N,N’-Carbonyldiimidazole | 1,1′-Carbonyldiimidazole | CAS 530-62-1

Item Name:
Carbonyldiimidazole
N,N’-Carbonyldiimidazole
1,1′-Carbonyldiimidazole
Di(1H-imidazol-1-yl)methanone
CAS No.: 530-62-1
MF: C7H6N4O
MW: 162.149

Category:

N,N’-Carbonyldiimidazole, also known as 1,1′-Carbonyldiimidazole, Carbonyldiimidazole, Di(1H-imidazol-1-yl)methanone, is a derivative of imidazole. Its imidazole structure has a closed large P bond, and there is a pair of lone pair electrons on the unbound sp2 orbital of one of the nitrogen atoms. These features gives Carbonyldiimidazole strong chemical reactivity, which means it can react with functional groups such as ammonia, alcohols, and acids to synthesize many compounds that are difficult to obtain if using general synthesizing methods.

1,1′-Carbonyldiimidazole is widely used as an enzyme and protein binder, intermediate in antibiotic synthesis, especially as a bonding agent for synthesizing peptide compounds.

Properties of N,N’-Carbonyldiimidazole

Carbonyldiimidazole is white crystalline powder,  which is often used to turn amines into amides, carbamates, and urea or convert alcohols into esters. It is soluble in water and organic solvents such as alcohols and ethers.  1,1′-Carbonyldiimidazole is highly deliquescent and reacts with water into imidazole and carbon dioxide.

Melting Point:  117-122°C(lit.)
Boling Point:  288.83°C (rough estimate)
Flash Point: 250.8°C

Applications of N,N’-Carbonyldiimidazole

Carbonyldiimidazole is mainly used in organic synthesis as a formyl transfer reagent and an activator of carboxylic acids. It has higher application value than similar reagents DCC and EDC, due to its high reactivity, low cost, and simple post-treatment.

N,N’-Carbonyldiimidazole can also be used as a peptide reagent functioning as condensation agent to synthesize triphosphate nucleosides, peptides, and esters, as well as an important intermediate in the synthesis of acyl imidazole and pyruvamide. It is used for protecting biochemical synthesis groups and connecting protein peptide chains and also widely used as an activator in organic synthesis, especially in the fields of biochemistry and pharmaceuticals.

As an activator, Carbonyldiimidazole can be used to quickly make amphiphilic urea oligomers with good antibacterial properties. It can also be used to synthesize Hydroxyquinium derivatives with amide structures that can self assemble under solid-state conditions or make Heterocyclic organic compounds with urea structure through Monomer self cyclization.