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Difluoromethyl trifluoromethanesulfonate, Trifluoromethanesulfonic acid difluoromethyl ester
C2HF5O3S
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Quality Level
Assay
95%
form
liquid
density
1.584 g/mL at 25 °C
storage temp.
2-8°C
SMILES string
O=S(OC(F)F)(C(F)(F)F)=O
InChI
1S/C2HF5O3S/c3-1(4)10-11(8,9)2(5,6)7/h1H
InChI key
DAANAKGWBDWGBQ-UHFFFAOYSA-N
Related Categories
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).
Application
Difluoromethyl triflate (TfO-CHF2) can be used as a reagent:
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.
- 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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B
WGK
WGK 3
Flash Point(F)
135.0 °F
Flash Point(C)
57.22 °C
Regulatory Information
危险化学品
Certificates of Analysis (COA)
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Synthesis of difluoromethyl ethers with difluoromethyltriflate.
Angewandte Chemie (International ed. in English), 52(7), 2092-2095 (2013-01-12)
Difluoromethyl Triflate
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 203(03), 1-1 (2001)
Difluoromethoxylation of N-Heteroaromatics
Synfacts, 14(03), 0239-0239 (2018)
Tri-and difluoromethoxylated N-based heterocycles- Synthesis and insecticidal activity of novel F3CO-and F2HCO-analogues of Imidacloprid and Thiacloprid
Journal of Fluorine Chemistry, 203(03), 155-165 (2017)
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