Everyone Healthy medication library
Benzimidazole Drug Class
Medicines in this drug class are grouped together in the Everyone Healthy medication database. This page is educational only and should not be used as personal prescribing advice.
Drug class overview
Benzimidazole overview
Benzimidazole
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]
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]
| Benzimidazole | |
|---|---|
 |
|
| Identifiers | |
| CAS number | 51-17-2  |
| PubChem | 5798 |
| ChemSpider | 5593 |
| SMILES | |
| InChI | |
| InChI key | HYZJCKYKOHLVJF-UHFFFAOYAX |
| Properties | |
| Molecular formula | C7H6N2 |
| Molar mass | 118.14 g mol−1 |
| Melting point |
170–172 °C |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Harmful (Xn) |
| R-phrases | R20 R21 R22 R36 R37 R38 |
| S-phrases | S26 S36 |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| Infobox references | |
Preparation
Benzimidazole is commercially available. The usual synthesis involves condensation of o-phenylenediamine with formic acid,[4] or the equivalent trimethyl orthoformate:
- C6H4(NH2)2 + HC(OCH3)3 → C6H4N(NH)CH + 3 CH3OH
By altering the carboxylic acid used, this method is generally able to afford 2-substituted benzimidazoles.[4] Benzimidazole also has fungicidal properties. It acts by binding to the fungal microtubules and stopping hyphal growth. It also binds to the spindle microtubules and blocks nuclear division.
See also
- Benzimidazoline
- 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
- polybenzimidazole, a high performance fiber
References
- ^ H. A. Barker, R. D. Smyth, H. Weissbach, J. I. Toohey, J. N. Ladd, and B. E. Volcani (February 1, 1960). "Isolation and Properties of Crystalline Cobamide Coenzymes Containing Benzimidazole or 5,6-Dimethylbenzimidazole". Journal of Biological Chemistry 235 (2): 480–488. PMID 13796809. http://www.jbc.org/cgi/reprint/235/2/480.
- ^ 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:.
- ^ a b E. C. Wagner and W. H. Millett (1943), "Benzimidazole", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0065; Coll. Vol. 2: 65
Further reading
Grimmett, M. R. (1997). Imidazole and benzimidazole synthesis. Boston: Academic Press. ISBN 0-12-303190-7.
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