tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

CAS: 69739-34-0 | C7H15F3O3SSi | 264.33 g/mol

Catalog Number	Quantity
A12174.06 also known as A12174-06	5 g

Catalog number A12174.06

also known as A12174-06

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Chemical Identifiers

CAS69739-34-0

IUPAC Nametert-butyldimethylsilyl trifluoromethanesulfonate

Molecular FormulaC7H15F3O3SSi

InChI KeyWLLIXJBWWFGEHT-UHFFFAOYSA-N

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

Specifications

Appearance (Color)Clear colorless to yellow

Identification (FTIR)Conforms

Refractive Index1.3835-1.3880 @ 20?C

Assay (Aqueous acid-base Titration)≥97.5 to ≤102.5%

FormLiquid

tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.

Solubility
Slightly miscible with chloroform.

Notes
Moisture sensitive. Store in a cool place. Incompatible with strong acids.

RUO – Research Use Only

General References:

Powerful silylating agent (see Appendix 4) and Lewis acid; compare tert-Butyl dimethyl chlorosilane, A13064 and 3429. Silylation of hindered alcohols can be effected with TBDMS-OTf and 2,6-lutidine, where other reagents are unsuccessful: Tetrahedron Lett., 22, 3455 (1981).
Has been used in a sequence for the conversion of N-Boc to N-Cbz: Tetrahedron Lett., 26, 5543 (1985). For an alternative method for this transformation, see Benzyl 2,2,2-trichloroacetimidate, A12387.
Treatment of ɑß-unsaturated esters containing a suitably-placed ketone function with the reagent and triethylamine results in tandem intramolecular Michael-aldol reactions to give cyclobutanone derivatives: J. Am. Chem. Soc., 115, 8107 (1993).
For general reactions of trialkylsilyl perfluoroalkanesulfonates, see Trimethyl silyl trifluoromethanesulfonate, A12535; reviews: Synthesis, 1 (1982); Adv. Silicon Chem., 1, 189 (1991).
Cheng, B.; Trauner, D. A Highly Convergent and Biomimetic Total Synthesis of Portentol. J. Am. Chem. Soc. 2015, 137 (43), 13800-13803.
Florence, G. J.; Wlochal, J. Synthesis of the Originally Proposed Structure of Palmerolide C. Chem. Eur. J 2012, 18 (45), 14250-14254.