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Sigma-Aldrich

Trifluoromethanesulfonic anhydride

99%

Synonym(s):

Triflic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
358-23-6
Molecular Weight:
282.14
Beilstein:
1813600
EC Number:
206-616-8
MDL number:
MFCD00000408
UNSPSC Code:
12352101
PubChem Substance ID:
24850557
NACRES:
NA.22

vapor density

5.2 (vs air)

Quality Level

200

vapor pressure

8 mmHg ( 20 °C)

Assay

99%

form

liquid

refractive index

n20/D 1.321 (lit.)

bp

81-83 °C (lit.)

density

1.677 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F

InChI

1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8

InChI key

WJKHJLXJJJATHN-UHFFFAOYSA-N

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General description

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is an electrophilic reagent that is an efficient source of trifluoromethyl. It is commonly used in organic chemistry to convert oxygen-containing compounds to triflates and for the electrophilic activation and subsequent conversion of amides, sulfoxides, and phosphorus oxides.

Application

Catalyst for glycosylation for synthesis of polysaccharides

Reagent for stereoselective synthesis of mannosazide methyl uronate donors

Activator for direct glycosylation with anomeric hydroxy sugars
Trifluoromethanesulfonic anhydride can be used as :
  • A Reactant in the synthesis of Dipentaerythritol hexatriflate via triflatation method and Azido-diphenyl-acetic acid.
  • Catalyst for glycosylation for synthesis of polysaccharides.
  • Reagent for stereoselective synthesis of mannosazide methyl uronate donors.
  • Activator for direct glycosylation with anomeric hydroxy sugars
  • A methylation reagent to synthesize trifluoromethylated compounds by direct introduction of CF3 group to (hetero)arenes.
  • A reagent to prepare substituted tetrazoles from secondary amides using sodium azide.
  • A reagent in Bischler−Napieraiski cyclization reaction along with 4-(N,N-dimethylamnino)pyridine.

accessory

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Description
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recommended

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Signal Word

Danger

Hazard Statements

H272,H302,H314,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Ox. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

not determinedboils before flash

Flash Point(C)

not determinedboils before flash

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’.

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The conversion of secondary amides to tetrazoles with trifluoromethanesulfonic anhydride and sodium azide
Thomas EW
Synthesis, 1993(08), 767-768 (1993)
Chimica Oggi, 22, 48-48 (2004)
Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent
Ouyang Y, et al.
Angewandte Chemie (International Edition in English), 57(23), 6926-6929 (2018)
Synthesis, 735-735 (1993)
Aldrichimica Acta, 16, 15-15 (1983)
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