6478-79-1

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Dichloro-2-methylbenzimidazole is used as an antiparasitic agent for treating infections caused by various parasites. Its antiparasitic activity is attributed to its ability to disrupt the normal functioning of the parasites, leading to their elimination from the host.
Used in Drug Metabolism Research:
5,6-Dichloro-2-methylbenzimidazole is used as an inhibitor of aminopyrine demethylase, an enzyme involved in the metabolism of certain drugs. This property makes it a valuable tool in studying the role of aminopyrine demethylase in drug metabolism and its potential as a target for drug development.
Used in Veterinary Medicine:
5,6-Dichloro-2-methylbenzimidazole is used as a veterinary medicine for treating parasitic infections in animals. Its broad-spectrum antiparasitic activity makes it effective against a variety of parasites, helping to improve the health and well-being of animals.
Used in Crop Protection:
5,6-Dichloro-2-methylbenzimidazole can be used in crop protection as a potential antiparasitic agent against pests that affect agricultural crops. Its ability to inhibit the growth and reproduction of parasites can help protect crops from damage and improve overall crop yield.
Used in Environmental Management:
5,6-Dichloro-2-methylbenzimidazole may also find applications in environmental management, particularly in controlling parasitic organisms that pose threats to aquatic ecosystems or other natural habitats. Its antiparasitic properties can contribute to the preservation of biodiversity and the overall health of the environment.

InChI:InChI=1/C8H6Cl2N2/c1-4-11-7-2-5(9)6(10)3-8(7)12-4/h2-3H,1H3,(H,11,12)

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 64-19-7 acetic acid 
• 78-39-7 Triethyl orthoacetate 
• 64-17-5 ethanol 
• 141-97-9 ethyl acetoacetate 
• 121-44-8 triethylamine 
• 75-07-0 acetaldehyde 
• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 127-19-5 N,N-dimethyl acetamide 
• 141-82-2 malonic acid 

Downstream Products

• 611233-53-5 5,6-dichloro-2-methyl-1-undecylbenzimidazole 
• 171354-91-9 5,6-dichloro-1-heptyl-2-methylbenzimidazole 
• 163403-28-9 5,6-dichloro-2-methyl-1-octylbenzimidazole 
• 611233-49-9 5,6-dichloro-1-(3-cyanopropyl)-2-methylbenzimidazole 
• 2818-64-6 5,6-dichloro-1,2-dimethyl-1H-benzimidazole 
• 906639-70-1 2-(5,6-dichloro-1H-benzoimidazol-2-yl)-1-(furan-2-yl)-ethanol 
• 1374116-63-8 C₁₉H₂₀Cl₂N₂O₇ 
• 78621-34-8 C₁₃H₁₄Cl₂N₂O₄ 
• 1360442-71-2 C₁₃H₁₄Cl₂N₂ 
• 1449030-60-7 methyl 3-(5,6-dichloro-2-methyl-1H-benzimidazol-1-yl)propanoate 
• 1449030-66-3 3-(5,6-dichloro-2-methyl-1H-benzimidazol-1-yl)propanehydrazide 

Relevant academic research and scientific papers

Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid

Metal-free catalyzed intermolecular tandem Michael addition/cyclization has been developed for the synthesis of benzo[4,5]imidazo[1,2-a]pyridines from α-bromocinnamaldehyde and 2-substituted benzimidazoles. The reaction promoted by a simple inorganic base displays moderate to good yields and good functional group tolerance. The optical properties of some typical products have been investigated. We found that, due to the presence of the benzene ring at the C1-position of benzo[4,5]imidazo[1,2-a]pyridines which restricts intramolecular motion, as a new type of aggregation-induced emission (AIE) luminogen (AIEgen), they show very good solid-state fluorescence with quantum yields up to 88.80%. Importantly, the AIE performance of compound3bcan be useful to detect the nitroaromatic explosive picric acid (PA) with a detection limit and quenching constant of 42.5 nM and 7.27 × 104M?M, respectively.

Preparation method 2 -substituted benzimidazole derivative

The invention belongs to the field of fine chemical product production, and particularly relates to 2 -substituted benzimidazole derivative preparation method which comprises the following steps: (1) taking O-phenylenediamine and aldehyde as raw materials, carrying out catalytic condensation, cyclization and oxidation reaction in a eutectic solvent. (2) Water is added to the reaction system, the separated product is filtered, and the eutectic solvent is recycled. (3) After recrystallization, a target product is obtained. The method has the advantages of simple operation process, easily available raw materials, low cost, high purity of the target product and no catalyst participation, can effectively prevent isomer formation, and is beneficial to large-scale production.

