394-59-2

Usage

Uses

Used in Chemical Synthesis:
4-(Trifluoroacetyl)toluene is used as a reagent for the synthesis of 5-methylene-2-(trifluoromethyl)morpholin-3-one derivatives, which possess fungicidal activity. This application is particularly relevant in the agricultural and pharmaceutical industries, where these derivatives can be employed as active ingredients in fungicides to protect crops and treat fungal infections, respectively.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(trifluoroacetyl)toluene may be utilized as a key intermediate in the development of new drugs with potential applications in various therapeutic areas. Its unique chemical structure allows for the creation of novel compounds with improved pharmacological properties, such as enhanced efficacy, selectivity, and reduced side effects.
Used in Agricultural Industry:
Within the agricultural industry, 4-(trifluoroacetyl)toluene plays a crucial role in the synthesis of fungicides that protect crops from various fungal diseases. By incorporating 4-(TRIFLUOROACETYL)TOLUENE into the development process, chemists can create more effective and targeted fungicides, leading to increased crop yields and reduced reliance on harmful chemical treatments.

InChI:InChI=1/C9H7F3O/c1-6-2-4-7(5-3-6)8(13)9(10,11)12/h2-5H,1H3

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 108-88-3 toluene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 76-05-1 trifluoroacetic acid 
• 110-86-1 pyridine 
• 874-60-2 4-methyl-benzoyl chloride 
• 340-07-8 N-(trifluoroacetyl)piperidine 
• 106-38-7 para-bromotoluene 
• 383-63-1 ethyl trifluoroacetate, 
• 58593-90-1 1-(4-tolyl)-2,2,2-trifluoro-1-chloroethylisocyanate 
• 22007-37-0 O-methyl (4-methoxyphenyl)carbamothioate 
• 113445-98-0 1-isocyanato-1-(4-methylphenyl)-2,2,2-trifluoroethyl 4-bromobenzoate 
• 98-88-4 benzoyl chloride 
• 96254-05-6 2-(trifluoroacetyloxy)pyridine 

Downstream Products

• 446-65-1 2,2,2-trifluoro-1-(4-methylphenyl)ethanol 
• 35462-71-6 1-(1,1,1,3,3,3-hexafluoropropan-2-yl)-4-methylbenzene 
• 1979-52-8 1-methyl-4-(perfluoroprop-1-en-2-yl)benzene 
• 19302-08-0 1-((Z)-2-Chloro-2-fluoro-1-trifluoromethyl-vinyl)-4-methyl-benzene 
• 19302-09-1 1-((E)-2-Chloro-2-fluoro-1-trifluoromethyl-vinyl)-4-methyl-benzene 
• 72487-05-9 (R)-4-methyl-α-(trifluoromethyl)-benzenemethanol 
• 76953-97-4 1-(4-methylphenyl)-1-(trifluoromethyl)ethanol 
• 131437-10-0 1,1,1,3,3-pentafluoro-2-(4-methylphenyl)-4-penten-2-ol 
• 58808-59-6 4-(trifluoroacetyl)benzoic acid 
• 75703-25-2 2,2,2-trifluoro-1-(4-methylphenyl)-1-ethanone oxime 
• 80446-60-2 (S)-4-methyl-α-(trifluoromethyl)-benzenemethanol 
• 87736-79-6 C₁₆H₁₄F₃NO₃S 
• 61204-09-9 1,1,1-tris-(p-tolyl)-2,2,2-trifluoroethane 

Relevant academic research and scientific papers

Grafting organic and biomolecules on H-terminated porous silicon from a diazirine

A diazirine compound, 1,4-(1-azi-2,2,2-trifluoroethyl)benzoic acid, was used as a stable carbene precursor to react with Si-H terminated porous silicon (PSi) under microwave irradiation. After formation of a molecular monolayer, the end carboxyl group was

Click-Addressable Cassette for Photoaffinity Labeling

A small molecule 1 was designed to contain an alkyne, a trifluoromethyl phenyldiazirine, and a free piperidine-NH for facile conjugation to protein binding ligands. This "cassette" 1 was synthesized via a relatively direct route involving only routine steps. In this proof-of-concept study, putative ligands for carbonic anhydrase IX and for TrkC were conjugated to 1. Photoaffinity labeling was performed using purified extracellular regions of both these protein-receptors, and using cells that express these receptors (isolation via a pull-down procedure), labeling of the protein was observed in all four experiments.

