Table VIIl,17 Aliphatic ketones

Ketone B.P. M.P. 2,4-Dinitro- Semi- Benzylidene Phenyl- p-Nitro- Other derivatives °C
oc oc phenylhydrazone carbazone derivative hydrazone phenyl-
oc oc oc oc hydrazone
oc

Acetone 56 128 190 112 42 149 Oxime, 59

Ethyl methyl ketone 80 115 146 129
Methyl vinyl ketone 80 141
Biacetyl 88 315 (Di) 279 (Di) 53 243 (Di) 230 Dioxime, 234
Jsopropyl methyl ketone 94 120 114 109
Methyl propyl ketone 102 144 112 117 Oxime, 58
Diethyl ketone 102 156 139 31 144 Oxime, 69
Pinacolone (I-butyl methyl ketone) 106 125 158 41 Oxime, 78
lsobutyl methyl ketone 117 95 132 79 Oxime, 58
Di-isopropyl ketone 124 88 160 Oxime, 34
Ethyl propyl ketone 124 130 112
Butyl methyl ketone 128 107 125 88 Oxime, 49
4-Methylpent-3-en-2-one 130 203 164 142 134 Oxime, 49
Cyclopentanone 131 146 210 190 55 154 Oxime, 57
Pentane-2,4-dione 139 209 Oxime, 149
2-Methylcyclopentanone 139 184
Dipropyl ketone 144 75 133
Acetoin (acetyl methyl carbinol) 145 318 185
Acetol (hydroxyacetone) 146 129 196 103 Oxime, 71
Heptan-2-one 151 89 127 207 73
Cyclohexanone 156 162 167 118 81 147 Oxime, 91
2-Methylcyclohexanone 165 137 197 132 Oxime, 43
4-Hydroxy-4-methylpentan-2-one 166 203 209 Oxime, 58
Di-isobutyl ketone 168 92 122
Methyl acetoacetate 170 152 d"f/" 1.077, n/f 1.420
3-Methylcyclohexanone 170 155 191 122 94 119
4-Methylcyclohexanone 171 134 203 99 110 128 Oxime, 39
Hexyl methyl ketone 173 58 123 93
Cycloheptanone 180 148 162 108
Cyclohexyl methyl ketone 180 140 177 154 Oxime, 60
f
Ethyl acetoacetate 181 93 133 dlY" 1.025, nt 1.420
Dibutyl ketone 188 90
(+)-Fenchone 193 140 184 Oxime, 167
Hexane-2,5-dione 194 257 (Di) 220 120 (Di) Dioxime, 137
Methyl levulinate 196 142 143 96
f
djY" 1.050, nr 1.423
Phorone (I) 199 28 118 221 Oxime, 48
P-Thujone 202 114 174 Oxime, 55
Ethyl levulinate 206 102 148 104
° f
dl2 1.011, n1 1.423
( - )-Menthone 209 146 189 53 Oxime, 59
Isophorone (2) 215 130 199 77 68 Oxime, 79
Pulegone 224 147 174 Oxime, 119
Undecan-6-one 226 14 °
dj2 0.825, n/f 1.429
(+ )-Carvone 230 191 163 110 175 Oxime, 73
Tridecan-7-one 255 33 97
a-Ionone 130/13 151 143 (108) 113 Oxime, 90
{J-Jonone 139/18 128 149 173
2,2'-Furoin 135 217 81 Oxime, 161
2,2'-Furil 165 215 184 199 Dioxime, 100
(+)-Camphor 209 179 177 238 98 233 217 Oxime, 119

Chloroacetone 119 125 150

I,1-Dichloroacetone 120 163
1,3-Dichloroacetone 173 45 133 120
Table VIII,18 Aromatic ketones

