Skip to Content
MilliporeSigma
All Photos(1)

Documents

531413

Sigma-Aldrich

2,2-Difluoro-2-(fluorosulfonyl)acetic acid

97%

Synonym(s):

(Fluorosulfonyl)difluoroacetic acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
FSO2CF2CO2H
CAS Number:
1717-59-5
Molecular Weight:
178.09
MDL number:
MFCD01320807
UNSPSC Code:
12352100
PubChem Substance ID:
24877815
NACRES:
NA.22

Assay

97%

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.36 (lit.)

bp

153 °C (lit.)

density

1.723 g/mL at 25 °C (lit.)

SMILES string

OC(=O)C(F)(F)S(F)(=O)=O

InChI

1S/C2HF3O4S/c3-2(4,1(6)7)10(5,8)9/h(H,6,7)

InChI key

VYDQUABHDFWIIX-UHFFFAOYSA-N

General description

2,2-Difluoro-2-(fluorosulfonyl)acetic acid reagent is employed as a difluorocarbene source for difluoromethylation of phenolic hydroxyl groups.

Application

2,2-Difluoro-2-(fluorosulfonyl)acetic acid may be used in the following processes:
  • Preparation of 1-difluoromethyl-2-oxo-1,2-dihydropyridine analogs by reacting with the corresponding 2-chloropyridines.
  • Prepration of silyl fluorosulfonyldifluoroacetate as new highly efficient difluorocarbene reagent for cyclopropanation of alkenes.
  • Regio- and stereoselective free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H310,H314

Hazard Classifications

Acute Tox. 2 Oral - Skin Corr. 1A

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides
Zhu, J. M.; et al.
Science China: Chemistry, 54, 95-102 (2011)
Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): a new, highly efficient difluorocarbene reagent
Dolbier, William R.; et al.
Journal of Fluorine Chemistry, 125, 459-469 (2004)
Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides.
Zhu JM, et al.
Science China: Chemistry, 54(1), 95-102 (2011)
Preparation and use of a new difluorocarbene reagent
Dolbier, W. R., Jr.; et al.
Organic Syntheses, 80, 172-176 (2003)
Makoto Ando et al.
Organic letters, 8(17), 3805-3808 (2006-08-11)
[reaction: see text] A novel one-pot synthesis of N-difluoromethyl-2-pyridones is described. N-(Pyridin-2-yl)acetamide derivatives were excellent precursors for the preparation of N-difluoromethyl-2-pyridone derivatives. Difluoromethylation of 2-acetaminopyridine derivatives was achieved with sodium chlorodifluoroacetate as a difluorocarbene source in the presence of a
View All Related Papers

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