Henry E. (Henry Enfield) Roscoe.

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long, strongly refractive needles, which melt at 127 and readily
sublime. It forms a yellow solution in alkalis. On fusion with
caustic potash resorcinoldicarboxylic acid is formed ; this crys-
tallizes from water in fine, white needles, which decompose on
heating into resorcinol and carbon dioxide. 1 Its constitution has
not boon accurately determined, but the position of the side-
chains is probably OH : OH : CO 2 H : C0 2 H = 1:3:4:6, since
in this arrangement the carboxyls stand in both the ortho-
and the para-relation to the hydroxyls.

Diliydroxyterephthalic acwZ,(OH:OH:C0 2 H :C0 2 H=1 :4:2:5).
This body, which is also known as quinolditarboxylic acid,
is obtained by passing air into an alkaline solution of suc-
cinosuccinic ether (Part II. p. 211) and decomposing the pro-

1 Lewv and Tiemann. licr. Deulsch. Chtm. Ges. x. 2210.

L L 2



516 AROMATIC COMPOUNDS.

duct with sulphuric acid. 1 It may also be readily prepared by
saponifying the ether, and crystallizes from hot water in brownish
yellow, hair-like needles, but from alcohol in deep yellow plates,
while it separates from ether in rhombic tablets or prisms, which
are coloured greenish yellow and show a light blue fluorescence.
A hot supersaturated solution, however, first deposits asymmetric
white and green crystals, the latter of which are less acutely
pointed than the former. On further cooling the rhombic prisms
appear and replace the asymmetric crystals when the solution is
again gently warmed. If, however, the latter are isolated, the
white plates are converted on cooling into the green, which again
become white on warming, so that by alternate heating and cooling
the same crystal can be obtained in either modification an in-
definite number of times. Since the shape of the crystal alters
with the colour, it can be made to present the appearance of a
concertina, alternately elongated and compressed by causing the
changes of temperature to follow one another rapidly. 2

The aqueous solution of the acid shows a faint emerald green
fluorescence, while that of the alcoholic solution is light blue ; it is
coloured a pure deep blue by ferric chloride. When rapidly heated
the acid decomposes with formation of quinol and other products. 3

Normal sodium dihydroxytereplithalate, C 6 H 4 O 2 (CO 2 Na) 2 +
2H 2 O, crystallizes on the spontaneous evaporation of its aqueous
solution, in flat, light brown prisms.

Acid sodium dihydroxyterephthalatc, C 6 H 4 O 2 (CO 2 Na)CO 2 H +
2H 2 O, forms light yellow, lustrous prisms.

Basic sodium dihydroxytercphthalate, C 6 H 2 (ONa) 2 (CO 2 Na) 2 +
12H 2 O. The acid dissolves in caustic soda forming a deep
yellow solution with a strong green fluorescence ; on the addition
of very concentrated caustic soda the basic salt separates in
large transparent crystals, which possess a large number of faces
and appear a faint greenish yellow by transmitted, but light blue
by reflected light.

2271 Dietkyl diliydroxyterephthalate, C 6 H 4 O 2 (C0 2 .C 2 H^) 2 , is
formed by the addition of bromine to a solution of succinosuccinic
ether in carbon disulphide, 4 and by the action of sodium on an
ethereal solution of dibromaceto-acetic ether, 5 CH 3 .CO.CBr 2 .C0 2 .
C 2 H 5 . The latter formation corresponds to that of succino-

1 Herrmann, Ber. Dcutsch. Chcm. Ges. x. 111.

2 Lehmann, ZcitscJi. Kryst. x. 3 ; Herrmann, Ber. Dcutsch. Chcm. Ges. xix. 2229.

3 Herrmann, Ann. Chcm. Plmrm. ccxi. 335.

4 Herrmann, ibid. ccxi. 372; Ber. Dcutsch. Chcm. Gfcs. xvi. 1411; Duisberg,
ibid. xvi. 133 ; Ebert, Ann. Chcm. Pharm. ccxxix. 45. 5 Wcdel, ibid, ccxix 71.



