidine. C 14 H 13 ON. 
MW. 211. Leaflets. M.p. 62. Sol. EtOH. 

Et ether : benzylidene - p - phenetidine. 
15 H 16 ON. MW, 225. Leaflets. M.p. 76 
(71). Sol. Et 2 0, C 6 H 6 . Mod. sol. EtOH, 
AcOH. B,HCl : decomp. at 138-9. 



Benzyl ether : C 20 H 17 OS'. MW, 287. Cryst. 
from pet. ether. 3Lp. 118. Spar. sol. EtOH. 
Acetyl deriv. : needles. M.p. 92. 
Benzoyl deriv. : needles. M.p. 144. 

Philipp, Ber., 1892, 25, 3248. 

Pope, Fleming, J. Chem. Sac., 1908, 93, 

1915. 

Benzylideaeaniline (Benzalaniline) 
C 6 H 5 N:CH-C 6 H 5 

C 13 H 1X H MW, 181 

Needles or leaflets. M.p. 48 (54). B.p. 
300. Sol. EtOH, Et 2 0. Insol. H 2 0. Volatile 
in steam. Hot min. acids - >- benzaldehyde -j- 
aniline. NaHg > benzylaniline. 

Picrate : m.p. 183 (173). 

Styphnate : pale yellow cryst. from EtOH. 
M.p. 193. 

Bigelow, Eatnough, Organic Syntheses* 

CoUective Vol. I, 73. 
Strain, J. Am. Chem. Soc. 9 1928, 50, 2218. 

BenzyKdene~p-anisidine. 

See under Benzylidene-^-aminophenol. 
Benzylideneazine (Benzalazine, dibenzyl* 
idenehydrazine) 



U H 12 N 2 MW, 208 

YeUow prisms. M.p. 93. Sol. Et 2 O, CHC1 3 , 
C 6 H 6 , hot EtOH. Part, volatile in steam. 
Decomp. on dist. to stilbene, benzonitrile, etc. 
Hot dil. min. acids > benzaldehyde + 
hydrazine. NaHg > dibenzyJhydrazine. Na 
+EtOH > benzylamine. 
B 3 HCl : yellow powder. M.p. 150. 
3MBr : m.p. 165. 
Picrate : yellow needles. M.p. 148. 
Styphnate : yellow needles from EtOH. M.p. 
152. 

Curtius, Jay, J. praJct. Chem., 1889, 39* 

44. 
Thiele, Ann., 1910, 376, 244 (Note 2). 

Benzylidenebiuret 



C 9 H 9 2 N 3 MW, 191 

M.p. 272-3. Sol. caustic alkalis. Spar. sol. 
Et 2 0, CHCls. Insol. CS 2 . 

SchiS, Ann. 9 1896, 291, 369. 

Benzylidene bromide (Benzol bromide, 
co 'dibromotoluene) 

C 6 H 6 -CHBr 2 
C 7 H 6 Br 2 MW, 250' 

B.p. 156/23 mm. D 18 1-51. < 1-541. 
Vorlander, Ann., 1905, 341, 22. 

2-Benzylidenebutane . 

See p-Methyl-p-ethylstyrene. 



1-Benzylidenebutyric Acid 



275 



Benzylidene fluoride 



1-BenzyHdenebutyric Acid. 

See a-Ethyleinnamie Acid. 
3-BenzylIdenebiityricAcId (Cinnamylcicetic 
CKid, 2-styrylpropionic acid) 

C 6 H 5 -CH:CH-CH 2 CH 2 -COOH 

CuHiA " MW, 176 

Leaflets. M.p. 90-1. Sol. Et O, CHCij, 
CS 2 . Mod. sol. hot H 2 O. Alk. KMn0 4 > 
succinic 4- benzoic acids. 

Erlemneyer, Kreutz, Ber., 1905, 38, 3505. 

Benzylidene chloride (Benzol chloride. 
co -dichlorotolueTie ) 



B enzylidenediacetamide 



C 7 H 6 C1 2 " " MW, 161 

F.p. 17. M.p. 16. B.p. 207 (203-5 /756 
mm.). Sol. EtOH, Et 2 O. Insol. HgO. D 14 
1*2557. Hyd. by alkalis, cone. H 2 S0 4 , or 
H 2 + iron catalyst, to benzaldehyde." 

Staudinger, Ber., 1909, 42, 3976. 
Lorges, Chem. Abstracts, 1925, 19, 1700. 
Meyer, Monatsh., 1915, 36, 729. 
Kharasch, Brown, J. Am. Chem. Sac., 
1939, 61, 2142. 

Benzylidene-o-chloroaniline 




C 13 H 10 NC1 MW, 215-5 

YeUowish needles from pet. ether. M.p. 34. 

Fischer, Neber, Ber., 1912, 45, 1094. 

Benzylidene-iw-chloroaiiiline . 

Viscous oil. B.p. 338. 

Lachowicz, Monatsh., 1888, 9, 697. 

BenzyHdene-p-chloroaniline . 

Leaflets. M.p. 62. 
B,HCl : m.p. 194 deconip. 

Hantzsch, Schwab, Ber., 1901, 34, 829. 

Benzylidenecyanoacetic Acid. 

See a-Cyanocinnamic Acid. 
BenzyHdenedeoxybenzoin (1 : 2-Diphenyl- 
1-benzoylethylene ) 



CH-C 6 H 5 
C 21 H 16 MW, 284 

Needles. M.p. 101-2. Sol. AcOH, CS 2 , 
C 6 H 6 , hot EtOH. An isomeric modification has 
m.p. 88-9, and is more sol. than higher-melting 
form. 

Oxime : silky needles. M.p. 208-9. 

Phenylhydrazone : m.p. 163--4 . 

Note The " oxime " and " phenylhydr- 
azone " are probably cyclic comps. 

Stobbe, Niedenzu, Ber., 1901, 34, 3908. 
Thiele, Ruggli, Ann., 1912, 393, 71. 



C n H K 2 N 2 MW, 206 

M.p. 245. Sol. EtOH. Mod. sol. hot H 2 0. 
Spar, sol Et 2 O. HC1 > benzaldehyde, AcOH 
and NH 4 CL 

Chattavay, Swinton, /. Chem. Soc., 1912, 
101, 1206. 



Benzylidene diacetate 
glycol diacetate) 



(Phenylmethylene, 



,208 

M.p. 46. B.p. 220, 154/20 mm. Sol. 
EtOH, Et 2 O. D 20 1-11. 

Nef, Ann., 1897, 298, 277. 

Peski, Eec. trav. chim., 1921, 40, 103. 

Knoerenagel, Ann., 1913, 402, 117. 

Benzylidene-diacetic Acid. 
See 2-Phenylglutaric Acid. 
Benzylidene-diacetophenone (2-Phenyl- 
1 : 3-dibenzoylpropane, pfenyl-diphenacylmethane) 

C 6 H 5 -CH(CH 2 -CO-C 6 H 5 ) 2 
C 23 H 20 2 MW, 328 

Prisms. M.p. 85. Deconip. on dist. > 
acetophenone + chalkone. 
Oxime : needles. M.p. 144. 
Dioxime : needles. M.p. 164. 
Di-semicarbazone : m.p. 232-3. 

Kostanecki, Rossbach, Ber., 1896, 29, 

1493. 

Dieckmann, Fischer, Ber., 1911, 44, 973. 
Kohler, Jones, /. Am. Chem. Soc., 1919, 
41, 1255. 

B enzylidene-diurethane 

C 6 H 5 -CH(NH-CO-OC 2 H 5 ) 2 
C 13 H 18 4 N 2 MW, 266 

M.p. 178-9. Sol. hot EtOH.Aq. Sublimes. 
Lehmann, Ber., 1901, 34, 370. 

BenzyMdene-ethylamine 



C d H n ISr MW, 133 

B.p. 195/749 mm. Df 0-937. Sol. EtOH, 
Et 2 O. Insol. H 2 0. 

Zaunschirm, Awn., 1888, 245, 279. 
Auwers, Ottens, Ber., 1924, 57, 446. 



Benzylidene fluoride (Benzal fluoride, 
fluorotoluen&) 

C 6 H 5 -CHF 2 

C 7 H 6 F 2 MW, 128 

B.p. 139-95. B 19 1-13696. Heat of comb. 
Ct, 853-9 CaL Cone. H 2 S0 4 or H 2 at 200 ^ 
benzaldehyde + HF. 

Swarts, J. Chim. phys., 1919, 17, 31. 



l-Benzylideneglutaric Acid 
1-Benzylideneglutaric Acid 



C 12 H 12 O 4 



27(5 Benzylidenemalonic Acid 

Benzoyl deny.: C 6 H/CKN;NH-CO-C 6 H 5 . 

^^^ ft rt ~ \EtOH. 



CH 2 *COOH 



MW, 220 



Keedles from H 2 0. M.p. 177. Sol. Et 2 O. 
Spar. sol. CS 25 CHCI S . C 6 H 6 , ligroin. 

Fittig, Roedel, Ann., 1894, 282, 336. 

i : 2-Benzylide2aeglyceroI (Glycerol 1 : 2- 

benzylidene ether) 



o. , 2 , 66 . . . 

2-Me ether: needles from C 6 H 6 -4igroin. M.p. 



C 10 H 12 3 

B.p. I43-4/2 mm. Df 1-1916. ng 1-5389. 
Readily liydrolysed by dil min. acids. 

3-Jfo ether: C U H 14 3 . MW, 194. B.p. 
138-41 C /10 mm. ng 1-5128. 

Hill, Whelen, Hibbert, J. Am. Ghem. Soc., 
1928, 50, 2235. 

1 : 3-BenzyIideneglycerol (Glycerol 1:3- 
benzylidenz ether, 2-phenyl-m-dioxanol-5) 
Exists in two isomeric forms. 
(i). Needles from C 6 H 6 -ligroin. M.p. 83-5. 
Sol. EtOH, Et 2 O, C 6 H 6 . Insol. H 

2 

52. 

%-Q-Acetyl : m.p. 115-16. 
2-Q-Benzoyl : cryst. from ligroin. M.p. 103. 
(ii). Needles from C 6 H 6 -ligroin. M.p. 62-5- 
63. Part, isomerised on standing. 
$-Oaproyl : m.p. 31. 
$-Gaprylyl : m.p. 35. 
^Elaidyl: m.p. 43-5-4. 
$-Oleyl : m.p. 4-5. 

2-Q~Benzoyl : plates from ligroin. M.p. 80-1. 
Very labile. 

Tbe two isomers form a 1 : 1 mol. comp. 
M.p. 65-6. 

Hill, Wlielen, Hibbert, J. Am. CJiem. Soc., 

1928, 50, 2235. 
Davies, Heilbron, Jones, J. CTiem. Soc., 

1934, 1234. 

Verkade, van Boon, Eec. trav. chim., 
1942, 61, 831. 

Benzylidenehydrazine (BenzaUehyde Jiydr- 
azone) 



C 7 H 8 N 2 MW, 120 

Leaflets. M.p. 16. B.p. 140/14 mm. Sol. 

EtOH. Decomp. by acids, alkalis, H 2 0. Un- 

stable in moist air. Reduces OTEL 3 .Ag]Sr0 3 . 

]Sjfo[g >. benzylhydrazine. 
Acetyl deriv. : C 6 H 5 -CH:N-NH-COCH 3 . 
MW, 162. Needles. M.p. 134. 



C 9 H 10 ON 2 . 
Sol. EtOH, 



3IW 5 224. M.p. 206. Sol 

Curtius, Franzen. Ber. 9 1902. 35. 3236. 
Benzylidenehydrazinoacetic Acid 



, 178 

Silky needles. M.p. 156-7. Sol. hot EtOH. 
Spar. sol. H 2 0, Et 2 0. 

Ciirtius, Ber., 1890, 23, 3030. 

BenzyUdene-m~liydrazmobenzoic Acid 

(m- Carboxyphenyl-benzylidenehydrazine ) 

COOH 



C 14 H 12 2 N 2 MW, 240 

Plates. M.p. 173. Sol. EtOH, AcOH. 
Spar. sol. H 2 0. Does not reduce Fehling's. 
WoH, Scbiff, Ber., 1900, 33, 2754. 

Benzylidene-p-hy dr azinobenz oic Acid 

(p-Garboxyphenyl-benzylidenehydrazine). 
Et ester: C 16 H 16 O 2 N 2 . MW>268. M.p. 160. 
Thorns, Ritsert, Chem. Zentr., 1921, I, 
584. 

a-BenzyHdeneliydrociiiiiainic Acid. 
See cc-Benzylcinnamic Acid. 
BenzyHdene-lactic Acid. 
See Styrylglycollic Acid. 
4-Benzylidene-lepidine . 
See 4-Styrylquinoline. 
Benzylidenelutidine. 
See Methylstyrylpyridine, 
Benzylidenemalonic Acid (Benzalmalonic 
acid] 



c 6 H 5 -CH:c< COOH 



C 10 H 8 4 MW, 192 

Prisms. M.p. 195-6 decomp. Sol. hot 
H 2 O, EtOH, Me 2 CO, AcOEt. Spar. sol. CS 2 , 
cold H 2 0, AcOH, CHC1 3 , C 6 H 6 , ligroin. Heat 
of comb. 1056-8 Cal. k (first) = 4-08 X 10" 3 
at 25; k (second) == 3-15 X 10" 6 . 

Di-Me ester: 12 H 12 4 . MW, 220. M.p. 
45. B.p. 171/10 mm. 

ffl ester : C 12 H 12 4 . MW, 220. M.p. 85. 

Di-Et ester: C 14 H 16 4 . MW, 248. M.p. 32. 
B.p. 215-17 /30 mm., 196/14 mm., 176-775 
mm. Df 1-1045. <* 4 1-5389. 

Di-isopropyl ester : b.p. 127-30/0-5 mm. 
rig 1-5197. 

