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531413

Sigma-Aldrich

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

97%

Synonym(s):

(Fluorosulfonyl)difluoroacetic acid

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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

Quality Level

100

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

Related Categories

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

CorrosionSkull and crossbones
GHS05,GHS06

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

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’.

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Preparation and use of a new difluorocarbene reagent
Dolbier, W. R., Jr.; et al.
Organic Syntheses, 80, 172-176 (2003)
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)
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
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