Pular para o conteúdo
Merck
Todas as fotos(1)

Documentos

225649

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

99%

Sinônimo(s):

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

Faça loginpara ver os preços organizacionais e de contrato
Todas as fotos(1)

About This Item

Fórmula linear:
CF3SO3Si(CH3)3
Número CAS:
27607-77-8
Peso molecular:
222.26
Beilstein:
1868911
Número CE:
248-565-4
Número MDL:
MFCD00000406
Código UNSPSC:
12352103
ID de substância PubChem:
24853510
NACRES:
NA.22

Nível de qualidade

200

Ensaio

99%

forma

liquid

índice de refração

n20/D 1.36 (lit.)

pb

77 °C/80 mmHg (lit.)

densidade

1.228 g/mL at 25 °C (lit.)

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

Procurando produtos similares? Visita Guia de comparação de produtos

Categorias relacionadas

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.
It can be used:
  • As a silylating agent for the synthesis of trimethylsilyl-enol ethers from esters of α-diazoacetoacetic acid.
  • To activate benzyl and allyl ethers for the alkylation of sulfides.
  • To facilitate the conversion of Diels-Alder adducts of Danishefsky′s diene to cyclohexenones without the formation of methoxy ketone by-product.
  • To prepare difluoroboron triflate etherate, a powerful Lewis acid especially in acetonitrile solvent.
  • As a reagent in a Dieckmann-like cyclization of ester-imides and diesters.

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

acessório

Nº do produto
Descrição
Preços

Pictogramas

FlameCorrosion
GHS02,GHS05

Palavra indicadora

Danger

Frases de perigo

H226 - H314

Classificações de perigo

Flam. Liq. 3 - Skin Corr. 1B

Perigos de suplementos

EUH014

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

Já possui este produto?

Encontre a documentação dos produtos que você adquiriu recentemente na biblioteca de documentos.

Visite a Biblioteca de Documentos

Os clientes também visualizaram

Slide 1 of 2

1 of 2

Trifluoromethanesulfonic acid ReagentPlus®, ≥99%

Sigma-Aldrich

347817

Trifluoromethanesulfonic acid

Trichloroacetonitrile 98%

Sigma-Aldrich

T53805

Trichloroacetonitrile

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
BF 3? OEt 2 and TMSOTf: A synergistic combination of Lewis acids.
Myers EL, et al.
Chemical Communications (Cambridge, England), 42, 4434-4436 (2006)
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
Method for sulfide S-benzylation or S-allylation using trimethylsilyl triflate activated benzyl or allyl ethers.
Vedejs E & Eustache J.
The Journal of Organic Chemistry, 46(16), 3353-3354 (1981)
Exibir todos os documentos relacionados

Nossa equipe de cientistas tem experiência em todas as áreas de pesquisa, incluindo Life Sciences, ciência de materiais, síntese química, cromatografia, química analítica e muitas outras.

Entre em contato com a assistência técnica