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Benzimidazole

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Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a white solid that appears in form of tabular crystals.^[2]

Benzimidazole

Names

Preferred IUPAC name

1H-1,3-Benzimidazole

Other names

1H-Benzo[d]imidazole

Identifiers

CAS Number

51-17-2^Y

3D model (JSmol)

Interactive image

Beilstein Reference

109682

ChEBI

CHEBI:41275^Y

ChEMBL

ChEMBL306226^Y

ChemSpider

5593^Y

DrugBank

DB02962

ECHA InfoCard

100.000.075

EC Number

200-081-4

Gmelin Reference

3106

KEGG

C02009^Y

PubChem CID

5798

UNII

E24GX49LD8^Y

CompTox Dashboard (EPA)

DTXSID8024573

InChI

InChI=1S/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)^Y

Key: HYZJCKYKOHLVJF-UHFFFAOYSA-N^Y
InChI=1/C7H6N2/c1-2-4-7-6(3-1)8-5-9-7/h1-5H,(H,8,9)

Key: HYZJCKYKOHLVJF-UHFFFAOYAX

SMILES

c1ccc2c(c1)[nH]cn2

Properties

Chemical formula

C₇H₆N₂

Molar mass

118.139 g·mol⁻¹

Melting point

170 to 172 °C (338 to 342 °F; 443 to 445 K)

Acidity (pK_a)

12.8 (for benzimidazole) and 5.6 (for the conjugate acid)^[1]

Hazards

GHS labelling:

Pictograms

Signal word

Warning

Hazard statements

H302, H315, H319, H335

Precautionary statements

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Safety data sheet (SDS)

External MSDS

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is ^YN ?)

Infobox references

Preparation

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Benzimidazole was discovered during research on vitamin B₁₂. The benzimidazole nucleus was found to be a stable platform on which drugs could be developed.^[3] Benzimidazole is produced by condensationofo-phenylenediamine with formic acid,^[4] or the equivalent trimethyl orthoformate:

C₆H₄(NH₂)₂ + HC(OCH₃)₃ → C₆H₄N(NH)CH + 3 CH₃OH

2-Substituted derivatives are obtained when the condensation is conducted with aldehydes in place of formic acid, followed by oxidation.^[5]

Reactions

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Benzimidazole is a base:

C₆H₄N(NH)CH + H⁺ → [C₆H₄(NH)₂CH]⁺

It can also be deprotonated with stronger bases:

C₆H₄N(NH)CH + LiH → Li [C₆H₄N₂CH] + H₂

The imine can be alkylated and also serves as a ligand in coordination chemistry. The most prominent benzimidazole complex features N-ribosyl-dimethylbenzimidazole, as found in vitamin B₁₂.^[6]

N,N'-Dialkylbenzimidazolium salts are precursors to certain N-heterocyclic carbenes.^[7]^[8]

Applications

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Benomyl is a fungicide with a benzimidazole core

Benzimidazole derivatives are among the most frequently used ring systems for small molecule drugs listed by the United States Food and Drug Administration.^[9] Many pharmaceutical agents belong to the benzimidazole class of compounds. For example:

Angiotensin II receptor blockers such as azilsartan, candesartan, and telmisartan.
Anthelmintic agents such as albendazole, ciclobendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, triclabendazole, and thiabendazole. These drugs work by binding tubulin, a vital part of the cytoskeleton and mitotic spindle. Benzimidazoles are selectively toxic towards parasitic nematodes, selectively binding and depolymerising their tubulins.^[10]
Antihistamines such as astemizole, bilastine, clemizole, emedastine, mizolastine, and oxatomide.
Benzimidazole fungicides such as benomyl, carbendazim, fuberidazole, and thiabendazole. These drugs selectively bind to and depolymerise fungal tubulin.^[10]
Benzimidazole opioids such as bezitramide, brorphine, clonitazene, etodesnitazene, etonitazene, etonitazepipne, etonitazepyne, isotonitazene, metodesnitazene, and metonitazene.
Proton-pump inhibitors such as dexlansoprazole, esomeprazole, ilaprazole, lansoprazole, omeprazole, pantoprazole, rabeprazole, and tenatoprazole.
Typical antipsychotics such as benperidol, clopimozide, droperidol, neflumozide, and oxiperomide, and pimozide.
Other notable pharmaceutical agents which contain a benzimidazole group include abemaciclib, bendamustine, dabigatran, daridorexant, and glasdegib.

Inprinted circuit board manufacturing, benzimidazole can be used as an organic solderability preservative.^{[citation needed]}

Several dyes are derived from benzimidazoles.^[11]

References

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^ Walba, Harold; Isensee, Robert W. (1961). "Acidity Constants of Some Arylimidazoles and Their Cations". The Journal of Organic Chemistry. 26 (8): 2789–2791. doi:10.1021/jo01066a039.

^ "Benzimidazole | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2023-01-11.

^ Bennet-Jenkins, E.; Bryant, C. (1996). "Novel sources of anthelmintics". International Journal for Parasitology. 26 (8–9): 937–947. doi:10.1016/s0020-7519(96)80068-3. ISSN 0020-7519. PMID 8923141.

^ E. C. Wagner, W. H. Millett (1939). "Benzimidazole". Organic Syntheses. 19: 12. doi:10.15227/orgsyn.019.0012.

^ Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405

^ H. A. Barker; R. D. Smyth; H. Weissbach; J. I. Toohey; J. N. Ladd & 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. doi:10.1016/S0021-9258(18)69550-X. PMID 13796809.

^ R. Jackstell; A. Frisch; M. Beller; D. Rottger; M. Malaun; 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.

^ H. V. Huynh; J. H. H. Ho; T. C. Neo; 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.

^ Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J Med Chem 2014, 57, 5845.>

^ ^a ^b Wang, C. C. (January 1984). "Parasite enzymes as potential targets for antiparasitic chemotherapy". Journal of Medicinal Chemistry. 27 (1): 1–9. doi:10.1021/jm00367a001. ISSN 0022-2623. PMID 6317859.

^ Horst Berneth "Methine Dyes and Pigments" in Ullmann's Encyclopedia of Industrial Chemistry, 2008, Wiley-VCH, Weinheim. doi:10.1002/14356007.a16_487.pub2

Benzimidazole

Contents

Preparation

Reactions

Applications

See also

References

Further reading

Languages