Merck
CN
All Photos(1)

Documents

85325

Sigma-Aldrich

Silver trifluoromethanesulfonate

purum, ≥98.0% (Ag)

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
Ag(OTf), Silver (trifluoromethyl)sulfonate, Silver triflate, Trifluoromethanesulfonic acid silver salt
Linear Formula:
CF3SO3Ag
CAS Number:
2923-28-6
Molecular Weight:
256.94
Beilstein:
3598402
EC Number:
220-882-2
MDL number:
MFCD00013226
PubChem Substance ID:
329769373
NACRES:
NA.22

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. 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
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

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).
P.J. Garegg et al.
Acta Chemica Scandinavica. Series B, 33, 116-116 (1979)
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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service