6593. p-Nitrobiphenyl

Nomenclature

CAS number: 92-93-3
4-Nitro-1,1′-biphenyl; 4-nitrobiphenyl; p-nitrodiphenyl; PNB.
C12H9NO2; mol wt 199.21.
C 72.35%, H 4.55%, N 7.03%, O 16.06%.

Description and references

Prepn: G. Schultz, Ann. 174, 210 (1874); O. Kühling, Ber. 28, 42 (1895); E. Bamberger, ibid. 404; R. L. Jenkins et al., Ind. Eng. Chem. 22, (1) 31 (1930); K. Dimroth et al., Ber. 101, 2215 (1968). Crystal structure: M. Prasad et al., J. Indian Chem. Soc. 13, 519 (1936); C.A. 31, 12715 (1937). Review of carcinogenic risk: IARC Monographs vol. 4, 113-117 (1974).

Chemical structure

Properties

Needles from alcohol, mp 113.7°. bp760 340°; bp30 223.7-224.1°. Insol in water. Slightly sol in cold alc; more readily sol in hot alc; sol in chloroform, ether. uv spectrum: D. F. DeTor, H. J. Scheifele, J. Am. Chem. Soc. 73, 1442 (1951).

Caution

Potential symptoms of overexposure are headache, drowsiness and dizziness; dyspnea; ataxia, lassitude; methemoglobinemia; urinary burning; acute hemorrhagic cystitis. Potential occupational carcinogen. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH PB2003-100121, 2003) p 226.

Use

Formerly in prepn of p-biphenylamine, q.v.