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Skeletal formula
Ball-and-stick model
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 91-59-8 YesY
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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
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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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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.


  1. Steinberg GD, Kim HL. Bladder Cancer. eMedicine.com. URL: http://www.emedicine.com/MED/topic2344.htm. Accessed on: May 9, 2007.

See also

nl:2-naftylamine pt:2-Naftilamina