Anthracene

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).
Anthragallol Anthralin Anthramycin Anthranol Anthraquinone

Anthracene[1]
Anthracene
Anthracene 3D
Identifiers
CAS number 120-12-7 YesY
PubChem 8418
ChemSpider 8111 YesY
UNII EH46A1TLD7 YesY
DrugBank DB07372
KEGG C14315 YesY
ChEBI CHEBI:35298 YesY
ChEMBL CHEMBL333179 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C14H10
Molar mass 178.23 g mol−1
Appearance Colorless
Density 1.25 g/cm³ at 19.85 °C, Solid
0.969 g/cm³ at 220 °C, liquid
Melting point 218 °C; 424 °F; 491 K
Boiling point 340 °C; 644 °F; 613 K
Solubility in water insoluble
Solubility methanol: 0.0908 g/100 mL
hexane: 0.164 g/100 mL
Hazards
EU classification Dangerous for the Environment
Flash point 121 °C; 250 °F; 394 K
Autoignition temperature 540 °C; 1,004 °F; 813 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Anthracene is a solid polycyclic aromatic hydrocarbon of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400-500 nm peak) fluorescence under ultraviolet light.[2]