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Benzimidazole

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Benzimidazole
Skeletal formula with numbering convention

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IUPAC name
1H-benzimidazole
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51-17-2 7pxY ChEBI CHEBI:41275 7pxY ChEMBL ChEMBL306226 7pxY ChemSpider 5593 7pxY Jmol-3D images Image
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This page is a soft redirect. Properties

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C7H6N2 Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Melting point Script error: No such module "convert". Acidity (pKa) 12.8 (for benzimidazole) and 5.6 (for the conjugate acid) [1] colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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SDS External MSDS EU classification Harmful (Xn) R-phrases R20 R21 R22 R36 R37 R38 S-phrases S26 S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[2]

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.[3][4]

Preparation

Benzimidazole is commercially available. The usual synthesis involves condensation of o-phenylenediamine with formic acid,[5] 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.[5] 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

References

  1. ^ Walba, H. & Isensee, R. W. Acidity constants of some arylimidazoles and their cations. J. Org. Chem. 26, 2789-2791 (1961).
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ a b E. C. Wagner and W. H. Millett (1943). "Benzimidazole". Org. Synth. ; Coll. Vol. 2, p. 65 .

Further reading

  • Grimmett, M. R. (1997). Imidazole and benzimidazole synthesis. Boston: Academic Press. ISBN 0-12-303190-7. 

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