78164-31-5

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethylbenzotrifluoride is used as a reagent for the preparation of bromodomain targeting degronimers for target protein degradation. Bromodomains are protein domains that recognize acetylated lysine residues on histones and other proteins, playing a crucial role in gene expression regulation and cellular processes. Targeting bromodomain proteins with degronimers can modulate their activity and lead to the degradation of specific target proteins, offering a promising therapeutic strategy for various diseases, including cancer and inflammatory disorders.

InChI:InChI=1/C9H9F3/c1-6-3-4-8(5-7(6)2)9(10,11)12/h3-5H,1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 95-47-6 o-xylene 
• 71740-88-0 1,2-dimethyl-4-trifluoromethyl-cyclohexadiene-(1,4) 
• 41818-96-6 1,3-dimethyl-2-(trifluoromethyl)benzene 
• 93683-27-3 perfluoro-2,4-dimethyl-3-ethylpent-3-yl radical 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 619-04-5 3,4-dimethylbenzoic acid 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 31599-61-8 3,4-dimethyliodobenzene 
• 583-71-1 4-bromo-o-xylene 
• 401797-00-0 2-(3,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 86845-29-6 1,3-dimethyl-5-trifluoromethylbenzene 

Downstream Products

• 835-58-5 4-(trifluoromethyl)phthalic acid 
• 41818-96-6 1,3-dimethyl-2-(trifluoromethyl)benzene 
• 80245-28-9 1,2-dimethyl-3-(trifluoromethyl)benzene 
• 86845-29-6 1,3-dimethyl-5-trifluoromethylbenzene 
• 26238-14-2 5-trifluoromethylbenzofuran-1,3-dione 
• 1997-41-7 5-trifluoromethylphthalimide 
• 1483-45-0 4-trifluoromethylphthalodinitrile 
• 20036-05-9 4-trifluoromethylphthalamide 

Relevant academic research and scientific papers

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides

While acid fluorides can readily be made from widely available or biomass-feedstock-derived carboxylic acids, their use as functional groups in metal-catalyzed cross-coupling reactions is rare. This report presents the first demonstration of Pd-catalyzed

Trifluoromethylation of Arylsilanes with [(phen)CuCF3]

A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF3] as the CF3source under mild, oxidative conditions with high functional-group compatibility. This transformation complements prior trifluoromethylation of arenes in several ways. Most important, this method converts arylsilanes formed by the silylation of aryl C?H bonds to trifluoromethylarenes, thereby allowing the conversion of arenes to trifluoromethylarenes. The unique capabilities of the reported method are demonstrated by the conversion of a C?H bond into a C?CF3bond in active pharmaceutical ingredients which do not undergo this overall transformation by alternative functionalization processes, including a combination of borylation and trifluoromethylation.

Introducing a new radical trifluoromethylation reagent

Perfluoro-3-ethyl-2,4-dimethyl-3-pentyl radical (PPFR) is a persistent radical stable at room temperature, but easily decomposes at 90 °C to produce a CF3 radical which is able to react with a variety of aromatic compounds to afford the corresponding trifluoromethyl derivatives, usually as mixtures of regioisomers in good to excellent overall yields.

Copper-catalysed process for the production of substituted or unsubstituted trifluormethylated aryl and heteroaryl compounds

The present invention relates to a process for the production of triffluoromethylated unsubstituted or substituted aryl or heteroaryl compounds which comprises reacting an unsubstituted or substituted aryl or heteroaryl halide with a trifluoroacetate of formula (I) or (II), wherein R1 is hydrogen or a C1-C5 alkyl group and M an alkali metal or an ammonium ion, in the presence of a copper salt as catalyst and an anorganic halogenide salt or a trifluoroacetacid salt as activator compound.

A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuRF]

A versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuRF]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF3] is now commercially available and has been prepared on 20g scale. Copyright

Silver-mediated trifluoromethylation of arenes using TMSCF3

The silver-mediated C-H trifluoromethylation of aromatic substrates using TMSCF3 is described. The development, optimization, and scope of these transformations are reported. AgCF3 intermediates are proposed.

Phototransposition reactions of methyl-substituted benzotrifluorides: Proof of the role of trifluoromethyl-substituted carbon

Irradiation in acetonitrile of any one of the six isomers of dimethylbenzotrifluoride 8 resulted in efficient photoisomerization to the others. The dominant processes in these phototransposition reactions divides the isomers into two triads. The first consists of 8-2,6 (2,6-dimethylbenzotrifluoride), 8-2,3, and 8-3,4; the second consists of 8-3,5, 8-2,4, and 8-2,5. Moreover, irradiation of 2,6-dideuterio-4-methylbenzotrifluoride 5-d2 resulted in formation of 5,6-dideuterio-3-methylbenzotrifluoride 6-d2. These observations demonstrate that it is the trifluoromethyl-substituted carbon that is the migratory one in these reactions.

A New Method for the Trifluoromethylation of Aromatics

A new method is described for introducing a CF3-group, by a single-step synthesis, into aromatic compounds.This trifluoromethylation is done by means of a mixture consisting of HF/CCl4 and the aromatic compounds.The reaction is thought to be of a Friedel-Crafts type and limited to aromatics which are not substituted by electron withdrawing groups.