6398. 1-Naphthylamine

Nomenclature

CAS number: 134-32-7
1-Naphthalenamine; 1-aminonaphthalene; α-naphthylamine; naphthalidine.
C10H9N; mol wt 143.19.
C 83.88%, H 6.34%, N 9.78%.

Description and references

Prepd by reducing α-nitronaphthalene with Fe and HCl: West, J. Chem. Soc. 127, 494 (1925); from 1-naphthalenecarboxylic acid and hydroxylamine: Snyder et al., J. Am. Chem. Soc. 75, 2014 (1953). Review of carcinogenic risk: IARC Monographs 4, 87-96 (1974).

Chemical structure

Properties

Needles, becoming red on exposure to air, or a reddish, cryst mass; unpleasant odor. Sublimes; volatile with steam. d 1.13. mp 50°. bp 301°. Flash pt 157°C. Sol in 590 parts water; freely sol in alc, ether. Reduces warm ammoniacal silver nitrate. Keep well closed and protected from light.

Derivative

Hydrochloride.
C10H9N.HCl; mol wt 179.65.
C 66.86%, H 5.61%, N 7.80%, Cl 19.73%.

Properties

Cryst powder; becomes bluish on exposure to air and light. Sol in about 27 parts water; sol in alcohol, ether. Protect from light.

Derivative

Sulfate dihydrate.
(C10H9N)2.H2SO4.2H2O; mol wt 420.48.
C 57.13%, H 5.75%, N 6.66%, S 7.63%, O 22.83%.

Properties

White to yellowish cryst powder. Slightly sol in water or alcohol.

Caution

Potential symptoms of overexposure to 1-naphthylamine are dermatitis; hemorrhagic cystitis; dyspnea, ataxia and methemoglobinemia; hematuria; dysuria. Potential occupational carcinogen. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 222.

Use

Manufacturing dyes; toning prints made with cerium salts; the hydrochloride with sulfanilic acid is a reagent for nitrate.