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

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.

Decarboxylative and Deaminative Alkylation of Difluoroenoxysilanes via Photoredox Catalysis: A General Method for Site-Selective Synthesis of Difluoroalkylated Alkanes

A general method for site-selective difluoroalkylation of alkyl carboxylic redox esters with difluoroenoxysilanes through photoredox-catalyzed decarboxylative reaction has been developed. The reaction can also be extended to aliphatic amine derived pyridinium salts. This method has the advantages of high efficiency, mild reaction conditions, and broad substrate scope, including primary, secondary, and sterically hindered tertiaryl alkyl substrates, providing a general and practical route for applications in organic synthesis and pharmaceutical studies.

A Hammett Study of Clostridium acetobutylicum Alcohol Dehydrogenase (CaADH): An Enzyme with Remarkable Substrate Promiscuity and Utility for Organic Synthesis

Described is a physical organic study of the reduction of three sets of carbonyl compounds by the NADPH-dependent enzyme Clostridium acetobutylicum alcohol dehydrogenase (CaADH). Previous studies in our group have shown this enzyme to display broad substrate promiscuity, yet remarkable stereochemical fidelity, in the reduction of carbonyl compounds, including α-, β- and γ-keto esters (d -stereochemistry), as well as α,α-difluorinated-β-keto phosphonate esters (l -stereochemistry). To better mechanistically characterize this promising dehydrogenase enzyme, we report here the results of a Hammett linear free-energy relationship (LFER) study across three distinct classes of carbonyl substrates; namely aryl aldehydes, aryl β-keto esters and aryl trifluoromethyl ketones. Rates are measured by monitoring the decrease in NADPH fluorescence at 460 nm with time across a range of substrate concentrations for each member of each carbonyl compound class. The resulting v 0 versus [S] data are subjected to least-squares hyperbolic fitting to the Michaelis-Menton equation. Hammett plots of log(V max) versus σ X yield the following Hammett parameters: (i) for p -substituted aldehydes, ρ = 0.99 ± 0.10, ρ = 0.40 ± 0.09; two domains observed, (ii) for p -substituted β-keto esters ρ = 1.02 ± 0.31, and (iii) for p -substituted aryl trifluoromethyl ketones ρ = -0.97 ± 0.12. The positive sign of ρ indicated for the first two compound classes suggests that the hydride transfer from the nicotinamide cofactor is at least partially rate-limiting, whereas the negative sign of ρ for the aryl trifluoromethyl ketone class suggests that dehydration of the ketone hydrate may be rate-limiting for this compound class. Consistent with this notion, examination of the 13 C NMR spectra for the set of p -substituted aryl trifluo romethyl ketones in 2percent aqueous DMSO reveals significant formation of the hydrate (gem -diol) for this compound family, with compounds bearing the more electron-withdrawing groups showing greater degrees of hydration. This work also presents the first examples of the CaADH-mediated reduction of aryl trifluoromethyl ketones, and chiral HPLC analysis indicates that the parent compound α,α,α-trifluoroacetophenone is enzymatically reduced in 99percent ee and 95percent yield, providing the (S)-stereoisomer, suggesting yet another compound class for which this enzyme displays high enantioselectivity.

Engineering bromodomains with a photoactive amino acid by engaging 'Privileged' tRNA synthetases

Site-specific placement of unnatural amino acids, particularly those responsive to light, offers an elegant approach to control protein function and capture their fleeting 'interactome'. Herein, we have resurrected 4-(trifluoromethyldiazirinyl)-phenylalan

Oxidation of α-trifluoromethyl and non-fluorinated alcohols: Via the merger of oxoammonium cations and photoredox catalysis

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields.

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Br?nsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Rapid Mapping of Protein Interactions Using Tag-Transfer Photocrosslinkers

Analysing protein complexes by chemical crosslinking-mass spectrometry (XL-MS) is limited by the side-chain reactivities and sizes of available crosslinkers, their slow reaction rates, and difficulties in crosslink enrichment, especially for rare, transie