Ketone B.P. M.P. 2,4-Dinitro- Semi- Oxime Phenyl- p-Nitro- Other derivalives °C
oc oc phenylhydrazone carbazone oc hydra zone phenyl-
oc oc hydrazone
oc
Acetophenone 202 20 250 (237) 199 59 105 185 Benzylidene, 58
2-Hydroxyacetophenone 215 210 117 110
2-Methylacetophenone (1) 216 159 203 61
Benzyl methyl ketone 216 27 156 198 69 87 145
Propiophenone (2) 218 19 191 174 53 147
3-Methylacetophenone (3) 220 207 198 55
lsobutyrophenone (4) 222 163 181 94 73
4-Methylacetophenone (5) 224 28 258 205 88 96 198
Benzyl ethyl ketone 226 136
Butyrophenone (<i) 230 12 190 188 50
m-Methoxyacetophenone 240 196
Valerophenone (7) 242 166 166 52 162
o-Methoxyacetophenone 245 183 83 114
a-Tetralone 129/12 257 217 89 (103) 84 231 Benzylidene, 105
/J-Tetralone 138/16 18 215 88 109
1-Acetylnaphthalene 302 34 229 139 149 Picrate, 116; benzylidene,
Phenyl o-tolyl ketone (8) 310 190
Phenyl m-tolyl ketone 314 221 101
Dibenzyl ketone 331 35 100 146 125 129 Benzylidene, 162
p-Methoxyacetophenone 258 39 220 198 87 142
a-Hydrindone 242 42 258 233 146 128 235 Benzylidene, 113
Benzalacetone 262 42 227 186 116 157 166 Benzylidene, 112
Benzophenone 306 49 238 165 144 137 155
2-Acetylnaphthalene 301 56 262 236 145 177 Picrate, 85
Phenyl styryl ketone (9) 347 58 245 168 115 119 Picrate, 97
Phenyl p-tolyl ketone 326 60 200 122 154 109
Deoxybenzoin (10) 320 60 206 148 98 116 163 Benzylidene, 102
p-Methoxybenzophenone 355 62 180 138 132 199
Fluorenone (11) 341 83 284 195 152 269
a-Hydroxyacetophenone 86 146 70 112 Benzoyl, 118; acetyl, 49
Di-p-tolyl ketone 335 95 229 163 100
Benzi! 347d 95 189 244 (Di) 237 235 (Di) 290 Quinoxaline, 126
m- Hydroxyacetophenone 96 195
p-Hydroxyacetophenone 109 261 199 145 151
Di benzylideneacetone 112 180 189 143 153 173 Picrate, 114
p-Benzoquinone 116 186 243 (Di) 140 Picrate, 79
Acenaphthenone 121 175 90 Picrate, 113
1,4-Naphthoquinone 125 247 198 278
Benzoin 344 137 245 206 151 (99) 159 Benzoyl, 125; acetyl, 83
1,2-Naphthoquinone 146 184 162 138 235
Resacetophenone (13) 147 218 199 159 Dibenzoyl, 81; diacetyl, 3
9,10-Phenanthraquinone 207 313 158 165 245
Phloroacetophenone (14) 219 Tribenzoyl, 118; triacetyl,
Anthraquinone 285 224 183
Halogeno-ketones

m-Chloroacetophenone 228 232 88 176

o-Chloroacctophenone 229 206 160 (179) 113 215
p-Chloroacetophenone 236 20 231 201 95 114 239
o-Bromoacetophenone 112/10 177
m-Bromoacetophenone 131/16 8 238
a-Bromoacetophenone (15) 51 146 89
p-Bromoacetophenone 256 51 230 208 129 126
p-Chlorobenzophenone 323 78 185 156 (95) 106
VIII PRACTICAL ORGANIC CHEMISTRY PHYSICAL CONSTANTS OF ORGANIC COMPOUNC

Table VIII,18 Aromatic ketones (continued)

Ketone B.P. M.P. 2,4-Dinitro­ Semi­ Oxime Phenyl­ p-Nitro­ Other derivatives °C
oc oc phenylhydrazone carbazone oc hydrazone phenyl­
oc oc hydrazone
oc

Halogeno-ketones (continued)

p-Bromobenzophenone 350 82 230 169 126

p-Iodoacetophenone 85
<X,p-Dibromoacetophenone (16) 109 115

Nitro- and amino-ketones

o-Nitroacetophenone 159/16
o-Aminoacetophenone 251 20 290 109 108
m-Ni troacetophenone 81 228 257 132 135
p-Nitroacetophenone 81 132
m-Aminoacetophenone 99 196 148
p-Aminoacetophenone 294 106 250

(I) Methyl o-tolyl ketone. (9) Chalkone.