DIHYDROXYTEREPHTHALIC ACID. 517

succinic ether from monobromaceto-acetic ether. It crystallizes
from ether in short, thick prisms or long flat needles, and from
benzene in rectangular, rhombic tablets, which have the colour
of uranium glass and show a light blue fluorescence. It melts
at 133 133'5 and sublimes at a higher temperature in lustrous,
green, flat plates possessing a beautiful blue fluorescence. Its
alcoholic solution is coloured bluish green by traces of ferric
chloride. It dissolves in alkalis forming a deep yellow solution,
with which a concentrated solution of an alkali produces a deep
orange-red precipitate.

Dicthyldiacetoxyter&phthalate, C 6 H 2 (OCO.CH 3 ) 2 (CO 2 .C 2 H 5 ) 2 , is
prepared by heating the ethyl ether with acetyl chloride, and
crystallizes from alcohol in colourless, lustrous plates, which melt
at 115 (Wedel).

Mondhyl dihydroxyterephthalate, C 6 H 2 (OH) 2 (C0 2 .C 2 H 5 )CO 2 H.
When the diethyl ether is dissolved in dilute caustic potash
and the unattacked portion removed after some time by acetic
acid, barium chloride precipitates the barium salt of the acid
ether from the filtrate ; this salt can readily be recrystallized from
hot water, and hydrochloric acid added to its solution precipitates
the mono-ethyl ether of dihydroxyterephthalic acid. It is a
strong monobasic acid, crystallizes from hot water in fine, yellow
needles, and is deposited on the evaporation of its alcoholic solu-
tion in light yellow, transparent, vitreous prisms, which melt at
184. Its solution is coloured bluish violet by ferric chloride.

If the diethyl ether is boiled with alcoholic hydrochloric acid
and zinc, it is again reduced to succinosuccinic ether, which can
therefore be regarded as the ether of a dihydroxydihydrotere-
phthalic acid. The latter is formed in the first stage of the
reaction, but immediately changes into the isomeric compound: 1



II II

HC\/COH H 2 C\/CO

c c

H/ /X \CO 2 .C 2 H 6 H/\CO r <\H

The latter formula is rendered probable by the formation of the
substance from bromaceto- acetic ether, CH 3 .CO.CHBr.CO 2 .C 2 H 6 ,
which occurs with elimination of hydrobromic acid ; it also forms a
i Bcr. Deut*ch. Chcm. Oes. xix. 428.



518 AROMATIC COMPOUNDS.

di-imide, is converted into an oximido-compound by hydroxyl-
amine (Baeyer), and yields both a phenylhydrazide and a di-
phenylhydrazide. 1 On the other hand it yields a diacetyl-com-
pound on heating with acetyl chloride (Wedel), which is more readily
obtained by adding sodium ethylate to its ethereal solution, a
rose-coloured precipitate of C 6 H 4 9! Na 2 (CO 2 .C 2 H 5 ) 2 being formed,
which is immediately converted by acetyl chloride into the com-
pound C 6 H 4 (OC 2 H 3 O) 2 (CO 2 .C 2 H 5 ) 2 (Baeyer). The latter com-
pounds must be looked upon as derivatives of the dihydroxy-
dihydroterephthalic acid into which succinosuccinic ether or
quinonetetrahydrodicarboxylic acid so readily changes.

Dihydroxyterephthalic acid also probably exists in two
forms, as quinoldicarloxylic acid, C 6 H 2 (OH) 2 (CO 2 H) 2 , and as
guinonedikydrodicarboxylic acid, C O 2 H 4 (CO 2 H) 2 , which readily
change into one another. The latter formula is required by
its formation from dibromaceto-acetic ether, while its whole
behaviour corresponds to the former. It may be assumed that
the green modification is the quinone-acid, while the colourless
is the quinol derivative (Herrmann).

