2-Naphthylamine
From Wikipedia, the free encyclopedia
| 2-Naphthylamine | |
|---|---|
 |
|
| Chemical name | 2-Aminonaphthalene |
| Other names | 2-Naphthylamine ß-Naphthylamine |
| Chemical formula | C10H9N |
| Molecular mass | 143.19 g/mol |
| CAS number | [91-59-8] |
| Density | 1.061 g/cm3 |
| Melting point | 111-113 °C |
| Boiling point | 306 °C |
| SMILES | NC2=CC1=CC=CC=C1C=C2 |
| Disclaimer and references | |
2-Naphthylamine 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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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, HO2C•C6H4•CH2•CH2•CO2H. Numerous sulfonic acids derived from 2-naphthylamine are known. Of these, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.