(2) Ethyl phenyl ketone. (ID) Benzyl phenyl ketone.
(3) Methyl m-tolyl ketone. (11) Diphenylcne ketone.
(4) Isopropyl phenyl ketone. (12) Phcnacyl alcohol.
(5) Methyl p-tolyl ketone. (13) 2,4-Dihydroxyacetophenone.
(6) Phenyl propyl ketone. (14) 2,4,6-Trihydroxyacetophenone.
(7) Butyl phenyl ketone. (15) Phenacyl bromide.
(8) 2-Methylbenzophenone. (16) p-Bromophenacyl bromide.
VIII PRACTICAL ORGANIC CHEMISTRY PHYSICAL CONSTANTS OF ORGANIC COMPOUND

..
Table VIIl,32 Primary and secondary aliphatic amines

Amine B.P. ,p:,0· 10•

no Benzene- Toluene-p- Phenyl- 1-Naphthyl- Picrate N-Substi- Benzamide Acetamide
cc sulphonamide sulphon- thiourea thiourea cc toted phthal- 'C , cc
cc amide cc cc imide
'C 'C

Methylamine -7 30 75 113 192 215 134 80

Ethylamine 17 58 63 106 121 165 78 71
Isopropylamine 35 0.689 1.374 26 51 101 143 150 86 100
t-Butylamine 46 198 134
Propylamine 49 0.717 1.388 36 52 63 103 135 66 84
Allylamine 55 0.762 1.420 39 64 98 140 70
s-Butylamine 63 0.725 1.393 70 55 101 140 76
lsobutylamine 68 0.735 1.397 53 78 82 137 151 93 57
Butylamine 77 0.741 1.401 65 109 151 34 42
Isopentylamine 97 0.749 1.408 65 102 97 138
Pentylamine 105 0.754 1.411 69 103 139
Hexylamine 129 0.766 1.418 96 77 79 127 40
Cyclohexylamine 134 0.867 1.459 142 158 149 104
Heptylamine 155 0.775 1.425 75 121
Ethanolamine 171 1.022 1.454 160 127
Octylamine 177 0.782 1.429 112
( - )-Menthylamine 212 0.854 135 157 145

Benzylamine 185 0.982 1.544 88 116 147 172 196 115 105 60
1-Phenylethylamine 187 189 120 57
2-Phenylethylamine 198 0.854 69 66 135 174 130 116 114

1,2-Diaminoethane 117 (1) 0.898 1.457 168 160 102 233 244 172
1,2-Diaminopropane 120 0.874 137 193 139
1,3-Diaminopropane 136 0.889 1.460 250 148 101
1,4-Diaminobutane 159 (2) 224 168 255d 177 137
1,5-Diaminopentane 180 119 148 135
1,6-Diaminohexane 205 (3) 154 220 158

Dimethylamine 7 47 79 135 168 158 41

Diethylamine 56 0.707 1.386 42 60 34 108 155 42
Di-isopropylamine 84 0.717 1.392 94 140
Dipropylamine 110 0.738 1.405 51 161 75
Diallylamine 111
Di-s-butylamine 135 0.753 1.411
Di-iso butylamine 137 0.746 1.409
Dibutylamine 159 0.760 1.418 86 123 59
Di-isopentylamine 186 0.771 1.423 118
Dipentylamine 205 0.777 1.427
Dicyclohexylamine 255d (4) 119 173 153 103
Diethanolamine (5) 270d (6) 1.097 1.478 130 99 110
Pyrrolidine 89 0.854 1.424 123 112
Piperidine 106 0.861 1.453 94 96 152 48
2-Methylpiperidine 118 55 135 45
3-Methylpiperidine 126 138
4-Methylpiperidine 128
Morpholine 130 1.000 1.455 119 147 136 148 75
Pyrrole 131 0.969 1.509 69d
Piperazine 140 (7) 292 (di) 173 280 196 144
(mono) (di) (di)
1,2,3,4-Tetrahydroisoquinoline 232 154 195 129 46
1,2,3,4-Tetrahydroquinoline 250 67 76
(m.p. 20)
VIII PRACTICAL ORGANIC CHEMISTRY PHYSICAL CONSTANTS OF ORGANIC COMPOUND

