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Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. The most prominent benzimidazole in nature is N-ribosyl-dimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin B12.
It is produced commercially as an parasiticide. The usual synthesis involves condensation of trimethylorthoformate and o-phenylenediamine:
- C6H4(NH2)2 + HC(OCH3)3 → C6H4N(NH)CH + 3 CH3OH
Benzimidazole, as well as the analog imidazole have been used as carbon skeletons for N-heterocyclic carbenes. The NHCs are usually used as ligands for transition metal complexes. They are often prepared by deprotonating an N,N'-disubstituted benzimidazolium salt at the 2-position with a base.
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