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Merck

483346

Sigma-Aldrich

Silver trifluoromethanesulfonate

≥99.95% trace metals basis

Sinónimos:

AgOTf, Silver triflate, Trifluoromethanesulfonic acid silver salt

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About This Item

Fórmula lineal:
CF3SO3Ag
Número de CAS:
Peso molecular:
256.94
Beilstein:
3598402
Número CE:
Número MDL:
Código UNSPSC:
12161600
ID de la sustancia en PubChem:
NACRES:
NA.22
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Nivel de calidad

Ensayo

≥99.95% trace metals basis

idoneidad de la reacción

core: silver
reagent type: catalyst

mp

286 °C (lit.)

cadena SMILES

[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

Clave InChI

QRUBYZBWAOOHSV-UHFFFAOYSA-M

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Aplicación

  • 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]

Pictogramas

Corrosion

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

Eye Dam. 1 - Skin Irrit. 2

Código de clase de almacenamiento

13 - Non Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Certificados de análisis (COA)

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Visite la Librería de documentos

Trifluoromethanesulfonic?Carboxylic Anhydrides, Highly Active Acylating Agents.
Effenberger F and Epple G
Angewandte Chemie (International Edition in English), 11(4), 299-300 (1972)
Silver mediated acetylenic oxy cope rearrangement.
Bluthe N, et al.
Tetrahedron, 42(5), 1333-1344 (1986)
Perfluoroalkanesulfonic esters: methods of preparation and applications in organic chemistry.
Stang P J, et al.
Synthesis, 1982(02), 85-126 (1982)
Asymmetric synthesis via electrophile-mediated cyclisations.
Fox D N and Gallagher T
Tetrahedron, 46(13-14), 4697-4710 (1990)
Yu Hsien Lin et al.
Chemical communications (Cambridge, England), 48(88), 10910-10912 (2012-10-02)
β-Glycosyl imidinium triflate is generated from participating thioglycoside donors for disarmed-armed iterative glycosylations and one-pot oligosaccharide synthesis.

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    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

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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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