Skip to Content
Merck
All Photos(2)

Documents

792764

Sigma-Aldrich

Difluoromethyl triflate

95%

Synonym(s):

Difluoromethyl trifluoromethanesulfonate, Trifluoromethanesulfonic acid difluoromethyl ester

Sign Into View Organizational & Contract Pricing


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.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

135.0 °F

Flash Point(C)

57.22 °C


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service