Title: Phenanthrene
CAS Registry Number: 85-01-8
Molecular Formula: C14H10
Molecular Weight: 178.23
Percent Composition: C 94.34%, H 5.66%
Literature References: Isomeric with anthracene. Occurs in coal tar, q.v., and in products of incomplete combustion. Isoln: Ostermayer, Fittig, Ber. 5, 933 (1872); Glaser, ibid. 982. Purification (from contaminating carbazole and anthracene): Clar, Ber. 65, 852 (1932). Formation from toluene, bibenzil, 9-methylfluorene or stilbene by passage through red-hot tube: Graebe, Ber. 7, 48 (1874); Ann. 167, 161 (1879); Ber. 37, 4145 (1904). Also from coumarone and benzene: Kraemer, Spilker, Ber. 23, 85 (1890). Pschorr synthesis from o-nitrobenzaldehyde and phenylacetic acid: Ber. 29, 500 (1896). From diphenylethylene: Cook, Hewett, J. Chem. Soc. 1933, 1098. Diene synthesis from 1-vinylnaphthalene and maleic anhydride: Cohen, Warren, ibid. 1937, 1315. From o-phenylbenzoic acid: Schönberg, Warren, Chem. Ind. (London) 58, 199 (1939). By irradiation of stilbene: Mallory et al., J. Am. Chem. Soc. 84, 4361 (1962). Synthesis by double succinoylation of benzene: Rahman et al., J. Org. Chem. 28, 3571 (1963). Structure: Trotter, Acta Crystallogr. 16, 605 (1963). Review of carcinogenic risk: IARC Monographs 32, 419-430 (1983); of toxicology and human exposure: Toxicological Profile for Polycyclic Aromatic Hydrocarbons (PB95-264370, 1995) 487 pp.
Properties: Monoclinic plates from alcohol. d25 1.179; mp 100°; bp 340°. Sublimes in high vacuum. Absorption spectrum: Clar, Lombardi, Ber. 65, 1412 (1932); Mayneord, Roe, Proc. Roy. Soc. London A 152, 317 (1935). Practically insol in water. Sol in organic solvents, especially in aromatic hydrocarbons. One gram dissolves in 60 ml cold, 10 ml boiling 95% alcohol, 25 ml abs alcohol, 2.4 ml toluene or carbon tetrachloride, 2 ml benzene, 1 ml carbon disulfide, 3.3 ml anhydr ether. Soluble in glacial acetic acid. Solns exhibit a blue fluorescence. Forms molecular compds with picric acid, picryl chloride, dinitrobenzene and similar nitro compounds. LD50 i.p. in mice: 700 mg/kg (IARC).
Melting point: mp 100°
Boiling point: bp 340°
Density: d25 1.179
Toxicity data: LD50 i.p. in mice: 700 mg/kg (IARC)
CAUTION: Can cause photosensitization of skin. |