7396. Picene

Nomenclature

CAS number: 213-46-7
3,4-Benzchrysene; 1,2,7,8-dibenzphenanthrene; dibenzo[a,i]phenanthrene; β,β-binaphthyleneethene.
C22H14; mol wt 278.35.
C 94.93%, H 5.07%.

Description and references

Found in tar oils from soft coal: Burg, Ber. 13, 1834 (1880); Lang et al., ibid. 97, 494 (1964); in petroleum residues from the cracking process: Meyer, Hofmann, Monatsh. Chem. 37, 681 (1916). Synthesis from cholic acid by selenium dehydrogenation: Ruzicka et al., Helv. Chim. Acta 17, 200 (1934); from o-xylylenedicyanide with o-nitrobenzaldehyde by a double Pschorr synthesis: Waldmann, Pitschak, Ann. 527, 183 (1937); by a diene synthesis with tetrahydrodinaphthyl and maleic anhydride: Weidlich, Ber. 71, 1203 (1938); from 9,10-dihydrophenanthrene: Phillips, J. Am. Chem. Soc. 75, 3223 (1953); from ethyl 4,6-dioxoheptane-1,5-dicarboxylate: Nasipuri, Chem. Ind. (London) 1956, 795.

Chemical structure

Properties

Fluorescent plates from ethyl acetate, mp 366-367°. bp 518-520°. Absorption spectrum: Mayneord, Roe, Proc. R. Soc. London A152, 319 (1935). Difficultly sol in most solvents. Somewhat sol in boiling benzene, chloroform, glacial acetic acid; more sol in cumene (isopropylbenzene).