Trimethylsilyl chloride

Chemical compound

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Trimethylsilyl chloride (abbreviated TMSCl) is an organosilicon compound with the formula (CH₃)₃SiCl. It is a colorless liquid that is widely used in organic synthesis.

Structure and properties

Trimethylsilyl chloride is a volatile, colorless liquid with a pungent odor. It is soluble in organic solvents such as benzene, toluene, and diethyl ether. The compound is sensitive to moisture, reacting with water to produce hydrochloric acid and hexamethyldisiloxane.

Synthesis

Trimethylsilyl chloride is typically produced by the reaction of silicon tetrachloride with methylmagnesium chloride or methyl lithium:

SiCl₄ + 3 CH₃MgCl _ (CH₃)₃SiCl + 3 MgCl₂

This reaction is carried out in an inert atmosphere to prevent the hydrolysis of the product.

Applications

Trimethylsilyl chloride is primarily used as a silylating agent in organic synthesis. It is used to protect hydroxyl groups by converting them into trimethylsilyl ethers, which are more stable under certain conditions. This protection is particularly useful in multi-step synthesis processes where the hydroxyl group needs to be preserved.

TMSCl is also used in the preparation of other organosilicon compounds, such as trimethylsilyl azide and trimethylsilyl cyanide, which are useful intermediates in organic synthesis.

Safety

Trimethylsilyl chloride is corrosive and can cause burns upon contact with skin or eyes. It should be handled in a well-ventilated area, and appropriate personal protective equipment should be worn. Due to its reactivity with water, it should be stored in a dry environment.

Related pages

• Organosilicon chemistry
• Silyl ether
• Silicon tetrachloride