Trimethylsilyl chloride
chemical compound
Trimethylsilyl chloride, also known as chlorotrimethylsilane, is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
Preparation
TMSCl is prepared on a large scale by the direct process, the reaction of methyl chloride with a silicon-copper alloy. The principal target of this process is dimethyldichlorosilane, but substantial amounts of the trimethyl and monomethyl products are also obtained. The relevant reactions are (Me = methyl, CH3):
x
MeCl
+
Si
⟶
{
Me
3
SiCl
,
Me
2
SiCl
2
,
MeSiCl
3
,
etc.
{\displaystyle x\ {\ce {MeCl + Si}}\longrightarrow {\begin{cases}{\ce {Me3SiCl}},\\[2pt]{\ce {Me2SiCl2}},\\[2pt]{\ce {MeSiCl3}},\\[2pt]{\text{etc.}}\end{cases}}}
Typically about 2–4% of the product stream is the monochloride, which forms an azeotrope with MeSiCl3.
Reactions and uses
TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in hydrolysis to give the hexamethyldisiloxane:
2
Me
3
SiCl
+
H
2
O
⟶
Me
3
Si
−
O
−
SiMe
3
+
2
HCl
{\displaystyle {\ce {2 Me3SiCl + H2O -> Me3Si-O-SiMe3 + 2 HCl}}}
The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce anhydrous solutions of hydrochloric acid in alcohols, which find use in the mild synthesis of esters from carboxylic acids and nitriles as well as, acetals from ketones. Similarly, trimethylsilyl chloride is also used to silanize laboratory glassware, making the surfaces more lipophilic.
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