4267
T3D4213
2-Aminonaphthalene
2-Aminonaphthalene is an aromatic amine. It is used to make azo dyes. It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Aminonaphthalene is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by heating 2-naphthol with ammonium acetate to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with ferric chloride. When reduced by sodium in boiling amyl alcohol solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H. Numerous sulfonic acidsderived from 2-aminonaphthalene are known. Of these, the delta-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs. 2-Aminonaphthalene is found in cigarette smoke and suspected to contribute to the development of bladder cancer.
91-59-8
7057
C10H9N
White powder.
113°C
0.189 mg/mL at 25°C
1, carcinogenic to humans. (L135)
2014-08-29T05:53:29Z
2014-12-24T20:26:42Z
C02227
27878
true
NC1=CC2=CC=CC=C2C=C1
C10H9N
InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2
InChIKey=JBIJLHTVPXGSAM-UHFFFAOYSA-N
143.1852
143.073499293
Exogenous
Solid
2.28
HMDB41802
CHEMBL278164
6790