2963-64-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 4137, 1987 DOI: 10.1021/jo00227a041

InChI:InChI=1/C14H12N2/c1-10-6-2-3-7-11(10)14-15-12-8-4-5-9-13(12)16-14/h2-9H,1H3,(H,15,16)

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 95-54-5 1,2-diamino-benzene 
• 53724-30-4 o-Methyl-dithiobenzoesaeure 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 1042161-52-3 (2-Azido-phenyl)-[1-o-tolyl-meth-(E)-ylidene]-amine 
• 89-95-2 2-methyl-benzyl alcohol 
• 1262136-90-2 C₁₄H₁₃IN₂ 
• 1262136-91-3 C₁₄H₁₃BrN₂ 
• 1262136-92-4 C₁₄H₁₃ClN₂ 
• 529-19-1 2-Methylbenzonitrile 
• 615-43-0 2-iodophenylamine 
• 10228-77-0 N-(o-methylbenzylidene)aniline 
• 62-53-3 aniline 

Downstream Products

• 1421623-26-8 2-(2-methyl-6-((triisopropylsilyl)ethynyl)phenyl)-1H-benzo[d]imidazole 
• 1417819-00-1 1-methyl-6-phenylbenzo[4,5]imidazo[2,1-a]isoquinoline 
• 79881-93-9 N-vinyl-2-(o-tolyl)benzimidazole 

Relevant academic research and scientific papers

[Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)]: Synthesis, crystal structure, catalytic activity and DFT study

Metal-organic hybrid complexes often exhibit large surface area, pore volume, fascinating structures and potential applications including catalytic applications. Hence a new metal-organic hybrid complex [Diaquo{bis(p-hydroxybenzoato-κ1O1)}(1-methylimidazole- κ1N1)}copper(II)] was synthesized using conventional method. Physico-chemical characterization of the complex was performed with FTIR spectroscopy, single crystal X-ray diffraction, TGA, EPR and FESEM. Single crystal X-ray diffraction study suggests it to be three dimensional with space group P212121 (orthorhombic). The crystal achieves its three-dimensional structure and stability through extensive intermolecular hydrogen bonding. Hirshfeld surface analysis, catalytic activity and DFT study of the complex was also performed. The synthesized complex acts as good catalyst in benzimidazole synthesis with good recyclability as catalyst up to 5th run.

An Unexpected Formation of 2-Arylbenzimidazoles from α,α-Diiodo-α’-acetoxyketones and o-Phenylenediamines

An unusual reactivity of the α,α-diiodo-α’-acetoxyketones with o-phenylenediamines is reported through the formation of 2-arylbenzimidazoles. A systematic study through a series of fruitful control experiments and isolation of key intermediates unravelled the unprecedented domino mechanism. This process involves a stepwise two-carbon fragmentation pathway through domino and sequential amidation–aziridination–decarbonylation–I2-mediated aminative cyclization–oxidation reactions. This strategy employs no additives like oxidant, metal catalyst, bases, and represents yet another novel reactivity profile of the building blocks α,α-diiodo-α’-acetoxyketones.

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

Preparation method of 2-substituted benzimidazole compound

The invention discloses a preparation method of a 2-substituted benzimidazole compound, and belongs to the field of synthesis of benzimidazole compounds. The 2-substituted benzimidazole compound is synthesized in an organic solvent by taking an o-nitroaniline compound, aromatic aldehyde, o-dinitrobenzene and aromatic aldehyde as raw materials and taking Co particles wrapped by a nitrogen-doped carbon material as a catalyst. According to the method, the 2-substituted benzimidazole compound can be prepared at room temperature, the reaction conditions are mild, the yield is as high as 95%, the selectivity is as high as 99%, and the method is economical, environmentally friendly and wide in substrate applicability. The used catalyst is easy to prepare, low in cost and good in reusability, canbe separated by utilizing magnetism, and is convenient to recover, so that the method has a relatively strong industrial application prospect.

Visible-Light Photoredox Catalyzed Double C-H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides

A visible-light photoredox catalyzed radical cascade cyclization of simple ethers with cyanamides is developed at room temperature. This strategy involves sequential inert Csp3-H/Csp2-H functionalizations through intermolecular addition reaction of oxyalkyl radicals to N-cyano groups followed by radical cyclization of iminyl radicals in situ generated with C-2 aryl rings. This method allows for efficient synthesis of tetracyclic benzo[4,5]imidazo[1,2-c]quinazolines. Importantly, this is the first example of an intermolecular-intramolecular radical cascade cyclization reaction of cyanamides.

