Title: Naphthacene
CAS Registry Number: 92-24-0
Synonyms: Tetracene; 2,3-benzanthracene; rubene; chrysogen
Molecular Formula: C18H12
Molecular Weight: 228.29
Percent Composition: C 94.70%, H 5.30%
Literature References: Occurs in coal tar. Contaminates commercial anthracene to which it imparts a yellow color. Isoln: Cook
et al., Proc. Roy. Soc. London B111, 455 (1932). Isoln from crude anthracene by chromatography: Winterstein
et al., Z. Physiol. Chem. 230, 159 (1934). Synthesis by condensing succinic acid and phthalic anhydride in the presence of sodium acetate: Gabriel, Michael,
Ber. 10, 1559, 2207 (1877);
11, 1682 (1878); Roser,
Ber. 17, 2744 (1884); Nathanson,
Ber. 26, 2582 (1893); Gabriel, Leupold,
Ber. 31, 1159, 1272 (1898); Wanag,
Ber. 70, 274 (1937); from 1-naphthol and phthalic anhydride: Deichler, Weizmann,
Ber. 36, 547, 719 (1903);
DE 298345 (1916); from 1,5-dihydroxynaphthalene and phthalic anhydride: Bentley
et al., J. Chem. Soc. 91, 411, 1588 (1907); from tetralin and phthalic anhydride: Schroeter,
Ber. 54, 2242 (1921);
DE 346673 (1918);
cf. Fieser,
J. Am. Chem. Soc. 53, 2329 (1931). Other syntheses: Coulson,
J. Chem. Soc. 1935, 77; Weizmann
et al., ibid. 1939, 398.
Properties: Orange leaflets from xylene. d 1.35. Sublimes
in vacuo. mp 341° (open capillary tube), mp 357° (copper block). Absorption spectrum: Clar,
Ber. 69, 607 (1936). Fluorescence maxima: Krishman, Seshan,
Z. Kristallogr. 89, 538 (1934). Difficultly sol in most solvents. Solns show slight green fluorescence in daylight. Does not form a picrate.
Melting point: mp 341° (open capillary tube); mp 357° (copper block)
Density: d 1.35
