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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:
2923-28-6
Molecular Weight:
256.94
Beilstein:
3598402
EC Number:
220-882-2
MDL number:
MFCD00013226
UNSPSC Code:
12161600
PubChem Substance ID:
329769373
NACRES:
NA.22
Pricing and availability is not currently available.

grade

purum

Quality Level

100

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

Related Categories

General description

Silver trifluoromethanesulfonate p-complexes of monoenes, dienes, trienes, monoynes and diynes have been prepared.[1] It reacts with 2-fluoro- and 3-fluoro-4-alkoxystilbazoles to afford the mesomorphic complexes.[2] Iodine monochloride/AgOTf constitutes an efficient promoter system for the O-glycoside synthesis.[3]

Application

Silver trifluoromethanesulfonate (AgOTf) may be employed as a reagent during glucosylation of several alcohols.[1] AgOTf in combination with p-nitrobenzenesulfenyl chloride may be employed as an activator for the glycosylation.[4]
It may be used for the synthesis of the following:
  • cystine-containing peptides[5]
  • 3-aminoalkylated indoles[6]
  • benzo[b]oxepines and 2H-chromenes[7]
  • diversely substituted iminoimidazoazines[8]

Other Notes

Reagent for the substitution of halides by triflate.; Reagent for the glycosylation of glycosyl halides[9][10][11]; Reagent used for the deprotection of protected thiols[12]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H315,H318

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6139
BCCH3866
BCCD9289
BCCD0497
BCCB7994

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The glucosylation of several alcohols with tetra-O-benzyl-. ALPHA.-D-glucopyranose and a mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine.
Koto S, et al.
Bulletin of the Chemical Society of Japan, 53(6), 1761-1762 (1980)
P.J. Garegg et al.
Acta Chemica Scandinavica. Series B, 33, 116-116 (1979)
V. Pozsgay et al.
The Journal of Organic Chemistry, 46, 3761-3761 (1981)
David Crich et al.
Carbohydrate research, 343(10-11), 1858-1862 (2008-04-01)
p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 degrees C in CH(2)Cl(2).
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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