A similar case has been observed by Baeyer with regard to
phloroglucinol, which forms a trioxin.e with hydroxylamine, the
trihydroxybenzene being converted into triketohexhydrobenzene
(Part III. p. 394.) : 2

Phloroelncinol. Triketohexhydrobeiizene.

OH CO

A H fl

HO yCH

HO-C\/C-OH

CH

Analogous cases have long been known to chemists ; among
the simplest are nitrous acid arid cyanic acid, which are exceed-
ingly unstable in the free state, but yield stable modifications of

two kinds:

Methyl nitrite. Potassium cyanatc.

CH 3 O N=O K O CEzN

Nitromethane. Methyl isocyauatc.

CH 3 -N/ "> CH 3 -N=C-0



1 Knorr, Bcr. Dentsch. Chem. G'cs. xvii. 2055.
8 Ibid, xviii. 3454 ; xix. 159, 1800.



TRI- AND TETRA-HYDROXYPHTHALIC ACIDS. 519

The constitution of these compounds can therefore be repre-
sented with equal accuracy by different structural, or, as Laar l
names them, tautomeric formulae. The atoms are in continual
motion within the molecule, and one form is converted into the
other when the light and most rapidly moving atoms of hydrogen
are more strongly attracted by one or other of the remaining
atoms. If, however, the hydrogen be replaced by a heavier
atom or molecule, the latter no longer escapes from the sphere
of attraction, and the mobile form is converted into a stable
one.



TRIHYDROXYPHTHALIC ACIDS, C H(OH) 3 (C0 2 H) 2 .

2272 Gallocarloxylic acid, C 8 H 6 7 + 3H 2 O, is formed, together
with pyrogallolcarboxylic acid (p. 378), when pyrogallol or gallic
acid is heated to 130 with ammonium carbonate. It requires
3,000 parts of water at for solution, and crystallizes from hot
water in very fine needles, which become anhydrous at 180
and melt above 270 with evolution of carbon dioxide. Dilute
ferric chloride colours its solution violet, while the concentrated
reagent produces a greenish brown colouration. When heated
in the air with water and an excess of calcium carbonate, the
latter is coloured reddish violet, and when an ammoniacal solu-
tion of the acid is mixed with a solution of bicarbonate of
calcium, a deep violet coloured precipitate is formed, which may
therefore be obtained with spring water containing calcium
carbonate. 2



TETRAHYDROXYPHTHALIC ACIDS,

C 6 (OH) 4 (C0 2 U) 2 .

2273 Tetrahydroxyterephthalic acid. When an ethereal or
alcoholic solution of ethyl dihydroxyterephthalate is treated with
anhydrous nitrogen trioxide, it is converted into ethyl diTiydr-
oxyquinonctcreplithalate, C 6 O 2 (OH) 2 (CO 2 .C ? H 5 ) 2> crystallizing n
yellow prisms, which are slightly soluble in cold water, alec
and ether, more readily in chloroform. The solutions have

i Bcr. Dcutsch. Ckcm. Ges. xviii. 648 ; xix. 730.
3 Brunner and Scnhofor, Monalsk. Ctvm. i. 468.



520 AROMATIC COMPOUNDS.

deep yellowish red colour. When the ether is heated with caustic
soda, a basic salt of dihydroxyquinoneterephthalic acid is formed,
and immediately decomposes on the addition of acids into carbon
dioxide and dihydroxyqidnone, C 6 O 2 H 2 (OH) 2 , which forms small,
black-brown crystals. Nitranilic acid, C b 2 (NO 2 ) 2 (OH) 2 , is
always formed if dihydroxyterephthalic acid be submitted to the
same treatment.

