Merck
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176176

Sigma-Aldrich

Trifluoromethanesulfonic anhydride

≥99%

Synonym(s):
Triflic anhydride
Linear Formula:
(CF3SO2)2O
CAS Number:
Molecular Weight:
282.14
Beilstein:
1813600
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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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Application

Trifluoromethanesulfonic anhydride can be used as:
  • A trifluoromethylation reagent for the synthesis of 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.

Catalyst for glycosylation for synthesis of polysaccharides

Reagent for stereoselective synthesis of mannosazide methyl uronate donors

Activator for direct glycosylation with anomeric hydroxy sugars

Packaging

1, 4 kg in glass bottle
50, 250, 500 g in glass bottle
5, 10 g in ampule

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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