Diallyl ester: b.p. 144-770-5 mm. < 
1-5489. 

Di-l-menthyl ester : needles from EtOH. 
M.p. 95. 



Bexizytidene-1-raphthylaxnine 



Beiijzylimiziodlacetic Acid 



DicMoride : C 10 H 6 2 CL>. MW, 229. Xeedies 
from pet. ether. M.p. 77*. 

Diamide: C IQ B., Q O^ t) . MW, 190. M.p. 
189-90. 

Mononitrile : see a-Cyanocinriamio Acid. 

Di-nitrile : C 10 H 6 X 2 . MW, 154. M.p. 87. 

Knoevenagei, Ber., 1898, 31, 2605. 
Claisen, Crismer, Ann., 1883, 218, 131. 
Staudinger, Ott, Ber., 1911, 44, 1636. 
Odell, Hines, J. Am. Chem. Soc., 1913, 
35, 82. 

BenzyKdene-1-napMhylamine (Benml-&.- 
no/phthyla m ine) 




MW,231 

YeUow leaflets. M.p. 73. Sol. EtOH. Et 2 0. 
Insol. H 2 0. 

Bucherer, Schwalbe, Ber., 1906, 39, 2812. 

BenzyKdene-2-napMhylamiiie (Benzal-$- 

naphthylamine) . 

Pale yellow needles. M.p. 103. Sol. CHC1 3 . 
Mod. sol. hot EtOH. 

BMCltlHcf): yellow cryst. M.p. 162-3. 
Unstable. 

Claisen, Ann., 1887, 237, 273. 

B enzylidene-m-nitr oaniline 




C 13 H 10 0>N 2 MW, 226 

Yellow needles. M.p. 73 (66). 

Miller, Plochl, Ber., 1892, 25, 2053. 
Bogoslovskii, Vatulya, J. Gen. Chem. 
U.S.S.S., 1945, 15, 653. 

Benzylidene-p-nitroaniline. 

YeUow needles. M.p. 117-18. Sol. hot 
EtOH, Me 2 CO, C 6 H 6 . Spar. sol. Et 2 0. Insol. 
ligroin. 

Schwalbe, Ber., 1902, 35, 3302. 

Benzylidenephenetidine. 

See under Benzylideneaminophenol. 
Benzylidenephthalide 




C 15 H 10 2 MW, 222 

Monoclinic prisms. M.p. 108. Sol. hot 

EtOH. Insol. H 2 0. 
Allo-. 
Pale yellow cryst. M.p. 185-7. 

Weiss, Sauermann, Ber., 1925, 58, 2736. 



Benzylidenepinacolin. 

See tert. -Butyl styryl Ketone. 
1-Benzylidenepropionic Acid. 
See a-Methylcizmamic Acid. 
2-Benzylidenepropionic Acid. 
See Styrylacetic Acid. 
BenzyKdeneqnmaldine. 
See 2-Styrylqninoline. 
Benzylidenesuccinic Acid. 
See Phenylitaconic Acid. 
Benzylidenethiosemicarbazide. 
See UTider Benzaldehyde. 
B enzylidene-o-t oluidine 

CH, 



C 14 H 13 N ' MW, 195 

Practically colourless oil. B.p. 314 (309- 
10/745 mm.), 176/15 mm. Df 1-041. < 
1-635. 

Lachowicz, Monatsh., 1888, 9, 698. 

Auwers, Ottens, Ber., 1924, 57, 446. 

Mailhe, Bull. soc. chim., 1919, 25, 321. 

B enzylidene-m-toluidine . 

Pale yellow oil. B.p. 315/775 mm. 

B 2 HCl : m.p. 199-200. 

Law, J. Chem. Soc., 1912, 101, 154. 

Benzylidene-p-toluidine. 
Yellowish cryst. M.p. 35. B.p. 318/755 
mm., 178/11 mm. 

Law, J. Chem. Soc., 1912, 101, 154. 

Strain, J. Am. Chem. Soc., 1928, 50, 2218. 

Benzylidene-m-2-xylidine (Benzal-m~xyli- 
dine) 

CH 3 



MW, 209 



on. 



Busch, Ber., 1899, 32, 1009. 



Benzylidene-m-4-xylidine. 

Yellow oil. B.p. above 300. 

Michaehs, Ann., 1893, 274, 235. 

Benzylidene-p-xylidine (Benzal-p-xylidine) . 
Pale yellow cryst. M.p. 102-3 (96). DiL 
min. acids > ^p-xylidine + benzaldehyde. 
MchaeHs, Ann., 1893, 274, 235. 

Benzyliminodiacetic Acid 



CuH 13 4 N - MW, 223 

Needles. M.p. 197-8 decomp. Behaves to 
alkalis as monobasic acid. 



1-BenzyHndole 



2T8 



4-Benzyl-levulinic Acid 



Nitrate: colourless needles. M.p. 117 de- Picrate: yellow prisms from EtOH. M.p. 



comp. 

Hydrockloride : decomp. at 197. 
Diamide: C^H^OAV MW, 221. Pale 
yellow needles 4- 1H*0" m p. 159, aahyd. 166. 
Di-nitrile: CnH^X,. MW, 185. Prisms. 
M.p. 45 3 . Hydrochloride : m.p. 105. 

Dubsky, Dlngemanse, Ber., 1921, 54, 
2659. 

1 -BenzyMndole (S-Benzylindole) 



C 15 H 13 N 




X-CH 2 -C 6 H 5 

MW, 207 

Needles. M.p 45. Sol. EtOH, Et 2 3 CHC1 3 , 

C 6 H 6J ligroin. 

Antrick, Ann., 1885, 227, 363. 

2-Benzylindole . 

Cryst. from pet. ether. M.p. 86. 
N-lfe: C 16 H 15 ISr. MW, 221. Cryst. from 
Et 2 0-pet. ether. M.p. 65. Picrate: brick 
red needles from Et 2 0. M.p. 97. 

Picrate : brick red needles from MeOH. M.p. 
115. 

Julian, Pikl, J. Am. Chem. Soc., 1933, 55, 
2108. 

3-Benzylindole . 

M.p. 111. 

Picrate : m.p. 113. 

Robinson, Cornforth, West, B.P. 550,060, 
(Chem. Abstracts, 1944, 38, 1077). 

Benzyl iodide (&-Iodotoluene) 

C 6 H 5 -CH 2 I 
C 7 H 7 I MW, 218 

Cryst. M.p. 24. B.p. 93 /10 mm. Decomp. 
on dist. at ord. press. Sol. EtOH, Et 2 0, C 6 H 6 . 
Spar. sol. CS 2 . Insol. H 2 0. D 25 1-7335. 

Kumpf, Ann., 1884, 224, 126. 
Spath, Monatsh., 1913, 34, 1995. 
Fischer, Ber. s 1915, 48, 101. 

4-Benzylisophthalic Acid. 

See Diphenylmethane-2 : 4-dicarboxylic Acid. 
1 -Benzylisoquinoline (Phenyl-l-isoquinolyl- 
methane) 




C 16 H 13 N " ' ~ MW,219 

Prisms from CHCl 3 -pet. ether. M.p. 56. 

B.p. 211-13/11 mm., 140~50/1 mm. 
B,HCl: needles from EtOH-Et 2 0. M.p. 

175. 
B 2 ,H 2 PtCL : reddish needles from H 9 0. 

M.p. 216. 



. 

MetModide : yellow needles. M.p. 247-8. 
Rugheimer, Ber. y 1900, 33, 1719. 
Spath, Berger, Kuntara, Ber., 1930, 63, 

139. 
Pictet, Grains, Ber., 1910, 43, 2387. 

3-Benzylisoquinoline (PJienyl-%-isoqidnolyl- 
metkane). 

" B.p. 311' 



Sol. C 6 H 6 . 



Spar. 



Prisms from EtOH. M.p. 104. 
23 mm. Very sol. CHC1 3 . ~ " " 
sol. Kgroin. 

B,HN0 3 : needles. M.p. 136-7. 

Bz,H<>PtCl : needles + 1H 2 O. M.p. anhvd. 
216-17 ". 

Picrate : needles. M.p. 199. 

Riigheimer, Ber. 9 1900, 33, 1719. 

4-Benzylisoquinoline (PhenylA-isoquinolyl- 
metkane). 

Colourless plates. M.p. 118. B.p. 238/23 
nun. Spar, volatile in steam. 

BfrH^PtClfrlH^O : m.p. anhyd. 219-20. 

B^SOt : m.p. 208-9. 

MetModide : m.p. 188. 

Ethiodide : m.p. 188-9. 

Picrate : m.p. 191. 

Riigheimer, Friling, Ann., 1903, S26, 265. 

Benzyl isothiocyanate (Benzyl mustard oil) 

C 6 H 5 -CH 2 N:CS 

MW, 149 

Occurs in cress oil. B.p. 243, 124-6/12 
mm. Insol. H 2 0. 

Schneider, Clibbens, Hullweck, Steibelt, 
Ber., 1914, 47, 1248. 

1-Benzyl-lactic Acid. 

See l-Hydroxy-2-phenylisobutyric Acid. 
2-Benzyl-lactic Acid. 
See l-Hydroxy-3-phenylbutyric Acid. 
2Benzyl-levulinic Acid (2-Aceto-3~phenyl- 
n-butyric acid) 



C 8 H 7 NS 



C 12 H 14 3 MW, 206 

Cryst. from dil. EtOH. M.p. 99. B.p. 
230-50/4 mm. Decomp. on dist. at ord. 
pressures. NaHg >- 3-hydroxy-2-benzyl-n- 
valeric acid. 

Erdmann, Ann., 1889, 254, 202. 

4-Benzyl-levulinic Acid (3-Keto-5-phenyl- 
caproic acid, S-keto-S-phenyl-n-hexoic acid) 

C 6 H 5 -CH 2 -CH 2 -CO-CH 2 -CH 2 -COOH 
C 12 H 14 3 MW, 206 

Needles from H 2 0. M.p. 89. Sol. CHCL, 
hot H 2 0. Spar. sol. CS 2 . H 2 S0 4 > reddish- 
yellow col. 

Erdmann, Ann., 1890, 258, 131. 



Benzylmaleic Acid 



279 



AVBenzyl-l-napMhylaxnine 



Benzylmaleic Acid. 
See Phenylcitraconic Acid. 
Benzylmalonic Acid (%-Phenylisosuccinic 
acid) 



C 10 H 10 4 MW, 194 

M.p. 117 (121). Sol H 2 0, EtOH, Et 2 O, hot 
C 6 H 6 . Heat of eomb. C p 1085-9 Gal., C, 1085-6 
CaL k (first) = 1-51 X 10-* at 25 ; k (second) = 
0-49 X 1CH at 100. Heat at 180 > C0 2 + 
iiydrocinnamic acid. 

Di-Me ester: C^H^O,. MW, 222. B.p. 
282-5. 

Di-Et ester: C 14 H 18 O 4 . MW, 250. B.p. 
300, 169/12 mm. DJJ 1-077. 

Di-n-butyl ester : C 18 H> 6 4 . MW, 306. B.p. 
154. n% 1-4760. 

Di-p-nitrobenzyl ester : C,>4H 20 O 8 N 2 . MW, 
464. M.p. 119-5. 

Dichloride: C 10 H 8 9 C1 2 . MW, 231. B.p. 
141/15 mm. 

Diamide : C 10 H 12 2 N 2 . MW 5 192. Needles. 
M.p 225. 

M ono-n itrile : see a-Cyanohydrocinnamic Acid. 

Di-nitrile : benzylmalonitrile. C 10 H 8 N 2 . 
MW, 156. M.p. 91 (79). B.p. 174/23 mm. 
Sol. EtOH, Et 0. 

Di-hydrazide: needles. M.p. 164. B,2HCl : 
m.p. 135. 

Dianilide : m.p. 217. 

Claisen, Crismer, Ann., 1883, 218, 139. 
Hantzsch, Osswald, JBer., 1899, 32, 649. 
Leuchs, J&er., 1911, 44, 1509. 
Darapsky, J. praJct. Chem., 1917, 96, 301. 
Wojcik, AdHns, J. Am. Chem. Soc., 1934, 
56, 2424. 

Benzylmenthol (1 -Methyl-4:-i8opropyl-2-ben- 
zylcyclohexanol-3) 

CH-CH 3 



2 9 9H 



CH 2 -C 6 H 5 



H 2 C CHOH 

CH-CH(CH 3 ) 2 

C 17 H 26 MW, 246 

Exists in two forms, (i). Cryst. from Et 2 : 
m.p. 111-2. (ii). Oil : b.p. 180-3/10 mm. 

WaUach, Ann., 1899, 305, 263. 
Benzyl Mercaptan (Thiobenzyl alcohol) 



C 7 H 8 S MW, 124 

B.p. 194-5. D 20 1-058. Oxidises in air to 
dibenzyl disulphide. 

Me ether : methyl benzyl sulphide. C 8 H 10 S. 
MW, 138. B.p. 195-8. 

Et ether : ethyl benzyl sulphide. C 9 H 12 S. 
MW, 152. B.p. 214-16 (218-24). 



Phenyl ether : phenyl benzyl sulphide. 
C 13 H 12 S. ^IW 5 200. M.p. 42. 

Benzyl ether : see Dibenzyl sulphide. 

Smythe, J. Chem. Soc., 1913, 104, i, 174. 
Hess, Leaper, TJ.S.P., 1,729,615, (Chem. 

Abstracts, 1929, 23, 5474). 
Adams, Bramlet, Tendick, J. Am. Chem. 

Soc., 1920, 42, 2369. 

National Aniline Co., U.S.P., 1,842,414, 
(Chem. Abstracts, 1932, 26, 1618). 

