6399. 2-Naphthylamine

Nomenclature

CAS number: 91-59-8
2-Naphthalenamine; 2-aminonaphthalene; β-naphthylamine.
C10H9N; mol wt 143.19.
C 83.88%, H 6.34%, N 9.78%.

Description and references

Prepd by heating β-naphthol with ammonium sulfite and NH4OH at 150°: DE 117471 (1900); Frdl. 6, 190; from 2-naphthalenecarboxylic acid and hydroxylamine: Snyder et al., J. Am. Chem. Soc. 75, 2014 (1953). Review of carcinogenic risk: IARC Monographs 4, 97-111 (1974).

Chemical structure

Properties

White to reddish crystals; volatile with steam. d498 1.061. mp 111-113°. bp 306°; also stated as 294°. Sol in hot water, alcohol, ether. Reduces warm ammoniacal silver nitrate.

Derivative

Acetate.
C10H9N.CH3COOH; mol wt 203.24.
C 70.92%, H 6.45%, N 6.89%, O 15.74%.

Properties

White to yellowish scales or flakes; slight odor of acetic acid. Very sol in water or alcohol; sol in ether. Keep well closed and protected from light.

Caution

Potential symptoms of overexposure to 2-naphthylamine are dermatitis; hemorrhagic cystitis; dyspnea; ataxia; methemoglobinemia, hematuria; dysuria. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 222. 2-Naphthylamine is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-179.

Use

Formerly in manuf of dyes, as antioxidant in rubber.