Nomenclature
CAS number: 120-12-7
C
14H
10; mol wt 178.23.
C 94.34%, H 5.66%.
Description and references
Obtained from coal tar, q.v.: Dumas, Laurent, Ann. 5, 10 (1833); Laurent, Ann. 34, 287 (1840); Anderson, Ann. 122, 294 (1862); J. Chem. Soc. 15, 44 (1862); Auerbach, Das
Anthracen und seine Derivate (Braunschweig, 1880); Perkin, J. Soc. Arts 27, 572 (1879); Lunge, Coal Tar and Ammonia (1916); Barnett, Anthracene and Anthraquinone (London, 1921);
Nanson, Text. Color. 48, 605, 678, 751 (1926); 49, 19, 246, 557, 593 (1927); Houben,
Fischer, Das Anthracen und die Anthrachinone (Leipzig, 1929); Borrmann, Der Teer (Leipzig, 1940); Schumann, Kokereiteer (Stuttgart, 1940). Extensive patent literature on purification.
Prepn of very pure anthracene from synthetic anthraquinone: Clar, Ber. 72, 1645 (1939). 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.
Properties
Monoclinic plates from alc. Sublimes. When pure,
colorless with violet fluoresence; when impure (due to tetracene,
naphthacene), yellow with green fluorescence. Strongly triboluminescent
and triboelectric. d427 1.25. mp 218°. bp760 342°. Absorption spectrum: Clar, Ber. 65, 506 (1932). Less soluble than the
isomeric phenanthrene. Insol in water; one gram dissolves in 67 ml
abs alcohol, 70 ml methanol, 62 ml benzene, 85 ml chloroform, 200
ml ether, 31 ml carbon disulfide, 86 ml carbon tetrachloride, 125
ml toluene. Anthracene darkens in sunlight. According to Downs, US 1303639 (1919), when solns of crude anthracene
in coal tar naphtha are exposed to ultraviolet irradiation, the anthracene
is precipitated as dianthracene (para-anthracene) which
is reconverted to anthracene by sublimation. Forms molecular addn
products with nitro compounds.Derivative
Picric acid complex.
Properties
mp 139°.Derivative
sym-Trinitrobenzene complex.
Properties
mp 164°.Derivative
Trinitrotoluene complex.
Properties
mp 162°.Use
Important source of dyestuffs (manuf anthraquinone,
alizarin dyes).