Ethyl tctrakydroxylerephthalatc, C ( .(OH) 4 (CO 2 .C 2 H 5 ) 2 , is ob-
tained by passing sulphur dioxide into a faintly alkaline solution
of the dihydroxyquinone ether, and crystallizes from hot chloro-
form in golden yellow plates, melting at 178. It is converted
by cold caustic soda solution into sodium tetrahydroocyterc-
phthalate, C 6 (OH) 4 (CO 2 Na) 2 , which crystallizes in yellow prisms.
On decomposition with sulphuric or hydrochloric acid, tetra-
hydroxyphthalic acid yields carbon dioxide and tetrahydroxy-
benzene, C 6 H 2 (OH) 4 , which forms yellow needles, melting at
148 . 1

1 Loewy, Her. Dcutsch. Chcm. Gcs. xix. 2385.



INDEX



INDEX.



ACETBHOMAMIDE, 113

Acetmetamidobenzoic acid, 248
Acetmetatoluidc, 62
'i-Acetmetaxylide, 407
s-Acetmetaxylide, 407
y-Acetmetaxylide, 406
Acetmethylparatolnide, 65
Acetometahydroxybeiizideiie acetate.

293

Acetortho-amidobeuzoic acid, 239
Acctorthotoluide, 59
-Acetorthoxylide, 406
r-Acetorthoxylide, 406
Acetoxime benzyl ether, 98
Acetparamidobenzoic acid, 253
Acetparatoluide, 66
Acetparaxylide, 407
Acetphthali7nide, 464
Acctylbenzenylamidoxime 214
Acetylisovamllic acid, 354
Acetylmetahydroxybenzaldehyde, 293
Acetylopianic acid, 506
Acetylorthamidobenzaldehyde, 149
Acetylparahydroxybenzaldehyde, 295
Acetylpamhydroxybenzidene acetate,

296

Acetylparamidobenzaldehyde, 150
Acetylsalicylic acid, 308
Acetyl salicylaldehyde, 288
Acetylsinapic acid, 377
Acetylvanillic acid, 353
Aeetylvanillin, 347
Acid ammonium hippurate, 189
Acid ammonium phthalate, 456
Acid barium liydroxamate, 208
Acid barium orthosulphobenzoate, 268
Acid bariumphthalate, 457
Acid calcium benzarsenate, 277
Acid ethyl hemipinate, 511
Acid ethyl metasulphobenzoate, 271
Acid ethyl a-nitrophthalate, 474
Acid ethyl v-nitrophthalate, 474
Acid metatoluidinc oxalate, 61
Acid o-mcthyl hcmipinate, 510
Acid /8-mcthyl hemipinate, 511



Acid methyl sulphiuidephthalate, 478
Acid paratoluidine oxalate, 64
Acid potassium benzarsenate, 277
Acid potassium benzhydroxamate, 208
Acid potassium benzophosphinate, 276
Acid potassium hemipinate, 510
Acid potassium sulphiuidephthalate,

Acid potassium sulphoparahydroxy-

benzoate, 336
Acide quiniqiie, 382
Acid silver sulphinidephthalate, 478
Acid sinapin sulphate, 375
Acid sodium benzhydroxamate, 208
Acid sodium dilivdroxyterephthalate,

516
Addition products of isophthalic acid,

481
Addition products of phthalic acid,

469
Addition products of terephthalic acid,

486

Adjacent Dinitroparatoluidine, 71
Adjacent metadihydroxybenzoic acid,

360

Aes-cioxaUc acid, 363
Aldehydes, 447
Aldehydovanillic acid, 508
Aldehydohydroxybcnzoic acids, 491,

502

Alizaric acid, 450
Allyl benzoate, 162
Aloi'sol, 402
Amarine, 140
Amarythrin, 428
Amido-anisic acid, 338
Amido-azotoluenes, 77
Amidobenzenyl-phenylene-ainidinc,206
Amidobenzoic acid percyanide, 248
Amidobenzylamines, 120
Amido-derivatives of the xylenes, 405
Amidol^emipinic acid, 511
Amidohemipinylphenylphydrazide,512
Amido-isophthalic acid, 482
Amidomeconin, 501
Amidometa-azotoluene, 78
Amidometatoluic acids, 418



524



INDEX.



