2-Naphthylamine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
2-Naphthylamine
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 91-59-8 YesY
ChemSpider 6790 YesY
KEGG C02227 YesY
ChEBI CHEBI:27878 YesY
ChEMBL CHEMBL278164 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H9N
Molar mass 143.19 g mol−1
Appearance White to red crystals
Density 1.061 g/cm3
Melting point 111 to 113 °C (232 to 235 °F; 384 to 386 K)
Boiling point 306 °C (583 °F; 579 K)
Acidity (pKa) 3.92
Related compounds
Related compounds 2-Naphthol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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[edit]

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.

See also[edit]

References[edit]

  1. ^ CDC - NIOSH Pocket Guide to Chemical Hazards