2-Naphthylamine
| 2-Naphthylamine | |
|---|---|
| Skeletal formula | |
| Ball-and-stick model | |
| 2-Aminonaphthalene | |
| Other names 2-Naphthylamine β-Naphthylamine | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 91-59-8 
|
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C10H9N |
| Molar mass | 143.19 g/mol |
| Density | 1.061 g/cm3 |
| Melting point |
111-113 °C |
| Boiling point |
306 °C |
| style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds | |
| Related compounds | 2-Naphthol |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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, 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.
Role in disease
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.[1]
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.
References
- ↑ Steinberg GD, Kim HL. Bladder Cancer. eMedicine.com. URL: http://www.emedicine.com/MED/topic2344.htm. Accessed on: May 9, 2007.
