benzimidazole

ベンズイミダゾール

関

Albendazole; Mebendazole; Thi- abendazole

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/06 23:40:38」(JST)

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Benzimidazole
IUPAC name 1H-benzimidazole
Identifiers
CAS number	51-17-2 Y
PubChem	5798
ChemSpider	5593 Y
UNII	E24GX49LD8 Y
KEGG	C02009 Y
ChEBI	CHEBI:41275 Y
ChEMBL	CHEMBL306226 Y
Jmol-3D images	Image 1 Image 2
SMILES n2c1ccccc1nc2 c1ccc2c(c1)[nH]cn2
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
Properties
Molecular formula	C7H6N2
Molar mass	118.14 g mol−1
Melting point	170–172 °C
Acidity (pKa)	12.8 (for benzimidazole) and 5.6 (for the conjugate acid)
Hazards
MSDS	External MSDS
EU classification	Harmful (Xn)
R-phrases	R20 R21 R22 R36 R37 R38
S-phrases	S26 S36
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y (verify) (what is: Y/N?)
Infobox references

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.

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.

Preparation

Benzimidazole is commercially available. The usual synthesis involves condensation of o-phenylenediamine with formic acid, 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. 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
• Polybenzimidazole, a high performance fiber
• 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
• benzimidazole fungicides

References

Further reading

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

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• A self-assembled Pd2L4 cage that selectively encapsulates nitrate.

• Zhou LP1, Sun QF.
• Chemical communications (Cambridge, England).Chem Commun (Camb).2015 Dec 7;51(94):16767-70. doi: 10.1039/c5cc07306e. Epub 2015 Oct 13.
• A M2L4 cage with D4 symmetry was self-assembled from four anthracene-bridged benzimidazole ligands and two Pd(II) ions. The cage features a concise hydrophobic pocket wrapped up by the anthracene walls with eight hydrogen-bond donors pointing inward, which provide a specific binding site for nitrate
• PMID 26459954

• Vibrationally resolved (1)Lb ((1)A')↔S0 ((1)A') electronic spectra of benzimidazole and indene: Influence of Duschinsky and Herzberg-Teller effects on weak dipole-allowed transitions.

• Yang P1, Pang M1, Li M1, Shen W1, He R2.
• Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Dec 5;151:375-84. doi: 10.1016/j.saa.2015.06.101. Epub 2015 Jun 30.
• Geometrical optimizations of the ground and first excited states of benzimidazole and indene were performed using the density functional theory (DFT) and its time-dependent extension methods (TD-DFT), respectively. Their vibrationally resolved (1)Lb ((1)A')↔S0 ((1)A') absorption and fluorescence s
• PMID 26143330

Japanese Journal

• 1,3,5-Tris(phenyl-2-benzimidazole)-benzene cathode buffer layer thickness dependence in solution-processable organic solar cell based on 1,4,8,11,15,18,22,25-octahexylphthalocyanine

• Jpn. J. Appl. Phys. 54(4S), 04DK11, 2015-03-24
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• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 91(3), 610-625, 2015-03-01
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• NAID 130005095014

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★リンクテーブル★

リンク元	「駆虫薬」
拡張検索	「2-pyridinylmethylsulfinylbenzimidazole」「dichlororibofuranosylbenzimidazole」「dimethylbenzimidazole」「benzimidazole ring」

「駆虫薬」

　　[★]

英

anthelmintic, anthelmintics

ラ

anthelmintica

関

http://en.wikipedia.org/wiki/Anthelmintic

antiplatyhelmintic agents	Antitrematodals (schistosomicides)	binds tubulin	benzimidazole (Triclabendazole#)
		acetylcholinesterase inhibitor	phosphonic acid (metrifonate)
		Other/unknown	quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen)
	anticestodals (taeniacides)	binds tubulin	benzimidazole (albendazole#)
		Other/unknown	salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen)
antinematodal agents (macrofilaricides)		binds tubulin	benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole)
		chloride channel	macrolide (ivermectin#)
		NMDA	tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel)
		Other/unknown	piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#)  · tribendimidine

「2-pyridinylmethylsulfinylbenzimidazole」

　　[★]

2-ピリジニルメチルスルフィニルベンズイミダゾール、2-ピリジニルメチルスルフィニルベンゾイミダゾール

「dichlororibofuranosylbenzimidazole」

　　[★]

ジクロロリボフラノシルベンズイミダゾール

「dimethylbenzimidazole」

　　[★]

ジメチルベンズイミダゾール

「benzimidazole ring」

　　[★]

ベンズイミダゾール環