1885-46-7

Basic information

• Product Name: Trifluoromethanesulfonic acid difluoromethyl ester
• Synonyms: Difluoromethyl triflate;Difluoromethyl trifluoromethanesulfonate;Trifluoromethanesulfonic acid difluoromethyl ester;Difluoromethyl triflate 95%
• CAS NO: 1885-46-7
• Molecular Formula: C₂HF₅O₃S
• Molecular Weight: 200.084556
• Mol File: 1885-46-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 48.5-49 °C
• Flash Point: 57℃
• Appearance: /
• Density: 1.584 g/mL at 25 °C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Trifluoromethanesulfonic acid difluoromethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoromethanesulfonic acid difluoromethyl ester(1885-46-7)
• EPA Substance Registry System: Trifluoromethanesulfonic acid difluoromethyl ester(1885-46-7)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2920 3(8) / PGII
• WGK Germany: 3
• Hazardous Substances Data: 1885-46-7(Hazardous Substances Data)

Usage

Uses

Difluoromethyl triflate (TfO-CHF2) can be used as a reagent: In difluoromethylation reaction. To prepare difluoromethoxylated heterocycles by reacting with hydroxylated N-based heterocycles. To synthesize trifluoromethylated arenes by treating with diaryliodonium salts in the presence of copper and tetrabutylammonium difluorotriphenylsilicate (TBAT).It allows for a simple method toward the preparation of difluoromethyl ethers and thioethers under basic conditions from alcohols and thiols. Difluoromethyl phenols can also be obtained in a single pot from boronic acids and C-H activation of arenes.

General Description

Difluoromethyl triflate (HCF2OTf) is an easy to handle, air-stable and non-ozone-depleting liquid reagent for difluoromethylation. It can be prepared by reacting trifluoromethyltrimethylsilane (TMSCF3) and triflic acid in the presence of titanium tetrachloride (TiCl4).

Upstream product

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

Downstream Products

• 1206980-28-0 2-chloro-5-(difluoromethoxy)pyridine 
• 1206978-15-5 2-chloro-4-(difluoromethoxy)pyridine 
• 947249-27-6 2-bromo-3-(difluoromethoxy)pyridine 
• 1214345-30-8 3-bromo-2-(difluoromethoxy)pyridine 
• 1084812-45-2 3-chloro-6-(difluoromethoxy)pyridazine 
• 1214377-45-3 2-chloro-6-(difluoromethoxy)pyridine 
• 791-25-3 diethyl 2-(difluoromethyl)-2-phenylmalonate 
• 943-08-8 2-[(difluoromethyl)sulfanyl]-1,3-benzothiazole 
• 145742-68-3 5-chloro-2-(difluoromethoxy)benzaldehyde 
• 1214348-81-8 2-bromo-4-chloro-1-(difluoromethoxy)benzene 
• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 70097-65-3 1-(benzyloxy)-4-(trifluoromethyl)benzene 
• 2367-02-4 1-phenoxy-4-(trifluoromethyl)benzene 
• 402-52-8 methyl 4-(trifluoromethyl)phenyl ether 

Relevant articles and documents

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.

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.

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