Amidomethylnorhemipinic acid, 514
Amido-opianylphenylhydrazide, 508
Amidortho-azotoluene, 77
-Amido-orthocresol, 26, 51
y-Amido-orthophenol, 26
Amido-orthotoluic acids, 415
Anrido-<|/-meconin, 501
a-Amidoparacresol, 20
-Amidoparacresol, 30
y-Amidoparacresol, 30
Amidoparahydroxybenzoic acid, 335
a-Amidoparatoluic acid, 421
Amidophenylmetabenzoglycocyamine,

253

Ainidophthalic acids, 475
a-Amidophthalic acid, 475
v-Amidophthalic acid, 475
a-Amidosalicylic acid, 317
3-Amidosalicylic acid, 318
Amido-substituted benzylamines, 116
Amidosulphobenzoic acids, 275
Amidoterephthalic acid, 489
Amidotoluenes, 54
Amido-uramidobenzoyl, 242
Amidoxylenes, 405
Ammonium benzidene sulphate, 137
Ammonium benzoate, 160
Ammonium gallate, 368
Ammonium metahydroxybenzoate, 321
Ammonium parahydroxybenzoate, 328
Ammonium salicylate, 303
Ammonium terephthalate, 484
Amygdalacere, 131
Amygdalin, 130
Amyl benzoate, 162
Amyl hippurate, 191
Amyl orsellinate, 433
Amyl salicylate, 306
Anhydridesofparahydroxybenzoicacid,

331

Anhydro-amidohemipinic acid, 512
Anhydro - amidomethylnorhemipinic

acid, 514

Anhydrobenzodiamidobenzene, 205
Anhydrous benzoic acetic acid, 167
Aniletic acid, 316
Anilido-ethoxytolu-quinone anilido,

49

Anilidohydroxytoluquinone, 49
AnilidohydroxytoliKjuinone anilide, 49
Aniline, 297

Aniline lourde speciale, 56
Aniline oil, 55
Aniline orange, 31
Anis-amide, 333
Anis-anilide, 333
Anisbenzanishydroxylamine, 3 12
Anisbcnzethylhydroxylamine, 340
Anisbenzhydroxamic acid, 340
Anis-dibenzhydroxylamine, 341
Anise alcohol, 284
Anisenyloxime compounds, 339
Anisethylbenzhydroxylamine, 341
Anishydroxamic acid, 339



Anisic acid, 329

Anisic acid, substitution products of,

336

Anisic anhydride, 332
Anisonitril, 334
Anisuric acid, 333
Anisyl chloride, 332
Anthranil, 240

Anthranilcarboxylic acid, 240
Anthranilic acid, 297
Antimony derivatives of toluene, 86
Archil, 42

Arsendiparatolyl chloride, 85
Arsendiparatolyl trichloride, 85
Arsenditolyl oxide, 85
Arsenic Compounds of Benzyl, 125
Arsenic derivatives of toluene, 84
Arsenobenzoic acid, 277
Arsenorthotolyl chloride, 85
Arsenorthotolyl dioxide, 86
Arsenorthotolyl oxide, 85
Arsenparatolyl chloride, 84
Arsentolyl oxide, 85
Arsentribenzoic aoid, 278
Arsentritolyl dichloride, 85
Asymmetric diamido-azotolnene, 80
Asymmetric dibenzyl thiocarbamide,

124

Asymmetric dibenzyl urea, 123
Asymmetric ethylbenzoyl urea, 178
Asymmetric metadihydroxy ben zoic

acid, 359
Asymmetric diphenylbenzenylam id i 1 1 c,

204

Azo-aceto-acetic benzoic acid, 267
Azobenzenesalicylic acid, 319
Azobenzoic acids, 265
Azo- derivatives of benzoic acid 265
Azo-derivatives of toluene, 75
Azomalonic-benzoic acid, 268
Azonitrom^thanebenzoic acid, 267
.Azo-orcin, 52
Azophenylmethyl, 181
Azo-opianic acid, 512
Azotoluenes, 75
a-Azotoluidine, 79
0-Azotoluidine, 79
Azoxybenzoic acids, 265
a- Azoxy toluidine, 78
3-Azoxytoluidine, 79



