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483346

Sigma-Aldrich

Silver trifluoromethanesulfonate

≥99.95% trace metals basis

Synonym(s):

AgOTf, Silver triflate, Trifluoromethanesulfonic acid silver salt

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About This Item

Linear Formula:
CF3SO3Ag
CAS Number:
2923-28-6
Molecular Weight:
256.94
Beilstein:
3598402
EC Number:
220-882-2
MDL number:
MFCD00013226
UNSPSC Code:
12161600
PubChem Substance ID:
24871884
NACRES:
NA.22

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

Gold Catalysts — 21st Century ′Gold Rush′
  • 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
GHS05

Signal Word

Danger

Hazard Statements

H315,H318

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

Certificates of Analysis (COA)

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Silver mediated acetylenic oxy cope rearrangement.
Bluthe N, et al.
Tetrahedron, 42(5), 1333-1344 (1986)
Asymmetric synthesis via electrophile-mediated cyclisations.
Fox D N and Gallagher T
Tetrahedron, 46(13-14), 4697-4710 (1990)
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)
Lingyong Jiang et al.
Organic & biomolecular chemistry, 10(40), 8102-8107 (2012-09-06)
A silver triflate-catalyzed tandem reaction of N'-(2-alkynylbenzylidene)hydrazide with pyridyne is presented. Different outcomes are obtained, depending on the pyridynes utilized in the transformation.
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