324-15-2

Usage

Benzimidazole derivative

The compound is derived from benzimidazole, which is a heterocyclic aromatic organic compound known for its importance in medicinal chemistry.

3-fluorophenyl group

A phenyl ring (a six-carbon ring with bonded hydrogen atoms) attached to the benzimidazole ring, with a fluorine atom at the 3-position (the meta-position) of the phenyl ring.

Potential pharmaceutical applications

The compound has potential use in the development of drugs targeting specific biological pathways, making it a valuable building block for the synthesis of various biologically active compounds.

Versatile chemical

Due to its unique structure and properties, 1H-Benzimidazole, 2-(3-fluorophenyl)can be used in the synthesis of a wide range of compounds, making it a versatile chemical in medicinal chemistry.

Fluorine substituent

The presence of a fluorine atom in the compound may confer unique pharmacological properties, such as increased potency, selectivity, and metabolic stability, enhancing its potential as a drug candidate.

InChI:InChI=1/C13H9FN2/c14-10-5-3-4-9(8-10)13-15-11-6-1-2-7-12(11)16-13/h1-8H,(H,15,16)

Upstream product

• 455-38-9 3-fluorobenzoic acid 
• 95-54-5 1,2-diamino-benzene 
• 456-48-4 3-Fluorobenzaldehyde 
• 70090-82-3 1-fluoro-3-(propa-1,2-dien-1-yl)benzene 
• 455-37-8 3-fluorobenzamide 
• 615-43-0 2-iodophenylamine 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 456-47-3 3-fluoro-benzenemethanol 
• 100-82-3 (3-fluorophenyl)methanamine 
• 455-36-7 1-(3-fluorophenyl)ethanone 
• 615-36-1 2-bromoaniline 
• 4403-69-4 2-amino-1-benzylamine 
• 88-74-4 2-nitro-aniline 

Downstream Products

• 1096130-33-4 C₂₃H₁₈FN₅ 
• 1096130-27-6 2-(3-fluorophenyl)-1-(1-phenyl-1H-[1,2,3]-triazol-4-yl-methyl)-1H-benzo[d]imidazole 
• 1096130-31-2 C₂₃H₁₈FN₅ 
• 1096130-29-8 C₂₃H₁₅F₄N₅ 
• 1096130-25-4 C₂₂H₁₄F₃N₅ 
• 1096130-23-2 C₂₃H₁₇F₂N₅ 
• 1096130-21-0 C₂₃H₁₈FN₅O 
• 1096130-19-6 C₂₃H₁₈FN₅O 
• 1096130-17-4 C₂₂H₁₅F₂N₅ 
• 1096130-15-2 C₂₂H₁₄F₃N₅ 
• 1096130-13-0 2-(3-fluorophenyl)-1-[1-(2,3,4-trifluorophenyl)-1H-[1,2,3]-triazol-4-yl-methyl]-1H-benz[d]imidazole 

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.

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.

Oxidative coupling of primary amines to imines catalyzed by CoCl2·6H2O

A high-performance, readily available and eco-friendly cobalt catalyst has been suggested for the first time for the additive-free oxidative coupling of primary amines to imines. Different substituted benzylamine and heteroaryl methanamine compounds could be transformed into their corresponding imines in good to excellent yields over this catalyst. Meanwhile, it has been demonstrated that this catalyst can also afford the oxidative coupling of various benzylamines with o-phenylenediamine to produce benzimidazole derivatives in medium to good yields.

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

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.

Antimicrobial evaluation of myricetin derivatives containing benzimidazole skeleton against plant pathogens

A series of novel myricetin derivatives containing benzimidazole skeleton were constructed. The structure of compound 4g was further corroborated via X-ray single crystal diffractometer. The antimicrobial bioassays showed that all compounds exhibited potent inhibitory activities against Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (Rs) and Xanthomonas oryzae pv. Oryzae (Xoo) in vitro. Significantly, compound 4q showed the best inhibitory activities against Xoo, with the EC50 value of 8.2 μg/mL, which was better than thiodiazole copper (83.1 μg/mL) and bismerthiazol (60.1 μg/mL). In vivo experimental studies showed that compound 4q can treat rice bacterial leaf blight at 200 μg/mL, and the corresponding curative and protection efficiencies were 45.2 and 48.6%, respectively. Meanwhile, the antimicrobial mechanism of the compounds 4l and 4q were investigated through scanning electron microscopy (SEM). Studies showed that compounds 4l or 4q can cause deformation or rupture of Rs or Xoo cell membrane. These results indicated that novel benzimidazole-containing myricetin derivatives can be used as a potential antibacterial reagent.

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.

Direct synthesis of 2-substituted benzimidazoles: Via dehydrogenative coupling of aromatic-diamine and primary alcohol catalyzed by a Co complex

A Co(ii) complex with a stable structure was designed and synthesized with quinalic acid and Co (OAc)2·4H2O. The single crystal structure of the complex was characterized by X-ray diffraction. A dehydrogenative coupling of aromatic diamines and primary alcohols was developed by using the Co(ii) complex as the catalyst to synthesize 2-substituted benzimidazole. A series of 2-substituted benzimidazoles were obtained with good to excellent yields under mild reaction conditions. In addition, a compound with inhibitory Parkinson's activity was synthesized on a gram-scale by using this method. Finally, the reaction mechanism was proposed and the energy changes in the reaction process were simulated by density functional theory (DFT).

2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES

A genus of compounds encompassed by formula (III) and their use is disclosed: Formula (III). The compounds activate Ppargc1a and, as a consequence, are useful for treating a variety of neurodegenerative diseases such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, Parkinson's disease, Huntington's disease, frontotemporal degeneration, dementia with Lewy bodies, motor neuron diseases, and a demyelinating disease.

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.