Benzyl Mercaptan carboxylic Acid. 
See ca-Mercapto-o-toluic Acid. 
Benzylmesitylene. 
See Phenylmesitylmethane. 
B enzylmethylaniline . 
See MethylbenzylaniHne. 
BenzyLnaphthalene, 
See Phenylnaphthylmethane. 
4 - Benzyl - 1 -naphthol (Phenyl^-hydroxy- 
naphthylmethane) 

OH 




C 17 H 14 MW, 234 

Prisms from C^H 6 . M.p. 125-6. 
Acetyl : m.p. 87-8. 
Benzoyl : m.p. 103. 

Me ether : C 18 H 16 0. MW, 248. M.p. 85-7. 
Dziewonski, DziecielewskL, Chem. Ab- 
stracts, 1928, 22, 2164. 
Behagel, Preiensehner, Ber., 1934, 67, 
1375. 

1 - Benzyl - 2 - naphtliol (Phenyl~2-hydroxy- 
naphthylmethane) 

CH 2 -C 6 H 5 




C 17 H 14 ^ ~ MW,234 

Needles from 85% formic acid. M.p. 110. 
B.p. 247~50/15 mm. 

Behagel, Freiensehner, Ber., 1934, 67, 

1375. 
Cf. Bakunin, Altieri, Gazz. chim. ital., 

1903, 33, ii, 488. 

JV-B enzyl-1-naphthylamine ( 1 -Naphthyl- 
benzylamine) 

NH-CH 2 -C 6 H 5 




C 17 H 15 N ' " MW,233 

Needles. M.p. 73. Sol. EtOH, Et 2 0. 

Erote*, Tommasi, Bull. soc. chim., 1873, 

20, 67. 
Berlhigozzi, Gazz. chim. ital., 1920, 50, i, 

215. 
Zechmeister, Truka, Ber., 1930, 63, 2883. 



A T ~Benzyl~2-napMhylamine 

A T -Benzyl-2-napMhyIamiiie 
benzylamine). 

Prisms from Et 2 0. M.p. 6S C . B.p. 405. 
Sol. C 6 H 6 , ligroin. IDTOo > nitroso deriv. 
BMCl : m.p. 219. 
^-Benzoyl ; m.p. 115. 
Picrate : m.p. 140-1. 
Nitroso : m.p. 112. 

Ciusa, Cremonini Gazz. chim. ital. 9 1928, 

58, 153. 
Zechmeister, Truka, Ber., 1930, 63, 2883. 



4-Benzyl~ I - naphthylamine 

aminonaphlhylmethane) 



5/ 



C 17 H 15 N 
M.p. 114-5. 
N-Acetyl : violet cryst. M.p. 208-9. 

DziewonsM, DziecielewsM, Chem. Ab- 
stracts, 1928, 22, 2164. 

6 - Benzyl - 2 - naphthylamine (Phenyl - 6 - 

amino-2-naphthylmethane) . 
Needles. M.p. 95. Turns blue in air. 
N-Acetyl : needles. M.p. 189. 

DziewonsM, WodelsM, Chem. Zentr., 1933, 
I, 774. 

Benzyl 1-naphthyl Ether 

0-CH 2 -C 6 H 5 



MW, 234 



280 Benzylpenaldic Acid 

'2-Saphtkyl- Benzyl 2-zraphth.yl Ketone. 

Needles from EtOH. M.p. 99-5. 
Oxime : m.p. 129. 
PJienylhydrazone : m.p. 165-7. 
Picrate : m.p. 143. 

Luce, Compt. rend., 1925, 180, 145. 

Boiggli, Eeinert, Helv* Chim. Ada, 1926, 
9,67. 

Benzyl naphthyl sulphide. 

See under TMonaphthol. 

sym, .-Benzyl-1-naphthylthiourea 

C 6 H 5 -CH 2 -NH-CS-NH-C 10 H 7 
18 H 16 N 2 S MW, 292 

Cryst. from EtOH. M.p. 172-3. 

Dixon, J. Chem. Soc., 1891, 59, 558. 

siftn.-Benzyl-2-naplitliylthiotirea. 
Plates from EtOH. M.p. 165-6. 

Dixon, J. Chem. Soc., 1891, 59, 558. 

$ym . -B enzyl- 1-naphth.ylur e a 

C 6 H 5 -CH 2 -NH-CO-NH-C 10 H 7 



(Phenyl-4:- 



HW, 233 



C 18 H 16 ON 2 



MW, 276 







C 17 H U 
M.p. 61. B.p. 200/12 mm. 

v. Braun, Reich, Ann., 1925, 445, 233. 

Benzyl 2-naphthyl Ether. 
Leaflets from EtOH. M.p. 99. Sol. EtOH, 
Et 2 0, CHC1 3 , C 6 H 6 . 

Staedel, Ann., 1883, 217, 47. 
Gomberg, Buckler, J. Am. Chem. 8oc., 
1920, 42, 2059. 

Benzyl 1-naphthyl Zetone 
CO-CH 2 -C 6 H 5 



Leaflets. M.p. 203. Cryst. from EtOH. 
French, Wirtel, J. Am. Chem. Soc., 1926, 
48, 1736. 

Benzyl nitrate 

C 6 H 5 -CH 2 -0-N0 2 
C 7 H 7 3 N MW, 153 

Oil. B.p. 106/20 mm. Explodes on heating 
to 180. 

Brunner, Ber., 1876, 9, 1745. 
Nef, Ann., 1899, 309, 171. 

Benzyl nitrite 

C 6 H 5 -CH 2 -0-NO 
C 7 H 7 2 N MW, 137 

OH. B.p. 80~3/35 mm., 71/18 mm. Df 
1-075. ri 1-4989. Decomp. spontaneously. 
Baeyer, Villiger, Ber., 1901, 34, 755. 
Chretien, Longi, Compt. rend., 1945, 220, 
746. 

Benzyl-p-nitrosoaniline (p-Nitrosophenyl- 
benzylamine, p-nitrosobenzylaniline) 




C 18 H 14 MW, 246 

Plates from EtOH. M.p. 66-7. Sol. EtOH, 
Et 2 0. HI >- b enzyl- 1-naphthylmethane. 
Oxime : m.p. 148-52 decomp. 
Phenylhydrazone : m.p. 101. 
Picrate : m.p. 101-2. 

Luce, Compt. rend., 1925, 180, 145. 
Buggli, Eeinert, Helv. Chim. Acta, 1926, 
9, 67. 



C 13 H 12 ON 2 ~ MW, 212 

Greenish cryst. with blue cast. M.p. 129. 
Sol. C 6 H 6 . Spar. sol. cold EtOH, Et 2 0. 
(NH4) 2 S > benzyl-j)-phenylenediamine. 

Nitrosamine : unstable. M.p. 77. 

Boddinghaus, Ann., 1891, 263, 300. 

Benzyloxyethanol . 

See Hydroxyethyl benzy 1 Ether. 
Benzylpenaldic Acid. 
See Penaldic-G Acid. 



BenzylpenicUlenic Acid 



281 



2-Benzylpiperidine 



Benzylpenicillenic Acid. 

See Penicillenic-G Acid. 

Benzylpenicillin . 

See Penicillin-G. 

Benzylpenicilloic Acid. 

See Peniciiloie-Q Acid. 

Benzylpenillamine . 

See Perollamine-G. 

BenzyipenilMc Acid. 

See PenUHc-G Acid. 

Benzylpenilloaldeliyde . 

See PeraOoaldehyde-G. 

Benzylpenilloic Acid. 

See Pemlloie-G Acid. 

Benzylpenillonic Acid. 

See Pemllonic-G Acid. 

Benzylphenacylacetic Acid. 

See 2-Phenyl-2'-benzoylisobutyric Acid. 

Benzylphenacylamine (^-Benzylaminoaceto- 
phenone) 

C 6 H 5 -CO-CH 2 -NH-CH 2 -C 6 H 5 
C 15 H 15 ON MW, 225 

Free base unstable. 

B,HCl: cryst. from EtOH. M.p. 215. 
Spar. sol. cold H 2 0. 

B,HBr: needles. M.p. 201-3. Spar. sol. 
cold H 2 0. 

PJienylhydrazone : leaflets. M.p. 76. 

Picrate : yellow needles. M.p. 151-2. 

Busch, Hefele, J. praJct. CJiem., 1911, 83, 

425. 
Gabriel, Ber., 1914, 47, 1336. 

jp-Benzylphenetole . 

See under 4-Hydroxydiphenylmethane. 
BenzylpkenoL 
See Hydroxydiphenylmethane. 
Benzyl-1-phenylethylamine (a-Phenylethyl- 
benzylamine) 



C 6 H 5 -CH 2 -NH-CH-C 6 H 5 
C 15 H 17 N MW, 211 

d-. 

[a + 56-2 in EtOH. 

B,HCl : m.p. 177. 



d-Tartrate: plates + 2H 2 0. M.p. 62. 
Stable in air. 

1-. 

B.p. 171/15 mm. [oc]| - 56-1 in EtOH. 
d-Tartrate : prisms + 3H 2 from H 2 O. M.p. 
72. Decomp. in air. 

<-. 

B.p. 171/15 mm. Sol. EtOH, Et 2 0. InsoL 
H 2 O. 

B,HCl : prisms from H 2 O, M.p. 184. Mod. 
sol. H 2 0. 

B,HNO Z : needles. M.p. 124. Mod. sol. 
H 2 0. 



66 - SoL 

Oxalate : plates from EtOH.Aq. M.p. 193. 
Spar. sol. H 2 0, EtOH. 

Parck, /. prakt. Chem., 1912, 86, 284. 

Benzyl-2-plieiiylet]iyla2n2iie ($- 

benzylamine) 



C 15 H 17 N MW, 211 

B.p. 327-8, 86-7/15 mm. Misc. with EtOH, 
Et 2 0. 

BJSCl : m.p. 265-6 (254). 
Bjai : m.p. 233. 
B^H^SO^ : m.p. 191-2. 
N-Nitroso : m.p. 142. 
IX-Benzoyl : m.p. 123. 
Picrate : m.p. 146. 

v. Braun, Blessing, Zobel, Ber., 1923, 
56, 1988. 

Benzyl phenyletliyl Ketone (2-Keto-l : 4- 
diphenylbutane) 

C 16 H 16 5 ~ MW,224 

B.p. 206/11 mm. decomp. 
Oxime : m.p. 120. 

Goldschmiedt, Krczmaf, Monatsh., 1901, 
22, 665. 

JV-Benzylpip eridine ( 1 -Benzylpiperidine) 
CH 2 



CH 2 



N- 



C 12 H 17 N MW, 175 

B.p. 133-4 /21 mm., 113/13 mm. InsoL H 2 O. 
Dl 6 0-9625. Tif 1-5227. 
B,HCl : m.p. 178. 

B 2y H 2 PtCl Q : m.p. 191-3. Spar. sol. prac. all 
solvents. 

N-OaAZe : needles + JH 2 from Me 2 CO- 
Et 2 0. M.p. 148. B,HCl : m.p. 135. Picrate: 
m.p. 128. 

Bailie, Tafel, Ber., 1899, 32, 74. 
v. Braun, Ber., 1904, 37, 2920. 
Haase, Wolffenstein, Ber., 1904, 37, 3232. 
I.G., D.K.P., 620,510, (Chem. Abstracts, 
1936, 30, 732). 

2 - Benzylpiperidine (Phenyl - 2 -piperidyl- 
methane). 

Needles. M.p. 32. B.p. 267-8, 139-40/19 
mm., 128/12 mm. Sol. EtOH, Et 2 0. InsoL 

H 2 0. 

B HCl : needles from AeOEt. M.p. 137. 
B 2 ,H 2 PtCl Q : m.p. 216-17 decomp. 
B,HAuCl : m.p. 168-70. 
N-Acetyl : b.p. 189/12 mm. 



3-Benzylpiperidine 282 

N-Benzoyl : m.p. 68. 

'N-Benzenesulphonyl : prisms from ligroin. 
M.p. 65. 

Picjate : dark yellow prisms. M.p. 156-7. 
Methiodide : nT.p. 226. 

Tschitschfbabffl, Chem. Zentr., 1902, II, 

597. 

Bryans, Pyman, J. Chem. Soc. y 1929, 550. 
Overhoff, Wibaut, Eec. trav. chim , 1931, 

50, 972. 
Adkins, Kuick, Farlow, Wojcik, J. Am. 

Chem. Soc., 1934, 56, 2425. 
Veer, Goldschmidt, Eec. trav. chim., 1946, 

65, 793. 

3-Benzylpiperidine (Phenyl-3-piperidyl- 
methane). 

Viscous liquid. B.p. 278-9. Insol. H 2 0. 
Strong base. Absorbs C0 2 from air. 

B 2 ,HJPtCl^ : m.p. 191-2 decomp. 

B,HAuCl : yellow powder. M.p. 138-40. 
Tschitschibabin, Ber., 1903, 36, 2711. 

4 -Benzylpiperidine (Phenyl - 4 -piperidyl- 
methane). 

M.p. 6-7. B.p. 279, 150-2/17 mm. Sol. 
EtOH,Et 2 0. Insol. H 2 0. D? 0-9972. Absorbs 
C0 2 from air. 

B,HCl: white leaflets from AcOEt. M.p. 
172-3. 

: m.p. 197. 
V: m.p. 145-6. 

Picrate : golden yellow leaflets from EtOH. 
M.p. 187-8. 

"N-Benzenesulphonyl : needles from EtOH. 
M.p. 118. 

Tschitschibabin, Chem. Zentr., 1902, II, 
597. 



m.p. 183. 
Picrate : prisms from benzene. M.p. 140-1. 

Laforge, /. Am. Chem. Soc., 1928, 50, 

2484. 

Bryans, Pyman, J. Chem. Soc., 1929, 549. 
Veer, Goldschmidt. Bee. trav. chim., 1946, 

65, 793. 

