6592. o-Nitrobiphenyl

Nomenclature

CAS number: 86-00-0
2-Nitro-1,1′-biphenyl; o-nitrodiphenyl; ONB.
C12H9NO2; mol wt 199.21.
C 72.35%, H 4.55%, N 7.03%, O 16.06%.

Description and references

Prepn from diazotized o-nitroaniline and benzene by a modified Gomberg reaction: Elks et al., J. Chem. Soc. 1940, 1284. Prepd industrially by direct nitration of biphenyl (yields ≈50% para, 35% ortho).

Chemical structure

Properties

Orthorhombic bipyramidal plates from ethanol. Characteristic sweetish odor. mp 36.7°. d425 1.44. d4015.5 (liq) 1.189. The technical liquid weighs ≈10 lbs/gal. bp760 325°; bp30 205°; bp13 170°; bp4 166°. nD25 (tech liq) 1.613. Flash pt 179°C (354°F). uv max: 325 nm. Dipole moment: 3.79. Viscosity of tech liquid (cP): 12 (45°); 38 (25°). Insol in water. Sol in methanol, ethanol, tetrahydrofurfuryl alcohol, acetone, DMF, carbon tetrachloride, perchlorethylene, mineral spirits, turpentine, glacial acetic acid.

Use

Plasticizer for resins, cellulose acetate and nitrate, polystyrenes; fungicide for textiles; wood preservative; dye intermediate.