3278. 4,4′-Dinitrocarbanilide

Nomenclature

CAS number: 587-90-6
N,N′-Bis(4-nitrophenyl)urea; DNC; 4,4′-dinitrodiphenylurea.
C13H10N4O5; mol wt 302.24.
C 51.66%, H 3.33%, N 18.54%, O 26.47%.

Description and references

Prepd by heating 4-nitroaniline and diphenyl carbonate for 3 hrs at 200°: Vittenet, Bull. Soc. Chim. Fr. [3] 21, 149 (1899); by nitration of diphenylurea with 68.28% HNO3 in concd H2SO4 at 0°: Kogan, Kutepov, J. Gen. Chem. USSR 21, 1297 (1951), C.A. 46, 2003d (1952); by the action of dil HNO3 on diphenylurea at up to 100°: eidem, SU 78379 (1949), C.A. 48, 7056i (1954).

Chemical structure

Properties

Yellow needles from alc, mp 312° (dec). Sublimes above 310°. Moderately sol in boiling nitrobenzene; sparingly sol in boiling alc, somewhat more sol in a mixture of glacial acetic acid and nitric acid. Practically insol in acetone, chloroform, benzene, dioxane, acetic acid, ether and linseed oil. Solubilities in g/100 ml solvent at 25°: water 2 × 10-6; ethanol 0.007; ethyl acetate 0.015; petr ether 0.0; xylene <0.01; methyl Cellosolve 0.1; dimethyl acetamide 0.14; dimethyl sulfoxide 0.47.