Table VIII,32 Primary and secondary aliphatic amines (continued)

Amine B.P. cc M.P. cc dzo•

40 Derivatives 'C

Ester-amides (derivatives ofaminoformic acid, NH 2 COOH)

Methyl carbamate 177 54

Ethyl carbamate (urethan) 184 50 N-p-Nitrobenzoyl, 152; Benzylidcne, 179
Propyl carbamate 195 61
Butyl carbamate 204d 54
Pentyl carbamate 57
lsopentyl carbamate 67
N-Methylurethan (Ethyl N-methyl carbamate) 170
N-Ethylurethan (Ethyl N-ethyl carbamate) 170 0.981 1.422
N-Propylurethan 192
N-Butylurethan 202
N-s-Butylurethan 194
N-Phenylurethan (Ethyl N-phenyl carbamate) 237 53 N-Acetyl, 59; N-Benzoyl, 161; N-Nitroso, 62
Ethyl oxanilate 67 N-Acetyl, 65

Nore.-Esters of carbamic acid upon boiling with aniline yield carbanilide (m.p. 238 cq, am­ (1) M.p. 8 °C. (5) Di-2-hydroxyethylamine.
monia and the corresponding alcohol. (2) M.p. 28 °C. (6) M.p. 28T
(3) M.p. 42 °C. (7) M.p. 104 cc; Hydrate, 6H 2 0, m.p. 44 cc.
(4) M.p. 20 °C.

Table VIII,33 Primary aromatic amines

Amine B.P. M.P. Acetamide Benzamide Benzene- Toluene-p- Benzylidene Picrate 3-Nitro- 2,4-Dinitro- Formyl Phenyl
cc cc cc cc cc sulphon- sulphon- derivative oc phthalimide phenyl derivative thiourea
''C
amide amide "C derivative oc oc
cc cc oc
Aniline 183 114 163 112 103 54 138 156 47 154
Benzylamine 185 60 105 88 116 199 143 156
1-Phenylethylamine 187 57 120
2-Phenylethylamine 198 51 116 69 167 135
o-Toluidine 200 112 144 124 110 213 150 126 59 136
m-Toluidine 203 66 125 95 114 200 130 161 104
p-Xylidine (1) 214 15 142 140 232 150
p-Ethylaniline 215 94 151
m-2-Xylidine (2) 215 11 177 168 212 180 176 148
o-Ethylaniline 216 112 147
m-4-Xylidine (3) 216 130 192 130 181 209 156 114 152
m-5-Xylidine (4) 220 10 144 136 209 77 153
o-Anisidine (5) 225 5 88 60 89 127 200 185 151 83 136
3,4-Dimethylaniline 226 49 99 118 154
N,N-Methylphenylhydrazine 227 92 153 132
o-Phenetidine (6) 229 79 104 102 164 164 164 62 137
Mesidine (7) 232 216 206 167 193 193
Phenylhydrazine 242 23 128 168 145 172
m-Phenetidine 248 96 103 157 158 52 138
m-Anisidine 251 80 68 169 158 138 57
o-Aminoacetophenone 251d 20 77 98 148
p-Phenetidine 254 135 173 143 107 76 69 173 l lR 76 1'1R
VIII PRACTICAL ORGANIC CHEMISTRY PHYSICAL CONSTANTS OF ORGANIC COMPOUNDS

Table VIIl,33 Primary aromatic amines (continued)

Amine B.P. M.P. Acetamide Benzamide Benzene- Toluene-p- Benzylidene Picrate 3-Nitro- 2,4-Dinitro- Formyl Phenyl
C cc cc cc cc sulphon- sulphon- derivative cc phthalimide phenyl derivative thiourea
amide amide cc cc derivative cc cc
'C cc cc

