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Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

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

99%

Sinônimo(s):

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

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10 G
R$ 535,00
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10 G
R$ 535,00
50 G
R$ 1.819,00
250 G
R$ 3.113,00

About This Item

Fórmula linear:
CF3SO3Si(CH3)3
Número CAS:
Peso molecular:
222.26
Beilstein:
1868911
Número CE:
Número MDL:
Código UNSPSC:
12352103
ID de substância PubChem:
NACRES:
NA.22

R$ 535,00


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Nível de qualidade

Ensaio

99%

Formulário

liquid

índice de refração

n20/D 1.36 (lit.)

p.e.

77 °C/80 mmHg (lit.)

densidade

1.228 g/mL at 25 °C (lit.)

grupo funcional

fluoro
triflate

cadeia de caracteres SMILES

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

chave InChI

FTVLMFQEYACZNP-UHFFFAOYSA-N

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Aplicação

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]

Pictogramas

FlameCorrosion

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Flam. Liq. 3 - Skin Corr. 1B

Perigos de suplementos

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

77.0 °F - closed cup

Ponto de fulgor (°C)

25 °C - closed cup

Equipamento de proteção individual

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


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Os clientes também visualizaram

Slide 1 of 2

1 of 2

BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
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)
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
Efficient, trimethylsilyl triflate-mediated conversion of Diels-Alder adducts of 1-methoxy-3-[(trimethylsilyl) oxy]-1, 3-butadiene (Danishefsky's diene) to cyclohexenones.
Vorndam PE
The Journal of Organic Chemistry, 55(11), 3693-3695 (1990)
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

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