483346
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:
Molecular Weight:
256.94
UNSPSC Code:
12161600
NACRES:
NA.22
PubChem Substance ID:
EC Number:
220-882-2
Beilstein/REAXYS Number:
3598402
MDL number:
InChI key
QRUBYZBWAOOHSV-UHFFFAOYSA-M
InChI
1S/CHF3O3S.Ag/c2-1(3,4)8(5,6)7;/h(H,5,6,7);/q;+1/p-1
SMILES string
[Ag+].[O-]S(=O)(=O)C(F)(F)F
assay
≥99.95% trace metals basis
reaction suitability
core: silver, reagent type: catalyst
mp
286 °C (lit.)
Quality Level
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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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Irrit. 2
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
ppe
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)
Silver mediated acetylenic oxy cope rearrangement.
Bluthe N, et al.
Tetrahedron, 42(5), 1333-1344 (1986)
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)
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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