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Usage

Uses

Used in Organic Synthesis:
2-(1H-Benzimidazol-2-yl)-4-bromophenol is used as a key intermediate for the synthesis of various organic compounds. Its bromophenol group facilitates the formation of carbon-carbon bonds, making it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(1H-Benzimidazol-2-yl)-4-bromophenol is used as a building block for the development of new drugs. The benzimidazole group is known for its diverse applications, and when combined with the bromophenol group, it offers a unique structure that can be exploited for designing novel therapeutic agents.
Used in Chemical Research:
2-(1H-Benzimidazol-2-yl)-4-bromophenol is used as a research compound in chemical studies. Its complex structure and functional groups make it an interesting subject for exploring new reaction pathways and understanding the properties of similar compounds.
Used in Antimicrobial Applications:
Due to its phenolic nature, 2-(1H-Benzimidazol-2-yl)-4-bromophenol is used as an antimicrobial agent. The hydroxyl group imparts antiseptic properties, which can be harnessed for applications in disinfectants and sanitizing products.

InChI:InChI=1/C13H9BrN2O/c14-8-5-6-12(17)9(7-8)13-15-10-3-1-2-4-11(10)16-13/h1-7,17H,(H,15,16)

Upstream product

• 51800-88-5 2-[(2-amino-phenylimino)-methyl]-4-bromo-phenol 
• 95-54-5 1,2-diamino-benzene 
• 1761-61-1 5-bromosalicyclaldehyde 
• 1616869-69-2 C₁₅H₁₀BrNO₃ 
• 106-41-2 4-bromo-phenol 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 2316-64-5 5-bromo-2-hydroxybenzyl alcohol 
• 61131-72-4 2-(2-nitrovinyl)-4-bromophenol 
• 29979-27-9 N¹,N²-bis(5-bromo-2-hydroxybenzylidene)-1,2-phenylenediimine 
• 87745-36-6 Methyl-carbamic acid 4-bromo-2-((E)-2-nitro-vinyl)-phenyl ester 

Relevant academic research and scientific papers

The ninhydrin core as carbonyl source to access 2-(2′-hydroxyaryl)benzimidazoles exploiting the ortho selectivity of ninhydrin-phenol adducts

Although ninhydrin is an essential analytical tool in biochemical and forensic sciences, for the past several years, it has been employed as efficient building block for diverse organic scaffolds. In the present work, the ortho selectivity of ninhydrin-phenol adducts has been exploited to obtain 2-(2′-hydroxyaryl)benzimidazoles which are well known excited state intramolecular proton transfer (ESIPT) fluorophores. Under acidic condition, 3-(2-hydroxyaroyl)isoindolin-1-one intermediate generated in situ from ninhydrin-phenol adducts was treated with o-phenylenediamine resulting benzimidazole scaffolds via a two-step one pot strategy.

Synthesis and fungicidal activity of novel 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-ones

[Figure not available: see fulltext.] A series of 6H-benzimidazo[1,2-c][1,3]benzoxazin-6-one derivatives were synthesized in moderate to good yield by reaction of 2-(1H-benzimidazol-2-yl)phenols with triphosgene, and the structures of the target compounds

Reusable nano-zirconia-catalyzed synthesis of benzimidazoles and their antibacterial and antifungal activities

In this article, a zirconia-based nano-catalyst (Nano-ZrO2 ), with intermolecular C-N bond formation for the synthesis of various benzimidazole-fused heterocycles in a concise method is reported. The robustness of this reaction is demonstrated

Synthesis of new TCH/Ni-based nanocomposite supported on SBA-15 and its catalytic application for preparation of benzimidazole and perimidine derivatives

A stable nickel-decorated SBA-15 nanocomposite (Ni/TCH@SBA-15) was synthesized through surface modification of silica nanoparticles with 3-chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) followed by metal–ligand coordination with Ni (II). The structure of this organometallic nanocomposite was characterized by Fourier transform-infrared, field emission-scanning electron microscopy, EDAX, transmission electron microscopy, atomic absorption spectroscopy and N2 adsorption–desorption (Brunauer–Emmett–Teller) techniques. The catalytic performance of Ni/TCH@SBA-15 (NNTS-15) was determined for the synthesis of 2-aryl-substituted benzimidazoles and 2,3-dihydroperimidines. The excellent yields within shorter reaction times, simplicity of catalytic methods, non-toxicity and clean reactions, mild reaction conditions and easy work-up procedure are the important merits of these synthetic protocols. Moreover, the Ni (II) bonded to the SBA-15 surface was stable under the catalytic reaction conditions resulting in its efficient recycling and reuse.

