Passa al contenuto
Merck
Tutte le immagini(1)

Key Documents

225649

Sigma-Aldrich

Trimethylsilyl trifluoromethanesulfonate

99%

Sinonimo/i:

TMS triflate, TMSOTf, Trifluoromethanesulfonic acid trimethylsilylester

Autenticatiper visualizzare i prezzi riservati alla tua organizzazione & contrattuali


About This Item

Formula condensata:
CF3SO3Si(CH3)3
Numero CAS:
Peso molecolare:
222.26
Beilstein:
1868911
Numero CE:
Numero MDL:
Codice UNSPSC:
12352103
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

99%

Forma fisica

liquid

Indice di rifrazione

n20/D 1.36 (lit.)

P. eboll.

77 °C/80 mmHg (lit.)

Densità

1.228 g/mL at 25 °C (lit.)

Stringa SMILE

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
FTVLMFQEYACZNP-UHFFFAOYSA-N

Cerchi prodotti simili? Visita Guida al confronto tra prodotti

Applicazioni

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.

Accessorio

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

FlameCorrosion

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Flam. Liq. 3 - Skin Corr. 1B

Rischi supp

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

77.0 °F - closed cup

Punto d’infiammabilità (°C)

25 °C - closed cup

Dispositivi di protezione individuale

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


Scegli una delle versioni più recenti:

Certificati d'analisi (COA)

Lot/Batch Number

Non trovi la versione di tuo interesse?

Se hai bisogno di una versione specifica, puoi cercare il certificato tramite il numero di lotto.

Possiedi già questo prodotto?

I documenti relativi ai prodotti acquistati recentemente sono disponibili nell’Archivio dei documenti.

Visita l’Archivio dei documenti

I clienti hanno visto anche

Slide 1 of 2

1 of 2

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)

Il team dei nostri ricercatori vanta grande esperienza in tutte le aree della ricerca quali Life Science, scienza dei materiali, sintesi chimica, cromatografia, discipline analitiche, ecc..

Contatta l'Assistenza Tecnica.