9740. Triphenylene

Nomenclature

CAS number: 217-59-4
9,10-Benzphenanthrene; 1,2,3,4-dibenznaphthalene; isochrysene.
C18H12; mol wt 228.29.
C 94.70%, H 5.30%.

Description and references

Occurs in coal tar: Kaffer, Ber. 68, 1812 (1935). Synthesis from cyclohexanone: Mannich, Ber. 40, 163 (1907); Nenitzescu, Curcaneanu, Ber. 70, 346 (1937); from 9-phenanthrylmagnesium bromide and succinic anhydride: Bergmann, J. Am. Chem. Soc. 59, 1441 (1937); from 1,2,3,4-tetrahydrophenanthrene: Bachmann, Struve, J. Org. Chem. 4, 472 (1937); by reaction of 3 mols o-bromoiodobenzene in the presence of lithium: Heaney, Millar, Org. Synth. 40, 105 (1960).

Chemical structure

Properties

Long needles from alc or chloroform. Sublimes; d 1.302; mp 199°; bp 425°. Absorption spectrum: Clar, Lombardi, Ber. 65, 1414 (1932). Solns have blue fluorescence. Does not react with maleic anhydride.