1819. N,N′-Carbonyldiimidazole

Nomenclature

CAS number: 530-62-1
1,1′-Carbonylbis-1H-imidazole.
C7H6N4O; mol wt 162.15.
C 51.85%, H 3.73%, N 34.55%, O 9.87%.

Description and references

Prepd from phosgene and imidazole in dry tetrahydrofuran or dry benzene: Staab, Ann. 609, 75 (1957); Anderson, Paul, J. Am. Chem. Soc. 80, 4423 (1958).

Chemical structure

Properties

Crystals from tetrahydrofuran or benzene, mp 115.5-116°. Should be handled under exclusion of atmospheric moisture. Hydrolyzed by water in a few sec with evolution of CO2.

Use

In the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.