3-Benzylpyridine ($-Benzylpyridine, phenyl- 
3-pyridylmethane) . 

Needles. M.p. 34. B.p.286/740inm. Sol. 
EtOH, Et 2 0. Insol. H,0. 

B,HNO^: m.p. 140. " 

BfrHoPtCls : m.p. 200-2 decomp. 

Picrate : m.p. 119 (126-7). 

Tschitschibabin, Ber., 1903, 36, 2711. 
Laforge, J. Am. Chem. Soc., 1928, 50, 
2484. 

4-Benzylpyridine (y-Benzylpyridine, phenyl- 
4:~pyridylmethane) . 

B.p. 287/742 mm., 180-1/31 mm. Sol. 
EtOH, Et*0. DJ 1-0756. 
B,HNO~: m.p. 110. 
BiJBJPtClt : m.p. 207. 
Picrate : fine needles. M.p. 140-1. 
BfrZnClt : m.p. 161. 

Laforge, J. Am. Chem. Soc., 1928, 50, 

2484. 

Veer, Goldschmidt, Eec. trav. chim., 1946, 
65, 793. 



Acid (I-Keto-3-phenyl- 



B enzylpy r uvic 

butyric acid) 

C 6 H 5 -CH 2 -CH 2 -CO-COOH 
C 10 H 10 Oa MW, 178 

Plates. M.p. 48-50. Cryst. + 1|H 2 from 

Bryans, Pyman, J. Chem. Soc., 1929, 550. H 2 0. Sol. hot H 2 0, EtOH, Et^O, C 6 H 6 , 
Overhoff, Wibaut, Eec. trav. chim., 1931, CHC1 3 . Spar. aol. CS 2 . 

Amide : 10 H n O 2 N. MW, 177. M.p. 180. 

Phenylhydrazone : m.p. 144-5. 

Oxime : m.p. 165. 

Semicarbazone : m.p. 175 decomp. 

Fittig, Petkow, Ann., 1898, 299, 28. 



50, 973. 

Veer, Goldschmidt, Eec. trav. chim., 1946, 
65, 793. 



1-Benzylpropionaldeh.yde . 

See a-Methylhydrocinnamaldeliyde. 
1-Benzylpropionic Acid. 
See a-Methylhydrocinnamic Acid. 
2-Benzylpropionic Acid. 
See 3-Ph.enylbutyric Acid. 
2-Benzylpyridine (a-Benzylpyridine, phenyl- 
2 -pyridylmethane ) 



4-Benzylquinoline 

methane) 



( Plienyl-y-quinolyl- 





CH 2 -C 6 H 5 



C 12 H n ]Sr MW, 169 

B.p. 276/742 mm., 148-9/16 mm., 93-4/l 

mm. Sol EtOH, Et 2 0. Insol. H 9 0. Dg 1-067. 
B,HN0 3 : m.p. 116. 



C 16 H 13 ISI MW, 219 

Yellow, viscous oil. B.p. 223/19 mm. 
B^H 2 S0^2H 2 0: m.p. 105-8, anhyd. 132-3. 
Picrate: m.p 178. 
Methiodide : orange plates. M.p. 226. 

Rabe, Pasternack, Ber., 1913, 46, 1026, 
1032. 



3-BenzylsaJicylic Acid 



283 



BenzyltMourea 



3-Benzylsalicyiic Acid (~2-Hydrovydiphenyl- 
methane-3'Carboxylic acid, $-benzyl-o~hydroxy- 
benzoic acid) 

COOH 

OH 



MW, 228 
M.p. 133-5. 

Monsanto Chein. Co., U.S.P., 2,042,343, 
(Chem. Abstract*, 1936, 3D, 4998). 

5-Benzyisalicylic Acid (4c>Hydroxydiphenyl- 
methane~3-carboxylic acid, 5-benzyl-o-hydroxy- 
benzoic acid). 

Needles from H 9 0. M.p. 135-6. Sol. EtOH, 
Et 2 0, CHC1 3? C^. FeCl 3 > violet-blue col. 

Me ester : C 15 H U O 8 . MW, 242. M.p. 79- 
80. B.p. 134-8/l mm. 

Me ether: C 15 H 14 3 . MW,242. M.p. 201-3. 

Foldi, Ber., 1928, 61, 1609. 
Oliverio, Piccalagua, Chem. Abstracts, 
1934, 28, 6135. 

1-Benzylsemicarbazide (a.-Benzylsemicarb- 
azide) 



C 8 H n ON 3 MW, 165 

Prisms from 20% EtOH. M.p. 155. Sol. 
EtOH, Me 2 CO, AcOH. Mod. sol. CHC1 3 , H 2 0, 
AcOEt. Spar. sol. Et 2 0, C 6 H 6 . Insol. ligroin. 
Reduces Fehling's slowly in cold. 

Hale, Lange, J. Am. Chem. Soc., 1920, 42, 
115. 

2-Benzylsemicarbazide ($-Benzylsemicarb- 
azide) 

H 2 N-CO*Is-]SfH 2 



C 8 H 31 ON 3 MW, 165 

Prisms from CHCl 3 -ligroin. M.p. 135-6. 
Sol. EtOH, Me 2 CO, CHC1 3 , AcOH. Mod. sol. 
H 2 0, C 6 H 6 . Spar. sol. Et 2 0. Insol. ligroin. 
Slowly reduces warm Fehling's. Above m.p. >- 
1 -benzylsemicarbazide. 

Bougault, Leboucq, Compt. rend., 1928, 

186, 957. 
Hale, Lange, J. Am. Chem. Soc., 1920, 

42, 115. 

4-Benzylsemicarbazide (-Benzylsemicarb- 
azide) 

C 6 H 5 -CH 2 -NH-CO-NH-NH 2 

CgH-uONg MW, 165 

White cryst. powder. M.p. 111. Sol. H 2 0, 
Et 2 0, EtOH, CHC1 3 , hot C 6 H 6 . Insol. pet. 
ether. 

B,HCl: white needles. M.p. 224-5. Sol. 
H 2 O, EtOH. 

'N-Acetyl : m.p. 145. 



Oxalate : m.p. 135 2 decomp. 

Hopper. Chem. Abstracts, 1928, 22, 3640. 
Wilson, Hopper, Crawford, J. Chem. Soc., 
1922, 121, 866. 

Benzylstyrylacetic Acid. 

See 1 : 4-Diphenyl-l-butylene-3-carboxvlic 

Acid. 

Benzyl styryl Ketone (syni.-Pheni/lbenzi/l- 
ideneacetone) 

C 6 H 5 -CH 2 -CO*CH:CH-C 6 H 5 

c 16 H 14 o mv, 222 

Cryst. M.p. 71. Sol. C 6 H 6J EtOH-Et 2 0. 
Distils undecomp. Brilliant yellow sol. in cone. 
H S0 4 . 

Oxime : m.p. 102-3. 

Goldschmiedt, Krczmaf , Monatsh., 1901, 
22, 659. 

Benzylsuccinic Acid 

C 6 H 5 -CH 2 -CH-COOH 
CH 2 -COOH 

C 1]L H 12 4 MW, 208 

Needles or leaflets. M.p. 161. Sol. hot 
H 2 0, EtOH, EtoO. Spar. sol. CHC1 3 . CS 2 , C 6 H 6 . 
fc = 9-1 x 10- 5- at 25. 

Di-Me ester: C 13 H 16 4 . MW, 236. B.p. 
159/7 mm., 128-35/l-5 mm. 
Imide : m.p. 97-8. 
Di-hydrazide : m.p. 146. 
Anhydride: C U H 10 3 . MW, 190. Needles. 
M.p. 102. Sol. EtjO, CHC1 3 . C 6 H 6 . 

Fittig, Brooke, Ann., 1899, 305, 40. 
Reynolds, Am. Chem. J., 1911, 46, 209. 
Haworth, Jones, Way, J. Chem. Soc., 
1943, 10. 

Benzyl sulpbide. 

See Dibenzyl sulphide. 
Benzyl sulphone. 
See Dibenzyl sulphone 
Benzylsulpbonic Acid. 
See Toluene-a-sulphonic Acid. 
Benzyl sulpnoxide. 
See Dibenzyl sulph oxide. 
Benzyl tbiocyanate 

C 6 H 5 -CH 2 -SCN 

C 8 H 7 NS MW, 149 

Prisms. M.p. 43 (36-8). B.p. 256 (235 
decomp.). Sol. Et 2 0, CS 2 , hot EtOH. Insol. 
H 0. 

Barbaglia, Ber., 1872, 5, 687. 

Benzyltbiourea (Benzylthiocarbamide, car- 
pasemine) 

C 6 H 5 -CH 2 *NH-CS-NH 2 
C 8 H 10 N 2 S MW, 166 

Isolated from seeds of Carica papaya^ Linn. 
Prisms. M.p. 165. Spar. sol. cold EtOH. 
Insol. cold H 2 0. 

Acetate : m.p. 131. 



BenzyltMouretliane 



284 



Berberal 



Jfethiodide : m.p. 103-5 3 . 

DIxon, J, C%ez. Soc., 1891, 59, 552. 

Pause, Paranjpe, Proc. Indian Aca-d. Sci., 
1943, ISA, 140. 

BenzyltMonretliaiie (Benzylth iocarbam Ic 
ester) 



C 10 H 13 ONS " " MW, 195 

B.p. 125-30/0-3-0-4 mm. Heat with C 2 H 5 I 

> Isonierlc comp. C 6 H 5 CH>XH-CO-SC 2 H 5 . 

Schneider, Clibbens, Hiifiweck, Steibelt, 

Ber., 1914, 47, 1248. 

B enzyltoluene. 

See Phenyltolylmethane. 

JV-Benzyl-o-toluidine (o-Tolylbenzylamine) 

CH 3 
/\NH-CH 2 -C 6 H 5 



C 14 H 15 N ' MW, 197 

Cryst. M.p. 56 from EtOH, 60 from Et 2 0. 
B.p. 200-10/15-25 mm., 176/10 mm. Sol. 
most org. solvents. Insol. H 2 0. Rapidly turns 
green on exposure to light. D 5 1-01416. n* 
1-58611. 
B,HCl : m.p. 165-6. 

Courtot, Petitcolas, Butt. soc. chim., 1926, 

39, 452. 
Law, J. Chem. Soc., 1912, 101, 158. 

N - Benzyl - m - toluidine (m - Tolylbenzyl- 
amine). 

Pale yellow oil. B.p. 312, 179*5/10 mm. 
Df 1-00833. < 5 1-58451. 
B,HCl : m.p. 199-200. 

Courtot, Petitcolas, Bull. soc. chim., 1926, 

39, 452. 
Law, J. Chem. Soc., 1912, 101, 158. 

N - Benzyl - p - toluidine (p Tolylbenzyl- 
amine) . 

Leaflets. M.p. 19-20. B.p. 312-13, 205- 
15/10-15 mm., 181/10 mm. Sol. EtOH, 
Et 2 0. Insol. H 0. Df 1-00641. < 5 1-58324. 
B,HCl : needles. M.p. 181-2. 

Courtot, Petitcolas, Bull. soc. chim., 1926, 

39, 452. 

Law, J. Chem. Soc., 1912, 101, 158. 
Kirssanow, Iwastchenko, Bull. soc. chim., 
1935, 2, 2121. 

Benzylurea (Benzylcarbamide) 

C 6 H 5 -CE 2 -NH-CO*NHo 

C 8 H 10 ON 2 " MW, 150 

Needles from EtOH. M.p. 147-8. Sol. 
EtOH. Mod. sol. hot H 2 0. 

Paterno, Spica, Ber., 1876, 9, 81. 

Benzylurethane (Benzylaminoformic ethyl 
ester) 

C 6 H 5 -CH 2 -NH-CO-OC 2 H 5 
C 10 H 13 2 N MW, 179 



Leaflets from Hgroin. M.p. 48-9 (44). 

Basterfield, Wright, J. Am. Chem. Soc., 
1926, 48, 2367. 

3-Benzylvaleric Acid. 

See 4-Phenylisocaproic Acid. 

Benzylvaler olactone . 

See under 3-Hydroxy-2-benzyl-w- valeric Acid. 

Berbamine 



CH 9 




MW, 608 

Alkaloid ofBerberis vulgaris and jB. thunbergii. 
Leaflets + 2H 2 from EtOH. M.p. anhyd. 
156. Cryst. from pet. ether, m.p. 197-210. 
[aft 5 + 108-6 in CHC1 3 . 

Me ether: C 38 H 4 oO 6 N 2 . MW, 622. M.p. 
182 

Et ether: C 39 H M 6 N 2 . MW, 636. M.p. 188. 

Bruchhausen, Gericke, Arch, pharm., 

1931, 269, 119. 

Riidel, Arch, pharm., 1891, 229, 631. 
Santos, Chem. Abstracts, 1930, 24, 1647. 



Berberal 



OCH 3 




MW, 383 

Glistening plates. M.p. 148-50. Hyd. > 
co-aminoethylpiperonal-carboxylic anhydride + 
^-opianic acid. 

Perkin, Robinson, J. Chem. Soc., 1910, 

97, 321. 
Perkin, J. Chem. Soc., 1890, 57, 1079. 



Berberic Acid 



285 



Bergaptol 



Berberic Acid (5 : Q-Dihydroxy-2-methyl- 

benzoic acid, 3 : 4-dihydroxy-o-toluic acid) 
CH, 



OH 

C 8 H 8 4 MW, 168 

Needles + 1H 2 0. M.p. anhyd. 165 decomp. 
Sol. EtOH, Et 2 O, hot H 2 O. H 2 S0 4 > yellow 
col. in cold, green on heating. EeCl 3 > bluish- 
green. Dist. > homocatechol C0 2 . 
Perkin, J. Chem. Soc., 1889, 55, 88. 