Rhodium catalyzed 2-alkyl-benzimidazoles synthesis from benzene-1,2-diamines and tertiary alkylamines as alkylating agents

Substituted 2-alkyl-benzimidazoles were synthesized from benzene-1,2-diamine and tertiary amines as alkylating agent under polystyrene supported rhodium (Rh@PS) nanoparticles (NPs) catalyzed conditions. The heterogeneous rhodium catalyst was applied first time for the synthesis of 2-alkyl-benzimidazoles. The reaction followed through oxidation of alkylamines, transamination, and oxidative cyclisation with benzene-1,2-diamines for the corresponding products synthesis with good yields. The process is applicable for vast substrate scope, several functional groups are tolerable, and the Rh@PS catalyst is recyclable up to four cycles without significant loss in catalytic activity.

Sustainable photocatalytic synthesis of benzimidazoles

Among the 17 Sustainable Development Goals presented by the United Nations in 2015, great attention is devoted to the production of goods and chemicals by use of renewable raw materials, by recycling of products and by extensive use of renewable energy sources. In this context, photocatalysis attracted great attention for the possibility to exploit Solar light to promote the desired chemical reactions. Besides its use in degradation of pollutants and in the production of fuels, some efforts have been devoted in the development of photocatalytic processes for the synthesis of fine chemicals with high added-value. In this work, we investigated the sustainable photocatalytic synthesis of benzimidazole derivatives through a one-pot, tandem process starting from a nitro compound and ethanol. By a photocatalytic approach, ethanol is dehydrogenated producing the hydrogen required for reduction of nitro groups and the aldehyde required for cyclization and production of the benzimidazole unit. Co-doping of TiO2 with B and N is beneficial to increase the photocatalytic activity in H2 production from ethanol. The effect of various metal co-catalysts (Pt, Pd Ag, Cu) have been evaluated on H2 production rate and on selectivity in the synthesis of substituted benzimidazoles: Pt showed the highest selectivity in the desired products while Pd demonstrated a great activity for hydrodehalogenation, with potential interest for degradation of persistent pollutants.

A benzimidazole and synthetic method of derivative thereof (by machine translation)

The present invention provides a benzimidazole and its derivative synthesis method, the method through the imidazole chloride catalyzed O-phenylenediamine cyclized, realizes the multi-functional chain dibasic and imidazole and 2 - substituted benzimidazole synthesis, method is simple and economic, and the practicability is strong. This invention does not have any other catalyst or additive, synthetic method has good functional group tolerance and excellent yield and purity, reaction time is short, and does not need the harsh reaction conditions, is suitable for industrial production. (by machine translation)

Supported Rhodium (Rh@PS) Catalyzed Benzimidazoles Synthesis Using Ethanol/Methanol as C2H3/CH Source

An effective and stable polystyrene supported rhodium (Rh@PS) nano-catalyst has been synthesized by following reduction-deposition approach and applied for the selective benzimidazoles synthesis from 1,2-phenylenediamines and ethanol/methanol as C2H3/CH source. The ethanol/methanol in the presence of trace amounts of aerobic oxygen under Rh@PS catalysed condition, first participated in oxidation of alcohol followed by consecutive condensation, cyclization and hydrogen elimination reactions with 1,2-phenylenediamine gave the desired products in good yields. The Rh@PS catalyst in a single system performed both oxidation and reduction reactions in a selective/specific manner and applied for large substrate scope. Easy recovery, handling, stability, recyclability of the catalyst and less chance of metal contamination with the products are the added advantages of the process. (Figure presented.).

Imidazolium chloride-catalyzed synthesis of benzimidazoles and 2-substituted benzimidazoles from o-phenylenediamines and DMF derivatives

A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields.

Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis

An oxidant, base and metal free methodology has been developed for the synthesis of various 2-substituted and non-substituted benzazoles, quinazolines and quinazolinones using oxalic/malonic acids as an in situ carbon source. This methodology is applicable for a wide range of substituted o-phenylenediamine, o-aminothiophenol, o-aminophenol and o-aminobenzamide containing various functional groups and provides good to excellent yields of the corresponding product. Furthermore an easy workup procedure, high yield and easy isolation of products are key features of this methodology. The developed protocol is also applicable for the gram scale synthesis of benzimidazoles.

Discovery of the First Potent and Selective Inhibitors of Human dCTP Pyrophosphatase 1

The dCTPase pyrophosphatase 1 (dCTPase) regulates the intracellular nucleotide pool through hydrolytic degradation of canonical and noncanonical nucleotide triphosphates (dNTPs). dCTPase is highly expressed in multiple carcinomas and is associated with cancer cell stemness. Here we report on the development of the first potent and selective dCTPase inhibitors that enhance the cytotoxic effect of cytidine analogues in leukemia cells. Boronate 30 displays a promising in vitro ADME profile, including plasma and mouse microsomal half-lives, aqueous solubility, cell permeability and CYP inhibition, deeming it a suitable compound for in vivo studies.

Gadolinium (III) chloride catalyzed facile synthesis of 2-substituted benzimidazoles under solvent-free conditions

A series of 2-substituted benzimidazoles have been prepared from o-diamines and 1,3-dicarbonyl compounds using Gadolinium chloride as a catalyst under solvent free condition in good yields. Gadolinium chloride has been demonstrated as a mild and efficient catalyst.