6651. Nitrourea

Nomenclature

CAS number: 556-89-8
N-Nitrocarbamide.
CH3N3O3; mol wt 105.05.
C 11.43%, H 2.88%, N 40.00%, O 45.69%.
NH2CONHNO2.

Description and references

Prepd by the action of concd sulfuric acid upon urea nitrate: Thiele, Lachman, Ann. 288, 281 (1895); Ingersoll, Armendt, Org. Synth. 5, 85 (1925). By dropwise addition of HCl to a cooled mixture of silver cyanate and nitramide in water: Davis, Blanchard, J. Am. Chem. Soc. 51, 1794 (1929).

Properties

Platelets from alcohol + petr ether dec 158.4-158.8°. pK (20°) 2.15. Absorption spectrum: Baly, Desch, J. Chem. Soc. 93, 1753 (1908). Explosive. Soluble in hot water, but water solns are unstable. Decompn in aq alkaline solns is almost instantaneous. Freely sol in acetone, alcohol, acetic acid. Sparingly sol in petr ether, chloroform, benzene. Stable to oxidizing agents. Can be detonated, but is not sensitive to percussion or heating.