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91737

Trifluoromethanesulfonic anhydride

Name: Trifluoromethanesulfonic anhydride
Brand: SIAL

purum, ≥98.0% (T)

Synonym(s):

Tf₂O, Triflic anhydride

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About This Item

Linear Formula:

(CF₃SO₂)₂O

CAS Number:

358-23-6

Molecular Weight:

282.14

UNSPSC Code:

12352101

NACRES:

NA.22

PubChem Substance ID:

329770073

EC Number:

206-616-8

Beilstein/REAXYS Number:

1813600

MDL number:

MFCD00000408

Assay:

≥98.0% (T)

Form:

liquid

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Properties

vapor density

5.2 (vs air)

Quality Level

200

vapor pressure

8 mmHg ( 20 °C)

grade

purum

assay

≥98.0% (T)

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

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

Description

Application

Trifluoromethanesulfonic anhydride can be used in the preparation of azido sugars such as 6-azido fucose. It can also be used as a promoter for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the absence of catalyst.
Tf2O in combination with:

Diphenyl sulfoxide, forms an efficient promoter system for the activation of thioglycosides for glycosylation reactions.
2-chloropyridine, can be used for secondary amide activation.
Potassium iodide, can effectively mediate the deoxygenation of sulfoxides to form sulfides.
Hydrogen peroxide, for the selective oxidation of sulfanes to sulfoxides in the presence of oxidatively sensitive functional groups.

Tf2O can react with:

Ketones in the presence of a base to form vinyl triflates.
Magnesium alkoxides to form corresponding symmetrical or unsymmetrical ethers.
Sodium azide for the in situ preparation of triflyl azide.

Catalyst for glycosylation for synthesis of polysaccharides

Reagent for stereoselective synthesis of mannosazide methyl uronate donors

Activator for direct glycosylation with anomeric hydroxy sugars