368-94-5

Usage

Uses

Used in Synthetic Chemistry:
4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE is used as a reagent in synthetic chemistry for the creation of other chemicals, leveraging its high reactivity to facilitate various chemical reactions and syntheses.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE is used as an intermediate in the synthesis of pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Chemical Research:
4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE is utilized as a research tool in chemical laboratories, enabling scientists to study its properties and explore its potential applications in various chemical processes and reactions.
Used in Specialty Chemicals Production:
4-(TRIFLUOROMETHYL)BENZOYL FLUORIDE is employed in the production of specialty chemicals, where its unique reactivity and properties are harnessed to create specific compounds for various applications, such as agrochemicals, dyes, and other industrial chemicals.

InChI:InChI=1/C8H4F4O/c9-7(13)5-1-3-6(4-2-5)8(10,11)12/h1-4H

Upstream product

• 100-21-0 terephthalic acid 
• 14815-86-2 4-trichloromethylbenzoyl chloride 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 7664-39-3 hydrogen fluoride 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 99-94-5 p-Toluic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 711-33-1 4-trifluoromethyl propiophenone 

Downstream Products

• 37156-44-8 4-nitrophenyl 4-trifluoromethylbenzoate 
• 1195962-88-9 (1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-yl 4-(trifluoromethyl)benzoate 
• 728-86-9 phenyl[4-(trifluoromethyl)phenyl]methanone 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 
• 506421-62-1 2-(4-(trifluoromethyl)phenyl)-quinoline 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 501374-30-7 5,5-dimethyl-2-(4-trifluoromethyl-phenyl)-[1,3,2]dioxaborinane 
• 447455-27-8 morpholino(4-(trifluoromethyl)phenyl)methanone 
• 113845-69-5 4-(4-trifluoromethylphenyl)morpholine 
• 455-18-5 4-CF₃C₆H₄CN 

Relevant academic research and scientific papers

Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination

We describe a novel reagent system to obtain acyl fluorides directly from three different functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is achieved via a combination of trichloroisocyanuric acid and cesium fluoride, which facilitates the synthesis of various acyl fluorides in high yield (up to 99%). It can be applied to the late-stage functionalization of natural products and drug molecules that contain a carboxylic acid, an aldehyde, or an alcohol group.

Deoxyfluorination of Carboxylic Acids with KF and Highly Electron-Deficient Fluoroarenes

A deoxyfluorination reaction of carboxylic acids using potassium fluoride (KF) and highly electron-deficient fluoroarenes is reported here, giving acyl fluorides in moderate to excellent yield (57-92% based on NMR integration and 34-95% for isolated examples).

Synthesis method of acyl fluoride

The invention belongs to the technical field of synthesis of organic compounds, and relates to a synthesis method of acyl fluoride. The invention relates to a synthesis method of acyl fluoride, which is characterized in that carboxylic acid trifluoromethy

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Cyclopropanes are an important class of building blocks in organic synthesis. Herein, a ring-opening/arylcarboxylation/acylation cascade reaction for the 1,3-difunctionalization of aryl cyclopropanes enabled by cooperative NHC and organophotoredox catalysis is reported. The cascade works on monosubstituted cyclopropanes that are in contrast to the heavily investigated donor–acceptor cyclopropanes more challenging to be difunctionalized. The key step is a radical/radical cross coupling of a benzylic radical generated in the photoredox catalysis cycle with a ketyl radical from the NHC catalysis cycle. The transformation features metal-free reaction conditions and tolerates a diverse range of functionalities.

Efficient cleavage of tertiary amide bonds: Via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system

A novel approach for the efficient cleavage of the amide bonds in tertiary amides is reported. Based on the selective radical abstraction of a benzylic hydrogen atom by a CuBr2/Selectfluor hybrid system followed by a selective cleavage of an N-C bond, an acyl fluoride intermediate is formed. This intermediate may then be derivatized in a one-pot fashion. The reaction proceeds under mild conditions and exhibits a broad substrate scope with respect to the tertiary amide moiety as well as to nitrogen, oxygen, and carbon nucleophiles for the subsequent derivatization. Mechanistic studies suggest that the present reaction proceeds via a radical-polar crossover process that involves benzylic carbon radicals generated by the selective radical abstraction of a benzylic hydrogen atom by the CuBr2/Selectfluor hybrid system. Furthermore, a synthetic application of this method for the selective cleavage of peptides is described. This journal is

Synthesis of Acyl Fluorides via DAST-Mediated Fluorinative C-C Bond Cleavage of Activated Ketones

A new protocol for preparation of acyl fluorides was developed by recognizing activated ketones as starting materials. The method provides a different scope compared with previously reported methods that employ carboxylic acids as substrates. A working hypothesis of pull-and-push-driven fluorinative C-C bond cleavage was successfully demonstrated by the simple addition of diethylaminosulfur trifluoride (DAST) derivatives to α-oximinoketones. The designed reaction system led to a highly efficient and chemoselective reaction. The wide availability of the ketones allowed for a range of synthetically useful aryloyl and aliphatic acyl fluorides including those containing chiral skeletons. The method is mild, fast, scalable, and potentially one-pot operative.

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions

Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp2)-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.

Phosphine-Catalyzed Intermolecular Acylfluorination of Alkynes via a P(V) Intermediate

We report the phosphine-catalyzed intermolecular carbofluorination of alkynes using acyl fluorides as fluorinating reagents. This reaction promises to be a useful method for the synthesis of highly substituted monofluoroalkene derivatives since acyl fluor

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.