Berberilic Acid 

OCH 3 

^0/\COOH HOOC/\OCH 3 
-Ol JCH 2 -CH 2 -NH-COl J 

MW, 417 

Cryst. M.p. 177-82 > anhydride. Sol. 
EtOH. Heat > ca-aminoethylpiperonal-car- 
boxylic anhydride + isovanillie acid. 

Di-Me ester: C^H^OgN. MW, 445. M.p. 
173-4. 

Anhydride : see Berberilic Anhydride. 

Perkin, J. Chem. Soc., 1890, 57, 1048. 
Berberilic Anhydride (Anhydroberberilicacid) 

OCH 3 

H^/VT I-OOH og rNocH, 




C 20 H 17 8 N ' " MW, 399 

Lustrous cryst. M.p. 236-7. Sol. hot 
AcOH. Spar. sol. EtOH, C 6 H 6 , Me 2 CO, ligroin. 

Me ester: C 21 H 19 8 ^- MW, 413. M.p. 178-9. 

Acetyl deriv. : C 22 H 19 OgN. MW, 441. M.p. 
139-40. 

Chloride: C 20 H 16 7 NC1. MW, 417-5. M.p. 
167. 

Amide: C 20 H 18 7 N 2 . MW, 398. M.p. 203. 

Anilide: C 26 H 22 7 N 2 . MW,474. M.p. 199. 

Perkin, J. Chem. Soc. 3 1890, 57, 1037. 
Berberine 

" |OCH 3 
'OCH 3 

HOH 




C 20 H 19 5 N MW, 353 

Alkaloid from Hydrastis canadensis, Herberts 
vulgaris and other plants. Yellow needles. 
M.p. 145. Cryst. from H 2 with 6H 2 0, from 
CHCL with 1 CHCL. Sol. 22 parts H 2 O at 
20. Sol. EtOH. Spar. sol. CHC] 3 , C 6 H 6 . 



Prac. insol. Et 2 0. Optically inactive. Zn -f- 
H 2 S0 4 >* tetrahvdroberberine. 

B } HCl,2B 2 Q : yellow cryst. Spar. sol. H*O. 
Insol. Et 2 O, CHC! 3 , cold EtOH. 
B,H^80^ : sol. 100 parts H 2 0. 

Haworth, Perkin, E/ankin, J. Chem. Soc., 

1924 ? 125, 1686. 
Perkin, Bay, Robinson, J. Chem. Soc., 

1925, 127, 740. 

Mizuno, Yoshida, Jap. P., 99,230, (Chem. 
Abstracts, 1934, 28, 2468). 

BerBeronic Acid (Pyridine-2 : 4 : 5-tricarb- 
oxylic add) 

COOH 



HOOCf 



JCOOH 



C 8 H 5 6 N MW, 211 

Cryst. from H 2 in prisms with 2H 2 0. Loses 
1H 9 on standing in air. M.p. 235, anhyd. 
243. Sol. hot H 2 O. Spar. sol. hot EtOH. 
Insol. Et 2 0, C 6 H 6 f CHC1 3 . FeCIg ^ blood- 
red col. 

Mumm, Hiineke, Ber., 1918, 51, 150. 
Bergamottin (Bergaptol geranyl ether) 



H 
H' 



9H 2 -CH:C-CH 2 -CH 2 -CH:C-CH 3 
CH 

V 



C 21 H 22 4 MW, 338 

Constituent of bergamot oil. Cryst. from 
Et 2 O-pet. ether, M.p. 59-61. Decomp at 
200-230 in high vac. >- bergaptol. 

Spath, Kainrath, Ber., 1937, 70, 2272. 
Bergapten (Bergaptol methyl ether) 
CH 3 CH 

sq A X V 
HC V\A/ CO 



C 12 H 8 4 MW, 216 

Constituent of bergamot oil (about 5%). 
Needles from EtOH. M.p. 188. Spar. sol. 
EtOH. Sublimes. KOH fusion > phloro- 
glucinol. 

Thorns, Baetcke, Ber., 1912, 45, 3705. 
Cf. Karrer et aL, Helv. Chim. Acta, 
1920, 3, 541 ; 1921, 4, 718. 



Bergaptol 



OH CH 

V 



U H 6 4 



H( V V/ Y CO 



MW,202 



Bergenin 



286 



Betuligenol 



Constituent of bergamot oil. Xeedles from 
AcOEt. H-p. 277-8 (evac. tube). 
Me ether : see Bergapten. 
Geranyl ether : see Bergamottin. 

Spath, Socias, Ber., 1934, 67, 59. 
Spath, Kubiczek, Ber., 1937, 70, 1253. 



Bethogenin 



Bergenin 



OH CH 



H 



'0 
C 14 H 16 9 ^ MW,328 

Occurs in root of Saxifraga siberica. Prisms 
+ IKp from H 2 0. M.p. anhyd. 138-9 
(130), soHdrfying and re-melting at 230. 
[ tt ] D 37.3 in EtOH, - 47-3 in H 2 0. Re- 
duces warm Fehling's. Bitter taste. 
Penta-acetyl : m.p. 199-203 (192-5-3-5). 
Di-Me ether: C 16 H 90 9 . MW, 356. Cryst. 
+ 2H 2 0. M.p. 89, aoahyd. 194-6. 

Tschitschibabin, Kirssanow, Korolew, 

Woroschzow, Ann., 1929, 469, 98. 
Garreau, Machelart, Compt. rend., 1880, 

91, 942. 
Ssadikow, Guthner, Biochem. Z. 9 1927, 

190, 347. 
Morelle, Compt. rend., 1881, 93, 646. 

Bessisterol. 

See a-Spinasterol. 

Betaine (Anhydride or lactone of carboxy- 
methyltrimethylammonium hydroxide, lycine, oxy- 
neurine) 

(CE 3 ) 3 N-CH 2 -COO~ 
C 5 H U 2 N MW, 117 

Occurs in beetroot, cottonseed, etc. Prisms 
or leaflets. M.p. 293. Isomerises at the m.p. 
to methyl ester of dimethylaminoacetic acid. 
Crystallises from aq. solvents with 1H 2 0, in 
which the free acid HO-N(CH 3 ) 3 -CH 2 COOH is 
present (k = 7-0 x 10~ 13 at 25). The H 2 is 
lost at 100, giving betaine. Hydrated form 
sol. H 2 0, EtOH. Spar, sol Et 2 0. Cone. 
KOH.Aq. > trimethylamine. 

BMCl : acidol. M.p. 227-8 decomp. 

B,HBr : m.p. 233 decomp. 

B,HI : m.p. 200 (188-9). 

B,HAuCl : plates, m.p. 200-9, and rhombo- 
hedra m.p. 248-50 decomp. 

Picrate : yellow prisms from H 2 0. M.p. 183. 

Waterman, Proc. Acad. Sci. Amsterdam, 

1918, 20, 88. 
Beychler, Bull soc. chim. Belg., 1923, 32, 

247. 
Takayama, U.S.P., 1,870,319, (Ohem. 

Abstracts, 1932, 26, 5783). 

Betelphenol. 
See Chavicol. 




CH-CH, 



MW, 444 



Isolated from Beth root via crypt ogenin. 
Colourless needles from MeOH. M.p. 193-^r . 
Ppd. from EtOH by digitonin. [a]|f 98-4 
in dioxan. 

Acetyl : cryst. from EtOH-C 6 H 6 . M.p. 230- 
2. W!> 4 -944 in dioxan. 

Benzoyl : needles from MeOH-C 6 H 6 . M.p. 
212-15. [a]! 4 -65-1 in dioxan. 

Barusch, Noller, et al, J. Am. Chem. Soc., 
1942, 64, 2581 ; 1943, 65, 1786. 

Marker et al., /. Am. Chem. Soc., 1943, 
65, 1658 ; 1947, 69, 2167, 2386, 2395. 

Betol. 

See under 2-Naphthol. 
Betonicine 

HO-9H 9H 2 
HC CH-COO- 



MW, 159 



H 3 C CH 3 



Present in Betonica officinalis and Stachys 
silvatica, and is stereoisomeric with turicine. 
Prisms from EtOH. M.p. 252 decomp. [<x]g 
36-60 in H 2 0. Spar. sol. cold EtOH. 

B,HCl : needles or prisms from EtOH. M.p. 
232 decomp. 

B,HAuCl: yellow leaflets. Decomp. at 230-2. 

B 2 ,H 2 PtCl 6 : prisms + 2H 2 from H 2 0. M.p. 
225-6 decomp. 

Goodson, Clewer, /. Chem. Soc., 1919,, 

115, 923. 
Kiing, Z. physiol. Chem., 1913, 85, 217. 

Betulic Acid. 

See Betulinic acid. 

Bettiligenol (p-y-Hydroxybutylphenol) 
OH 



[ 2 -CH 2 -CHOH-CH 3 
C 10 H 14 2 MW, 166- 

Aglycone from betuloside. Cryst. M.p. 81-5. 
D 20 1-156. [a]gf, -18-5 in EtOH. 

Me ether : 11 H ie 2 . MW, 180. B.p. 158- 
9/14 mm., 130-l/4 mm. D 20 1-0361. <' 



Betiilin 



287 



Betulonic Acid 



1-5237. B [a]g -17-5 in EtOH. Ox. * 

anisic acid. p-Nitrobenzoyl : m.p. 285 decomp. 

Benzoyl : m.p. 68-9. [a]g 5 -12-8 in EtOH. 

Sosa, Ann. Chim., 1940, 14, 5. 
Delepine, Sosa, Bull. soc. chim., 1942, 9, 

771, 

Betulin (Betulinol) 



H 3 C 



H 





/OH, 



V 



H 3 C/ U M3H 2 

MW,442 

Triterpene alcohol present in birch bark. 
Needles from EtOH. M.p. 251-2. [a]g -f 
19-96 in Py. Mod. sol. hot EtOH, hot Et 2 0, 
hot CHClg, hot C 6 H 6 , hot AcOH, AcOEt. Spar, 
sol. ligroin. Insol. H 2 0. Sublimes with part 
decomp. H-COOH > allobetulin formate. 

Acetyl deriv. : leaflets from EtOH. M.p. 260. 

Diacetyl : prisms from EtOH. M.p. 216-7. 
[a] D + 22 in CHClg. 

Dipropionyl : m.p. 164-5. 

Dibutyryl : m.p. 107. 

Dibenzoyl : needles from Py-EtOH. M.p, 
181. [a]*? 5 +43. 

Di-p-bromobenzoyl : needles from EtOH-C 6 H 6 . 
M.p. 221-2. [ag? + 44. 

Di-m-nitrobenzoyl : needles from C 6 H 6 - 
EtOH. M.p. 267-8. [ag? + 38-4 in CHC1 3 . 

Di-anisoyl : cryst. from AcOH. M.p. 192-3. 
[afe 7 + 49 in CHC1 3 . 

Acid phthaloyl : needles from EtOH.Aq. M.p. 
180-2. [a]g +24-5. 

Allo-. 




Plates from EtOH. M.p. 260-1. [a]g 
+ 48-3. 

Formyl : needles. M.p. 311-12. [alg+51-l. 

Acetyl : plates. M.p. 277-8. [a] 1 ^ + 54-2. 

Benzoyl: leaflets from EtOHC 6 H 6 . M.p. 
275-6. [a]Jf + 70-3. 

m-Nitrobenzoyl : leaflets from EtOH-AcOH. 
M.p. 277-8. [aff + 69-2 in CHC1 3 . 

p-Bromobenzoyl : cryst. from EtOH-C 6 H 6 . 
M.p. 276. [a] 6 + 66-2 in CHC1 3 . 



Anisoijl: cryst. from AcOH. M.p. 295. 
[ a ]* j. 77-3 in CHC1 3 . 

Acid succinyl : leaflets from EtOH-C 6 H 6 . 
M.p. 265-6. [aJf+48 . 

Acid pJithaloyl : needles from EtOH. M.p. 
260-1. [ag 5 + 58. 

Ruzicka, Brenner, Helv. CMm. Acta, 

1940, 23, 1325. 
Ruzicka et aL, Helv. Chim. Acta, 1934, 

17, 426. 
Ruzicka, Briingger, Gustus, Helv. CMm. 

Ada, 1932, 15, 634. 
Ruzicka, Isler, Helv. Chim. Acta, 1936, 

19, 511. 

Schulze, Pieroh, Bar., 1922, 55, 2332. 
Dischendorfer, Grillmaver, Monatsh., 

1926, 47, 241, 419. 
Davy, Halsall, Jones, J. Chem. Soc., 1951, 

2696. 
Davy, Halsall, Jones, Meakins, ibid., 2702. 

Befrulinic Acid (Betulic acid, gratiolone) 



COOH 




C 30 H 48 3 J\iW, 456 

Unsaturated monobasic triterpene hydroxy- 
acid, isolated from Comics florida, Linn., 
Zizyphus vulgaris, Lamark, cabbage and other 
sources. Also obtained by ox. of betulin. Plates 
or needles +EtOH from EtOH. M.p. 316-18. 
Mllei *+ 7-89 in Py . Sol. Py. Spar. sol. EtOH, 
Me 2 CO, AcOEt, CHC1 3 , C 6 H 6 . Na salt almost 
insol. H 9 O. 

Acetyl: plates from EtOH. M.p. 289-91. 
M8.1 +7-70 in CHC1 3 . 
Benzoyl : m.p. 341-4 decomp. 
Me ester : needles from MeOH. M.p. 223-4. 
MSBi +8-01 in CHC1 3 . Acetyl : m.p. 290-2. 
Benzoyl : m.p. 248-50 decomp. 

Ruzicka, Lamberton, Christie, Helv. Chim* 

Acta, 1938, 21, 1706. 
Robertson, Soliman, Owen, J. Chem. 8oc, 9 

1939, 1267. 

Maurer, Meier, Reiff, Ber., 1939, 72, 1870. 
Davy, Halsall, Jones, J. Chem. Soc.,, 
1951, 2696. 

