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Sigma-Aldrich

Silver trifluoromethanesulfonate

≥99.95% trace metals basis

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Synonym(s):
AgOTf, Silver triflate, Trifluoromethanesulfonic acid silver salt
Linear Formula:
CF3SO3Ag
CAS Number:
Molecular Weight:
256.94
Beilstein:
3598402
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.95% trace metals basis

reaction suitability

core: silver
reagent type: catalyst

mp

286 °C (lit.)

SMILES string

[Ag+].[O-]S(=O)(=O)C(F)(F)F

InChI

1S/CHF3O3S.Ag/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1

InChI key

QRUBYZBWAOOHSV-UHFFFAOYSA-M

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Application

  • Silver trifluoromethanesulfonate (AgOTf ) is a reactive triflating agent, which converts alkyl, acyl and sulfonyl halides to corresponding triflate species.
  • It is a highly suitable electrophile to initiate acetylenic oxy-Cope rearrangement of substituted 5-hexen-1-yn-3-ols to synthesize corresponding α,δ-diethylenic aldehydes.
  • It can also be used in the diastereoselective cyclization of amino ketenes where the diastereoselectivity depends on Ag(I) concentration.

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Trifluoromethanesulfonic?Carboxylic Anhydrides, Highly Active Acylating Agents.
Effenberger F and Epple G
Angewandte Chemie (International Edition in English), 11(4), 299-300 (1972)
Perfluoroalkanesulfonic esters: methods of preparation and applications in organic chemistry.
Stang P J, et al.
Synthesis, 1982(02), 85-126 (1982)
Asymmetric synthesis via electrophile-mediated cyclisations.
Fox D N and Gallagher T
Tetrahedron, 46(13-14), 4697-4710 (1990)
Silver mediated acetylenic oxy cope rearrangement.
Bluthe N, et al.
Tetrahedron, 42(5), 1333-1344 (1986)
Shiqiang Yan et al.
Carbohydrate research, 354, 6-20 (2012-05-09)
An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the

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