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85325

Sigma-Aldrich

Silver trifluoromethanesulfonate

purum, ≥98.0% (Ag)

Synonym(s):

Ag(OTf), Silver (trifluoromethyl)sulfonate, Silver triflate, Trifluoromethanesulfonic acid silver salt

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About This Item

Linear Formula:
CF3SO3Ag
CAS Number:
Molecular Weight:
256.94
Beilstein:
3598402
EC Number:
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

Assay

≥98.0% (Ag)

form

crystals

reaction suitability

core: silver
reagent type: catalyst

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

General description

Silver trifluoromethanesulfonate p-complexes of monoenes, dienes, trienes, monoynes and diynes have been prepared. It reacts with 2-fluoro- and 3-fluoro-4-alkoxystilbazoles to afford the mesomorphic complexes. Iodine monochloride/AgOTf constitutes an efficient promoter system for the O-glycoside synthesis.

Application

Silver trifluoromethanesulfonate (AgOTf) may be employed as a reagent during glucosylation of several alcohols. AgOTf in combination with p-nitrobenzenesulfenyl chloride may be employed as an activator for the glycosylation.
It may be used for the synthesis of the following:
  • cystine-containing peptides
  • 3-aminoalkylated indoles
  • benzo[b]oxepines and 2H-chromenes
  • diversely substituted iminoimidazoazines

Other Notes

Reagent for the substitution of halides by triflate.; Reagent for the glycosylation of glycosyl halides; Reagent used for the deprotection of protected thiols

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo [b] oxepine and 2H-Chromene Synthesis.
Chan PWH, et al.
European Journal of Organic Chemistry, 2015(20), 4447-4456 (2015)
Mesomorphic complexes of silver trifluoromethanesulfonate and silver dodecylsulfate with 2-and 3-fluoro-4-alkoxy-4'-stilbazoles.
Bruce DW and Hudson SA.
Journal of Materials Chemistry, 4(3), 479-486 (1994)
Silver triflate catalyzed synthesis of 3-aminoalkylated indoles and evaluation of their antibacterial activities.
Rao VK, et al.
Organic and Medicinal Chemistry Letters, 1(1), 1-7 (2011)
Disulfide bond formation in S-acetamidomethyl cysteine-containing peptides by the combination of silver trifluoromethanesulfonate and dimethylsulfoxide/aqueous HCl.
Tamamura H, et al.
Tetrahedron Letters, 34(31), 4931-4934 (1993)
Silver Triflate-Catalyzed Cyclization of 2-Amino-6-propargyl-amineazines Leading to Iminoimidazoazines.
Chioua M, et al.
Advanced Synthesis & Catalysis, 356(6), 1235-1241 (2014)

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