BADIANIC ACID, 329
Barbatic acid, 402, 435
Barium amidohemipinate, 511
Barium benzoate, 161
Barium benzylsulphonate, 108
Barium chlorobenzylsulphoiiatc', 108
Barium diamidobenzoate, 259
Barium a-dinitrobenzoate, 234
Barium j9-dinitrobenzoate, 234
Barium y-dinitrobenzoate, 234



INDEX.



525



Barium 5-dinitrobenzoate, 235

Barium e-dinitrobenzoate, 235

Barium diuitrosalieylate, 317

Barium gallate, 369

Barium hippurate, 189

Barium homohydroxysalicylate, 438

Barium isophthalate, 479

Barium lecanorate, 434

Barium mecouinate, 500

Barium metabromobenzoate, 224

Barium metahydroxybenzoate, 321

B.irium metanitrobeuzoate, 231

Barium methylnoropianatc, 503

Barium opianate, 504

Barium opianylsulphite, 507

Barium ornithurate, 193

Barium orsellinate, 432

Barium orthobromobenzoate, 223

Barium orthonitrobenzoate, 230

Barium parabromobenzoate, 224

Barium parahydroxybenzoate, 328

Barium parauitrobenzoate, 232

Barium para-orsellinate, 43*5

Barium protocatechuate, 352

Barium pyrogallolcarboxylate, 379

Barium quinate, 384

Barium salicylaldehydc, 287

Barium salicylate, 303

Barium terephthalate, 484

Basic barium nitroparahydroxybenzo-

ate, 335

Basic copper potassium salicylate, 304
Basic copper quiuato, 384
Basic lead pyro-gallolcarboxylate, 379
Basic sodium dihydroxytereuhthalate,

516

Benzaldehyde, 129
Benzaldehyde-green, 135
Benzaldeliydc oxyiodide, 13-7
Ben/aldoxime, loO 1
Benzamic acid, 246
Benzamide, 172, 199
Benzamide hyd roehloride, 174
Benzanilide, '] 74
Be uzani I idim idoch loride, 203
Bunzanisbenzhydroxylamine, 341
Bunzanishydroxamic aoid, 340
Benzarsene chloride, 277
Beuzarsene iodide, 277
Benzai sonic acids, 277
] Jisiizarseiiious acid, 277
Bonzdianishydroxylamine, 342
Benzene, 297
Benzenyl alcohol, 194
Benzenyl amidines, 1 95
Beuzenylamidophenate, 206
Beiizenylnmidothiophenate, 206
Benzenylamidoxime, 212
Benzenylamidoximemetacarboxylic

