792764

Difluoromethyl triflate

95%

• Synonym(s): Difluoromethyl trifluoromethanesulfonate, Trifluoromethanesulfonic acid difluoromethyl ester
• Empirical Formula (Hill Notation): C₂HF₅O₃S
• CAS Number: 1885-46-7
• Molecular Weight: 200.08
• NACRES: NA.22
• PubChem Substance ID: 329768368
• UNSPSC Code: 12352108
• MDL number: MFCD28054469
• Assay: 95%
• Form: liquid

Properties

• Quality Segment: 100
• assay: 95%
• form: liquid
• density: 1.584 g/mL at 25 °C
• functional group: fluoro, triflate
• 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

Description

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:

• 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.

Safety Information

• pictograms: GHS02,GHS05,GHS07
• signalword: Danger
• hcodes: H226,H302,H314
• pcodes: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B
• Storage Class: 3 - Flammable liquids
• wgk: WGK 3
• flash_point_f: 135.0 °F
• flash_point_c: 57.22 °C