61078-14-6

Basic information

• Product Name: 1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole
• Synonyms: 1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole;1-Methyl-2-(methylsulfonyl)benzimidazole;1H-Benzimidazole, 1-methyl-2-(methylsulfonyl)-
• CAS NO: 61078-14-6
• Molecular Formula: C₉H₁₀N₂O₂S
• Molecular Weight: 210.2529
• EINECS: -0
• Mol File: 61078-14-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 132.0 to 136.0 °C
• Appearance: /
• CAS DataBase Reference: 1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole(61078-14-6)
• EPA Substance Registry System: 1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole(61078-14-6)

Safety Data

• Hazardous Substances Data: 61078-14-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole is used as a potential therapeutic agent for its ability to inhibit enzymes and modulate biological pathways. Its applications are being explored for treating various diseases and conditions, such as cancer and inflammation. The presence of the methylsulfonyl group may enhance its pharmacological activities, making it a promising candidate for further research and development in drug discovery.

Upstream product

• 57159-81-6 2-(methylsulfonyl)-1H-benzo[d]imidazole 
• 7732-18-5 water 
• 74-88-4 methyl iodide 
• 4344-61-0 1-methyl-2-(methylthio)-1H-benzimidazole 
• 134469-07-1 Benzimidazol-2-thiol 
• 7152-24-1 2-methylsulfanylbenzimidazole 
• 74-87-3 methylene chloride 

Downstream Products

• 27097-08-1 N-benzyl-1-methyl-1H-benzo[d]imidazol-2-amine 
• 6888-79-5 4-bromo-α-methylstyrene 
• 875-72-9 2-methylideneadamantane 
• 159635-49-1 tert-butyl 4-methylidenepiperidine-1-carboxylate 
• 28884-75-5 1,3,3-trimethyl-2-(3-methyl-1,3-butadienyl)-1-cyclohexene 
• 119433-76-0 (1S,4R)-1-isopropyl-4-methyl-2-methylene-cyclohexane 
• 1073-67-2 4-vinylbenzyl chloride 
• 6380-23-0 3,4-dimethoxystyrene 
• 826-74-4 1-vinylnaphthalene 
• 62108-28-5 4,8-dimethylnona-1,7-diene 
• 1849-01-0 1-methyl-2-benzimidazolone 
• 17088-21-0 1-vinylpyrene 
• 769-25-5 2,4,6-trimethylstyrene 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 

Relevant articles and documents

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone

The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.

Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents

A new Julia-type methylenation reagent, 1-methyl-2-(methylsulfonyl)benzimidazole (1e), reacts with a variety of aldehydes and ketones in the presence of either NaHMDS (-55 °C to rt) or t-BuOK (rt, 1 h) in DMF to give the corresponding terminal alkenes in high yields. The byproducts are easily removed, and the reaction conditions are mild and practical.

Mechanistic investigations and substrate scope evaluation of ruthenium-catalyzed direct sp3 arylation of benzylic positions directed by 3-substituted pyridines

A highly efficient direct arylation process of benzylic amines with arylboronates was developed that employs Ru catalysis. The arylation takes place with greatest efficiency at the benzylic sp3 carbon. If the distance to the activating aryl ring is increased, arylation is still possible but the yield drops significantly. Efficiency of the CH activation was found to be significantly increased by use of 3-substituted pyridines as directing groups, which can be removed after the transformation in high yield. Calculation of the energy profile of different rotamers of the substrate revealed that presence of a substituent in the 3-position favors a conformation with the CH2 group adopting a position in closer proximity to the directing group and facilitating C-H insertion. This operationally simple reaction can be carried out in argon atmosphere as well as in air and under neutral reaction conditions, displaying a remarkable functional group tolerance. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.

Substituted arylsulfonamides and benzamides

This invention relates to substituted arylsulfonamides and benzamides possessing aniarrhythmic activity, to pharmaceutical compositions and to methods for production thereof.