1571-85-3

Usage

Uses

Used in Pharmaceutical Industry:
1H-Benzimidazole, 6-nitro-2-phenylis used as a building block or intermediate for the synthesis of various biologically active compounds and pharmaceutical drugs. Its unique structural features and properties contribute to the development of new therapeutic agents.
Used in Agrochemical Industry:
1H-Benzimidazole, 6-nitro-2-phenylmay have potential use as an insecticide or fungicide in the agricultural industry. Its chemical properties can be harnessed to create effective pest control solutions, promoting crop protection and yield enhancement.

Upstream product

• 100-52-7 benzaldehyde 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 97-02-9 2,4-Dinitroanilin 
• 1663-61-2 triethoxymethylbenzene 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 1670-14-0 benzamidine monohydrochloride 
• 13296-94-1 2-bromo-4-nitroaniline 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 
• 932-90-1 Benzaldoxime 
• 93-97-0 benzoic acid anhydride 
• 98-88-4 benzoyl chloride 

Downstream Products

• 19250-69-2 N-(2-phenyl-1⁽³⁾H-benzoimidazol-5-yl)-benzamide 
• 300384-33-2 C₂₀H₁₄N₄O₃ 
• 1440142-00-6 C₂₀H₁₄ClN₃O 
• 1292833-61-4 C₂₁H₁₇N₃O₂ 
• 1767-25-5 2-phenyl-1H-benzo[d]imidazol-5-amine 
• 109747-07-1 1-benzyl-6-nitro-2-phenyl-1H-benzoimidazole 
• 109747-57-1 1-benzyl-5-nitro-2-phenyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Oxone-mediated annulation of 2-aminobenzamides and 1,2-diaminobenzenes with: Sec -amines via imine- N -oxides: New syntheses of 2,3-dihydroquinazolin-4(1 H)-ones and 1 H -benzimidazoles

An efficient and mild method for the preparation of 2,3-dihydroquinazolin-4(1H)-ones and 1H-benzimidazoles by the oxone-mediated reaction of sec-amines via imine-N-oxides with 2-amino-N-substituted benzamides and 1,2-diaminobenzenes respectively in THF-wa

New Synthetic Applications of Aryllead Triacetates. N-Arylation of Azoles

Treatment of a variety of azoles or their anions with p-tolyllead triacetate in the presence of copper(II) acetate afforded the corresponding N-aryl derivatives, normally in excellent yields.Room temperature arylation of an aminobenzimidazole derivative was chemoselectively directed to the amino group.

Cinnamide derived pyrimidine-benzimidazole hybrids as tubulin inhibitors: Synthesis, in silico and cell growth inhibition studies

An approach in modern medicinal chemistry to discover novel bioactive compounds is by mimicking diverse complementary pharmacophores. In extension of this strategy, a new class of piperazine-linked cinnamide derivatives of benzimidazole-pyrimidine hybrids have been designed and synthesized. Their in vitro cytotoxicity profiles were explored on selected human cancer cell lines. Specifically, structural comparison of target hybrids with tubulin-DAMA-colchicine and tubulin-nocodazole complexes has exposed a deep position of benzimidazole ring into the αT5 loop. All the synthesized compounds were demonstrated modest to interesting cytotoxicity against different cancer cell lines. The utmost cytotoxicity has shown with an amine linker of benzimidazole-pyrimidine series, with specificity toward A549 (lung cancer) cell line. The most potent compound in this series was 18i, which inhibited cancer cell growth at micromolar concentrations ranging 2.21–7.29 μM. Flow cytometry studies disclosed that 18i inhibited the cells in G2/M phase of cell cycle. The potent antitumor activity of 18i resulted from enhanced microtubule disruption at a similar level as nocodazole on β-tubulin antibody, explored using immunofluorescence staining. The most active compound 18i also inhibited tubulin polymerization with an IC50 of 5.72 ± 0.51 μM. In vitro biological analysis of 18i presented apoptosis induction on A549 cells with triggering of ROS generation and loss of mitochondrial membrane potential, resulting in DNA injury. In addition, 18i displayed impairment in cellular migration and inhibited the colony formation. Notably, the safety profile of most potent compound 18i was revealed by screening against normal human pulmonary epithelial cells (L132: IC50: 69.25 ± 5.95 μM). The detailed binding interactions of 18i with tubulin was investigated by employing molecular docking, superimposition and free energy analyses. Thus remarks made in this study established that pyrimidine-benzimidazole hybrids as a new class of tubulin polymerization inhibitors with significant anticancer activity.

Functional POM-catalyst for selective oxidative dehydrogenative couplings under aerobic conditions

Development of selective and efficient reusable catalytic systems for sustainable chemical production under benign conditions is attractive and received much attention. Herein, we report a rod-shaped octadecyl trimethylammonium functionalized Keggin-type polyoxometalate [PMO12O40] hybrids (OTA-POM) as an efficient heterogeneous catalyst for selective oxidative dehydrogenative couplings under aerobic conditions without any additive or external base. The catalyst recovery and subsequent five successive recyclability studies of hybrid POM confirms the heterogeneous nature of present catalytic system.

Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines

Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction ofortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

A one-pot synthesis of benzimidazoles via aerobic oxidative condensation of benzyl alcohols with o-phenylenediamines catalyzed by [MIMPs]+Cl-/NaNO2/TEMPO

The ionic liquid 1-methyl-3-(3-sulfopropyl)imidazolium chloride ([MIMPs]+Cl-) in combination with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and sodium nitrite (NaNO2) as a catalytic system demonstrates high efficiency in the one-pot two-step aerobic oxidative condensation of benzyl alcohols with 1,2-phenylenediamines to give benzimidazoles. Various benzimidazoles are obtained in good to excellent yields by this strategy.

Hypervalent iodine promoted: Ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates

The mild and efficient palladium-catalyzed ortho C(sp2)-H diversification of (NH)-free 2-substituted benzimidazole, quinazoline, and imidazopyridine is reported using hypervalent iodine as the key reagent. Acetoxy, aryl, iodide and nitro functi

A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media

A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions

The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.

Transcriptome analysis predicts mode of action of benzimidazole molecules against Staphylococcus aureus UAMS-1

Antimicrobial drug resistance is one of the most critical problems that plagued the human race in modern times. Discovery of novel antibiotics is important to counter this threat. Accordingly, herein we have reported the discovery of substituted benzimidazole class of molecules with antimicrobial property (specifically against Staphylococcus aureus). They were initially identified through a random screening and a novel catalytic synthetic strategy was utilized to access them. in vitro screening and phenotypic profiling revealed the antimicrobial nature. De novo transcriptome and gene analyses predicted the putative targets. This work provides a solid foundation for developing the benzimidazoles as a target specific antimicrobial preclinical candidate.