(Trifluoromethyl)trimethylsilane

Introduction

(Trifluoromethyl)trimethylsilane (TMSCF₃) is a flammable liquid with a boiling point of 54–55 °C, a flash point of –17 °C and density of 0.926 g/mL at 20 °C. It may be harmful if inhaled, swallowed, absorbed through skin and may cause respiratory tract, skin and eye irritation. TMSCF₃ was firstly synthesized by Rupert[ ¹ ] in 1984 via the condensation reaction of CF₃Br and TMSCl with (Et₂N)₃P. Nowadays, there are various synthetic methodologies to yield this compound. Among them, the approach of Pawelke is considered as the most efficient method.[ ² ] Following this method, the reaction of CF₃I and tetrakis(dimethylamino)ethylene formed an in situ mediated complex which reacted directly with TMSCl to afford TMSCF₃ in 94% yield. TMSCF₃ is versatile reagent for trifluoromethylation, such as transition-metal-catalyzed reaction, miscellaneous trifluoromethylation, and addition to carbonyl and imine groups. These reactions are extremely useful approaches in the pharmaceutical and agrochemical industry,[ ³ ] because they enhance metabolic stability (metabolic blocking) and alter the compound properties (liphophilicity, binding selectivity).

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