Benzimidazole
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| Benzimidazole |
</td></tr><tr><td style="background-color: #FFFFFF; vertical-align: top; white-space: nowrap;">Chemical formula </td><td style="background-color: #FFFFFF;">C7H6N2 </td></tr><tr><td style="background-color: #FFFFFF; vertical-align: bottom; white-space: nowrap;">Molar mass</td>
<td style="background-color: #FFFFFF;">118.136 g mol−1</td></tr><tr><td style="background-color: #FFFFFF; vertical-align: top; white-space: nowrap; width: 30%;">Systematic name</td> <td style="background-color: #FFFFFF;">1H-benzoimidazole</td></tr><tr><td align="center" style="background-color: #ddeeff;" colspan="2">Complete data</td></tr></table></div>
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.
[edit] See also
- Indole, an analog with CH in place of nitrogen in position 3.
- Purine, an analog with two additional nitrogen atoms in the six-membered ring.
- Simple aromatic rings
[edit] External links
pl:Benzimidazol th:เบนซิมิดาโซล
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