Betulinol. 

See Betulin. 

Betulonic Acid 
C 30 H 46 3 MW, 454 

Oxidation product of betulin. Needles or 
rosettes from EtOH. M.p. 253 decomp. [<%]]> 
+31 in CHC1 3 . 



Betuloside 



288 



Bilirubin 



Me ester: cryst. from Et,O-MeOH. M.p 
165. [a] D 31-5 in CHCI 3 ." Oxime : cryst 

from EtOH. M.p. 23S C deeomp. 

Semicarbazom : scales. M.p. 282-3. 

Ruzicka, Eey, Helv. Ckim. Ada, 1941, 

24, 529. 

Kawaguti, Kim, /. Pkann. Soc. Japan, 
1940, 60, 595. 

Betuloside (Betuligenol-2-d-glitcopyranoside) 
C 16 H 24 7 MW, 333 

Glucoside isolated from Betula alba. Colour- 
less cryst. powder. M.p. 190 corr. [a]|> 85 
-42-0~ in MeOH. [a]J? s -44-4 in H 2 0. 
Spar. sol. EtOH, Et 2 0, Me 2 CO, H 2 O. Sol. 
10% NaOH.Aq. Hyd. > glucose + betuli- 
genol. 

Dibenzoyl : m.p. 136-7 corr. [a]J> 8 36-7 in 
EtOH. 

Sosa, Ann. chim., 1940, 14, 5. 

BMlawanol 

C 21 H 32 2 MW, 316 

Constituent of the marking nut, Semecarpus 
anacardium. B.p. 215~245/4 mm. 
Hydro deriv. : m.p. 56-8. 

Bastogi, Sharma, Siddiqui, Journal of 
Scientific and Industrial Research 
(India], 1948, 78, No. 5, 61, (Ghem. 
Abstracts, 1948, 42, 7998). 



Bicuculline 




C 20 H 17 6 N MW, 367 

Constituent of Dicentra cucullaria, Gorydalis 
sempervirens, G. aurea, G. nobilis, Pero., and G. 
platycarpa. Plates from CHCl 3 -MeOH. M.p. 
215, (196, 177). Sol. CHC1 3 . Spar. sol. 
MeOH, EtOH. 

Manske, Can. J. Research, 1932, 7, 265 ; 
1933, 8, 210, 407 ; 1933, 9, 436 ; 1940, 
18, 288. 

Groenewoud, Robinson, /. Ghem. Soc., 
1936, 199. 

cis-Bicyclo-[3 : 3 : 0]-octane 
H 2 C CH CH 2 

HCv 
oO 

\_ 

JdLoG GJE1" 



B.p. 136-136-5. Df 0-8638. ri 14595. 
Cope, Sctunitz, J. Am. Ghem. Soc., 1950, 
72, 3056. 

Bicyclo-[4 : 2 : 0]-octane 



9 
C 



H 2 CH 



CH 

C 8 H 14 MW, 110 

B.p. 136. Df 0-8573. n$ 1-4613. 

Reppe, ScMchting, ELlager, Toepel, Ann., 
1948, 560, 1. 

czs-Bicyclo-[3 : 3 : 0]-octanone-2 

H 2 C CH CO 

H 2 C^ I \H 2 

H 2 C CH CH 2 

C 8 H 12 MW, 124 

B.p. 50/2-3 mm. Df 1-0060. ri 1-4766. 
Semicarbazone : cryst. from EtOH. M.p. 
178*8-180;2. 

2 : 4-Dinitrophenylhydrazone : two forms, (i) 
M.p. 1 10- 113. (ii) M.p. 140-140-2. 

Cope, Schmitz, J. Am. Chem. Soc., 1950, 

72, 3056. 
Cooke, Linstead, J. Ghem. Soc., 1934, 955. 

Bicyclo-[3 : 3 : 0>l-octenone-2 

H 2 CC CO 

H 2 C ,CH 2 

H 2 CC CH 2 

C 8 H 10 MW, 122 

M.p. 17-2-19. B.p. 62/0-9 mm. Df 1-0534. 
ri 1-5202. 

Semicarbazone : m.p. 230-232-2. 

Cope, Schmitz, /. Am. Ghem. Soc., 1950, 
72, 3056. 

Bigit aligenin . 

See Gitoxigenin. 

Bigit alin. 

See Gitoxin. 

Biguanide. 

See Diguanide. 

Bilineurine. 

See Choline. 

Bilirubin (Haematoidine) 



,CH 2 -CH 2 -COOH 



I CH 2 



MW, 110 




, 584 



Biliverdin 



289 



Bisabolene 



Occurs in blood, gallstones and urine. Brown 
cryst. Sol. CHC1 3 , C 6 H 6 , CS 2 . Spar. sol. EtOH, 
Et 2 0. Insol. H 2 0. Absorption max. at 420 muu 
Sol. aq. alkalis to orange-red sols. Ox. > 
biliverdin. 

Di-Me ester : orange cryst., m.p. 204-5 ; and 
red cryst., m.p. 168-9. 

Fischer, Lindner, Z. phmiol. Chem. 3 1926, 

161, 1. 
Eich, Bumstead, Chem. Abstracts, 1935, 

19, 2832. 

Barron, Medicine, 1931, 10, 77 (Bibl). 
Fischer, Haberland, Z. physiol. Ghem., 

1935 232 ^36 

Peterman, U.S.P., 2,049,134, (Ghem. Ab- 
stracts, 1936, 30, 6392). 
Fischer-Orth, Die Chemie des Pyrrols, 

1937,11,621. 
Fischer, PHeninger, Z. physiol. Chem., 

1941, 268, 197; 1942, 274, 231; 

Naturwiss., 1942, 30, 382. 

Biliverdin (Dihydrobilirubin, oocyan, utero- 
verdin) 

CH 3l == 1 CH:CH 2 CH 3fl r ,CH 2 -CH 2 -COOH 

~CH 



N 




N 



CH 2 :CHl=!CH 3 

Suggested structure 
C^H^O^ MW, 582 

Constituent of eggshells of birds and of dog 
placenta. Dark green plates or prisms with 
violet surface colour. M.p. above 300. Spar, 
sol. MeOH, CHC1 3 , Et 2 0. Absorption max. at 
680 m.fx, mm. at 500 mti. Gives Gmelin reaction 
with cone. HM) 3 in CHC1 3 . 

Di-Me ester: C 35 H 38 6 N 4 . MW,610. Cryst. 
from CHCl 3 -pet. ether. M.p. 220-1 corr. 
Absorption max. at 384 and 665 m^. 

Lemberg, Biochem. J., 1934, 28, 978; 

Ann., 1932, 499, 25. 
Lemberg, Barcroft, Proc. Roy. JSoc., 1932, 

110, 362. 
Lemberg, Legge, Chem. Abstracts, 1940, 

34, 6952. 
Fischer, Eeinecke, Z. physiol. Chem., 

1940, 265, 9. 

Fexier, Bull. soc. chim. biol., 1945, 27, 621. 
See also references under Bilirubin. 



Bilobol 



CH 2 -[CH 2 ] 6 -CH:CH-[CH 2 ] 5 -CH 3 





Constituent of fruit of Ginkgo biloba, Linn. 
Xeedles from pet. ether. 3I.p. 36-7. H -f- 
Pt >. hydrobiiobol. 

Di-Me ether: C^JELgO*,. 1IW, 346. B.p. 
250-2/6 mm. 

Fumkawa, 3d. Papers Inst. Phys. Ghem. 
Research, Tokyo, 1935, 26, 178. 

Biocyfcin 



-COOH 



C 16 H 28 4 N 4 S MW, 372 

Biotin complex occurring in yeast extract. 
Cryst. from Me 2 CO.Aq. M.p. 245-52 decomp. 
(slow crystallization), xn.p. 228-30 (rapid 
crystallization). Hyd. > iysine + biotin. 

Wright et al, Science, 1951, 114, 635. 
Folkers et al., J. Am. Ghem. jSoc., 1952, 

74, 1999, 2002. 
Wright et al., ibid., 1996, 2004. 

Biotin ( Vitamin E) 



NH 

H OH 
CH 2 CH*[CH 2 ] 4 *CO-XH-[CH 2 ] 4 - 



9H- 

CH 2 CH-[CH 2 ] 4 -COOH 



C 10 H 16 3 N 2 S MW, 244 

Occurs in yeast, eggs and liver. Bacterial 
growth factor and curative factor for " egg 
white injury." Needles from H 2 O. M.p. 230- 
2 decomp. Sol. H 2 0, EtOH. Spar. sol. 
CHC1 3 , Et 2 0, pet. ether. [a]f +92 in 
NaOH.Aq. 

Me ester : plates from MeOH-Et 2 0. M.p. 
166-7. Sublimes in vac. Sol. MeOH, EtOH, 
CHC1 3 . Spar. sol. C 6 H 6 . Insol. H 2 0, Et 2 0, pet. 
ether. [a]g +57 in CHC1 3 . 
f'J , du Vigneau, J. Biol. Ghem., 1942, 142, 
" f , - 615. 

' Hofmann, Advances in Enzymology, 1943, 
~f >-"^ 3, 289 (Review). 

Bisabolene (Limene) 



C CH 2 



H 2 C 



C-CH 



MW, 318 C 15 H 24 




Diet, of Org. Oomp. I. 



MW, 204 
19 



Bisabolol 



290 



Bixin 



Occurs in opoponax and bisabo! myrrli oils. 
Chief constituent of Chinese star-anise oil. 
B.p. I55~77"12 mm., 118-20^0-5 mm. Df 
0-9223. 7i? 1-4917. 

Trihydrochloride : m.p. 79-80. 

Ruzicka, van Teen. Ann., 1929, 468, 133. 
Ruzicka, Liguori, Helv. Chim. Ada, 1932, 

15,3. 
Jackson, Short, J. Soc. Chem. hid., 1936, 

5, ST. 

Grob, Sprecher, Helv. Chim. Act, 1952, 
35, 885. 



Bisabolol 



CHo 



jEL> G*GEL> 







H 



H 3 C 

C 15 H 26 MW, 222 

B.p. 154-6/12 mm. DJ 8 0-9216. rag 1-4939. 
Dry HC1 > bisabolene trihydrochloride. 

Ruzicka, Capato, Helv. Chim. Acta, 1925, 

8, 270. 
Ruzicka, Liguori, Helv. Chim. Acta, 1932, 

15,3. 

Bis-acenapMliylidene Diketone (Biacene- 
dione) 

09-9=9-90 





C i4 H 12 2 MW, 332 

Orange-red needles. M.p. 287-8. Spar. sol. 

AcOH, C 6 H 6 . Ox. > naphthalic anhydride. 

H 2 S0 4 > green col. 

Mono-phenylJiydrazone : brownish-red cryst. 

M.p. 105-10. 

Dziewonski, Litynski, Ber., 1925, 58, 
2539. 

Bis-trimethylethylene nitrosate. 

See Amylene nitrosate. 
Biurea (Dicarbamylhydrazine) 



Xeedles -f- 1H 8 0. M.p. 190 (193) decomp. 
Cryst. anhyd. from EtOH. Heat > cyanuric 
acid 4- XH 3 . CuS0 4 on KOH sol. > violet 
col. (Biuret reaction). 

N-Me deriv. : allophanic methyiamide. 
CH 3 NH-CO-KH-CO-I\ T H 2 . C 3 H 7 2 N 3 . MW, 
117. Cryst. from H 2 or EtOH. M.p. 166. 

N-Et deriv. : allophanic ethvlamide. 
C 2 H 5 -NH-CO-NH-CO-NH 2 . C 4 H 9 2 N 3 ."MW, 131. 
Prismatic needles from H 2 0. M.p. 153. De- 
comp. above m.p. 

Acetyl deriv.: CB^-CO-NH-CO-NH-CO-NHo. 
Needles from EtOH. M.p. 193. 

Benzoyl deriv. : cryst. from H 2 0. M.p. 220. 

m-Nitrobenzoyl deriv. : cryst. from H*0. 
M.p. 187-190. 

Thiele, Uhlfelder, Ann., 1898, 303, 95. 
Werner, Carpenter, J. Chem. JSoc., 1918, 

113, 699. 

Warren, Wilson, Ber., 1935, 68, 957. 
Adams, U.S.P., 2,401,599, (Chem. 

Abstracts, 1946, 40, 5449). 

Biuret Base (Triglycylglydne ethyl ester) 
NH 2 -CH 2 -CO-[NH-CH 2 -CO] 2 -NH-CH 2 -CO-OC 2 H 5 
C 10 H 18 5 N 4 MW, 274 

Plates. Sinters at 218, chars at 270 with- 
out melting. Sol. H 2 0. Prac. insol. EtOH. 
Et 2 O, C 6 Hg. Aq. sol. shows alk. reaction, and 
gives reactions of the proteins. 

B,HCl : leaflets. M.p. 212-14 decomp. 

B^HJPtClQ^H^O : orange plates. M.p. 112 
decomp. 

Picrate : m.p. 189. 

Fischer, Ber., 1904, 37, 2504. 
Curtius, ibid., 1284. 

Bixane (4 : 8 : 12 : IQ-Tetramethyleicosane) 
CH 3 -CH 2 -CH 2 *[CH 2 -CH(CH 3 )-CH 2 -CH 2 ] 4 -CH 3 
C 24 H 50 MW, 338 

Parent hydrocarbon of bixin series. Obtained 
by red. of bixin derivs. B.p. 218/15 mm., 
16270-5 mm. Spar. sol. EtOH, AcOH. Very 
sol. CHC1 3 , CC1 4 , CS 2 , pet. ether. Df 0-8054. 
ng 14502. 

Kuhn, Ehmann, Helv. Chim. Acta., 1929, 
12, 904. 



