1885-46-7

Usage

Uses

Used in Chemical Synthesis:
Trifluoromethanesulfonic acid difluoromethyl ester is used as a reagent for difluoromethylation reactions, allowing for the introduction of difluoromethyl groups into various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trifluoromethanesulfonic acid difluoromethyl ester is used as a reagent to prepare difluoromethoxylated heterocycles by reacting with hydroxylated N-based heterocycles. This application is crucial for the synthesis of bioactive molecules and drug candidates with potential therapeutic properties.
Used in Organic Chemistry Research:
Trifluoromethanesulfonic acid difluoromethyl ester is used as a reagent to synthesize trifluoromethylated arenes by treating with diaryliodonium salts in the presence of copper and tetrabutylammonium difluorotriphenylsilicate (TBAT). This method is valuable for the development of new organic compounds and materials with unique properties.
Used in the Preparation of Difluoromethyl Ethers and Thioethers:
Trifluoromethanesulfonic acid difluoromethyl ester is used as a reagent for the preparation of difluoromethyl ethers and thioethers under basic conditions from alcohols and thiols. This reaction provides a simple and efficient method for the synthesis of these valuable compounds.
Used in the Synthesis of Difluoromethyl Phenols:
Trifluoromethanesulfonic acid difluoromethyl ester is used as a reagent to obtain difluoromethyl phenols in a single pot from boronic acids and C-H activation of arenes. This approach streamlines the synthesis process and enhances the accessibility of these important chemical intermediates.

Upstream product

• 1493-13-6 trifluorormethanesulfonic acid 
• 693-85-6 3,3-difluoro-3H-diazirine 
• 1717-59-5 2,2-difluoro-2-(fluorosulfonyl)acetic acid 
• 2926-30-9 sodium triflate 
• 942128-13-4 2-(difluoromethylsulfinyl)bromobenzene 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 942128-14-5 2-(difluoromethylsulfinyl)biphenyl 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 65864-64-4 trimethyl(difluoromethyl)silane 

Downstream Products

• 1454765-40-2 3-(difluoromethoxy)-N,N-diethyl-5-methylbenzamide 
• 773134-78-4 4-difluoromethoxybenzoic acid ethyl ester 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 349-76-8 3'-(trifluoromethyl)acetophenone 
• 455-18-5 4-CF₃C₆H₄CN 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 
• 98-15-7 3-chlorotrifluoromethylbenzene 
• 455-13-0 4-Iodobenzotrifluoride 
• 52331-42-7 1-methyl-4-(trifluoromethyl)naphthalene 
• 1204313-91-6 (R)-tert-butyl (1-(naphthalen-1-yl)ethyl)(3-(3-(trifluoromethyl)phenyl)propyl)carbamate 
• 76783-59-0 ethyl 3-(trifluoromethyl)benzoate 
• 160001-85-4 1-(tert-butyl)-4-(trifluoromethyl)benzene 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 

Relevant academic research and scientific papers

Reaction of the Ruppert-Prakash reagent with perfluorosulfonic acids

A new property of Me3SiCF3 to undergo C-F bond activation upon interaction with perfluorosulfonic acids is described. The reaction is catalyzed by titanium tetrachloride and affords difluoromethyl perfluorosulfonates in good yields.

Deoxygenative tri- And difluoromethylthiolation of carboxylic acids with benzothiazolium reagents

Deoxygenative syntheses of fluorinated thioesters directly from carboxylic acids have been developed employing benzothiazolium reagents. The process using BT-SCF3 represents an attractive approach toward these SCF3containing compounds that avoids the use of metal ?SCF3 salts or preactivated acyl electrophiles. Moreover, the in situ activation of BT-SCF2H allows for an unprecedented nucleophilic difluoromethylthiolation reaction. DFT calculations support a mechanistic scenario involving a four-membered transition state where acyl substitution occurs without the formation of an unstable free ?SCF2H anion.

A fluorine scan of a tubulin polymerization inhibitor isocombretastatin A-4: Design, synthesis, molecular modelling, and biological evaluation

A novel series of tubulin polymerization inhibitors, based on fluorinated derivatives of isocombretastatin A-4 was synthesized with the goal of evaluating the effect of these compounds on the proliferative activity. The introduction of fluorine atom was performed on the phenyl ring or at the linker between the two aromatic rings. The modification of isoCA-4 by introduction of difluoromethoxy group at the para-position (3i) and substitution of the two protons of the linker by two fluorine atoms (3m), produced the most active compounds in the series, with IC50 values of 0.15–2.2 nM (3i) and 0.1–2 nM (3m) respectively, against a panel of six cancer cell lines. Compounds 3i and 3m had greater antiproliferative activity in comparison with references CA-4 or isoCA-4, the presence of fluorine group leads to a significant enhancement of the antiproliferative activity. Molecular docking studies indicated that compounds 3i and 3m occupy the colchicine binding site of tubulin. Evaluation of cytotoxicity in Human noncancer cells indicated that the compounds 3i and 3m were practically ineffective in quiescent peripheral blood lymphocytes, and may have a selective antiproliferative activity against cancer cells. Analyses of cell cycle distribution, and morphological microtubules organization showed that compound 3m induced G2/M phase arrest and, dramatically disrupted the microtubule network.

ANTIDIABETIC SPIROCHROMAN COMPOUNDS

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

Cu(i)-mediated 18F-trifluoromethylation of arenes: Rapid synthesis of 18F-labeled trifluoromethyl arenes

This report is concerned with an efficient, CuI-mediated method for the radiosynthesis of [18F]trifluoromethyl arenes, abundant motifs in small molecule drug candidates and potential radiotracers for positron emission tomography. Thr

New electrophilic difluoromethylating reagent

A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole derivatives, and phosphines. The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines.

Perfluoro- and Polyfluorosulfonic Acids. 21. Synthesis of Difluoromethyl Esters Using Fluorosulfonyldifluoroacetic Acid as a Difluorocarbene Precursor

Difluoromethyl alkanoates 5 and fluorinated and nonfluorinated alkanesulfonates 9 were synthesized in moderate yields by the reaction of alkali metal salts of acids with fluorosulfonyldifluoroacetic acid (3) in acetonitrile under mild conditions.The presumed intermediate anion FO2SCF2CO2- generates CF2: by elimination of SO2, CO2, and F-.The esters are formed by insertion of CF2: into the O-H of the acid, whereas HCF3 is formed by the competing capture of F-.Organic acids can be used indirectly in the reaction in the presence of inorganic salts such as Na2SO4 and KCl, with comparable yields of difluoromethyl esters.