6608. N-Nitroguanidine

Nomenclature

CAS number: 556-88-7
CH4N4O2; mol wt 104.07.
C 11.54%, H 3.87%, N 53.84%, O 30.75%.

Description and references

Exists in two forms. The α-form is the usual stable form. The β-form is converted into the α-form by dissolving in concd H2SO4 and pouring into ice water. Prepn of the α-form from guanidine nitrate and the β-form from guanidine sulfate: T. L. Davis et al., J. Am. Chem. Soc. 47, 1063 (1925). Modified prepn of the α-form: T. L. Davis, Org. Synth. 7, 68 (1927). Absorption spectrum: E. R. Riegel, K. W. Buchwald, J. Am. Chem. Soc. 51, 484 (1929)

Chemical structure

Properties

Needles, prisms from water, dec 225-250° (depending on speed of heating) giving off NH3 fumes. Slightly soluble in methanol (<0.5%), alcohol; practically insol in ether. Sol in concd acids from which it is precipitated by water. Sol in cold solns of alkalies (not of carbonates) with slow decompn.

Use

Explosive of moderate power. Can be exploded only with a detonator. Intermediate in the synthesis of pharmaceuticals.