1741-50-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-phenylbenzimidazole is used as a pharmaceutical agent for its potential biological activities. It has shown promise in anticancer, antiviral, and antifungal properties, making it a valuable compound for the development of new drugs to combat various diseases.
Used in Organic Light-Emitting Diodes (OLEDs):
5-Bromo-2-phenylbenzimidazole is used as a component in the development of organic light-emitting diodes. Its unique chemical properties contribute to the performance and efficiency of OLEDs, which are widely used in display and lighting technologies.
Used as a Fluorescence Probe for Nucleic Acids:
5-Bromo-2-phenylbenzimidazole is utilized as a fluorescence probe for nucleic acids. Its ability to interact with and fluoresce in the presence of nucleic acids makes it a valuable tool in molecular biology and diagnostics, aiding in the study and detection of genetic material.

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

Upstream product

• 202328-05-0 N-(2-nitro-4-bromophenyl)benzamide 
• 21719-91-5 N′-(4-bromophenyl)benzamidine 
• 7647-01-0 hydrogenchloride 
• 100-52-7 benzaldehyde 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 728-90-5 N-(2-nitrophenyl)benzanilide 
• 875-51-4 4-Bromo-2-nitroaniline 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 100-47-0 benzonitrile 
• 106-40-1 4-bromo-aniline 
• 1418298-88-0 C₁₃H₁₀BrIN₂ 
• 1242182-79-1 N-(3-bromophenyl)benzamidine 
• 591-19-5 m-Bromoaniline 
• 66416-72-6 4-bromo-2-iodoaniline 

Downstream Products

• 1257250-52-4 2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole 
• 1613695-61-6 C₁₈H₁₅N₃O 
• 1463056-15-6 4-amino-8-(2-phenyl-1H-benzo[d]imidazol-6-yl)cinnoline-3-carboxamide 
• 1257250-52-4 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

One-Pot Transformation of Lignin and Lignin Model Compounds into Benzimidazoles

It is a challenging task to simultaneously achieve selective depolymerization and valorization of lignin due to their complex structure and relatively stable bonds. We herein report an efficient depolymerization strategy that employs 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively convert different oxidized lignin models to a wide variety of 2-phenylbenzimidazole-based compounds in up to 94 % yields, by reacting with o-phenylenediamines with varied substituents. This method could take full advantage of both Cβ and/or Cγ atom in lignin structure to furnish the desirable products instead of forming byproducts, thus exhibiting high atom economy. Furthermore, this strategy can effectively transform both the oxidized hardwood (birch) and softwood (pine) lignin into the corresponding degradation products in up to 45 wt% and 30 wt%, respectively. Through a “one-pot” process, we have successfully realized the oxidation/depolymerization/valorization of natural birch lignin at the same time and produced the benzimidazole derivatives in up to 67 wt% total yields.

Benzimidazole compound as well as preparation method and application thereof

The invention provides a benzimidazole compound as well as a preparation method and application thereof. The structure of the benzimidazole compound is as shown in formula I in the specification. As a bipolar material, the benzimidazole compound provided

s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles

Developing green-safe, efficient and recyclable catalysts is crucial for the chemical industry. So far, organic photocatalysis has been proved to be an environmentally friendly and energy-efficient synthetic technology compared with traditional metal catalysis. As a versatile catalytic platform, hyper-crosslinked polymers (HCPs) with large surface area and high stability are easily prepared. In this report, we successfully constructed two porous HCP photocatalysts (TZ-HCPs) featurings-tetrazine units and surface areas larger than 700 m2g?1through Friedel-Crafts alkylation reactions. The rational energy-band structures and coexisting micro- and mesopores endow TZ-HCPs with excellent activities to realize the green synthesis of benzimidazoles (28 examples, up to 99% yield, 0.5-4.0 h) in ethanol. Furthermore, at least 21 iterative catalytic runs mediated by TZ-HCP1D were performed efficiently, with 96-99% yield. This study of TZ-HCPs sheds light on the wide-ranging prospects of application of HCPs as metal-free and green photocatalysts for the preparation of fine chemicals.

