1736-06-7

Usage

Uses

Used in Chemical Synthesis:
3'-METHYL-2,2,2-TRIFLUOROACETOPHENONE is used as a reactant in the synthesis of (trifluoromethyl)phenyldiazirines, which are valuable compounds for use in photoaffinity labelling. This application takes advantage of the compound's reactivity and its ability to form stable intermediates, allowing for the development of innovative techniques in chemical research and analysis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3'-METHYL-2,2,2-TRIFLUOROACETOPHENONE can be utilized as a key intermediate in the synthesis of various drug molecules. Its unique structure and reactivity enable the creation of novel compounds with potential therapeutic applications, contributing to the development of new medications and treatments for various diseases.
Used in Material Science:
3'-METHYL-2,2,2-TRIFLUOROACETOPHENONE may also find applications in material science, particularly in the development of new polymers and materials with specific properties. Its ability to form stable intermediates and participate in various chemical reactions can lead to the creation of advanced materials with improved characteristics, such as enhanced stability, durability, or specific functional properties.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 3203, 2001 DOI: 10.1021/jm010826r

Upstream product

• 591-17-3 meta-bromotoluene 
• 76-05-1 trifluoroacetic acid 
• 383-63-1 ethyl trifluoroacetate, 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 625-95-6 3-Iodotoluene 
• 181820-18-8 S-(tert-butyl)trifluorothioacetate 
• 17933-03-8 m-tolylboronic acid 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 620-23-5 m-tolyl aldehyde 
• 1737-23-1 1-(3-methylphenyl)-2,2,2-trifluoroethanol 
• 340-07-8 N-(trifluoroacetyl)piperidine 
• 329914-99-0 phenyl β-(trifluoroacetyl)vinyl sulfone 
• 78-79-5 isoprene 

Downstream Products

• 1737-23-1 1-(3-methylphenyl)-2,2,2-trifluoroethanol 
• 79663-86-8 1-(3-methylphenyl)-1-(trifluoromethyl)ethanol 
• 370104-05-5 1-(3-(bromomethyl)phenyl)-2,2,2-trifluoroethanone 
• 902453-29-6 N-(1-ethoxy-2,2,2-trifluoro-1-(3-methylphenyl)ethyl)-P,P-diphenylphosphinic amide 
• 370104-07-7 4-amino-5-fluoro-2-methyl-3-(3-trifluoroacetylbenzylthiomethyl)quinoline 
• 2676-99-5 2-(3-methylphenyl)-1,1,1-trifluorobutan-2-ol 
• 1096375-91-5 (R)-2,2,2-trifluoro-1-(1H-pyrrol-2-yl)-1-m-tolylethanol 
• 929099-10-5 2,2,2-trifluoro-1-(m-tolyl)ethanone oxime 
• 1256347-06-4 [2-methyl-4-(trifluoromethylsulfanyl)phenyl]-(m-tolyl)-S-trifluoromethylsulfonium trifluoromethanesulfonate 
• 1256347-08-6 [4-methyl-2-(trifluoromethylsulfanyl)phenyl]-(m-tolyl)-S-trifluoromethylsulfonium trifluoromethanesulfonate 
• 1338726-58-1 (E)-ethyl 2-(4-m-tolyl-4-(trifluoromethyl)oxetan-2-ylidene)acetate 

Relevant academic research and scientific papers

Domino C-F Bond Activation of the CF3 Group: Synthesis of Fluorinated Dibenzo[a,c][7]annulenes from 2-(Trifluoromethyl)-1-alkenes and 2,2′-Diceriobiaryls

The construction of ring-fluorinated seven-membered carbocycles was readily achieved via the domino SN2′-type/SNV reaction between 2-(trifluoromethyl)-1-alkenes and 1,4-carbodianions. The SN2′-type reaction of 2-(trifluoromethyl)-1-alkenes with 2,2′-diceriobiaryls generated the intermediary 1,1-difluoro-1-alkenes bearing a monoceriobiaryl moiety, which in turn underwent intramolecular SNV reaction to afford fluorinated 5H-dibenzo[a,c][7]annulenes.

Diels-Alder reactions of β-trifluoroacetylvinylsulfones

Diels-Alder reactions of β-trifluoroacetylvinylsulfones with 1,3-dienes in CH2Cl2 afforded corresponding mono- and polycycloadducts. A possibility of stereo- and regioselective cycloaddition was investigated. Elimination of sulfonyl group from cycloadducts leads to α,β-unsaturated trifluoromethylketones in good yields.