Methyl anthranilate 255 24 101 1 00 106 58

p-Aminodiethylaniline 261 1 04 1 72 1 12
Ethyl anthranilate 266d 13 61 98 93 1 12 57
Ethyl m-aminobenzoate 294 1 14
p-Aminodimethylaniline 262 41 1 32 228 98 188 1 68 108
p-Toluidine 200 45 1 54 1 58 120 1 18 181 156 1 37 53 141
o-Aminobiphenyl (8) 299 50 1 21 102 75
1-Naphthylamine c • 300 50 1 60 161 1 69 1 57 73 1 63 223 1 90 139 165
p-Aminobiphenyl (9) C 302 51 171 230 255 1 72
p-Anisidine 246 57 1 30 1 54 96 1 14 62 1 97 141 81 144
2-Aminopyridine 204 58 71 87 216 22 1
2,5-Diaminotoluene ( 1 0) 273 64 220 307
3-Aminopyridine 252 64 1 33 119
p-Tolylhydrazine 244d 65 130 146
m-Phenylenediamine 283 64 191 240 194 1 72 105 1 84 1 72 1 55
o-Nitroaniline 71 94 98 104 1 10 73 171 122
4-Amino-2-nitrotoluene 78 145 172 1 60 1 63
m-Aminoacetanilide 88 191 241
3,4-Diaminotoluene (1 1 ) 265 90 210 264 1 79
Ethyl p-aminobenzoate ( 1 2) 92 1 10 148 131
6-Nitro-2-aminotoluene 92 1 58 1 68
3-Nitro-2-aminotoluene 97 1 58
m-Aminoacetophenone 99 1 29 1 30
2,4-Diaminotoluene (13) 292 99 224 224 191 1 92 1 75 1 84 1 77
o-Phenylenediamine 257 1 02 1 86 301 1 86 202 1 06 208 1 70 t
p-Aminoacetophenone 294 106 167 205 128 203
2-Amino-4-nitrotoluene 107 151 186 1 72 1 16 1 79
2-Naphthylamine C 294 1 13 1 34 1 62 102 1 33 1 95 212 1 79 129 1 29
m-Nitroaniline 1 14 1 55 157 136 1 39 73 143 219 134 1 60
4-Amino-3-nitrotoluene 1 17 96 148 1 02 1 46 78
5-Nitro-1 -naphthylamine 119 220 183 199
l-Nitro-2-naphthylamine 126 1 23 1 68 1 56 1 60
p-Aminoazobenzene 1 26 145 21 1 130 1 62
Benzidine C 126 317 352 235 243 238
o-Tolidine ( 14) C 1 29 314 265 1 52 1 85 254
2-Amino-5-nitrotoluene 129 202 1 74 159 1 74
o-Aminoacetanilide 1 32
2,6-Dinitroaniline 138 197
p-Phenylenediamine 267 141 304 > 300 247 266 140 1 77 206
2-Nitro-1-naphthylamine 144 1 99 1 75
Anthranilic acid 146 1 85 181 214 217 127 1 68
p-Nitroaniline 148 216 199 139 191 1 15 100 255 1 94
p-Nitrophenylhydrazine 1 57d 205 193 1 20
4-Aminopyridine 158 1 50 202 216
p-Aminoacetanilide 1 63 304
Sulphanilamide ( 1 5) 1 66 219 284 211
m-Aminobenzoic acid 1 74 250 119 225
2,4-Dinitroaniline 1 80 121 220 219
p-Aminobenzoic acid 1 87 251 278 212 1 93 268
Picramide ( 1 6) 1 90 230 196 211
4-Nitro-1-naphthylamine 1 95 1 90 224 1 73 1 85
2,4-Dinitrophenylhydrazine 1 98d 198 207
2-Aminoanthraquinone 302 257 228 271 304
VIII PRACTICAL ORGANIC CHEMISTRY PHYSICAL CONSTANTS OF ORGANIC COMPOUND!

