Title: Carbazole
CAS Registry Number: 86-74-8
CAS Name: 9H-Carbazole
Additional Names: 9-azafluorene; dibenzopyrrole; diphenylenimine
Molecular Formula: C12H9N
Molecular Weight: 167.21
Percent Composition: C 86.20%, H 5.43%, N 8.38%
Literature References: Prepn: Bunyan, Cadogan, J. Chem. Soc. 1963, 42. Manuf from 2-biphenylamine: Conover, US 2481292 (1949 to Monsanto); Voltz et al., US 2891965 (1959 to Houdry Process Corp.); Nevitt, Seelig, US 3085095 (1963 to Standard Oil, Indiana); from 2-nitrobiphenyl: Larrison, US 2508791 (1950 to Allied Chem.); by hydrogenolysis of coal-hydrogenation products: Murray et al., US 2913397 (1959 to Union Carbide); from diphenylamine: Grotta, US 2921942 (1960 to American-Marietta); Bearse et al., US 3041349 (1962 to Martin-Marietta); Nevitt, Seelig, loc. cit. Purification: Rottschaefer, US 2459135 (1949 to GAF); Insinger, US 2464811 (1949 to Koppers Co.). Toxicity study: Eagle, Carlson, J. Pharmacol. Exp. Ther. 99, 450 (1950). Review of prepn and properties: W. C. Sumpter, F. M. Miller, Heterocyclic Compounds (Interscience, New York, 1954) pp 70-109.
Properties: Crystals from alcohol, benzene, toluene, glacial acetic acid, mp 245°. Sublimes. bp 355°, bp147 200°. d418 1.10. Exhibits strong fluorescence and long phosphorescence on exposure to ultraviolet light. Extremely weak base. Insol in water. One gram dissolves in 3 ml quinoline, 6 ml pyridine, 9 ml acetone, 2 ml acetone at 50°, 35 ml ether, 120 ml benzene, 135 ml abs alcohol. Slightly sol in petr ether, chlorinated hydrocarbons, acetic acid. Dissolves in concd H2SO4 without dec. KOH fusion yields N-potassium salt. LD50 orally in rats: >5 g/kg (Eagle, Carlson).
Melting point: mp 245°
Boiling point: bp 355°; bp147 200°
Density: d418 1.10
Toxicity data: LD50 orally in rats: >5 g/kg (Eagle, Carlson)
Use: Important dye intermediate. Used in making photographic plates sensitive to ultraviolet light. Reagent for lignin, carbohydrates, and formaldehyde. |