2622-74-4

Usage

Uses

Used in Pharmaceutical Development:
2-(4-Bromophenyl)benzimidazole is used as a key intermediate in the synthesis of various pharmaceuticals for its potential therapeutic applications. The presence of the bromophenyl group allows for further functionalization and modification, enabling the development of new drugs with improved pharmacological properties.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(4-Bromophenyl)benzimidazole serves as a versatile building block for the production of other compounds. Its unique chemical properties, including the presence of the bromophenyl group, make it a valuable component in the synthesis of a wide range of organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
2-(4-Bromophenyl)benzimidazole is utilized in medicinal chemistry for its potential as a lead compound in the discovery and optimization of new therapeutic agents. Its diverse pharmacological and biological activities, along with its unique chemical properties, make it a promising candidate for the development of novel drugs targeting various diseases and conditions.
Used in Chemical Research:
In the realm of chemical research, 2-(4-Bromophenyl)benzimidazole is employed as a model compound to study the reactivity, selectivity, and mechanisms of various chemical reactions. Its unique chemical properties, such as the presence of the bromophenyl group, provide valuable insights into the fundamental aspects of organic chemistry and contribute to the advancement of the field.

InChI:InChI=1/C13H9BrN2/c14-10-7-5-9(6-8-10)13-15-11-3-1-2-4-12(11)16-13/h1-8H,(H,15,16)

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 586-76-5 4-Bromobenzoic acid 
• 88-74-4 2-nitro-aniline 
• 1042161-44-3 (E)-2-azido-N-(4-bromobenzylidene)aniline 
• 1262137-05-2 C₁₃H₁₀Br₂N₂ 
• 873-75-6 4-bromobenzenemethanol 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 26510-95-2 ethyl 4-Bromobenzoylacetate 
• 21719-90-4 N-phenyl-4-bromobenzimidamide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 62-53-3 aniline 
• 7191-78-8 C₁₃H₁₁BrN₂ 
• 67628-23-3 4-bromo-N-chloro-N'-phenyl-benzamidine 

Downstream Products

• 92-52-4 biphenyl 
• 2562-77-8 2-([1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole 
• 157771-52-3 2-(4-bromophenyl)-1-propylbenzimidazole 
• 157771-53-4 2-(4''-methoxyterphenyl-4-yl)-1-propylbenzimidazole 
• 157771-46-5 2-(4'-methoxybiphenyl-4-yl)-1-propylbenzimidazole 
• 25739-25-7 2-(4-phenylethynyl-phenyl)-1H-benzoimidazole 
• 1021919-38-9 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole 
• 1000012-24-7 2-(4'-p-toluylphenyl)-1H-benzimidazole 
• 638141-30-7 2-(4-bromophenyl)-1-ethyl-1H-benzimidazole 
• 1238292-61-9 3,5,6-triphenylbenzo[4,5]imidazo[2,1-a]isoquinoline 
• 1447946-70-4 C₃₅H₂₂N₂ 
• 1447946-51-1 3-bromo-5,6-diphenylbenzo[4,5]imidazo[2,1-a]isoquinoline 

Relevant academic research and scientific papers

Synthesis and characterization of 2-substituted benzimidazoles and their evaluation as anticancer agent

In this work, we report a series of benzimidazole derivatives synthesized from benzene-1,2-diamine and aryl-aldehydes at room temperature. The synthesized compounds have been characterized on the basis of elemental analysis and various spectroscopic studi

Synthesis and temperature-induced morphological control in a hybrid porous iron-phosphonate nanomaterial and its excellent catalytic activity in the synthesis of benzimidazoles

A new organic-inorganic hybrid porous iron-phosphonate material, HPFP-1, has been synthesized under hydrothermal conditions by using hexamethylenediamine-N,N,N',N'-tetrakis-(methylphosphonic acid) (HDTMP) as the organophosphorus precursor. The morphology

Synthesis and characterization of green-emitting phosphorescent Ir(III) complexes based on phenyl benzimidazole ligand

Several new Ir(III) complexes with 2-(4-bromophenyl)-1H-benzo[d]imidazole or 2-(4-bromophenyl)- 1-methyl-benzo[d]imidazole ligands as cylcometalated ligand and acetylacetonate or picolinate as the ancillary ligand were synthesized and their structures and

Sequential oxidation and condensation of alcohols to benzimidazoles/ benzodiazepines by MoO3-SiO2 as a heterogeneous bifunctional catalyst

Sequential oxidation of alcohols to their corresponding aldehydes/ketones using H2O2 as a green oxidant and its further condensation with diamines to yield benzimidazoles/benzodiazepines with minimum side product formation under mild

1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles

In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]

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.

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.

Water extract of onion catalyst: An economical green route for the synthesis of 2-substituted and 1,2-disubstituted benzimidazole derivatives with high selectivity

An efficient, environmental friendly and substrate controlled method of synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o-phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2-diamines to afford 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2-substituted benzimidazoles 3 from aromatic aldehydes having electron-withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2-disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.

Tetrathienoanthracene-functionalized conjugated microporous polymers as an efficient, metal-free visible-light solid organocatalyst for heterogeneous photocatalysis

Owing to their advantages of superior inherent porosity, high chemical stability, light weight, and molecularly tunable optoelectronic properties, conjugated microporous polymers (CMPs) have been receiving increasing attention and research interest as pro

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.