2-Naphthylamine

Chembox new
Name = 2-Naphthylamine
ImageFile = 2-Naphthylamine.png ImageName =
IUPACName = 2-Aminonaphthalene
OtherNames = 2-Naphthylamine
β-Naphthylamine
Section1 = Chembox Identifiers
CASNo = 91-59-8
SMILES = NC2=CC1=CC=CC=C1C=C2
Section2 = Chembox Properties
Formula = C₁₀H₉N
MolarMass = 143.19 g/mol
Density = 1.061 g/cm³
MeltingPt = 111-113 °C
BoilingPt = 306 °C

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 It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by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 be contributory to the development of bladder cancer. [Steinberg GD, Kim HL. Bladder Cancer. eMedicine.com. URL: [http://www.emedicine.com/MED/topic2344.htm http://www.emedicine.com/MED/topic2344.htm] . Accessed on: May 9, 2007.]

References

ee also

*Naphthalene
*Naphthol
*1-Naphthylamine
*1,8-Bis(dimethylamino)naphthalene