39226-97-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-(trifluoromethyl)benzoic acid is used as a reactant for the preparation of trifluoromethylphenyl as P2 for ketoamide-based cathepsin S inhibitors. Cathepsin S inhibitors are of interest in the development of treatments for various diseases, including cancer and inflammatory conditions, due to their role in regulating immune responses and proteolytic processes.

InChI:InChI=1/C8H4ClF3O2/c9-6-4(7(13)14)2-1-3-5(6)8(10,11)12/h1-3H,(H,13,14)

Upstream product

• 313-12-2 2-amino-3-(trifluoromethyl)benzoic acid 
• 124-38-9 carbon dioxide 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 391-12-8 7-trifluoromethylisatin 

Downstream Products

• 129322-82-3 1-<2-chloro-3-(trifluoromethyl)phenyl>ethanone 
• 39959-94-9 2-chloro-3-trifluoromethylbenzamide 
• 850156-39-7 2-chloro-3-(trifluoromethyl)benzoyl chloride 
• 908123-86-4 tert-butyl 2-chloro-3-(trifluoromethyl)phenylcarbamate 
• 899431-48-2 5-(2-chloro-3-trifluoromethylphenyl)-1H-tetrazole 
• 899431-56-2 N-(2-chloro-3-trifluoromethylphenyl)-2-pyridin-3-ylacetamide 
• 899431-60-8 N-(2-chloro-3-trifluoromethylphenyl)-2-pyridin-3-ylthioacetamide 
• 62584-32-1 2-chloro-3-trifluoromethylbenzonitrile 
• 39226-96-5 2-chloro-3-(trifluoromethyl)benzylamine 
• 1213113-19-9 1-(2-Chloro-3-trifluoromethyl-phenyl)-ethylamine 
• 773135-43-6 ethyl 2-chloro-3-(trifluoromethyl)benzoate 
• 1005786-17-3 2-chloro-N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide 
• 1146411-56-4 4-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-1-(4-fluorophenyl)-2-piperazinone 
• 1146411-49-5 1-(2-chloro-4-fluorophenyl)-4-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-piperazinone 

Relevant academic research and scientific papers

Reagent-modulated optional site selectivities: The metalation of o-, m- and p-halobenzotrifluorides

Chloro(trifluoromethyl)benzenes and bromo(trifluoromethyl)benzenes undergo deprotonation at a position adjacent to the single halogen substituent when treated with alkyllithiums (at -75°C) and, respectively, lithium 2,2,6,6-tetramethylpiperidide (at -100°C) in tetrahydrofuran. Positional ambiguities, if existing, can be exploited to establish optional site selectivities. Thus, butyllithium reacts with 1-chloro-3-(trifluoromethyl)benzene under hydrogen/metal interconversion at the 2-position whereas sec-butyllithium attacks exclusively the 6-position. The latter mode of regioselectivity is also exhibited by 1-bromo-3-(trifluoromethyl)benzene in the presence of lithium 2,2,6,6-tetramethylpiperidide, only 2-bromo-4-(trifluoromethyl)phenyllithium being produced. 2-Bromo-6-(trifluoromethyl)phenyllithium is directly inaccessible, but is formed when 2-bromo-3-(trifluoromethyl)phenyllithium, generated at -100°C, is allowed to isomerize at -75°C.

Lithiations directed by carboxylic acid, fluorine and chlorine: The regioselective synthesis of polysubstituted benzoic acids and acetophenones

Lithiation/electrophilic quenching of ortho-lithiated benzoates allows the totally regiocontrolled synthesis of a wide range of 2,3-, 2,3,4-, and 2,3,4,5-polysubstituted benzoic acids and related acetophenones. Elsevier,.