2-Naphthylamine
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| Names | |
|---|---|
| IUPAC name
2-Aminonaphthalene | |
| Other names
2-Naphthylamine β-Naphthylamine | |
| Identifiers | |
91-59-8  | |
| ChEBI | CHEBI:27878 |
| ChEMBL | ChEMBL278164 |
| ChemSpider | 6790 |
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| Jmol-3D images | Image |
| KEGG | C02227 |
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| Properties | |
| Molecular formula |
C10H9N |
| Molar mass | 143.19 g·mol−1 |
| Appearance | White to red crystals |
| Density | 1.061 g/cm3 |
| Melting point | 111 °C (232 °F; 384 K) |
| Boiling point | 306 °C (583 °F; 579 K) |
| Vapor pressure | 1 mmHg (107° C)[1] |
| Acidity (pKa) | 3.92 |
| Hazards | |
| Flash point | 157 °C; 315 °F; 430 K |
| Related compounds | |
| Related compounds |
2-Naphthol |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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| Infobox 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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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, HO2CC6H4CH2CH2CO2H. 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.
Role in disease
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.[2]
It is activated in the liver but quickly deactivated by conjugation to glucuronic acid. In the bladder, glucuronidase re-activates it by deconjugation, which leads to the development of bladder cancer.