Benzotrithiophene and triphenylamine based covalent organic frameworks as heterogeneous photocatalysts for benzimidazole synthesis

Metal-free covalent organic frameworks (COFs) as visible-light active and recyclable photocatalysts afford an eco-friendly and sustainable option to classical photosensitizers, which usually require noble metals (iridium, ruthenium, rhodium, etc.) to produce photocatalytic activity. Most classical small molecule photosensitizers have poor recyclability with certain limitations. As a result, it is of great significance to develop a metal-free and easily recyclable COF photocatalyst. In this study, we designed and synthesized a new type of COF photocatalyst (BTT-TPA-COF) in which benzotrithiophene and triphenylamine units are alternately connected. It has high specific surface area, permanent porosity and good stability. In addition, this design strategy can effectively adjust the band gap, energy level and photoelectric performance of BTT-TPA-COF. As a metal-free photocatalyst, BTT-TPA-COF exhibits high-efficiency photocatalytic activity, excellent substrate tolerance and excellent recyclability for the synthesis of 2-arylbenzimidazole compounds. This research not only puts forward a design strategy for high-efficiency photocatalysts, but also broadens the application range of COF materials in photocatalytic organic reactions.

Al2O3/CuI/PANI nanocomposite catalyzed green synthesis of biologically active 2-substituted benzimidazole derivatives

This work is generally focused on the synthesis of an efficient, reusable and novel heterogeneous Al2O3/CuI/PANI nanocatalyst, which has been well synthesized by a simple self-assembly approach where aniline is oxidized into PANI and

Bandgap engineering in benzotrithiophene-based conjugated microporous polymers: a strategy for screening metal-free heterogeneous photocatalysts

Metal-free conjugated microporous polymers (CMPs) as visible-light active and recyclable photocatalysts offer a green and sustainable alternative to classical metal-based photosensitizers. However, the strategy for screening CMP-based heterogeneous photocatalysts has not been interpreted up to now. Herein, we present a general strategy for obtaining excellent solid photocatalysts, which is to implement bandgap engineering in the same series of materials. As a proof of concept, three conjugated porous materials containing benzo[1,2-b:3,4-b′:5,6-b′′]trithiophene building blocks (BTT-CMP1, BTT-CMP2 and BTT-CMP3) were successfully constructed. They possess permanent porosity with a large specific surface area and excellent stability. By changing the linker between benzotrithiophene units, the bandgaps, energy levels and photoelectric performances including the absorption, transient photocurrent responses and photocatalytic performances of BTT-CMPs could be handily modulated. Indeed, BTT-CMP2 displayed the best catalytic activity for visible-light-induced synthesis of benzimidazoles among the three CMP materials, even higher than that of small molecule photocatalysts. As a metal-free photocatalyst, interestingly, the screened BTT-CMP2 also showed extensive substrate applicability and outstanding recyclability. Additionally, we have the opinion that this strategy will prove to be a guiding principle for screening superior CMP-based photocatalysts and broaden their application fields.

Copper-catalyzed radical cascade cyclization for synthesis of CF3-containing tetracyclic benzimidazo[2,1-: A] iso-quinolin-6(5 H)-ones

Here, a general copper-catalyzed radical cascade carbocyclization reaction with 2-arylbenzoimidazoles and a Togni reagent was realized. Structurally diverse CF3-containing tetracyclic core benzimidazo[2,1-a]isoquinoline-6(5H)-ones were obtained in moderat

Method for catalytically synthesizing phenylbenzimidazole compound by using copper complex

The invention relates to a method for catalytically synthesizing a phenylbenzimidazole compound by using a copper complex, which comprises the following steps: in the presence of alkali, taking benzimidazole and halogenated hydrocarbon as raw materials, taking the copper complex containing meta-carborane ligand as a catalyst, and conducting reacting at room temperature to prepare the phenylbenzimidazole compound. Compared with the prior art, the method has the advantages that the halogenated hydrocarbon compound which is low in cost and easy to obtain is used as the substrate, the reaction of benzimidazole and halogenated hydrocarbon is efficiently catalyzed by using the copper complex, the phenylbenzimidazole compound is synthesized by a one-pot method, the reaction condition is mild, the universality is good, the catalytic efficiency is high, few byproducts are produced, the cost is relatively low, the product is easy to separate, and lots of waste residues cannot be generated.