453. 4-Amino-1-naphthol

Nomenclature

CAS number: 2834-90-4
4-Amino-1-naphthalenol; 4-hydroxy-α-naphthylamine.
C10H9NO; mol wt 159.18.
C 75.45%, H 5.70%, N 8.80%, O 10.05%.

Description and references

Prepd by treating α-naphthol with benzenediazonium chloride and reducing the benzeneazo-α-naphthol with sodium hydrosulfite: Conant et al., Org. Synth. 3, 7 (1923); cf. Fieser, Fieser, J. Am. Chem. Soc. 57, 493 (1935). From α-naphthylhydroxylamine by rearrangement in acetone: Neunhoffer, Liebich, Ber. 71B, 2247 (1938).

Chemical structure

Properties

Needles. Unless kept absolutely dry, it acquires a violet discoloration on storage and oxidizes to 1,4-naphthoquinone. Usually isolated as the hydrochloride, C10H9NO.HCl, needles, very sol in water.

Derivative

N-Acetyl deriv.

Nomenclature

4-Acetamido-1-naphthol; naphthacetol.
C12H11NO2; mol wt 201.22.
C 71.63%, H 5.51%, N 6.96%, O 15.90%.

Properties

Needles from alcohol, mp 188°, sparingly sol in water, sol in alcohol.

Use

Polymerization inhibitor; prepn of 2-allyl-4-amino-1-naphthol hydrochloride (an antihemorrhagic cpd); prepn of 1,4-naphthoquinone.