1-Cyanoimidazole

CAS 36289-36-8, Cat. No EN300-211455
Reagent for cyanation

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1-Cyanoimidazole is a mild and efficient electrophilic cyanating reagent for transferring cyano groups to various nucleophiles, including amines, thiols, and carbanions¹. Its scope includes primary and secondary amines, Grignard reagents, organolithium species, and thiols, offering high to excellent yields for most substrates. Applications include the formation of cyanoamines, cyanated carbanion products, and thiocyanates. Reactions proceed smoothly under mild conditions in solvents such as CH₂Cl₂ or DMA, with carbanion cyanations achieving excellent yields. However, thiols due to competing disulfide formation have generally lower yields. 1-Cyanoimidazole is a stable solid that should be handled under anhydrous conditions to maximize efficiency and minimize byproduct formation.

Synonyms: N-cyanoimidazole; imidazole-1-carbonitrile; 1-cyano-1H-imidazole; 1-cyanoimidazole; 1H-imidazole-1-carbonitrile