Green synthesis of benzimidazole derivatives under ultrasound irradiation using Cu-Schiff base complexes embedded over MCM-41 as efficient and reusable catalysts

We have synthesized two recoverable catalysts by covalently attaching complexes such as Cu-complex-phen and Cu-complex-bipy on MCM-41 through a greener synthetic route. FT-IR, EDX, SEM and TEM microscopy, XRD analysis, N2 adsorption and desorpt

A Magnetic Heterogeneous Biocatalyst Composed of Immobilized Laccase and 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) for Green One-Pot Cascade Synthesis of 2-Substituted Benzimidazole and Benzoxazole Derivatives under Mild Reaction Conditions

The design of reusable high-performance heterogeneous catalysts via the immobilization of chemical and biochemical species on magnetic nanoparticles increases the efficiency of catalytic systems by facilitating easy, fast, and clean separation processes. Laccase and 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl were separately immobilized on amine functionalized iron (II, III) oxide nanoparticles with covalent bonding using glutaraldehyde as a coupling reagent. The prepared catalyst was used to synthesize 12 benzoxazole and benzimidazole derivatives. The one-pot, two-step enzymatic aerobic oxidation reaction included the condensation of in situ-produced salicylaldehyde derivatives with aromatic amines, followed by an enzymatic dehydrogenation process. Optimal reaction conditions consisted of a citrate buffer (10 mM, pH 4.5) at 40 °C for an incubation time of 10 h and a heterogeneous catalyst containing immobilized laccase (80 mg, 100 U) and immobilized 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) (40 mg, 2 mol%). The catalyst retained more than 85% of its initial activity after 10 runs. In addition to the potential for reuse without significant losses in performance, eco-friendly attributes of this catalytic system include its high catalytic activity and the ease with which it can be recovered from the reaction mixture using an external magnet. (Figure presented.).

Br?nsted acidic reduced graphene oxide as a sustainable carbocatalyst: A selective method for the synthesis of C-2-substituted benzimidazole

Br?nsted acidic reduced graphene acts as an efficient and sustainable carbocatalyst for the selective synthesis of C-2-substituted benzimidazoles under ambient conditions. A massive influx of sulphonic acid group on reduced graphene oxide surface gives graphene sulfonic acid (G-SO3H), which acts as a Br?nsted acidic catalyst for the synthesis of a series of benzimidazoles under mild conditions. The present methodology is a revamp of the benzimidazole synthesis with broad functional group tolerance in shorter time. G-SO3H provides an operationally simple, metal-free condition and is amenable to gram-scale production. Pyridine adsorption studies prove the catalytically responsible Br?nsted acidity of the catalyst. The catalyst is highly stable for several cycles without any loss of activity, which is evidenced by the FT-IR, PXRD and TEM characterization of the reused catalyst.

Highly efficient AgNO3-catalyzed approach to 2-(benzo[d]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine

A new, convenient and efficient AgNO3-catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.

Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles

The benzimidazole ring is an important pharmacophore in contemporary drug discovery. Thus, effort to identifying new compounds containing benzimidazole scaffolds have gained much attention in recent years. In the present study, MCM-41 type mesoporous silica with large pore (l-MSN) supported ytterbium was successfully prepared by wet impregnation method. Among rare earth metal salts, ytterbium triflate has already been widely investigated as a catalyst in organic synthesis but less toxic ytterbium oxide has yet to be explored. Relatively high abundance and low cost of ytterbium with respect to many catalytically active metals (e.g. Pd, Au, Ru, Ir, Pt) offer an opportunity to develop sustainable catalysts for organic conversions. The catalyst has been characterized by various techniques including nitrogen adsorption, FT-IR, TEM, SEM, EDX technique and elemental mapping. The obtained materials exhibit high surface area and a narrow distribution of mesoporosity. The catalytic performance of the Yb@l–MSNs was tested by synthesis of 1,2-disubstituted benzimidazoles and 2-substituted benzimidazoles through the coupling of aldehydes with o-phenylenediamine. The catalyst resulted in excellent yields in short reaction times and the reaction showed tolerance toward both electron-donating and electron-withdrawing functional groups at room temperature. A particularly interesting finding was the solvent selectivity of this reaction; namely, 1,2-disubstituted benzimidazoles generated as major product in water-ethanol, while the 2-substituted benzimidazoles was generated exclusively in non-polar solvents like toluene.

Efficient preparation of acidic ionic liquid-functionalized reduced graphene oxide and its catalytic performance in synthesis of benzimidazole derivatives

Abstract: This article reports an efficient method with a simple workup for the facile synthesis of benzimidazole derivatives using an acidic ionic liquid covalently supported on graphene sheets. The catalyst was efficiently synthesized and characterized