Table VIIl,33 Primary aromatic amines (concinued)

Amine B.P. M.P. Acetamide Benzamide Benzene- Toluene-p- Benzylidene Picrate 3-Nitro- 2,4-Dinitro- Formyl Phenyl
cc "C cc cc cc sulphon- sulphon- derivative 'C phthalimide phenyl derivative thiourea
amide amide oc "C derivative oc oc
cc oc oc

C-Ha/ogeno-amines

o-Chloroaniline 209 88 99 130 105 34 1 34 136 1 50 77 156

2-Amin o-3-chlorotoluen e 215 120
4-Amin o-3-chlorotoluene 223 7 113 137 11 0
m-Chloroanilin e 230 79 122 121 138 177 172 1 84 58 1 24
2-Amin o-4-chlorotoluene 237 22 1 40
4-Amin o-3-bromotoluene 240 26 1 17 149
2-Amino-5-chlorotoluene 241 29 140 142 125
2-Amin o-6-chlorotoluene 245 159 173
m-Bromoaniline 251 18 88 1 20 1 80 187 143
m-Iodoaniline 25 1 19 15 1 128
2-Amin o-4-bromotoluene 255 32 165
o-Bromoaniline 229 32 99 11 6 90 129 161 146
2,5-Dichloroaniline 255 50 132 1 20 1 66
2-Amin o-5-bromotoluen e 240 59 157 115
o-Iodoaniline 60 110 139 112
2,4-Dichloroaniline 245 63 146 117 128 1 06 116
p-lodoaniline 63 184 222 86 1 09 153
p-Bromoanilin e 66 167 204 1 34 IOI (141) 67 180 202 1 58 148
p-Chloroaniline 232 71 1 79 1 93 122 96 (121) 62 178 199 1 67 1 02 152
2,4,6-Trichloroaniline 263 78 206 1 74 83 180
2,4-Dibromoaniline 79 146 1 34 124 146 17 1
2,6-Dibromoaniline 84 210 124
2,4-Diamin ochloroben zene 88 243 178 215
2-Chloro-4-nitroaniline 1 08 139 161 1 64
4-Chloro-2-nitroaniline 1 16 104 11 0
2,4,6-Tri bromoaniline 120 232 198 95 222

A mino-phenols t

2,4-Diaminophenol (17) 79d 222 (di) 231

m-Aminophenol 123 101 (di) 153 (di) 156
Picramic acid ( 18) 169 201 (N) 229 (N) 191 (N)
5-Amin o-2-hydroxytoluene 173 1 03 (di) 194 11 0
o-Aminophenol 174 1 24 (di) 184 (di) 141 1 39 89 199 129 146
p-Aminophen ol 186d 150 (di) 234 (di) 125 253 182 1 90 140 1 50
8-Amin o-2-naphthol 207 165 208
I -Amin o-2-na phthol dee. 206 235

* All aromatic amines should be treated as potentially carcinogenic (see Section 1,3,D,5); those
(8) o-Xenylamine. ( 1 4) 4,4' -Diamino-3,3'-dimethylbiphenyl.
marked C are subject to legal control in Great Britain or the USA or both.
(9) p-Xenylamine. ( 1 5) p-Aminobenzenesulphonamide.
t This compound is ben zimidazole. (10) 2,5-Tolylenediamine. (16) 2,4,6-Trinitroaniline.
t See also Table Vll l,35 and Table Vlll,34 for secondary and tertiary amines having a nuclear (11 ) 3,4-Tolylenediamine. (1 7) Hydrochloride = Amidol.
hydroxyl substituent. (12) Benzocaine. ( 18) 2-Amino-4,6-dinitrophenol.
( l ) 2,5-Dimethylaniline. (5) o-Methoxyaniline. ( 1 3) 2,4-Tolylenediamine.
(2) 2,6-Dimethylaniline. (6) o-Ethoxyaniline.
(3) 2,4-Dimethylaniline. (7) 2,4,6-Trimethylaniline.
(4) 3,5-Dimethylaniline.
VIII P RACTICAL O RGANIC CHEMISTRY
PHYSICAL CONSTANTS OF ORGANIC CO MPO U N DS

