4887-80-3

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXYBENZIMIDAZOLE is used as an active pharmaceutical ingredient for its anti-proliferative activity. It has been studied in preliminary in vivo toxicity tests against a panel of non-small cell lung cancer cell lines, showing potential as a therapeutic agent in the treatment of cancer.
Used in Chemical Research:
As an organic compound, 5-METHOXYBENZIMIDAZOLE can be used as a research chemical in the development of new drugs and materials. Its unique structure and properties make it a valuable tool for understanding various chemical reactions and interactions.
Used in Material Science:
5-METHOXYBENZIMIDAZOLE's chemical properties may also make it suitable for use in the development of new materials with specific characteristics, such as improved stability or reactivity. Further research and development in this area could lead to novel applications in various industries.

InChI:InChI=1/C8H8N2O/c1-11-6-2-3-7-8(4-6)10-5-9-7/h2-5H,1H3,(H,9,10)

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 64-18-6 formic acid 
• 96-96-8 4-methoxy-2-nitroaniline 
• 57-55-6 propylene glycol 
• 107-21-1 ethylene glycol 
• 67-56-1 methanol 
• 37052-78-1 6-methoxy-1H-benzoimidazole-2-thiol 
• 64-17-5 ethanol 
• 100-51-6 benzyl alcohol 
• 1758-73-2 Aminoiminomethanesulfinic acid 
• 4280-28-8 3,4-dinitroanisole 
• 73590-58-6 omeprazole 
• 124-38-9 carbon dioxide 

Downstream Products

• 112146-95-9 5-methoxy-6-nitro-1(3)H-benzimidazole 
• 41292-65-3 5-hydroxy-1H-benzimidazole 
• 79938-46-8 1-acetyl-5-methoxybenzimidazole 
• 79938-47-9 1-acetyl-6-methoxybenzimidazole 
• 1135119-72-0 C₂₂H₁₇F₃N₂O₄S 
• 1135119-69-5 C₂₂H₁₇F₃N₂O₄S 
• 1427722-22-2 (Z)-5-methoxy-1-styryl-1H-benzo[d]imidazole 
• 69445-55-2 1-(4-phenyl)-6-methoxy-1H-benzo[d]imidazole 
• 38205-85-5 1-(4-phenyl)-5-methoxy-1H-benzo[d]imidazole 
• 10394-42-0 6-methoxy-1-methylbenzimidazole 
• 10394-39-5 5-methoxy-1-methyl-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Novel approach to the synthesis of omeprazole: An antipeptic ulcer agent

A novel approach for the synthesis of omeprazole, a potent antiulcer drug, is described. The synthetic procedure involved the formation of an ester of the 5-methoxy thiobenzimidazole followed by coupling of the ester with the Grignard reagent of 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine. Copyright Taylor & Francis Group, LLC.

Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles

We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc

Highly efficient one pot synthesis of benzimidazoles from 2-nitroaniline and PhSiH3 as reducing agent catalyzed by Pd/C as a heterogeneous catalyst

This work reports an efficient route for the synthesis of benzimidazole from o-nitroaniline in the presence of carbon dioxide atmosphere, PhSiH3 as a reducing agent catalyzed by Pd/C as a catalyst. Benzimidazoles have become the focus of organic chemists, as benzimidazole is an important intermediate in medicinal chemistry. We have developed more efficient route for the synthesis benzimidazole and various substituted benzimidazoles have been synthesized in good to excellent yield. The TBD (1,5,7-Triazabicyclo [4.4.0] dec-5-ene) is selected as a base as it promotes the CO2 insertion. Benzimidazoles were synthesized through reduction of nitro group followed by cyclization of amine using CO2 as a carbon source. Moreover, the Pd/C catalyst can be recycled up to five recycle run without significant changes in the yield of the product.

Highly Efficient and Catalyst-Free Synthesis of Benzimidazoles in Aqueous Media

Abstract: A convenient and highly efficient, catalysts-free synthesis of benzimidazoles in an aqueous medium has been developed. The conditions of the synthesis were optimized, and its scope was successfully extended to various substrates with good to excellent yields. The experimental procedure is simple, and the products can be isolated by filtration followed by recrystallization from water.

Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.

Method for synthesizing benzimidazole from carbon dioxide and o-phenylenediamine compound

The invention discloses a method for synthesizing benzimidazole from carbon dioxide and an o-phenylenediamine compound, the method is characterized in that an amino-containing functionalized ordered mesoporous polymer is used as a catalyst, o-phenylenediamine and carbon dioxide are used as raw materials, dimethylaminoborane is used as a hydrogen reduction reagent, carbon dioxide and the o-phenylenediamine compound are catalyzed to react in an NMP solvent to generate a benzimidazole compound, wherein the dosage of a catalyst is 0.01-1mol% based on the nitrogen content of the o-phenylenediamine compound; the filling pressure of the carbon dioxide is 0.1-2MPa; the reaction temperature is 60-180DEG C; the molar ratio of the catalyst to the NMP is 1:50-100. Compared with the prior art, the catalyst has the advantages of simple preparation, high catalytic activity, capability of catalyzing the reaction of carbon dioxide and the o-phenylenediamine compound under mild conditions to generate benzimidazole and derivatives thereof, and the like.

Synthesis method of benzimidazole compound based on iron catalytic oxidation-reduction coupling reaction

The invention belongs to the field of organic synthesis, and relates to a benzimidazole compound synthesis method based on an iron catalytic oxidation-reduction coupling reaction. According to the method, o-nitroaniline compounds and alcohol compounds are used as raw materials, and the benzimidazole compounds are generated through iron-catalyzed redox coupling reaction in the presence of an iron catalyst and a proton donor. The method provided by the invention provides a new way for the synthesis of benzimidazole drugs and pesticides. Compared with a traditional benzimidazole compound synthesis method with o-phenylenediamine compounds and carboxylic acid or carboxylic acid derivatives as raw materials, the method has the advantages that the atom utilization rate of the whole process is increased, the production cost is reduced, and waste gas, waste liquid and waste solid generated in the production process is reduced.

Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical

A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.

K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles

We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.

Synthesis method of ammonium acetate mediated benzimidazole compound

The invention discloses a synthesis method of a benzimidazole compound mediated by ammonium acetate. The synthesis method comprises the following steps: adding an o-phenylenediamine compound, dimethylsulfoxide, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at 130-150 DEG C, cooling the reaction product to room temperature after the reaction is finished, and carrying out separation and purification on the product to obtain the benzimidazole compound. The invention develops a method for synthesizing a benzimidazole compound under the mediation of ammonium acetate by taking DMSO as a carbon source and an oxidant and an o-phenylenediamine compound as a substrate under the condition of no metal catalyst. The synthesis method does not need a metal catalyst, and the required carbon source and oxidant have the characteristics of low toxicity, low price, easiness in obtaining, stable performance and the like. The method has the advantages of easiness inoperation, few steps, mild reaction conditions, better functional group tolerance and the like, and provides a new valuable way for synthesizing benzimidazole compounds.