50562-01-1

Usage

Uses

Used in Chemical Reactions:
1-methyl-4-(2,2,2-trifluoroethyl)benzene is used as a solvent in various chemical reactions and processes. Its high thermal stability and resistance to chemical reactions make it suitable for use in demanding conditions.
Used in Production of Specialized Materials:
Due to its unique properties, 1-methyl-4-(2,2,2-trifluoroethyl)benzene is used in the production of specialized materials that require high thermal stability and resistance to chemical reactions.
Used in Electronics Industry:
1-methyl-4-(2,2,2-trifluoroethyl)benzene is also utilized in the electronics industry, where its properties are beneficial for the manufacturing of certain components and materials.
Used as an Intermediate in Synthesis:
1-methyl-4-(2,2,2-trifluoroethyl)benzene serves as an intermediate in the synthesis of other chemicals and pharmaceuticals, contributing to the development of new products and innovations.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-methyl-4-(2,2,2-trifluoroethyl)benzene is used as an intermediate for the synthesis of various drugs, taking advantage of its unique properties to create effective medications.
Safety Note:
It is crucial to handle 1-methyl-4-(2,2,2-trifluoroethyl)benzene with caution, as its high fluorination can make it toxic and potentially hazardous if not properly controlled. Proper safety measures should be implemented during its use and disposal.

Upstream product

• 106-42-3 para-xylene 
• 1680206-12-5 Grushin’s reagent 
• 398456-85-4 (4-methylbenzyl)zinc(II) bromide 
• 104-81-4 4-Methylbenzyl bromide 
• 104-87-0 4-methyl-benzaldehyde 
• 887144-94-7 Togni's reagent II 
• 52693-87-5 4-methylbenzaldehyde hydrazone 
• 5720-05-8 4-methylphenylboronic acid 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 
• 87671-54-3 4-methylbenzyl diphenylphosphinite 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 28321-07-5 1-(2,2-difluorovinyl)-4-methylbenzene 

Relevant academic research and scientific papers

Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes

Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free.

Csp3-Csp3 Bond-Forming Reductive Elimination from Well-Defined Copper(III) Complexes

Carbon-carbon bond-forming reductive elimination from elusive organocopper(III) complexes has been considered the key step in many copper-catalyzed and organocuprate reactions. However, organocopper(III) complexes with well-defined structures that can undergo reductive elimination are extremely rare, especially for the formation of Csp3-Csp3 bonds. We report herein a general method for the synthesis of a series of [alkyl-CuIII-(CF3)3]- complexes, the structures of which have been unequivocally characterized by NMR spectroscopy, mass spectrometry, and X-ray crystal diffraction. At elevated temperature, these complexes undergo reductive elimination following first-order kinetics, forming alkyl-CF3 products with good yields (up to 91%). Both kinetic studies and DFT calculations indicate that the reductive elimination to form Csp3-CF3 bonds proceeds through a concerted transition state, with a ΔH? = 20 kcal/mol barrier.

Copper-Mediated Trifluoromethylation of Benzylic Csp3?H Bonds

Trifluoromethyl-containing compounds play a significant role in medicinal chemistry, materials and fine chemistry. Although direct C?H trifluoromethylation has been achieved on Csp2?H bonds, direct conversion of Csp3?H bonds to Csp3?CF3 remains challenging. We report herein an efficient protocol for the selective trifluoromethylation of benzylic C?H bonds. This process is mediated by a combination CuIII?CF3 species and persulfate salts. A wide range of methylarenes can be selectively trifluoromethylated at the benzylic positions. A combination of experimental and theoretical mechanistic studies suggests that the reaction involves a radical intermediate and a CuIII?CF3 species as the CF3 transfer reagent.

Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization

The installation of trifluoromethyl groups has become an essential step across a number of industries such as agrochemicals, drug discovery, and materials. Consequently, the rapid introduction of this critical functional group in a predictable fashion would benefit current practitioners in those fields. This communication describes a mild trifluoromethylation of benzylic C-H bonds with high selectivity for the least hindered hydrogen atom. The reaction provides monotrifluoromethylation and proceeds in an environmentally friendly acetone/water solvent system. The method can be used to install benzylic trifluoromethyl groups on highly functionalized drug molecules.

METHOD FOR PRODUCING (FLUOROALKYL) ARENE

PROBLEM TO BE SOLVED: To provide a method for efficiently producing fluoroalkyl arene, which is important as synthetic raw materials for medicines and functional materials. SOLUTION: A fluoroalkyl arene is produced by the reaction between an aryl metal species represented by formula (2) and a fluoroalkyl halide represented by formula (3) in the presence of a cobalt compound and an ethylenediamine derivative. In the formula (2) shown in the following figure, R11-R15 independently represent H, a C1-C4 alkyl group or the like. In the formula (3): Y-Rf, Y is Cl or the like; Rf is a C2-C3 fluoroalkyl group. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl(2,2,2-trifluoroethyl)iodonium triflates

Highly electrophilic aryl(2,2,2-trifluoroethyl)iodonium triflates have been used for the first time as trifluoroethyl and aryl transfer reagents in Pd-catalyzed functionalization of arylboronic acids. Electron-rich arylboronic acids reacted with aryl(2,2,

Cobalt/diamine-catalyzed 1,1-difluoroethylation and 2,2,2-trifluoroethylation of aryl Grignard reagents with corresponding fluoroalkyl halides

Cobalt/diamine-catalyzed 1,1-difluoroethylation and 2,2,2-trifluoroethylation of aryl Grignard reagents with 1,1-difluoroethyl and 2,2,2-trifluoroethyl halides were investigated. With regard to the 1,1-difluoroethylation, 1,2-bis(dimethylamino)-2-methylpropane, which has been rarely used in the cross-coupling reactions, gave the highest yield among the diamine ligands tested. In the 2,2,2-trifluoroethylation, trans-1,2-bis(dimethylamino)cyclohexane provided the desired products in satisfactory yields with not only 2,2,2-trifluoroethyl iodide but also chloride. This Co/diamine catalyst was also effective for the coupling with other partially fluorinated alkyl halides in the presence of appropriate diamine ligands.

Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates

Trifluoroethylarenes are found in a variety of biologically active molecules, and strategies for accessing this substructure are important for developing therapeutic candidates and biological probes. Trifluoroethylarenes can be directly accessed via nucleophilic trifluoromethylation of benzylic electrophiles; however, current catalytic methods do not effectively transform electron-deficient substrates and heterocycles. To address this gap, we report a Cu-catalyzed decarboxylative trifluoromethylation of benzylic bromodifluoroacetates. To account for the tolerance of sensitive functional groups, we propose an inner-sphere mechanism of decarboxylation.

Synthesis of trifluoromethylated compounds from alcohols via alkoxydiphenylphosphines

The transformation of hydroxyl group in benzyl or allyl alcohols to trifluoromethyl was achieved via the reaction of the corresponding alkyloxydiphenylphosphine and CuCF3, generated in situ from methyl fluorosulfonyldifluoroacetate and CuI, under mild conditions. A plausible mechanism was proposed on the basis of experimental results.

SYNTHESIS AND USE OF FLUORINATED COMPOUNDS

The invention is directed to the preparation of fluorinated compounds and their use in organic synthesis. In particular, the invention is directed to methods of reacting compounds of structure with Rf-CH=N2 or (CF3)2C=N2 to form a perfluoroalkylate or -arylated compounds, and products derived from these reactions, where X, YB, and Rf are described herein.