2-Naphthylamine
Title: 2-Naphthylamine
CAS Registry Number: 91-59-8
CAS Name: 2-Naphthalenamine
Additional Names: 2-aminonaphthalene; b-naphthylamine
Molecular Formula: C10H9N
Molecular Weight: 143.19
Percent Composition: C 83.88%, H 6.34%, N 9.78%
Literature References: Prepd by heating b-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).
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.
Melting point: mp 111-113°
Boiling point: bp 306°; also stated as 294°
Density: d498 1.061
 
Derivative Type: Acetate
Molecular Formula: C10H9N.CH3COOH
Molecular Weight: 203.24
Percent Composition: 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.

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