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 
• 1042161-44-3 (E)-2-azido-N-(4-bromobenzylidene)aniline 
• 1262137-05-2 C₁₃H₁₀Br₂N₂ 
• 623-00-7 4-bromobenzenecarbonitrile 
• 106-41-2 4-bromo-phenol 
• 5877-51-0 N-(4-bromobenzylidene)aniline 
• 873-75-6 4-bromobenzenemethanol 
• 62-53-3 aniline 
• 55368-42-8 4-bromobenzamidine hydrochloride 
• 1493-27-2 ortho-nitrofluorobenzene 
• 106-38-7 para-bromotoluene 
• 25062-46-8 4-bromobenzaldehyde oxime 

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 
• 1000012-28-1 2-[4'-(4-fluorophenyl)phenyl]-1H-benzimidazole 
• 1000012-24-7 2-(4'-p-toluylphenyl)-1H-benzimidazole 
• 1000012-29-2 2-[4'-(4-chlorophenyl)phenyl]-1H-benzimidazole 
• 1000012-25-8 2-(4'-p-anisylphenyl)-1H-benzimidazole 
• 1000012-27-0 2-[4'-(4-formylphenyl)phenyl]-1H-benzimidazole 
• 1000012-26-9 4'-(1H-benzo[d]imidazol-2-yl)-[1,1'-biphenyl]-4-carbonitrile 
• 25739-25-7 2-(4-phenylethynyl-phenyl)-1H-benzoimidazole 
• 1135618-16-4 C₁₅H₁₄BrN₂⁽¹⁺⁾*I^(1-) 
• 1352574-72-1 methyl (2E)-3-[4-(1-methyl-1H-benzimidazol-2-yl)phenyl]acrylate 

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.

UV-visible light-induced photochemical synthesis of benzimidazoles by coomassie brilliant blue coated on W-ZnO@NH2nanoparticles

Heterogeneous photocatalysts proffer a promising method to actualize eco-friendly and green organic transformations. Herein, a new photochemical-based methodology is disclosed in the preparation of a wide range of benzimidazoles through condensation of o-phenylenediamine with benzyl alcohols in the air under the illumination of an HP mercury lamp in the absence of any oxidizing species catalyzed by a new photocatalyst W-ZnO@NH2-CBB. In this photocatalyst, coomassie brilliant blue (CBB) is heterogenized onto W-ZnO@NH2 to improve the surface characteristics at the molecular level and enhance the photocatalytic activity of both W-ZnO@NH2 and CBB fragments. This unprecedented heterogeneous nanocatalyst is also identified by means of XRD, FT-IR, EDS, TGA-DTG, and SEM. The impact of some influencing parameters on the synthesis route and effects on the catalytic efficacy of W-ZnO@NH2-CBB are also assessed. The appropriate products are attained for both the electron-withdrawing and electron-donating substituents in the utilized aromatic alcohols. Furthermore, preparation of benzimidazoles is demonstrated to occur mainly via a radical mechanism, which shows that reactive species such as ·O2-, OH and h+ would be involved in the photocatalytic process. Stability and reusability studies also warrant good reproducibility of the nanophotocatalyst for at least five runs. Eventually, a hot filtration test proved that the nanohybrid photocatalyst is stable in the reaction medium. Using an inexpensive catalyst, UV-vis light energy and air, as a low cost and plentiful oxidant, puts this methodology in the green chemistry domain and energy-saving organic synthesis strategies. Finally, the anticancer activity of W-ZnO nanoparticles is investigated on MCF7 breast cancer cells by MTT assay. This experiment reveals that the mentioned nanoparticles have significant cytotoxicity towards the selected cell line.

Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols

An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized by FT-IR, XRD, FE-SEM, TEM, VSM, TGA, EDX, DLS, and ICP analyses. The optimum range of parameters such as time, temperature, amount of catalyst, and solvent were investigated for the domino one-pot benzimidazole and Biginelli reactions to find the optimum reaction conditions. The catalyst was compatible with a variety of benzyl alcohols, which provides favorable products with good to high yields for all of derivatives. Hot filtration and Hg poisoning tests from the nanocatalyst revealed the stability, low metal leaching and heterogeneous nature of the catalyst. To prove the synergistic and cooperative effect of the catalytic system, the various homologues of the catalyst were prepared and then applied to a model reaction separately. Finally, the catalyst could be filtered from the reaction mixture simply, and reused for five consecutive cycles with a minimum loss in catalytic activity and performance. Graphic Abstract: A new magnetically recyclable Cu/Mn bimetallic catalyst has been developed for domino one-pot oxidation-condensation of benzimidazole and Biginelli reactions from alcohols. [Figure not available: see fulltext.]

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

Heterogenizing a Homogeneous Nickel Catalyst Using Nanoconfined Strategy for Selective Synthesis of Mono- And 1,2-Disubstituted Benzimidazoles

A homogeneous Ni-phenanthroline catalyst was successfully immobilized into the cavities of a metal-organic framework, ZIF-8. The as-synthesized heterogeneous catalyst, Ni-Phen@ZIF, represents the first MOF based catalyst that enables dehydrogenative coupling of alcohols with aromatic diamines for selective synthesis of both mono- and 1,2-disubstituted benzimidazoles. The catalyst survived under harsh basic conditions, characterized by SEM, TEM, BET, PXRD, and EDX elemental mappings. The presence of the nanoconfined Ni-phenanthroline complex and the formation of extra Lewis acid sites during catalysis in the Ni-Phen@ZIF structure, confirmed by TPD analysis and kinetic experiments, might be responsible for higher activity and selectivity.