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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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$71.94
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$155.48

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1 G
$71.94
5 G
$155.48

About This Item

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

$71.94

List Price$78.20Save 8%
Web-Only Promotion

Available to ship onApril 15, 2025Details

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Quality Level

100

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.[1][2]
  • 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.[3]
  • It can also be used in the diastereoselective cyclization of amino ketenes where the diastereoselectivity depends on Ag(I) concentration.[4]

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H315,H318

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT0371
MKCK2815
MKBZ3923V
MKBN2634V
MKBJ1075V

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Silver mediated acetylenic oxy cope rearrangement.
Bluthe N, et al.
Tetrahedron, 42(5), 1333-1344 (1986)
Trifluoromethanesulfonic?Carboxylic Anhydrides, Highly Active Acylating Agents.
Effenberger F and Epple G
Angewandte Chemie (International Edition in English), 11(4), 299-300 (1972)
Asymmetric synthesis via electrophile-mediated cyclisations.
Fox D N and Gallagher T
Tetrahedron, 46(13-14), 4697-4710 (1990)
Perfluoroalkanesulfonic esters: methods of preparation and applications in organic chemistry.
Stang P J, et al.
Synthesis, 1982(02), 85-126 (1982)
Gang Liu et al.
Chemical communications (Cambridge, England), 48(56), 7049-7051 (2012-06-12)
An unexpected silver triflate-catalyzed tandem reaction of N'-(2-alkynylbenzylidene)hydrazide with ketene through 6-endo-cyclization, [3+2] cycloaddition and rearrangement is reported. This reaction proceeds efficiently to generate the molecular complexity with the formation of four bonds in a one-pot procedure.
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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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