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Merck
CN

531413

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
NACRES:
NA.22
PubChem Substance ID:
24877815
UNSPSC Code:
12352100
MDL number:
MFCD01320807
Assay:
97%

Key Documents

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InChI

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

SMILES string

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

InChI key

VYDQUABHDFWIIX-UHFFFAOYSA-N

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.)

functional group

carboxylic acid, fluoro

Quality Level

100

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

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Skin Corr. 1A

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4206
MKCR7888
MKCQ0064
MKCD7887
MKCC6336

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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)
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
Free radical fluoroalkylation of terminal alkenes and alkynes with iododifluoromethanesulfonamides.
Zhu JM, et al.
Science China: Chemistry, 54(1), 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)
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