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:
Molecular Weight:
178.09
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
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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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