acid, 480
Benzenylamidoximeparacarboxylic

acid, 485
Beiizenylazoximebenzcnylcaiboxylic

acid, 468



Benzenylazoxime carbinol, 215

Benzenylazoximepropenylcarboxylic
acid, 215

Benzenyl compounds, 194

Benzenylethoxime chloride, 213

Benzenylethenylazoxime, 214

Benzenyl ethyl ether, 196

Benzenyloxime compounds, 2Q7

Benzenyloximic acid, 208

Benzenyl triacetate, 196

Benzenyl tribromide, 196

Benzenyl trichloride, 195

Benzenyltrichlorophosphoryl chloride,
311

Benzethylanishydroxylamine, 341

Benzethylbenzhydroxylamiue, 209

Benzhydroxamic acid, 208

Benzhydroxamide, 212

Benzhydroxylamiue, 207

Benzidene-acetamide, 143

Benzidenc-aniline, 140

Benzidene-aniline cyanhydrate, 141

Benzidene benzoate, 163

Benzidene benzobromohydrin, 170

Benzidene benzochlorohydrin, 169

Benzidene compounds, 136

Benzidene diacetate, 137

Benzidene dibromide, 136

Benzidene dichloride, 136

Benzidene dbhlorochromic acid, 6

Benzidene diethyl ether, 136

Benzidene di-iodide, 137

Benzidenedimethylparadiamido-
benzene, 142

Benzidenediphenylhydrazinc, 141

Benzidenedi-ureide, 143

Benzidene-orthodiamido-benzeiie, 141

Benzideneparadiainrdobenzenc, 142

Beuzidenephenylamiue hydrochloiide,
143

Benzidenephenyl hydrazin e, 141

Benzideuephenyldiamine, 142

Benzidene sulphide, 138

Benzidenetetra-ureide, 143

Benzidenetri-ttreide, 143

Benzidene ureides, 143

Benzidene urethane, 143

Benzidenoxime, 139

Benzimido-acelic ether, 201

Benzimido-amide, 202

Benzimido-ethers, 200

Benzimido-ethyl ether, 201

Benzimido-isobutyl ether, 201

Benzimido-thiobenzyl ether, 202

Benzimido-thio-ethyl ether, 201

Benzoene, 8

Benzoene monochlore, 7

Benzoic acid, 7, 108, 151, 297, 383

Benzoic acid, azo-derivatives of, 265

Benzoic acid, nitro-substitutiou pro-
ducts of, 227

Benzoic acid, salts and ethers of, 160

Benzoic anhydride, 166

Beiizoleic acid, 159



526



INDEX.



Benzonitril, 122, 197

Beiizonitril and its derivatives, 197

Benzophosphine chloride, 276

Benzophosphinic acid, 275

Benzolorthoalcoholsame, 442

Benzortho-amidobenzoic acid, 239

o-Benzothio-aldehyde, 133

0-Benzothio-aldehyde, 138

y-Benzofhio-aldehyde, 139

Benzo-trichloride, 195

Benzoxamidine, 213

Benzoyl, 285

Benzoyl acetyl oxide, 167

Benzoyl aniline, 174

Benzoylanthranil, 241

Benzoylazobenzene, 180

Benzoylbenzenylamidoxime, 214

Benzoyl- benzoic acid, 458

Benzoylbenzoximic acid, 209

Benzoyl bromide, 169

Benzoyl chloride, 168

Benzoyl derivatives of amines and

amido-bases, 174
Benzoyl dioxide, 167
Benzoyldiphenylamine, 175
Benzoyldiphenylhydrazine, 181
Benzoyl disnlphide, 171
Benzoyl ethylbenzhydroxamate, 209
Benzoyl fluoride, 170
Benzoyl-glycollic acid, 165
Benzoyl group, 128
Benzoylguanidine, 243
Benzoylguanidine, nitrate, 243
Benzoyl, halogen compounds of, 168
Benzoylhelicin, 289
Benzyl hydrosulphide, 138
Benzoyl iodide, 170
Benzoyl-lactic acid, 165
Benzoyl methylaniline, 175
Benzoylmethylpyrogallol dimethyl

ether, 164

Benzoylnitranilines, 175
Benzoyl, nitrogen compounds of, 172
Benzoylornithine, 193
Benzoylorthotoluide, 175
Benzoyl oxide, 166
Benzoyl, oxides of, 166
Benzoylparatoluide, 175
Benzoyl peroxide, 167
Benzoylphenylhydrazine, 1 79
Benzoylpropylpyro - gallol dimethyl

ether, 164

Benzoylpyro-gallol dimethyl ether, 164
Benzoylsalicin, 282
Benzoyl salicylaldehydc, 288
Benzoylsalicylamide, 312
Benzoylsalicylnitril, 313
Benzoyl sulphide, 171
Benzoylsulphimide, 269
Benzoyl, sulphur compounds of, 170
Benzoyl thiocyanate, 172
Benzoyl thio-urea, 179
Benzoyl urea, 178
Benzoylvanillic acid, 353



