67370-32-5

Usage

Chemical structure

A benzimidazole derivative with two chloride substituents attached to the phenyl ring

Potential uses

Anti-fungal and anti-bacterial agent, activity against cancer cells, treatment of skin conditions (allergic contact dermatitis, atopic dermatitis), fungicide in agriculture

Promise

Wide range of applications in the fields of medicine and agriculture

InChI:InChI=1/C13H8Cl2N2/c14-9-6-5-8(7-10(9)15)13-16-11-3-1-2-4-12(11)17-13/h1-7H,(H,16,17)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 18880-04-1 3,4-dichlorobenzyl bromide 
• 2642-63-9 3',4'-dichloroacetophenone 
• 615-43-0 2-iodophenylamine 
• 102-49-8 3,4-dichlorobenzyl amine 
• 51-44-5 3,4-dichlorbenzoic acid 

Downstream Products

• 1609007-48-8 (E)-1-(2-(3,4-dichlorophenyl)-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one 
• 1428958-95-5 2-(3,4-dichloro-phenyl)-1-(2-methanesulfonyl-pyrimidin-4-yl)-1H-benzoimidazole 
• 1428958-91-1 2-(3,4-dichloro-phenyl)-1-(2-methylsulfanyl-pyrimidin-4-yl)-1H-benzoimidazole 
• 1428959-05-0 {4-[2-(3,4-dichloro-phenyl)-benzoimidazol-1-yl]-pyrimidin-2-yl}-(tetrahydro-pyran-4-yl)-amine 
• 1081111-16-1 2-(3,4-dichlorophenyl)-1-{3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole 

Relevant academic research and scientific papers

Synthesis of benzimidazole based hydrazones as non-sugar based α-glucosidase inhibitors: Structure activity relation and molecular docking

In search for α-glucosidase inhibitors used in the treatment of diabetes mellitus, a series of unique benzimidazole based hydrazones derivatives were synthesized (5a-5p), which were then investigated for their in vitro α-glucosidase inhibitory potential.

Solvent-dependent metal-free chemoselective synthesis of benzimidazoles and 1,3,5-triarylbenzenes from 2-amino anilines and aryl alkyl ketones catalyzed by I2

A solvent-dependent I2-catalyzed chemoselective reaction was developed for the synthesis of benzimidazoles and 1,3,5-triarylbenzenes via the annulation of 2-amino anilines and aryl alkyl ketones or the cyclization of aryl alkyl ketones, respectively. With 1,4-dioxane as the solvent, sequential C[sbnd]N bond formation followed by C(CO)-C(CH3) bond cleavage leads to the formation of benzimidazoles in a highly selective manner while aldol-type self-condensation of aryl alkyl ketones predominates using PhNO2 or PhCl as the solvent to afford 1,3,5-triarylbenzenes.

Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light

ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ～ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.

Copper-Catalyzed Double C-N Bond Formation for the Synthesis of Diverse Benzimidazoles from N -Alkyl-2-iodoaniline and Sodium Azide

An efficient approach to the synthesis of benzimidazole derivatives has been achieved by copper-catalyzed double C-N bonds formation of N-alkyl-2-iodoaniline and sodium azide. The reaction was supposed to proceed through copper-catalyzed tandem reaction of SNAr reaction, aerobic oxidation of C(sp3)-H bond and intramolecular C-N bond formation sequence. Structurally diverse 2-aryl, alkenyl and alkyl benzoimidazole derivatives were assembled by this methodology.

Trichloroisocyanuric Acid/Triphenylphosphine-Mediated Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiazoles

A new and efficient method for preparation of benzimidazoles, benzoxazoles, and benzothiazoles from reactions of different carboxylic acids with o-phenylenediamine, o-aminophenol, and o-aminothiophenol in the presence of triphenylphosphine/trichloroisocyanuric acid system is presented. The desired products have been characterised on the basis of spectral (infrared, NMR, mass spectrometry) data, and the mechanism of their formation is proposed. The remarkable advantages are the inexpensive and readily available reagent, simple procedure, mild conditions, and good-to-excellent yields.

Iron(II) bromide-catalyzed oxidative coupling of benzylamines with ortho-substituted anilines: Synthesis of 1,3-benzazoles

An iron(II) bromide-catalyzed oxidative coupling of benzylamines with 2-amino/hydroxy/mercapto-anilines has been developed, allowing the synthesis of a diversity of substituted 1,3-benzazoles in good to excellent yields. This transformation is compatible with a wide range of functional groups. The method is practical, economical and employs molecular oxygen as an oxidant.

Synthesis of benzimidazoles by copper-catalyzed aerobic oxidative domino reaction of 1,2-diaminoarenes and arylmethyl halides

Arylmethyl halides are readily synthesized via halogenation from the basic raw materials, even in green processes. They are used to replace their downstream products to prepare medicinally important 2-aryl benzimidazoles. CuBr-catalyzed synthesis of 2-aryl benzimidazoles from arylmethyl halides and 1,2-diaminoarenes via a one-pot domino reaction is developed. This new synthetic method is simple, practical and cost saving, and tolerates wide functional groups. A mechanism of CuBr-catalyzed aerobic oxidative domino reaction via a one-pot four-step process is proposed.

Eco-friendly synthesis of 2-substituted benzimidazoles using air as the oxidant

A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the products, and moderate to good yields are the main advantages of this procedure.

Syntheses and biological evaluation of 1-heteroaryl-2-aryl-1H-benzimidazole derivatives as c-Jun N-terminal kinase inhibitors with neuroprotective effects

1-Heteroaryl-2-aryl-1H-benzimidazole derivatives were synthesized as inhibitors of c-Jun N-terminal kinases, JNK3. Their activities were evaluated through measurement of Kd using SPR, JNK3 kinase assay, and cell-viability of human neuroblastoma

Benzimidazoles: A new class of carbonic anhydrase inhibitors

Carbonic anhydrase inhibitory activity of benzimidazole derivatives 1-24 has been evaluated. Compounds 22 (IC50 = 7.47 ± 0.39 μM), 21 (IC50 = 10.31 ± 0.11 μM), 20 (IC50 = 23.1 ± 1.78 μM), 12 (IC50 = 12.16 ± 0.10