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Sigma-Aldrich

Difluoromethyl triflate

95%

Synonym(s):

Difluoromethyl trifluoromethanesulfonate, Trifluoromethanesulfonic acid difluoromethyl ester

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About This Item

Empirical Formula (Hill Notation):
C2HF5O3S
CAS Number:
Molecular Weight:
200.08
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

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:
  • 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.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

135.0 °F

flash_point_c

57.22 °C


Certificates of Analysis (COA)

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Synthesis of difluoromethyl ethers with difluoromethyltriflate.
Patrick S Fier et al.
Angewandte Chemie (International ed. in English), 52(7), 2092-2095 (2013-01-12)
Difluoromethoxylation of N-Heteroaromatics
Snieckus V and Richardson P
Synfacts, 14(03), 0239-0239 (2018)
Difluoromethyl Triflate
Besset T
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 203(03), 1-1 (2001)

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