Benzyl, 89

Benzylacetamide, 121

Benzyl acetate, 97

Benzyl alcohol, 7, 89 ; properties, 93 ;

substitution products of, 98
Benzylamidine, 202
Benzylamine, 112 ; properties, 113
Benzyl amine hydrochloride, 113, 114
Benzylamine nitrite, 114
Benzylamines, 110

Benzylamines, amido-substitutcd, 116
Benzylamines, substitution products of,

118
Benzylammonium benzyl carbamate,

113, 114

Benzylaniline, 117
Benzyl, arsenic compounds of, 125
Benzyl benzoate, 162
Benzylbenzoyl thio-urea, 179
Benzyl bromide, 97
Benzyl bromophenyl ether, 95
Benzyl carbamate, 123
Benzyl-carbimide, 122
Benzyl chloride, 7, 96
Benzyl chlorophenyl ether, 95
Bt-nzylcyananmide, 121
Benzylcyanuramide, 121
Benzyl-Derivatives of the Acid- Amides

and Allied Bodies, 121
Benzyldimethylselenine tri-iodide, 110
Benzyldimethylsulphine iodide, 106
Benzyl dimethylsulphine platinichlor-

ide, 107

Benzyl dioxysulphide, 107
Benzyl diphenylamine, 117
Benzyl diselenide, 109
Benzyl disulphide, 107
Benzyl, ethereal salts of, 96
Benzyl ethers, 94
Benzylethoxyl chloride, 100
Benzyl ethyl ether, 94
Benzyl ethyl sulphide, 106
Benzyl group, 89
Benzyl hydrosulphide, 105
Benzylhydroxyammonium chloride, 98
Benzyl iodide, 97
Benzyl-isocyauate, 122
Benzyl isocyauurate, 122
Benzyl isothiocyanate, 122
Benzylmetamine, 121
Benzyl methyl ether, 94
Benzyl mercaptan, 105
Benzyl mustard oil, 122
Benzyl nitrate, 97
Benzyl, nitrogen bases of, 110
Benzyl orthocresyl ether, 95
Benzyl oxalate, 98
Benzyl oxide, 94
Benzyl oxysulphide, 107
Benzyl paracresyl ether, 95
Benzyl phenylamine, 117
Benzyl phenyldimethylammoni urn

chloride, 117
Benzyl phenyl ether, 95



INDEX.



527



Benzylphosphinc, 124

Benzylphosphonium iodide, 124

Benzylquinol, 96

Benzylsalicylic acid, 306

Benzyl salicylaldehyde, 287

Benzylselenic acid, 109

Benzyl selenide, 109

Benzyl, selenium compounds of, 109

Benzyl selenocyanate, 123

Benzyl, silicon compounds of, 127

Benzyl sulphide, 106

Benzylsulphonamide, 109

Benzylsulphonic acid, 108

Benzylsulphonic chloride, 108

Benzyl, sulphur compounds of, 105

Benzyl thiocarbamide, 124

Benzyl thiocyanate, 122

Benzyl thiobenzoate, 171

Benzyl urea, 123

Benzyl urethane, 123

Beta-orcinol, 402

Boron and Silicon derivatives of Tolu-
ene, 87

Boron disalicylic acid, 304

Bromamidobenzoic acids, 255

Bromanisic acid, 336

Bromine substitution products, 41

Bromine substitution products of tolu-
ene, 10

Bromobenzidenedichlorochromyl chlo-
ride, 11

Bromobenzylbenzoate, 170

Bromogallic acid, 370

Bromomalophthalic acid, 470

Bromomeconin, 500

Bromometacresol, 27

a- Bromometatoluic acid, 417

/3-Bromometatoluic arid, 417

o-Bromometaxylene, 394

s-Bromometaxylene, 394

rt-IJromometaxylenol, 401

Bromonitrobenzoic acids, 236



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