1062. 1,2-Benzanthracene

Nomenclature

CAS number: 56-55-3
Benz[a]anthracene; 2,3-benzphenanthrene; tetraphene; benzanthrene; naphthanthracene.
C18H12; mol wt 228.29.
C 94.70%, H 5.30%.

Description and references

Occurs in coal tar, q.v.: Cook et al., J. Chem. Soc. 1933, 395. Synthesis from naphthalene and phthalic anhydride: Elbs, Ber. 19, 2209 (1886). From o-toluylnaphthalene: Fieser, Dietz, Ber. 62, 1827 (1929). From phenanthrene and succinic anhydride: Haworth, Mavin, J. Chem. Soc. 1933, 1012. Absorption spectrum: Capper, Marsh, J. Chem. Soc. 1926, 726; Clar, Ber. 65, 507 (1932); Mayneord, Roe, Proc. R. Soc. London A152, 299 (1935). Review: E. Clar, Polycyclic Hydrocarbons Vol. 1 & 2 (Academic Press, New York, 1964). Review of toxicology and human exposure: Toxicological Profile for Polycyclic Aromatic Hydrocarbons (PB95-264370, 1995) 487 pp.

Chemical structure

Properties

Plates from glacial acetic acid or alc. Greenish-yellow fluorescence. Sublimes. mp 155-157° (Fieser, Dietz); mp 160° [Fieser, Hershberg, J. Am. Chem. Soc. 59, 2502 (1937)]; mp 167° (I. G. Farbenind., DE 481819; DE 486766). Difficultly sol in boiling alc; sol in most other organic solvents. Insol in water.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-220.