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Revision as of 09:23, 11 December 2011

2-Naphthylamine
Skeletal formula
Ball-and-stick model
Names
IUPAC name 2-Aminonaphthalene
Other names 2-Naphthylamine
β-Naphthylamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.892 Edit this at Wikidata
KEGG
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2Key: JBIJLHTVPXGSAM-UHFFFAOYSA-N
  • InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2Key: JBIJLHTVPXGSAM-UHFFFAOYAA
SMILES
  • c12ccccc1ccc(N)c2
Properties
Chemical formula C10H9N
Molar mass 143.19 g/mol
Density 1.061 g/cm
Melting point 111-113 °C
Boiling point 306 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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.

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

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

See also

Categories: