2255. Chrysene

Nomenclature

CAS number: 218-01-9
1,2-Benzphenanthrene.
C18H12; mol wt 228.29.
C 94.70%, H 5.30%.

Description and references

Occurs in coal tar, q.v. Is formed during distillation of coal, in very small amount during distillation or pyrolysis of many fats and oils. Isoln from coal tar: Liebermann, Ann. 158, 299, 307 (1871). Purification by chromatography: Winterstein, Sch"on, Z. Physiol. Chem. 230, 146 (1934); Winterstein et al., ibid. 158. Synthesis by heating H2 and acetylene to 800°: Meyer, Ber. 45, 1633 (1912). From cholesterol on heating with palladium charcoal or activated charcoal: Schmid, Zentner, Monatsh. Chem. 49, 96 (1928). Review of toxicology and human exposure: Toxicological Profile for Polycyclic Aromatic Hydrocarbons (PB95-264370, 1995) 487 pp.

Chemical structure

Properties

Orthorhombic bipyramidal plates from benzene. d420 1.274. mp 254°. Sublimes easily in vacuo. bp 448°. Strong fluorescence under ultraviolet light. Absorption spectrum: Marchlewski, Moroz, Bull. Soc. Chim. Fr. [4] 33, 1406 (1923). Slightly sol in alc, ether, carbon bisulfide, glacial acetic acid. At 25° one gram dissolves in 1300 ml abs alc, 480 ml toluene. About 5% is sol in toluene at 100°. Moderately sol in boiling benzene. Insol in water. Slightly sol in cold organic solvents, but fairly sol in these solvents when hot, including glacial acetic acid.