6395. 1,4-Naphthoquinone

Nomenclature

CAS number: 130-15-4
1,4-Naphthalenedione; α-naphthoquinone; 1,4-dihydro-1,4-diketonaphthalene.
C10H6O2; mol wt 158.15.
C 75.94%, H 3.82%, O 20.23%.

Description and references

Prepn: Fieser, Org. Synth. coll. vol. I, 383 (2nd ed., 1941); Braude, Fawcett, ibid. coll. vol. IV, 698 (1963). Substituted 1,4-naphthoquinones occur in nature, e.g., phthiocol, q.v., various pigments, and the vitamins K.

Chemical structure

Properties

Yellow triclinic needles from alcohol or petr ether. Odor like that of benzoquinone. d 1.422. mp 126°. Begins to sublime below 100°. Sublimation rates: Kempf, J. Prakt. Chem. [2] 78, 236, 257. Easily volatile with steam. uv spectrum: Purvis, J. Chem. Soc. 101, 1318 (1912). Sparingly sol in cold water, slightly in petr ether, freely in hot alcohol, ether, benzene, chloroform, carbon bisulfide, acetic acid; sol in alkali hydroxide solns giving a reddish-brown soln.