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Merck

176176

Trifluoromethanesulfonic anhydride

99%

Synonym(s):

Triflic anhydride

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About This Item

Linear Formula:
(CF3SO2)2O
CAS Number:
Molecular Weight:
282.14
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
EC Number:
206-616-8
Beilstein/REAXYS Number:
1813600
MDL number:
Assay:
99%
Form:
liquid
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InChI key

WJKHJLXJJJATHN-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor density

5.2 (vs air)

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.)

functional group

fluoro, triflate

Quality Level

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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.

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

5.1B - Oxidizing hazardous materials

wgk

WGK 3

flash_point_f

not determinedboils before flash

flash_point_c

not determinedboils before flash

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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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)
Controlled star poly (2-oxazoline) s: Synthesis, characterization
Laetitia P,et al.
European Polymer Journal, 122, 109323-109323 (2020)
[11 C] phenytoin revisited: synthesis by [11 C] CO carbonylation and first evaluation as a P-gp tracer in rats
Joost V,et al.
EJNMMI Research, 2, 1-11 (2012)
The conversion of secondary amides to tetrazoles with trifluoromethanesulfonic anhydride and sodium azide
Thomas EW
Synthesis, 1993(08), 767-768 (1993)

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