Trimethylsilylmethanol

Trimethylsilylmethanol, also known as (trimethylsilyl)methanol or TMSM, is an organosilicon compound with the chemical formula (CH₃)₃SiCH₂OH. It is a colorless liquid at room temperature and is soluble in many organic solvents. The molecule consists of a trimethylsilyl group ((CH₃)₃Si-) attached to a hydroxymethyl group (-CH₂OH).

This compound finds application as a reagent in organic synthesis. It serves as a source of the trimethylsilylmethyl group, which can be introduced into other molecules through various chemical reactions. For instance, it can be used in silylation reactions to protect hydroxyl groups or to create specific carbon-carbon bonds. The hydroxyl group can also be further functionalized, allowing for the synthesis of more complex organosilicon compounds.

Trimethylsilylmethanol is typically prepared through the reaction of trimethylsilylmethylmagnesium chloride with formaldehyde or by the reduction of trimethylsilylcarboxylic acid derivatives. It is considered a relatively stable compound under normal laboratory conditions but should be stored away from moisture and strong oxidizing agents. Its physical properties, such as boiling point and density, are well-documented.