Direkt zum Inhalt
Merck

225649

Sigma-Aldrich

Trimethylsilyltrifluormethansulfonat

Trimethylsilyl trifluoromethanesulfonate
1 of 1 reviewers received a sample product or took part in a promotion

99%

Synonym(e):

TMS-triflat, TMSOTf, Trimethylsilyl-trifluormethansulfonat

Anmeldenzur Ansicht organisationsspezifischer und vertraglich vereinbarter Preise

Größe auswählen

10 G
€ 38,10
50 G
€ 143,00
250 G
€ 397,00

€ 38,10


Check Cart for Availability

Bulk-Bestellung anfordern

Größe auswählen

Ansicht ändern
10 G
€ 38,10
50 G
€ 143,00
250 G
€ 397,00

About This Item

Lineare Formel:
CF3SO3Si(CH3)3
CAS-Nummer:
Molekulargewicht:
222.26
Beilstein:
1868911
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22

€ 38,10


Check Cart for Availability

Bulk-Bestellung anfordern

Qualitätsniveau

Assay

99%

Form

liquid

Brechungsindex

n20/D 1.36 (lit.)

bp

77 °C/80 mmHg (lit.)

Dichte

1.228 g/mL at 25 °C (lit.)

Funktionelle Gruppe

fluoro
triflate

SMILES String

C[Si](C)(C)OS(=O)(=O)C(F)(F)F

InChI

1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3

InChIKey

FTVLMFQEYACZNP-UHFFFAOYSA-N

Suchen Sie nach ähnlichen Produkten? Aufrufen Leitfaden zum Produktvergleich

Anwendung

Trimethylsilyl trifluoromethanesulfonate has been used in combination with boron trifluoride etherate for the copper-catalyzed asymmetric allylic alkylation (AAA) of allyl bromides, chlorides, and ethers with organolithium reagents in the presence of a chiral ligand.[1][2]
It can be used:
  • As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.[3]
  • To activate benzyl and allyl ethers for the alkylation of sulfides.[4]
  • To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.[5]
  • To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.[6]
  • As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.[7]

It may also be used to catalyze:
  • Acylation of alcohols with acid anhydrides.[8]
  • Reductive coupling of carbonyl compounds with trialkylsilanes to form symmetrical ethers.[9]
  • Glycosidation of 4-demethoxydaunomycinones with 1-O-acyl-L-daunosamine derivatives.[10]

Zubehör

Produkt-Nr.
Beschreibung
Preisangaben

Piktogramme

FlameCorrosion

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Flam. Liq. 3 - Skin Corr. 1B

Zusätzliche Gefahrenhinweise

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

77.0 °F - closed cup

Flammpunkt (°C)

25 °C - closed cup

Persönliche Schutzausrüstung

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number

Die passende Version wird nicht angezeigt?

Wenn Sie eine bestimmte Version benötigen, können Sie anhand der Lot- oder Chargennummer nach einem spezifischen Zertifikat suchen.

Besitzen Sie dieses Produkt bereits?

In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

Kunden haben sich ebenfalls angesehen

BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
Thomas R Hoye et al.
Organic letters, 8(23), 5191-5194 (2006-11-03)
[Structure: see text] Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates
A simple method of preparing trimethylsilyl-and tert-butyldimethylsilyl-enol ethers of ?-diazoacetoacetates and their use in the synthesis of a chiral precursor to thienamycin analogs.
Ueda Y, et al.
Canadian Journal of Chemistry, 62(12), 2936-2940 (1984)
Eddie L Myers et al.
Chemical communications (Cambridge, England), (42), 4434-4436 (2006-10-24)
The combination of BF3.OEt2 and TMSOTf gives BF2OTf.OEt2, which is a more powerful Lewis acid than its components and especially effective in CH3CN solvent; the complex formed has been characterised by 1H, 19F, 11B and 31P (using Et3PO as an
Novel glycosidation of 4-demethoxyanthracyclinones by the use of trimethylsilyl triflate. Syntheses of optically active 4-demethoxydaunorubicin and 4-demethoxyadriamycin.
Kimura Y, et al.
Bulletin of the Chemical Society of Japan, 59(2), 423-431 (1986)

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

      Helpful?

Reviews

1 of 1 reviewers received a sample product or took part in a promotion

Active Filters

  1. 1 Ratings-Only Review

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

Setzen Sie sich mit dem technischen Dienst in Verbindung.