Table VIII,34 Secondary aromatic amines

Amine B.P. M.P. Acetamide Benzamide Benzene- Toluene-p- Picrate Formyl O ther derivatives · c
'C oc "C 'C sulphonamide sulphonamide 'C derivative
'C 'C 'C
N-Methylbenzylamine 18L
95
N-Methylaniline 194 103 63
79 95 145 Phthalamic acid, 194
N-Ethylbenzylamine 199
50 118 U rea (with PhNCOJ, 81
N-Ethylaniline 205 55 60
88 138 Phthalamic acid, 204
N-Methyl-m-toluidine 206 66
N-Methyl-o-toluidine 208 56 66 120 90
N-Methyl-p-toluidine 210 83 53 60 131 N-Nitroso, 52 •
N-Ethyl-o-toluidine 214 72
75
N-Ethyl-p-toluidine 217 39
71
N-Ethyl-m-toluidine 221 72
N-Propylaniline 222 47 54 Phthalamic acid, 225
N-Butylaniline 240 56
56 Phthalamic acid, 204
N-Methyl-1-naphthylamine 294 94
164
Dibenzylamine 300d 112 68 52
N-M ethyl-2-naphthylamine 317 51 84
78 145 N-Nitroso, 88 •
N-Ethyl-2-naphthylamin e 315 49
N-Ethyl-1-naphthylamine 325 68
o-Nitro-N-methylaniline 37 70
N-Benzylaniline 306 38 58 107 N-Nitroso, 36 *
119 140 48 N-Nitroso, 58 •
Diphenylamine 302 54 103 180 123 142 182 74 N-Nitroso, 67 •
m-Nitro-N-ethylaniline 60 89
N-Phenyl-1-naphthylamine 62 115 152
m-Nitro-N-methylaniline 68 95 155 83
Di-p-t olylamine 79 N-Nitroso, 76 •
330 88 125
43 (mono) 174 (mono) N-Nitroso, 101 •
p-Hydroxy-N-methylaniline 86 135 (mono) N-Nitroso, 136 •
o-Hydroxy-N-methylaniline 96 64 (di) 160 (mono)
p-Nitro-N-ethylaniline N-Nitroso, 130 •
96 119
N-Phenyl-2-naphthylamine N-Nitroso, 120 *
108 93 136
p-Nitro-N-methylaniline 152 152 111 120 N-Nitroso, 104 •
Indole 254 52 68
187 52 N-Nitroso, 171 •
Carbazole 355 246 69 98
137 185

• The particularly powerful carcinogenic properties of these compounds should be n oted.

VIII PRACTICAL O RGANIC CHEMISTRY PHYSICAL CONSTANTS OF ORGANIC COMPOUNDS

Table VIII,35 Tertiary amines

Amine B.P. cC M.P. Methiodide Picrate Methotoluene-p- Other derivatives cc

(/mmHg) oc oc 'C sulphonate 'C

Trimethylamine 3 230 216

Triethylamine 89 1 73 d�£· 0. 728; nil'° 1 .401
Triallylamine 1 55
0
Tripropylamine 1 56 208 1 17 Ethiodide, 238; d�£ 0.756; nil'° 1 .417
Tri bu ty!amine 212 1 86 1 06 Benzyl chloride, 185; d��· 0.778; n/J'° 1 .430
Tri-isopentylamine 245 125 d�r 0. 785; ntJ'° 1 .433
Tripentylamine 257 80d dir 0.791 ; nil'0 1 .437

