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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:

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Properties

Quality Level

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

Description

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.

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pictograms

Corrosion

signalword

Danger

hcodes

pcodes

P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P362 + P364

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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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)

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Global Trade Item Number

SKU	GTIN
483346-5G	04061833547878
483346-1G	04061826732830