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

New synthesis method of thiabendazole

The invention relates to a new synthetic route of a drug commonly named as thiabendazole. Thiazole-4-formaldehyde is used as a raw material, and is condensed with hydroxylamine hydrochloride to obtainthiazole-4-formaldoxime, thiazole-4-formaldoxime is subjected to chlorination by using NCS, and then reacts with aniline to obtain N-phenylthiazole-4-methylamine oxime, then N-phenylthiazole-4-methylamine oxime reacts with p-trifluoromethyl benzoyl chloride to obtain an amidoxime ester, and finally a visible-light-catalyzed free radical reaction is adopted for cyclization to obtain thiazole. According to the method, the visible-light-catalyzed free radical reaction is used to the synthesis of thiabendazole for the first time, the reaction conditions of a high temperature and a strong acid inthe traditional synthesis method are avoided, and thereby the reaction is greener and milder. The method has a broad spectrum, and can also be used for synthesis of imidazole compounds Ia-Ial.

Nickel catalysed construction of benzazoles: Via hydrogen atom transfer reactions

Herein we report a homogeneous, phosphine free, inexpensive nickel catalyst that forms a wide variety of benzazoles from alcohol and diamines by a reaction sequence of alcohol oxidation, imine formation, ring cyclization and dehydrogenative aromatization. A reversible azo/hydrazo couple, that is part of the ligand architecture steers both the alcohol oxidation and dehydrogenation of the annulated amine under fairly mild reaction conditions. Interestingly, both the alcohol oxidation and amine dehydrogenation steps are directly mediated by hydrogen atom transfer (HAT), which is greatly facilitated by the reduced ligand backbone. The kH/kD for the amine dehydrogenation step, measured at 60 °C is 5.9, fully consistent with HAT as the rate determining factor during this step. This is a unique scenario where two consecutive oxidation steps towards benzazole formation undergo HAT, which has been substantiated via kinetic studies, KIE determination and intermediate isolation. This journal is

Thiophene-embedded conjugated microporous polymers for photocatalysis

Various photoactive building blocks can be incorporated into porous organic polymers (POPs). The intrinsic properties, such as various synthetic methods, outstanding inherent porosity, easy tunability, rigid conjugated skeletons and high stability, endow the polymeric organic networks with wonderful potential to act as heterogeneous photocatalytic platforms. However, exploitation of efficient synthetic strategies for metal-free and nontoxic heterogenous photocatalysts, and further insights into the photocatalytic process in organic transformations are still necessary. In this context, we report the concise synthesis of two polymeric frameworks (BTP-CMP and TBTP-CMP) incorporated into bithiophene and thiophthene units via a "bottom-up"strategy. BTP-CMP and TBTP-CMP were employed as heterogeneous photocatalysts in the synthesis of benzimidazoles, and exhibited excellent catalytic activity (up to 98% yield, at least 15 iterative runs). Therefore, the thiophene-embedded networks can serve as stable efficient and recyclable heterogeneous photocatalysts. Additionally, based on the catalytic results of control experiments and the energy band structures of the materials and intermediates, a possible photocatalytic reaction mechanism has been proposed.

Method for generating nitrogen-containing heterocyclic ring products by catalyzing lignin and amino-containing compound with acid

The invention provides a method for generating nitrogen-containing heterocyclic ring products by catalyzing lignin and an amino-containing compound with acid, belonging to the technical field of lignin degradation. According to the invention, lignin and the amino-containing compound are catalyzed by acid to directly generate the nitrogen heterocyclic derivatives in one step, and excellent yield (60-100%) is obtained in degradation of lignin; meanwhile, the method disclosed by the invention has high atom utilization rate; and in traditional degradation of lignin to generate benzaldehyde or benzoic acid, beta-C and gamma-C mostly generate byproducts such as formaldehyde, formic acid or carbon dioxide and cannot be fully utilized, but however, beta-C and gamma-C in lignin can generate nitrogen-containing heterocyclic ring products of the same series together with amino-containing compound raw materials according to the method in the invention, and the method has great application value inthe aspect of medicine.

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.