321-51-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-fluorophenyl)-1H-benzimidazole is utilized as a potential drug candidate for its anticancer properties, given its ability to target and inhibit the growth of cancer cells. 2-(2-fluorophenyl)-1H-benzimidazole's structure, including the fluorophenyl group, may contribute to its mechanism of action, making it a subject of interest for further research and development in oncology.
Additionally, 2-(2-fluorophenyl)-1H-benzimidazole is considered for its antifungal applications, where it may be employed to combat fungal infections by disrupting essential fungal processes, thereby offering a new avenue for treatment in mycology.
Used in Research and Development:
In the scientific community, 2-(2-fluorophenyl)-1H-benzimidazole serves as a valuable compound for studying the structure-activity relationships of benzimidazole derivatives. Its unique structural features allow researchers to investigate how modifications to the benzimidazole core affect biological activity, potentially leading to the discovery of new and more effective drugs.
Furthermore, the compound may be used in the development of drug delivery systems, where its specific properties could be leveraged to improve the bioavailability, targeting, and overall efficacy of therapeutic agents. This application could be particularly relevant in the context of personalized medicine, where tailored drug delivery solutions are increasingly sought after.

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 88-74-4 2-nitro-aniline 
• 7191-81-3 C₁₃H₁₁FN₂ 
• 1072-85-1 o-fluorobromobenzene 
• 51-17-2 benzoimidazole 
• 446-51-5 2-fluorobenzyl alcohol 
• 615-36-1 2-bromoaniline 
• 615-43-0 2-iodophenylamine 
• 446-48-0 o-fluorobenzyl bromide 
• 445-29-4 o-fluoro-benzoic acid 

Downstream Products

• 1037289-22-7 5,6-diphenylbenzo[4,5]imidazo[2,1-a]isoquinoline 
• 28381-92-2 6-phenylbenzimidazolo<1,2-c>quinazoline 

Relevant academic research and scientific papers

Visible-Light-Driven Sulfonylation/Cyclization to Access Sulfonylated Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones

Visible-light-driven sulfonylation/cyclization of N-methacryloyl-2-phenylbenzoimidazoles has been successfully developed. Using commercially available sulfonyl chloride as sulfonylation reagent, a wide range of sulfonylated benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-ones with potential antitumor activity were provided in acceptable to excellent yields. This method has the advantages of mild reaction conditions and outstanding functional group tolerance, and provides a new strategy for the development of potential antitumor lead compounds.

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole-based hydrazones: A synergistic experimental-computational analysis

Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C23H18F2N4O (5a) and C25H22FN5O3

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.

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.

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

Nickel-Catalyzed C-F/N-H Annulation of 2-(2-Fluoroaryl) N-Heteroaromatic Compounds with Alkynes: Activation of C-F Bonds

The reaction of 2-(2-fluoroaryl) N-heteroaromatic compounds, such as benzimidazole and indole derivatives, with internal alkynes in the presence of a catalytic amount of a nickel complex results in C-F/N-H annulation with alkynes. The reaction shows a high functional group compatibility. The presence of a strong base, such as KOBu- tor LiOBu t, is required for the reaction to proceed.

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.

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).