C 2 H 6 2 N 4 
M.p. 244-6. 

Jacini, Qazz. chim. ital., 1937, 67, 715. 

Biuret (Allophanamide, ureidoformamide) 



C 2 H 5 2 N 3 



NH 2 -CO-NH-CO-NH 2 



Bixin (Norbixin methyl ester) 

MW? 118 CH 3 0-OC-CH:[CH-C(CH 3 ):CH-CH:] 4 -CH-COOH 
C 25 H 30 4 MW, 394 

From seeds of Bixa orellana, Linn. Violet 
prisms. M.p. 198. Sol. CHC1 3 , hot EtOH. 
Spar. sol. cold EtOH, Et 2 0, C ? H 6 , CS 2 , AcOH. 
Insol. H 2 0. Optically inactive. Absorption 
MW, 103 max. at 523-5, 489, and 457 mpi in CS 2 . 



p-Bixin 



291 



Borneol 



Jfe ester : norbixin dimethyl ester. C JEL 0.. 
MW, 408. M.p. 164 C . 

Kuhn, Winterstein, Helv. Chim. Ada, 

1928, 11, 427. 
Karrer, Helfenstein, Widmer, Itallie, 

ffeZw. OMm. Ada, 1929, 12, 741. 
Kuhn, Ehmann, ibid., 904. 
Blnkes, j&ec. trav. chim., 1929, 48, 603. 
Winterstein, Angew. Chem., 1934, 47, 

315 (Bibl). 

Holmes, Bromund, Science, 1935, 82, 202. 
Zechmeister, Escue, J. Am. Chem. Soc., 

1944, 66, 322. 

|3-Bixin. 

See Isobixin. 

Blepiiarin 
C 16 H 2 o0 10 MW, 372 

Optically active glycoside from Blepharis 
edulis, Pers. Contains 5 OH groups. M.p. 
222. [a]g* +121-5. CICOOEt > penta- 
carbethoxy deriv. 

Penta-acetyl ; needles from EtOH.Aq. M.p. 
161-5. 

Pentakis-p-nitrobenzoyl : m.p. 264 (from 
Py.Aq.). 

Me deriv. : m.p. 130 decomp. 

Lai, J. Indian Chem. Soc., 1940, 17, 269. 

Boldine 

CH 2 

^H, 
xX N-CH 3 
?H 

^2 




C 19 H 21 4 N MW, 327 

Constituent of leaves and stem of Peumus 

boldus, Mol. Plates from C 6 H 6 . M.p. 161-3 

(softens at 156) . Sensitive to light. Bitter taste. 

Di-Me ether : see Glaucine. 

Spath, Tharrer, Ber., 1933, 66, 904. 
Sehlitter, Ber. 9 1933, 66, 988. 

Boletol (5:7: 8-Trihydroxyanthraquinone-I- 
carboxylic acid, purpurin-S-carboxylic acid) 

HO CO COOH 



HO, 



C 15 H 8 7 




MW, 300 



Dyestuff from Boletus satanas and B. badias. 
Red needles from Et 2 0-ligroin. Carbonises at 
275-80. Sol. EtOH, Et 2 O. Spar. sol. H 2 0. 
H 2 2 > hemimellitic acid. 

Triacetyl : yellow prisms from AcOH. M.p. 
above 300. 



Leuco.- 

Penfa-acetyl : colourless prisms from AcOH. 
M.p. 252=. 

TrimetJiyl : diacetate : colourless prisms from 
MeOH. M.p. 213. 

Kogl, Deijs, Ann., 1934, 515, 10. 
Pastac, Chem. Zentr., 1941, I, 1303 
(Review). 

Bombicesterol . 
See Inagosterol. 

BoneDJiie 



^ MW, 564 

Occurs in the gephyrean worm Bonellia viridis. 
Fine dark green needles from Et 2 or toluene. 
Probably similar to mesopyrrochlorine. Forms 
complex salts with metals. 

Lederer, Compt. rend., 1939, 209, 528. 
Boninic Acid 

CH 2 -CH 2 -CH 3 OH 
/\_CO -- /NcOOH 



C 25 H 32 8 3ttW, 460 

Constituent of the lichen Hamalina boninensis, 
Y. Asahina. Plates from C 6 H 6 -pet. ether. 
M.p. 134-5. Sol. most org. solvents. Spar, 
sol. cold C 6 H 6 . Insol. pet. ether. FeCl 3 >- 
reddish-violet col. in EtOH. 

Me ester: C 26 H M 8 . MW, 474. Plates from 
EtOH. M.p. 86. FeCl 3 > red col. in EtOH. 

Asahina, Kusaka, Ber., 1937, 70, 1817. 

Borneol (Bornyl alcohol, Borneo camphor, 
2-hydroxycamphane) 




CH-OH 



C 10 H 18 



MW, 154 



d-. 

Hexagonal plates. M.p. 208. B.p. 212. 
Sol. EtOH, Et 2 0, C 6 H 6 , ligroin. Spar. sol. 
H 2 0. Sublimes. [a]f? + 3744 in EtOH. 
Heat of comb. C v 1464-7 Cal. Dil. HN0 3 * 
rf-camphor. PC1 5 > isobornyl chloride. 

Formyl : b.p. 98-9/15 mm., 90/10 mm. D 22 
1-009. < 1-47078. [a^ + 48-45. 

Acetyl: m.p. 29. B.p. 225-6, 106-7/15 
mm. Insol. H 2 0. [a] D liq. + 44-38. 

Benzoyl : m.p. 25-5. [a] D +43-9. 

ip-Nitrobenzoyl : plates. M.p. 137. Spar, 
sol. cold EtOH. Insol. H 2 0. 

Phenylurethane : m.p. 138. 

Me ether: C 11 H 20 0. MW, 168. B.p. 193-5, 
97_100/38 mm. Df 0-9162. wg 1-46237. 

Et ether : C 12 H 22 0. MW, 182. B.p. 204-5, 
97/20 mm. D? 0-9008. %5 145554. 



Bornesite 



292 



BoswelHc Acid 



Z-. 

Hexagonal plates. M.p. 204 (208-9). B.p. 
210/779 mm. Sublimes. [*$ 37-74 in 
EtOH. Heat of comb. C v 1472-5 Cal. 

Formyl : b.p. 215, 97/15 mm. Df 1-0058. 
M? - 4046, [*] D Uq. -4724 3 . 

Acetyl: m.p. 29. B.p. 223-4 (225-6). 
D? (liq.)0-9855. w# 146635. j>]f?iiq. 4445. 

Oxalate : m.p. 108. [a] D 45-2= in C 6 H 6 , 
51-6 in EtOH. 

Acid succinate : m.p. 60. [x] D 35-2 in 
EtOH. 

Benzoyl : m.p. 25-5. [^ -44-2. 

p-Nitrobenzoyl : m.p. 136. [a] D 33-1 in 



M.p. 210-5. 

Fujita, Cftm. Abstracts, 1928 3 22, 3406. 
Schwyzer, PAarm. .%., 1930, 75, 1275. 
Saisei Sydno K.K., Jap. P., 100,798, 

(Chem. Abstracts, 1934, 28, 3745). 
Hercules Powder Co., U.S.P., 1,961,398, 

(Chem. Abstracts, 1934, 28, 4746). 
Schering-Kahlbaum A.-G., D.R.P., 

582,043, (Chem. Abstracts, 1933, 27, 

5086). 
Hiickel, Kaluba, Ann., 1942, 550, 269. 

Bomesite. 

See under Inositol. 
Bornylamine (AmiTiocamphane) 



MW, 153 




GE 



CH CH 2 



C IO H 19 N 

d-. 

M.p. 163. Sublimes. Sol. most ord. org. 
solvents. InsoL H 2 0. [a]S +47-2 in EtOH. 

B,HCl: needles from H 2 O or EtOH. [a] D 
+23-3 in EtOH. 

B,HN0 3 : m.p. 240 decomp. 

N-Formyl : m.p. 93. [a]?? 43-17 in EtOH. 

N-Acetyl: white leaflets. M.p. 145. [oc] D 
4348 in EtOH. 

TS-Benzoyl : needles from EtOH. M.p. 138-5. 

"N-o-Nitrobenzoyl : needles from EtOH.Aq. 
M.p. 173. [a] 2 D - 22-39 in EtOH. 

N-m-Nitrobenzoyl : needles from EtOH.Aq. 
M.p. 161. [oc]S? - 27-91 in EtOH. 

'N-p-Nitrobenzoyl : needles from EtOH.Aq. 
M.p. 167. [ag> - 16-56 in EtOH. 

Picrate : m.p. 257 decomp. 

M.p. 163. B.p. 200-1. [a]! 50-8 in EtOH. 

B,HCl : m.p. 358. [afe 7 -23-5 in EtOH. 
[a]i 6 -22-3 in H 2 0. 

B,H^SO^ : [a]i> 5 14-8 in H 2 0. 

B^HzSO^ : [a]Jf -20-4 in H 2 0. 

B,HNO Z : decomp. at 202. [og? 21-5 
in EtOH. 



B,HJPtC\ : darkens at 270. 
Picrate : decomp. at 256. 

Goodson, J. Chem. Soc. 9 1927, 930. 
Frankland, Barrow, J. Chem. Soc., 1909. 

95, 2024. 

Ingersoll, Brown, Kim, Beauchamp, Jen- 
nings, J. Am. Chem. Soc., 1936, 58, 1810. 
Krestinskj^ Bard3 T shev, J. Gen. Chem., 
U.SJS.R., 1940, 10, 1894. 

Bornyl chloride (Chlorocamphane, " pinene 
hydrochloride," artificial camphor) 



HC1 




CH CH 2 

MW, 172-5 

Leaflets. Odour very similar to camphor. 
M.p. 132. B.p. 207. Sublimes. Sol. EtOH, 
Et 2 0. InsoL H 2 0. [a] ! D 4 + 30-96 in EtOH. 

Frankfurter, Frary, J. Am. Chem. Soc., 

1906, 28, 1461. 

Rostovskii, Sheremeteva, Chem. Abstracts, 
1936, 30, 1372. 

Bornylene (1:7: 7 -Trimethylbicyclo-[l : 2 : 2]- 
heptene-2) 




C 10 H 16 



H 2 - CH CH 



MW, 136 



M.p. 113. B.p. 146/750mm. Sublimes. 
[a] 2 B -22-27 in C 6 H 6 . KMn0 4 in C 6 H 6 > 
^-camphoric acid. 
(Z-. 

Cryst. from EtOH. M.p. 109-10. B.p. 
146. [aJ D +30-5 in toluene. KMn0 4 .Aq. 
> ^-camphoric acid. 

Meerwein, Joussen, Ber., 1922, 55, 2529. 
Henderson, Caw, J. Chem. Soc., 1912, 

101, 1416. 

Tschugaeff, Budrick, Ann., 1912, 388, 
288. 

Boron triethyl 

B(C 2 H 5 ) 3 

MW, 98 
Fuming liq. B.p. 95. D 23 0-6961. 

Stock, Zeidler, Ber., 1921, 54, 531. 
Boron trimetliyl 

B(CH 3 ) 3 

C 3 H 9 B MW, 56 

Gas at ord. temps. Forms add. comp. with 
1NH 3 , m.p. 56, b.p. 110. 

Stock, Zeidler, Ber., 1921, 54, 531. 
Boswellic Acid 

MW, 456 



C 6 H 15 B 



BoswelHc Acid 



293 



Bracteine 



Two isomeric hydroxytriterpene acids, iso- 
lated from frankincense (Oiibanum), in which 
the (3-acid predominates. 



Botogenin (1%-Ketodiosgenin) 



a-. 



/COOH 




Hexagonal plates from MeOH. M.p. 289 
corr. [<xg> 9 +114-5 in CHC1 3 . 

Me ester: C 31 H 50 3 . MW, 470. Plates from 
MeOH-Et 2 0. M.p. 214r~15 corr. [a]g> + 115-4 
in CHC1 3 . Acetyl: m.p. 229-30 corr. [a]* 9 
+68 in CHCLj. 

Formyl : needles from EtOH. M.p. 254-7 
corr. [ag? + 65-5 in CHClg. 

Acetyl: prisms from CHC1 3 . M.p. 241-3 
corr. [a]i 9 +65-3 in CHC1 3 . Chloride : cryst. 
from hexane. M.p. 195-6 corr. 

/COOH 



'C-H.q 




Suggested f ormula 

Prisms from MeOH. M.p. 238-40 corr. 
[a] D +237 in CHClg. Contains unreactive 
double bond but gives colours with C(N0 2 ) 4 and 
Liebermann-Burchard reagent. Replacement 
of -COOH by -CH 3 > a-amyrin. 

Me ester : prisms from CHCl 3 -MeOH. M.p. 
195 corr. [a] + 161 in CHC1 3 . Acetyl : m.p. 
197-198-5 corr. [a]g + 73-8 in CHCls. 

Formyl : needles from EtOH. M.p. 272-5 
decomp. corr. [a]^ + 91*6 in CHC1 3 . 

Acetyl: cryst. from MeOH. M.p. 273-5. 
[ag? + 68-9 in CHC1 3 . Chloride : m.p. 193. 

Winterstein, Stein, Z. physiol. Chem., 

1932, 208, 9. 

Trost, Chem. Zentr., 1937, II, 3759. 
Simpson, Williams, J. Chem. Soc., 1938, 

686, 1712. 

Euzicka, Wirz, Helv. Chim. Acta, 1939, 

22,948; 1940,23,132; 1941,24,248. 

Huzii, Osumi, J. Pharm. Soc. Japan, 

1940,. 60, 291. 

Jeger, Uber die Constitution der Triterpene, 
Fortschritte der Chemie Organischer 
Naturstoffe, Vol. 7, 1950, p. 1. 




