93. Acetyleneurea

Nomenclature

CAS number: 496-46-8
Tetrahydroimidazo[4,5-d]imidazole-2,5-(1H,3H)-dione; glycoluril; acetylenediureine; glyoxaldiureine; acetylene carbamide.
C4H6N4O2; mol wt 142.12.
C 33.80%, H 4.26%, N 39.42%, O 22.52%.

Description and references

Prepd by the sodium amalgam reduction of allantoin: Biltz, Schiemann, J. Prakt. Chem. 113, 77 (1926); from glyoxal and urea: Reibnitz, US 2731472 (1956 to BASF).

Chemical structure

Properties

Crystals, dec at about 300°. Slightly sol in cold, more sol in hot water; sol in warm mineral acids, warm ammonia.