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390755

Sigma-Aldrich

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate

97%

Synonym(s):

Difluoro(fluorosulfonyl)acetic acid methyl ester

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About This Item

Linear Formula:
FSO2CF2CO2CH3
CAS Number:
680-15-9
Molecular Weight:
192.11
Beilstein:
1812896
MDL number:
MFCD00144316
UNSPSC Code:
12352100
PubChem Substance ID:
24864345
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

reaction suitability

reaction type: click chemistry

refractive index

n20/D 1.351 (lit.)

bp

117-118 °C (lit.)

density

1.509 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C(F)(F)S(F)(=O)=O

InChI

1S/C3H3F3O4S/c1-10-2(7)3(4,5)11(6,8)9/h1H3

InChI key

GQJCAQADCPTHKN-UHFFFAOYSA-N

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Application

  • Useful reagent for the trifluoromethylation of alkyl halides.
  • Broadly applicable reagent for perfluoroalkylations for aryl iodides and bromides

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226 - H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

116.6 °F - closed cup

Flash Point(C)

47 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Journal of the Chemical Society. Chemical Communications, 705-705 (1989)
A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides.
Hiroyuki Morimoto et al.
Angewandte Chemie (International ed. in English), 50(16), 3793-3798 (2011-03-29)
David Orr et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(44), 14305-14316 (2014-09-13)
Vinyl cyclopropane rearrangement (VCPR) has been utilised to synthesise a difluorinated cyclopentene stereospecifically and under mild thermal conditions. Difluorocyclopropanation chemistry afforded ethyl 3-(1'(2'2'-difluoro-3'-phenyl)cyclopropyl) propenoate as all four stereoisomers (18a, 18b, 22a, 22b) (all racemic). The trans-E isomer (18a), prepared in

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