76889-76-4

Usage

Type of compound

Benzimidazole derivative

Common use

Building block in the synthesis of various pharmaceuticals and organic compounds

Medicinal chemistry interest

Potential biological activities, including enzyme inhibition and modulation of cellular processes

Studied properties

Potential antifungal and antiproliferative properties

Physical state at room temperature

Solid

Handling and storage

Standard laboratory conditions are typically used.

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 1042161-45-4 (E)-2-azido-N-(2-cyanobenzylidene)aniline 
• 22115-41-9 2-(bromomethyl)benzonitrile 
• 3010-03-5 piperidin-1-yl-acetonitrile 
• 716-79-0 2-phenyl-1H-benzoimidazole 
• 29134-29-0 N-cyanomethyl pyrrolidine 
• 3010-02-4 diethylaminoacetonitrile 
• 874-77-1 2-(4-methylpiperazin-1-yl)acetonitrile 
• 7468-67-9 o-formylbenzonitrile 
• 91-15-6 phthalonitrile 
• 27611-63-8 2-Cyanobenzoyl chloride 
• 76889-75-3 N-[3-Imino-2,3-dihydro-isoindol-(1Z)-ylidene]-benzene-1,2-diamine 
• 1608149-17-2 2-(((2-aminophenyl)amino)methyl)benzonitrile 

Downstream Products

• 16529-06-9 2-(2-carboxyphenyl)benzimidazole 
• 2717-05-7 1,2-benzoylenebenzimidazole 

Relevant academic research and scientific papers

One-Pot Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines and Isoquinolino[3,4-b]quinoxalines via Tandem Cyclization Strategies

Two operationally simple one-pot protocols have been developed for the synthesis of amino-functionalized benzo[4,5]imidazo[2,1-a]isoquinolines and isoquinolino[3,4-b]quinoxalines. Optimization data and substrate scope for these atom-economical transformat

Cd-MOF@PVDF Mixed-Matrix Membrane with Good Catalytic Activity and Recyclability for the Production of Benzimidazole and Amino Acid Derivatives

Mixed-matrix membranes (MMMs) incorporating metal-organic framework crystalline fillers as heterogeneous catalysts for organic transformation reactions have attracted more attention in catalysis science. Herein, a new 3D cadmium metal-organic framework (H3O)·[Cd(dppa)] (1) was first synthesized using the rigid 4-(3,5-dicarboxylphenyl)picolinic acid (H3dppa) as an organic ligand under solvothermal conditions, exhibiting a novel 6,6-connected network and good tolerance to various solvents. After activation, 1 showed good catalytic reactivity and selectivity for the synthesis of benzimidazole derivatives, affording solvent-dependent catalytic activity. Then, using the microcrystals of 1 and poly(vinylidene fluoride) (PVDF) as raw materials, 1@PVDF MMMs were successfully prepared by polymer solution casting. Notably, the integration of MOF and PVDF endows the mixed-matrix membrane 1@PVDF with great advantages in terms of more dispersive Lewis acid catalytic sites and recyclability. As expected, 1@PVDF not only displays good catalytic activity comparable to that of activated 1 but also exhibits remarkable recyclability and continuous usability for the production of benzimidazole and α-or β-amino acid derivatives. To the best of our knowledge, this is the first time that a Cd-based MOF and MMMs have been applied as a catalyst for the production of a β-amino acid. The combination of catalytic MOF and PVDF provides a way to simplify the design of a flow reactor and reduce the costs of manufacturing.

Solid Phase Synthesis of Biologically active Benzimidazole Derivatives Catalysed by CH3S03H-Si02 under Solvent free Condition

A simple an expeditious method was established for the synthesis of 2-Substituted-1H-Benzimidazole derivatives at 90°C using o-phenylenediamine and different aldehydes. It has been found that a mixture of Methanesulphonic acid-Si02to be an effective catal

Vanadyl Acetylacetonate-Copper (II) Trifluoro Methane Sulfonate Catalyzed Eco-friendly Synthesis of Substituted Benzimidazoles in Aqueous Media

Various substituted benzimidazoles have been successfully synthesized in aqueous medium by developing VO(acac)2–Cu(OTf)2 catalytic system. A green synthetic protocol has been created in presence of water and cetyltrimethyl ammonium bromide (CTAB) system in an organic solvent free condition. This chemoselective cyclocondensation cumoxidation process occurred in aqueous media. In this suitable method easily synthesized 2-Substituted benzimidazoles with good yields and no 1,2-disubstituted by-products were noticed. Excellent yields, environmentally benign and mild reaction condition, easy purification of the desired products are the main attractive features of this newly devised method.

Cu(OAc)2-Mediated benzimidazole-directed C-H cyanation using 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source

A new protocol for the Cu(OAc)2-mediated cyanation of arenes using benzimidazole as the directing group with 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was developed. A series of cyano derivatives were facilely and conveniently obtained in moderate to good yields by using this method. The C-H activation catalytic system was originally applied to the C(sp2)-H cyanation of the aryl/heteroaryl to synthesize 2-(1H-benzo[d]imidazol-2-yl)aryl nitriles. There were 19 new compounds in the synthesized 20 cyanide products. In this reaction, 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was originally employed in the C(sp2)-H cyanation of the arenes. In addition, a fluorescent material 5a was obtained by derivative reactions of the obtained cyanide product 3.

Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.

An unexpected role of carbon disulfide: A new and efficient method for the synthesis of 2-substituted benzimidazoles

A new and efficient methodology for the synthesis of 2-substituted benzimidazoles is described. In this procedure, CS2 unexpectedly facilitated the cyclization reaction between benzene-1,2-diamine and benzenecarbaldehydes in CH2Clsu

Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides

(Chemical Equation Presented) The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.

N-hydroxyphthalimide/cobalt acetate, a new catalytic oxidative system for the synthesis of benzimidazoles

Benzimidazoles are readily prepared from 1,2-phenylenediamine and an aldehyde using air and catalytic N-hydroxyphthalimide/Co(OAc)2 as the oxidant. Both electron-donating and electron-withdrawing groups are tolerated. Copyright Taylor & Francis Group, LLC.

Benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines as novel Na+/H+ exchanger inhibitors, synthesis and protection against ischemic-reperfusion injury

A novel series of benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines were designed and synthesized as Na+/H+exchanger inhibitors. Most of them were found to inhibit NHE1-mediated platelet swelling in a concentration-dependent manner, and to have significant cardioprotective effect against myocardial ischemic-reperfusion injury, among which compounds 10a and 34 were more potent than cariporide in both in vivo and in vitro tests.