86604-86-6

Basic information

• Product Name: 2-Chloro-6-(trifluoromethyl)-1H-benzimidazole
• Synonyms: 2-CHLORO-5-(TRIFLUOROMETHYL)BENZIMIDAZOLE;2-CHLORO-6-TRIFLUOROMETHYL-1H-BENZIMIDAZOLE;2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole;2-chloro-6-(trifluoromethyl)-1H-benzo[d]imidazole;2-chloro-5-(trifluoroMethyl)-1H-1,3-benzodiazole;1H-BenziMidazole, 2-chloro-6-(trifluoroMethyl)-;2-Chloro-6-(trifluoroMethyl)benziMidazole;-Chloro-6-(trifluoromethyl)benzimidazole
• CAS NO: 86604-86-6
• Molecular Formula: C₈H₄ClF₃N₂
• Molecular Weight: 220.58
• Mol File: 86604-86-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 186-188 °C
• Boiling Point: 322.1 °C at 760 mmHg
• Flash Point: 148.6 °C
• Appearance: /
• Density: 1.569 g/cm³
• Vapor Pressure: 0.000286mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.75±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-6-(trifluoromethyl)-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-6-(trifluoromethyl)-1H-benzimidazole(86604-86-6)
• EPA Substance Registry System: 2-Chloro-6-(trifluoromethyl)-1H-benzimidazole(86604-86-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 86604-86-6(Hazardous Substances Data)

Usage

Description

2-Chloro-6-(trifluoromethyl)-1H-benzimidazole is an organic compound that features a benzimidazole core with a chloro substituent at the 2nd position and a trifluoromethyl group at the 6th position. 2-Chloro-6-(trifluoromethyl)-1H-benzimidazole is known for its potential applications in the synthesis of various organic molecules and as a reagent in chemical reactions.

Uses

Used in Pharmaceutical Industry:
2-Chloro-6-(trifluoromethyl)-1H-benzimidazole is used as a reagent for preparing chiral 2-aminobenzimidazoles, which serve as recoverable organocatalysts. These organocatalysts are valuable in the synthesis of enantioselective pharmaceutical compounds, contributing to the development of more efficient and environmentally friendly synthetic routes.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Chloro-6-(trifluoromethyl)-1H-benzimidazole is utilized as a building block for the creation of complex organic molecules. Its unique structural features allow it to participate in various chemical reactions, facilitating the synthesis of target molecules with specific properties and functions.

InChI:InChI=1/C8H4ClF3N2/c9-7-13-5-2-1-4(8(10,11)12)3-6(5)14-7/h1-3H,(H,13,14)

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 368-71-8 4-(trifluoromethyl)-1,2-phenylenediamine 
• 133687-93-1 5-(trifluoromethyl)-1,3-dihydro-2H-benzoimidazol-2-one 

Downstream Products

• 1049799-23-6 C₂₀H₁₃ClF₃N₃O 
• 1170773-36-0 (1R,2R)-N₁-{6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl}cyclohexane-1,2-diamine 
• 1073558-62-9 3-phenyl-8-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]-1-oxa-3,8-diazaspiro-[4.5]decan-2-one 
• 1453097-16-9 3-methyl-4-(phenylmethyl)-1-(5-trifluoromethyl-1H-benzimidazol-2-yl)-1H-pyrazol-5-ol 
• 1073558-69-6 3-(3,4-dichlorophenyl)-8-[5-(trifluoromethyl)-1H-benzimidazol-2-yl]-1-oxa-3,8-diazaspiro-[4.5]decan-2-one 

Relevant articles and documents

Synthesis and in Vitro Activity of Polyhalogenated 2-phenylbenzimidazoles as a New Class of anti-MRSA and Anti-VRE Agents

A series of novel polyhalogenated 2-phenylbenzimidazoles have been synthesized and evaluated for in vitro antistaphylococcal activity against drug-resistant bacterial strains (methicillin-resistant Staphylococcus aureus, and vancomycin-resistant Enterococcus faecium. Certain compounds inhibit bacterial growth perfectly. 11 was active than vancomycin (0.78 μg/mL) with the lowest MIC values with 0.19 μg/mL against methicillin-resistant Staphylococcus aureus, 8 and 35 exhibited best inhibitory activity against vancomycin-resistant Enterococcus faecium (1.56 μg/mL). The mechanism of action for this class of compounds appears to be different than clinically used antibiotics. These polyhalogenated benzimidazoles have potential for further investigation as a new class of potent anti-methicillin-resistant Staphylococcus aureus and anti-vancomycin-resistant Enterococcus faecium agents.

Discovery of a Selective Aurora A Kinase Inhibitor by Virtual Screening

Here we report the discovery of a selective inhibitor of Aurora A, a key regulator of cell division and potential anticancer target. We used the atom category extended ligand overlap score (xLOS), a 3D ligand-based virtual screening method recently developed in our group, to select 437 shape and pharmacophore analogs of reference kinase inhibitors. Biochemical screening uncovered two inhibitor series with scaffolds unprecedented among kinase inhibitors. One of them was successfully optimized by structure-based design to a potent Aurora A inhibitor (IC50 = 2 nM) with very high kinome selectivity for Aurora kinases. This inhibitor locks Aurora A in an inactive conformation and disrupts binding to its activator protein TPX2, which impairs Aurora A localization at the mitotic spindle and induces cell division defects. This phenotype can be rescued by inhibitor-resistant Aurora A mutants. The inhibitor furthermore does not induce Aurora B specific effects in cells.

Design and synthesis of prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors as anti-prostate cancer drugs

A series of 1-aryl-3,4-substituted-1H-pyrazol-5-ol derivatives was synthesized and evaluated as prostate cancer antigen-1 (PCA-1/ALKBH3) inhibitors to obtain a novel anti-prostate cancer drug. After modifying 1-(1H-benzimidazol-2-yl)-3,4-dimethyl-1H-pyrazol-5-ol (1), a hit compound found during random screening using a recombinant PCA-1/ALKBH3, 1-(1H-5- methylbenzimidazol-2-yl)-4-benzyl-3-methyl-1H-pyrazol-5-ol (35, HUHS015), was obtained as a potent PCA-1/ALKBH3 inhibitor both in vitro and in vivo. The bioavailability (BA) of 35 was 7.2% in rats after oral administration. As expected, continuously administering 35 significantly suppressed the growth of DU145 cells, which are human hormone-independent prostate cancer cells, in a mouse xenograft model without untoward effects.