CH-CH, 



j 



BXX N/'V 

C 27 H 40 4 MW, 428 

Sapogeninof Dioscorea mexicana. Cryst. from 
EtOH. M.p. 262. 
Acetyl : cryst. from MeOH. M.p. 248. 

Marker et al., J. Am. Chem. Soc., 1947, 69, 
2167. 

Bourfoonal (^-Hydroxy-S-ethoxybenzaldehyde, 
vanillal, protocatechuic aldehyde 3-ethyl ether) 

CHO 



o*CH,-CH 3 



C 9 H 10 3 



MW, 166 

Strong vanilla-like 



M.p. 76-8 from EtOH. 
flavour. 
4-Acetyl : m.p. 48-9. 
4:-Benzyl : m.p. 57. 
Semicarbazone : m.p. 175. 
Phenylhydrazone : m.p. 124-6. InsoL org. 
solvents. 

2-NitroA-cyanophenylhydrazone : m.p. 308. 
Kloty, Am. J. Pharm., 1930, 102, 274. 
Shorygin, Bogacheva, Chem. Abstracts, 

1942, 36, 3627. 

Yakhilevich, Chem. Abstracts, 1942, 36, 
3628. 

Bractamine 

C 9 H 8 (NCH 3 )(OCH 3 )(OH) 
C n H 15 2 N MW, 193 

Alkaloid of Papaver bracteatum. Cryst. from 
EtOH. M.p. 216. Optically inactive. Sol. 
CHC1 3 , 10 % NaOH. Spar. sol. hot EtOH, Et 2 0. 
InsoL cold Py, xylene, H 2 0. FeCl 3 > green 
col. 

B,HCl : cryst. from EtOH-Et 2 0. M.p. 143. 

Picrate : m.p. 184-5. 

Methiodide : cryst. from EtOH. M.p. 220-1. 

Kisenev, Konovalova, /. Gen. Chem. 
U.S.S.K., 1948, 18, 142, (Chem. Ab- 
stracts, 1948, 42, 5037). 

Bracteine 

C 16 H 10 (NCH 3 )(OCH 3 ) 2 (OH) 2 
C 19 H 21 4 lSr MW, 327 

Alkaloid of Papaver bracteatum. Cryst. from 
Et 2 0. M.p. 230 decomp. [a]*? +120 in 



BrasHic Acid 



294 



Brazilein 



EtOH. Sol EtOH, CHC! 3 . Spar, sol Et.O. 
Insol. H 2 0. FeCL > green col. 

BJSCl : m.p. 258 s . 

BJSCIO^: m.p. 231-2 D . 

Mefhiodide : m.p. 205-15'. 

Eosenev, Elonovalova, J. Gen. CJiem* 
U.S.S.B., 1948, 18, 142 3 (CTiew. Ab- 
stracts, 1948, 42, 5037). 



BrasiHc Acid, 
See Brazilic Acid. 
Brassicasterol (7 

:n 3 




CH: 




&-Dikt/droe rgosterol) 

,/BUj Y 3 

M-CH:CH-CH-CH(CH 3 ) 2 



HO' 



C 28 H 4e O MW, 398 

Phytosterol from unrefined rapeseed oil. 

Plates -f 1H 2 from EtOH. M.p. 148. [aft 8 

644 in CHC1 3 . Ppt. with digitonin. Bed. 

>- ergostanol. 

Acetyl: plates from EtOH. M.p. 157-8. 
[a]? 65 in CHC1 3 . Tetrabromide : plates from 
CHCLj-EtOH. M.p. 209 decomp. 

Propionyl: plates from EtOH. M.p. 132. 
Tetrabromide : plates from CHCl 3 -EtOH. M.p. 
206 decomp. 

Benzoyl : needles from EtOH. M.p. 167. 

3 : 5-Dinitrobenzoyl : plates from EtOH-C 6 H 6 . 
M.p. 219. [oc]| 5 - 28 in CHC1 3 . 

Toluene--^ -sulpkonyl : m.p. 139-5-40*5. 
[a]|* -61-6 in CHC1 3 . 

Fernholz, Stavely, J. Am. Chem. Soc., 

1939,61,142; 1940, 62,428. 
Windaus, Welsch, Ber. 3 1909, 42, 612. 

Brassidic Acid (Brassic acid, A^-docosenoic 
acid, trans-ewcic add, isoerucic acid) 



C 22 H 42 2 MW, 338 

Present in rape-seed oil. Plates from EtOH. 
M.p. 61*5. B.p. 282/30 mm., 256/10 mm. 
Spar. sol. cold EtOH. DJ 7 0-8585. < oa 1-4347. 
Heat of comb. C p 3290-1 Oal., C, 3284-6 Cal. 
k = 3-25 X 10~ 7 at 18-1. 

Na salt : leaflets. M.p. 245-8. 

Me ester : C^H^O^. MW, 352. M.p. 34-5. 

Et ester: C^H^O*. MW, 366. Leaflets. 
M.p. 30-5. B.p. above~360. n% 1-4587. 

Phenyl ester: C 28 H 46 2 . MW, 414. M.p. 44. 
B.p. 285/12 mm. 



CH 



Chloride 
Amide : 
Nitrile : 
B.p. 257*117 mm. 

Anhydride : needles. M.p. 64 ( 



22 



^ 
22 H 41 N. 



OC1. MW, 356-5. M.p. 14. 
MW, 337. M.p. 94. 
MW, 319. M.p. 22. 



PJienylJiydrazide : m.p. 98. 

Mascarelli, Atti accad. Lincei, 1917, 26, 
I, 71, (Chem. Abstracts, 1918, 12, 362). 

Holde, Zadek, Ber., 1923, 56, 2052. 
Gonzales, Anales soc. espan. fis. quim. 

1926, 24, 156. 

Beimer, Wffl, Ber., 1886, 19, 3321. 
Rankoff, J. prakt. Chem., 1931, 131, 293. 
Keffler, Maiden, Bull. soc. chim. Belg. 3 

1935, 44, 467. 

Brassylic Acid (Undecane-l : 11-dicarboxylic 
add, tridecanedioic acid) 

HOOC-CH 2 -[CH 2 ] 9 -CH 2 -COOH 

C 13 H 24 4 MW, 244 

Needles from EtOH.Aq. or AcOEt. M.p. 114. 
Sol. EtOH, Et 2 0, CHC1 3 . Spar. sol. H 2 0, C 6 H 6 . 

Me ester: C U H 26 4 . MW, 258. M.p. 58. 

Di-Me ester : C 15 H, 8 4 . M^ T , 272. Plates. 
M.p. 36. B.p. 326-8*, 194/11 mm. 

Bi-M ester: C 17 H 32 4 . MW, 300. M.p. 
20. B.p. 204/12 mm. - 

M ester-chloride: 15 H 97 3 01. MW, 290-5. 
B.p. 185~8/5 mm. 

M ester-amide: C 15 H 29 3 K MW 3 271. M.p. 
912 

Diamide : C 13 H 26 2 N 2 . MW, 242. Needles. 
M.p. 177. Sol. EtOH. InsoL H>0. 

Di-nitrile : C 13 H 22 N . MW, 206. B.p. 210- 
215 /16 mm 

Monoanilide : m.p. 1 18*5-9-5. 

Di-anilide : m.p. 160-1. 

Di-p-bromoanilide : m.p. 202. 

Di-o-toluidide : m.p. 142. 

Di-p-toluidide : m.p. 156. 

Holde, Zadek, Ber., 1923, 56, 2052. 

Brazan (PTienylene-Z : %-naphthylene oxide) 




C 16 H 10 MW, 218 

Leaflets. M.p. 202. Cryst from EtOH. 
EtOH sol. shows greenish -blue fluor. 

Sabatier, Mailhe, Compt. rend., 1912, 155, 

260. 
Winterstein, Schon, Z. physiol. Chem., 

1934, 230, 166. 

Brazilein 

HO Q 



0-835. C 16 H 12 5 




OH 



MW, 284 



BrazHic Acid 



295 



Broraaiide 



Oxidation product of braziHn. Reddish- 
brown needles with grey metallic sheen. Sol. 
MeOH, EtOH, CHC1 3 , AcOH, C 6 H 6 . Spar. sol. 
Et 2 O. 

Tri-Me ether : amber prisms from EtOH. 
M.p. 177-8. 

Engels, Perkin, Robinson, J. Chem. Soc., 

1908, 1115. * 

Micovic, Robinson, J. Chem. Soc,, 1937,43. 
Brazilic Acid (Brasilia acid) 
CO 



CH,Ol 




9(OH)*CH 2 -COOH 



Ci 2 H 12 6 MW, 252 

Needles from H 2 or C 6 H 6 . M.p. 129-30. 
Very sol. EtOH, E\0, AcOH, hot C 6 H 6 . Sol. 
CHC1 3 . Spar. sol. pet. ether. 

Semicarbazone : cryst. Decomp. above 160. 
Perkin, /. Chem. Snc., 1902, 81, 226. 
PfeifFer, Heinrich, J. prakt. Chem., 1940, 
156, 241. 



Brazilin 



HO OH 




C 16 H M 5 MW, 286 

In Brazilwood. White or pale yellow cryst. 
from EtOH. Sol. H 2 0, EtOH, Et 2 0. Sol. aq. 
alkalis to deep carmine-red sols. 

Triacetyl deriv : needles. M.p. 105-6. 
Tetra-acetyl deriv. : needles. M.p. 149-51. 
Tri-Me ether : C 19 H 20 O 5 . MW, 328. Prisms. 
M.p. 139-40. In cone. H 2 S0 4 reddish-yellow 
sol. with green fluor. Acetyl : m.p. 174-6. 

Tetra-Me ether : C 20 H 2 o0 5 . MW, 342. Leaf- 
lets. M.p. 137-9. 

Perkin, Ray, Robinson, J. Chem. Soc., 

1928, 1504. 

Pfeiffer, Quehl, Tappermann, Ber. s 1930, 
63, 1301. 



Brein 



H 3 (X y 




Minor triterpene constituent of Manila elemi 
resin. Prisms from EtOH.Aq., needles from 
MeOH.Aq. M.p. 221-2. [aj -r 63-5 in CHC^, 
([]D + 143-4 C ). C(X0 2 ) 4 > yellow col. 
Liebermann-Burchard > reddish-brown col. 

Diformyl derir. : prisms from Me 9 CO.Aq. 
M.p. 220-1. [ajl 1 + 67 in CHC1 3 . 

Monoacetyl : crvst. from Et 2 0-Hght petroleum. 
M.p. 208-5-209. " 

Diacetyl deriv. : prisms from EtOH.Aq. M.p. 
197-8. [oc]i 7 + 70 in CHC1 3 , ([ajff +215-0). 

Dibenzoyl deriv. : cryst. from EtOH or 
Me 2 CO.Aq., m.p. 175-7. Rosettes of needles 
from ligroin, m.p. 209-10. [a]i> 7 +58 in 
CHC1 3 . 

Morice, Simpson, J. Chem. Soc., 1940, 

798 ; 1942, 198. 
Lieb, Mladenovic, Hoffmann, Monatsh., 

1940, 73, 219. 
Biichi, Jeger, Ruzicka, Helv. Chim. Acta-, 

1946, 29, 442. 

British. Anti-Lewisite. 

See 1 : 2-Dithioglycerol. 

Bromacetsil. 

See under Bromoacetaldehyde. 

Bromacetol. 

See 2 : 2-Dibromopropane. 

Bromal (Tribromoacetaldehyde) 

CBr 3 -CHO 
C 2 HOBr 3 MW 3 281 

B.p. 174, 78/26 mm., 61/9 mm. Df 
2-6650. Hot alkalis > bromoform + formic 
acid. 

Hydrate: bromal hydrate. OBr s CH(OH) a . 
C 2 H 3 2 Br 3 . MW, 299. Colourless monoclinic 
prisms + 1H 2 0. M.p. 53-5. 

Diacetyl : ~ tribromoethylidene diacetate. 
CBr 3 CH(OOC-CH 3 ) 2 . M.p. 77-8. 

Di-Et acetal : diethoxytribromoethane. 
CBr 3 CH(OC 2 H 5 ) 2 . B.p. 138~41/22-3 mm. 

Schaffer, JBer., 1871, 4, 366. 

Gaathaug, B.P. 430,608, (Chem. Ab- 

stracts, 1935, 29, 8003). 
Cristol, Haller, J. Am. Chem. Soc., 1946, 

68, 140. 
Balaban, B.P. 586,864, (Chem. Abstracts, 

1947, 41, 6664). 

Bromal Hydrate. 

See under Bromal. 
Bromalide 



Suggested structure 



MW, 442 



C 5 H 2 3 Br 6 MW, 590 

M.p. 158. Sol. Et 2 0. Insol. H 2 0. De- 
comp. by EtOH. 

Wallach, Ann., 1878, 193, 52. 



Bromaull 



296 



Bromoacetaldahyde 



Bromanil (Tetrabromo-p-benzoquinone, tetra- 

bromoquinone) 







Br 



'Br 



^v 



Golden-yellow cryst. M.p. 300. Mod. sol. 
hot EtOH. Spar. sol. cold Et 2 0. Insol. H 2 0. 
Sublimes. 

Kempf, Moehrke, Ber., 1914, 47, 2615. 
Graebe, Weltner, Ann., 1891, 263, 33. 
Holiday, B.P., 274,700, (Chem. Abstracts, 
1929, 23, 2990). 

Hodgson, Foster, J. Chem. Soc., 1942, 
583. 

Bromanilic Acid (3 : Q-Dibromo-2 : 5-dihydr- 
oxy-^-benzoquinone) 

P. 
Br/\OH 

HO!| 







C 6 H 2 4 Br 2 



MW, 298 



Dark red needles or bronzy leaflets . Sublimes . 
Sol. H 0, EtOH to purple sol. Yellow sol. in 
Et 2 0. 

Na salts: NaC 6 H0 4 Br 2