N,N-Dimethylbenzylamine 184 1 79 93
N,N-Dimethyl-o-toluidine 1 85 210 1 22
N,N-Dimethylaniline 1 93 228 1 64 161 Ethiodide, 136
N-Methyl-N-ethylaniline 201 1 25 1 34 Ethiodide, 102; p-nitroso, 66
N,N-Diethyl-o-toluidine 210 224 1 80
N,N-Dimethyl-p-toluidine 211 220 1 30 85 Benzyl chloride, 171
N,N-Dimethyl-m-toluidine 212 1 77 131
N,N-Diethylaniline 218 102 1 42 p-Nitroso, 84; benzyl chloride, 1 04
N,N-Diethyl-p-toluidine 229 184 1 10
N,N-Diethyl-m-toluidine 23 1 97
N,N-Di-n-propylaniline 245 1 56
N,N-Di-n-bu tylaniline 271 125 1 80
N,N-Dimethyl-1 -naph thylamine 273 1 45
N-Benzyl-N-methylaniline 306 1 64 127
N-Benzyl-N-ethylaniline 1 86/22 1 61 121
N,N-Dimethyl-2-naph thylamine 305 47 206
p-Bromo-N,N-dimeth y !aniline 264 55
Di benzy!aniline 300 70 1 35 1 32 p-Nitroso, 9 1
p-Hydroxy-N,N-dimethylaniline 76 201 o-Acetyl, 79
p-Nitroso-N,N-dimethylaniline 87 140
Tribenzylamine 380 92 1 84 190 Ethiodide, 1 90
Triphenylamine 365 1 27
p-Nitro-N,N-dimethylaniline 1 63

Pyridine 115 118 1 67 1 39 Ethiodide, 90

0(-Picoline (1 ) 129 227 1 69 1 50 Ethiodide, 1 23; picolinic acid, 1 36
2,6-Lutidine (2) 1 42 238 1 63 Dipicolinic acid, 226
y-Picoline 143 1 52 1 67 Isonicotinic acid, 308
/J-Picoline 144 92 1 50 Nicotinic acid, 228
2,4-Lutidine 1 59 113 1 83
2,5-Lutidine 1 60 1 69
2,3-Lutidine 1 64 1 88
2,4,6-Trimethylpyridine (3) 1 72 1 56
5-Ethyl-2-methylpyridine 1 78 1 66
3-Ethyl-4-methylpyridine 1 96 1 50
Ethyl nicotinate 223
Nicotine 246 218 Nicotinic acid, 228
Methyl nicotinate 204 38
2,2'-Bipyridyl 273 70 1 58

Quinoline 238 72 * (1 33)t 203 1 26 Ethiodide, 1 58

Isoquinoline 242 24 1 59 223 1 63 Ethiodide, 1 48
Quinaldine (4) 247 195 1 95 1 61 Ethiodide, 234
8-Methylquinoline 248 200
6-Methylquinoline 258 21 9 229 1 54 Benzyl chloride, 239
Lepidine (5) 262 1 74 21 1
2,4-Dimethylquinoline 264 264 194 Ethiodide, 21 4
VIII PRACTICA L ORGANIC CHEM ISTRY PHYSICAL CONSTANTS OF ORGANIC COM POU NDS

Table VIII,35 Tertiary amines (continued)

Amine B.P. M.P. Methiodide Picrate Methotoluene-p­ Other derivatives cc

oc oc oc cc sulphonate cc

6-Methoxyquinoline 284 26 236

7-Methylquinoline 252 39 237
8-Methoxyquinoline 283 50 1 60 1 43
2.6-Dimethylquinoline 267 60 237 191 1 75 Ethiodide, 227
8-Hydroxyquinoline 267 76 1 43 204
8-Nitroquinoline 92
6-Nitroquinoline 1 54 245
6-Hydroxyquinoline 1 93 236
3-Chloropyridine 1 49 135
3-Bromopyridine 1 70 1 65 1 56
2-Chloropyridine 1 70 1 20
2-Bromopyridine 1 94 1 27
3,5-Dibromopyridine 222 1 12 274 219
2,6-Dibromopyridine 249 1 19

6-Bromoquinoline 278 19 278 217

2-Chloroquinoline 267 38 1 22
6-Chloroquinoline 262 41 248 1 43 Ethiodide, 1 69
2-Bromoquinoline 49 210
Acridine Ill 224 208 Trinitrobenzene, 1 1 5
Hexamethylenetetramine 280 Sub. 190 1 79 205

• Monohydratc. t Anhydrous. {I) 2-Methylpyridine.

(2) 2,6-Dimethylpyridine.
(3) 1•-Collidine.
(4) 2-Methylquinoline.
(5) 4-Methylquinoline.