Benzimidazole

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Chemical structure of Benzimidazole_chemical_structure

Benzimidazole

Systematic (IUPAC) name
1H-benzoimidazole
Synonyms
BI
Identifiers
PubChem         5798
Chemical data
Formula C7H6N2 
Molar mass 118.136
Complete data

Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. The most prominent benzimidazole compound in nature is N-ribosyl-dimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin B12. [1]

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, in an extension of the well-elaborated imidazole system, has 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.[2][3]

See also

References

  1. H. A. Barker, R. D. Smyth, H. Weissbach, J. I. Toohey, J. N. Ladd, and B. E. Volcani (1960). "Isolation and Properties of Crystalline Cobamide Coenzymes Containing Benzimidazole or 5,6-Dimethylbenzimidazole". Journal of Biological Chemistry. 235 (2): 480–488.
  2. R. Jackstell, A. Frisch, M. Beller, D. Rottger, M. Malaun and B. Bildstein (2002). "Efficient telomerization of 1,3-butadiene with alcohols in the presence of in situ generated palladium(0)carbene complexes". Journal of Molecular Catalysis A: Chemical. 185 (1–2): 105–112. doi:10.1016/S1381-1169(02)00068-7.
  3. H. V. Huynh, J. H. H. Ho, T. C. Neo and L. L. Koh (2005). "Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity". Journal of Organometallic Chemistry. 690 (16): 3854–3860. doi:10.1016/j.jorganchem.2005.04.053.

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