384-32-7

Usage

Structure

Benzimidazole derivative with a methyl group at the 2-position and a trifluoromethyl group at the 4-position

Molar mass

216.17 g/mol

Boiling point

301.1°C at 760 mmHg

Uses

Building block in the synthesis of pharmaceuticals and agrochemicals, potential uses in the development of new materials and compounds for various technological applications

Safety precautions

Potential hazards and toxicity, should be handled and used with appropriate safety measures.

Upstream product

• 360-60-1 3-(trifluoromethyl)benzene-1,2-diamine 
• 64-19-7 acetic acid 
• 887144-97-0 Togni's reagent 
• 615-15-6 2-Methyl-1H-benzimidazole 
• 1445-45-0 Trimethyl orthoacetate 
• 24821-17-8 2-Nitro-6-(trifluoromethyl)aniline 
• 387-19-9 N-(2-nitro-3-(trifluoromethyl)phenyl)acetamide 
• 447-47-2 acetic acid-(2-amino-3-trifluoromethyl-anilide) 

Downstream Products

• 1168154-21-9 1-(3-methoxyphenyl)-2-methyl-4-(trifluoromethyl)-1H-benzimidazole 
• 1168154-49-1 2-methyl-1-{3-[3-(methylsulfonyl)phenoxy]phenyl}-4-(trifluoromethyl)-1H-benzimidazole 

Relevant academic research and scientific papers

Selective C-H trifluoromethylation of benzimidazoles through photoredox catalysis

The protocol presented here is a new strategy for visible light induced C-H trifluoromethylation at C4 of benzimidazoles using Togni's reagent in the presence of fac-Ir(ppy)3. Its advantages are its operational simplicity, mild reaction conditions, low catalyst loading and wide substrate scope in which electron-withdrawing, electron-donating groups and different protecting groups are tolerated.

Indium-mediated one-pot benzimidazole synthesis from 2-nitroanilines or 1,2-dinitroarenes with orthoesters

One-pot reduction-triggered heterocyclizations from 2-nitroanilines or 1,2-dinitroarenes to benzimidazoles were investigated in this study. In the presence of indium/AcOH in ethyl acetate at reflux, reaction of 2-nitroanilines or 1,2-dinitroarenes with R-C(OMe)3 (R=Me, Ph) produced excellent yields of the corresponding benzimidazoles within 30 min to 6 h depending on the substituents of the starting materials. Indium-mediated heterocyclization of 2-nitroanilines to benzimidazole was faster and had better yields than 1,2-dinitroarenes to benzimidazole under similar reaction conditions.

1-(3-Aryloxyaryl)benzimidazole sulfones are liver X receptor agonists

A series of 1-(3-aryloxyaryl)benzimidazoles incorporating a sulfone substituent (6) was prepared. High affinity LXR ligands were identified (LXRβ binding IC50 values 10 nM), some with excellent agonist potency and efficacy in a functional assay of LXR activity measuring ABCA1 mRNA increases in human macrophage THP1 cells. The compounds were typically stable in liver microsome preparations and had good oral exposure in mice.

BENZIMIDAZOLE COMPOUNDS

This invention relates generally to benzimidazole-based modulators of Liver X receptors (LXRs) and related methods (Formula I). wherein R2 is C6-C10 aryl or heteroaryl including 5-10 atoms, each of which is: (i) substituted with 1 R7, and (ii) optionally substituted with from 1-5 Re; and R1, R3, R4, R5, R6, R7, and Re are defined herein.