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633305

Sigma-Aldrich

Bismuth(III) trifluoromethanesulfonate

Synonyme(s) :

Bi(OTf)3, Bismuth tris(trifluoromethanesulfonate), Bismuth(III) triflate

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About This Item

Formule linéaire :
Bi(OSO2CF3)3
Numéro CAS:
88189-03-1
Poids moléculaire :
656.19
Numéro MDL:
MFCD02093669
Code UNSPSC :
12161600
ID de substance PubChem :
24882545
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

100

Pertinence de la réaction

core: bismuth
reagent type: catalyst

Pf

>300 °C (lit.)

Chaîne SMILES 

[Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

1S/3CHF3O3S.Bi/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

Clé InChI

NYENCOMLZDQKNH-UHFFFAOYSA-K

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Catégories apparentées

Application

Bismuth(III) trifluoromethanesulfonate may be used as a catalyst in the following processes:[1]
  • deprotection of acetals
  • cleavage of 2-tert-butoxy derivatives of thiophenes and furans
  • allylation of acetals to form homoallyl ethers
It may also be used as a substitute to corrosive triflic acid in Friedel-Crafts (FC) acylation and sulfonylation of arenes.[2]
Catalyzes direct substitution of allylic, propargylic, and benzylic alcohols with sulfonamides, carbamates, and carboxamides.[3]

Conditionnement

Bismuth(III) trifluoromethanesulfonate is an eco-friendly Lewis acid that can be prepared by reacting triflic acid with bismuth(III) trifluoroacetate.[4]

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
MKCK3885
MKCG9327
MKCF9864
MKCD1692
MKBZ8978V

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Consulter la Bibliothèque de documents

Bismuth (III) trifluoromethanesulfonate: An efficient catalyst for the sulfonylation of arenes.
Repichet S, et al.
The Journal of Organic Chemistry, 64, 6479-6482 (1999)
Bismuth (III) triflate in organic synthesis.
Gaspard-Iloughmane H and Le Roux C.
European Journal of Organic Chemistry, 2004(12), 2517-2532 (2004)
Maria Ricciardi et al.
ChemSusChem, 10(10), 2291-2300 (2017-04-05)
The disposal of any waste by recovering it within the production plant represents the ultimate goal of every biorefinery. In this scenario, the selective preparation of monoalkyl glyceryl ethers (MAGEs) starting from glycidol, obtained as byproduct in the epichlorohydrin production
Applications of bismuth (III) compounds in organic synthesis.
Leonard NM, et al.
Tetrahedron, 58(42), 8373-8397 (2002)
Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.
Hongbo Qin et al.
Angewandte Chemie (International ed. in English), 46(3), 409-413 (2006-12-06)
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Questions

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  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

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  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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