Benzimidazole
From Wikipedia, the free encyclopedia
| Benzimidazole | |
|---|---|
 |
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| IUPAC name | 1H-benzimidazole |
| Identifiers | |
| CAS number | [51-17-2] |
| PubChem | |
| SMILES | c1cccc2ncnc12 |
| Properties | |
| Molecular formula | C7H6N2 |
| Molar mass | 118.136 g/mol |
| Melting point |
170-172 °C |
| Hazards | |
| MSDS | Oxford MSDS |
| EU classification | Harmul (Xn) |
| S-phrases | S26 S36 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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 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]
[edit] See also
- Albendazole, a common use anthelmintic.
- 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
- Triclabendazole, most common drug against liver flukes
[edit] References
- ^ 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.
- ^ 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:.
- ^ 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:.
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