What is Trimethylsilyl trifluoromethanesulfonate?

Identification  

Product Name:    Trimethylsilyl trifluoromethanesulfonate    

Synonyms:    CT3795;Methanesulfonic acid, trifluoro-, trimethylsilyl ester;SILANE TMS-TRIFLATE;TMSOTF;TMS TRIFLATE;TRIMETHYLSILYL TRIFLATE;TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE;TRIMETHYLSILYL TRIFLUOROMETHANESULPHONATE    

CAS:    27607-77-8    

MF:    C4H9F3O3SSi

MW:    222.26

EINECS:    248-565-4

Properties

Melting point     25°C 

Boiling point     77 °C80 mm Hg(lit.)   

Density    1.228 g/mL at 25 °C(lit.)   

Vapor pressure     4.7 hPa (20 °C)    

Refractive index     n20/D 1.36(lit.)   

Fp     78 °F   

Storage temp.     2-8°C 

Form     Fuming Liquid    

Color     Clear colorless to light brown    

Specific Gravity    1.15    

Water Solubility     REACTS    

Sensitive     Moisture Sensitive    

Trimethylsilyl trifluoromethanesulfonate is composed by trifluoromethesulfonate and trimethylsilane group, under room pressure it is a clear colorless to light brown fuming liquid. Its reactivity is similar to trimethylchlorosilane, so it is often used in organic synthesis. Trimethylsilyl trifluoromethesulfonate can be used to convert aldehydes and ketones to silenol ethers.  At the same time, because of its similar reactivity to trimethylchlorosilane, it can also be used to protect alcohols.

Activity

Trimethylsilyl trifluoromethanesulfonate and Trimethylsilane trifluoromethesulfonate have similar reactivity, but Silyl enol ether obtained from it is slightly more stable than from that of Trimethylsilane trifluoromethesulfonate. Triethylsilane trifluoromethesulfonate is therefore a better choice for protecting alcohol groups or other similar reactions, such as to improve the stability of the reactants or to reduce side reactions, but it is correspondingly more difficult to remove the triethylsilane groups.

Catalyst uses

Trimethylsilyl Trifluoromethanesulfonate is a trialkylsilyl triflate used as a catalyst in organic synthesis. Trimethylsilyl Trifluoromethanesulfonate is used in combination with boron trifluoride eth yl ether to prepare a Lewis acid that is more powerful than its components and especially effective in acetonitrile solvent. Trimethylsilyl is a common reagent used in a Dieckmann-like cyclization of ester-imides and diesters.