One-Pot Successive Turbo Grignard Reactions for the Facile Synthesis of α-Aryl-α-Trifluoromethyl Alcohols

A novel straightforward one-pot methodology for two successive turbo Grignard reagent (iPrMgCl·LiCl) reactions, was developed for a facile synthesis of α-aryl-α-trifluoromethyl alcohols, motifs of value in pharmaceutical chemistry. The method displayed broad functional group tolerance, including reducible groups. Dual roles of iPrMgCl·LiCl were exploited in the tandem reaction with commercially available iodoarenes or iodoheteroarenes and 2,2,2-trifluoroethyl trifluoroacetate. The process encompasses three successive reactions in a one-pot process: the iPrMgCl·LiCl-mediated iodine/magnesium-exchange reaction of iodoarenes or iodoheteroarenes; nucleophilic addition of various generated aryl or heteroarylmagnesium reagents to 2,2,2-trifluoroethyl trifluoroacetate; and the reduction of in-situ generated aryl trifluoromethyl ketones with iPrMgCl·LiCl, to produce the corresponding α-aryl or α-heteroaryl-α-trifluoromethyl alcohols bearing various substituents, including reducible functional groups in good to excellent yields.

Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature

A palladium-catalyzed fluoroacylation of (hetero)aryl boronic acid with the fluorothioacetates is described at ambient temperature. A variety of aryl, and heteroaryl boronic acids are compatible in the reaction, affording the corresponding fluoroalkyl ketones in moderate to good yields. Further late-stage di-, and trifluoroacylation of drug molecule clofibrate and estrone demonstrated the synthetic practicability of this protocol.2009 Elsevier Ltd. All rights reserved.

N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application

The invention belongs to the technical field of medical chemical engineering intermediates and related chemistry, and relates to N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application. The N-phenyl-N-p-toluenesulfonyl trifluoroacetamide is taken as a trifluoroacetylation reagent, reacts with an arylboronic acid derivative in an anhydrous organic solvent under the action of a metalcatalyst, a ligand and an alkali, and is efficiently and highly selectively converted into a trifluoroacetophenone compound. According to a synthesis method of the trifluoroacetophenone compound, involved in the invention, reaction steps are few; the NTFTS which is stable in use, easy to store, cheap and easy to get is taken as a trifluoroacetyl source; environmental friendliness is realized; reaction conditions are mild; operation is easy; a high-yield and high-selectivity target product is obtained and has relatively good industrial production value and practical application value. The trifluoroacetophenone compound synthesized by utilizing the method can be further subjected to a functionalization reaction, and can be widely applied to the synthetic fields of medicine, pesticide, bioactive molecules, functional material molecules and the like.

Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate

A copper-mediated trifluoroacetylation of various arenediazonium salts with ethyl trifluoropyruvate is reported. The reaction proceeded smoothly under mild conditions at room temperature giving trifluoromethyl aryl ketones in moderate to good yields. A variety of functional groups, including methoxy, hydroxy, ester, ketone, trifluoromethyl, and halide groups, were well tolerated. A possible reaction mechanism involving an aryl radical intermediate was proposed and supported by experimental evidence. This reaction provides a new route to trifluoromethyl aryl ketones, notable synthetic targets, from the corresponding anilines.

Catalytic highly enantioselective transfer hydrogenation of β-trifluoromethyl nitroalkenes. An easy and general entry to optically active β-trifluoromethyl amines

In the presence of a thiourea catalyst, β-CF3 nitroalkenes react with Hantzsch esters in a highly enantioselective fashion, giving a broad range of β-CF3 amine precursors with a tertiary stereocentre at the β-position. This reaction

Catalytic asymmetric hydrogenation of α-CF3- or β-CF3-Substituted acrylic acids using Rhodium(I) complexes with a combination of chiral and achiral ligands

Only the mixture works! Acrylic acid derivatives with CF3 substituents in α or β position were efficiently hydrogenated in the presence of a RhI complex with a chiral secondary phosphine oxide (SPO; see scheme) and an achiral Ph3P as ligands. The corresponding propanoic acid derivatives were obtained with generally high conversion (>99 %) and high enantioselectivity (92->99 %). Copyright

Design, synthesis and evaluation of novel hydroxyamides as orally available anticonvulsants

Themisone, also known as Atrolactamide, was found, in the 1950s, to be a very potent anticonvulsant. It was hypothesized that the -CF3 substitution would maintain the anticonvulsant activity. Anticonvulsant testing of our novel compounds by the

A structure-based design approach to the development of novel, reversible AChE inhibitors

Chimeras of tacrine and m-(N,N,N-Trimethylammonio)trifluoroacetophenone (1) were designed as novel, reversible inhibitors of acetylcholinesterase. On the basis of the X-ray structure of the apoenzyme, a molecular modeling study determined the favored attachment positions on the 4-aminoquinoline ring (position 3 and the 4-amino nitrogen) and the favored lengths of a polymethylene link between the two moieties (respectively 5-6 and 4-5 sp3 atoms). Seven compounds matching these criteria were synthesized, and their inhibitory potencies were determined to be in the low nanomolar range. Activity data for close analogues lacking some of the postulated key features showed that our predictions were correct. In addition, a subsequent crystal structure of acetylcholinesterase complexed with the most active compound 27 was in good agreement with our model. The design strategy is therefore validated and can now be developed further.