Title: Anthracene
CAS Registry Number: 120-12-7
Molecular Formula: C14H10
Molecular Weight: 178.23
Percent Composition: C 94.34%, H 5.66%
Literature 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.
Melting point: mp 218°
Boiling point: bp760 342°
Density: d427 1.25
Derivative Type: Picric acid complex
Properties: mp 139°.
Melting point: mp 139°
Derivative Type: sym-Trinitrobenzene complex
Properties: mp 164°.
Melting point: mp 164°
Derivative Type: Trinitrotoluene complex
Properties: mp 162°.
Melting point: mp 162°
Use: Important source of dyestuffs (manuf anthraquinone, alizarin dyes). |