Trimethylsilyldiazomethane

Trimethylsilyldiazomethane (TMSD) is a chemical compound used as a reagent in organic chemistry. It is a colorless liquid that is stable at room temperature and is often used as a safer alternative to diazomethane in various chemical reactions.

Structure and Properties

Trimethylsilyldiazomethane is a diazomethane derivative where the methyl group is replaced by a trimethylsilyl group. It has a molecular formula of C4H10N2Si and a molar mass of 114.22 g/mol. The compound is a colorless liquid at room temperature and has a boiling point of 93-95 °C.

Synthesis

Trimethylsilyldiazomethane can be synthesized from trimethylsilyl chloride and diazomethane. The reaction is carried out in the presence of a base such as triethylamine.

Applications

Trimethylsilyldiazomethane is primarily used as a methylating agent in organic chemistry. It is often used as a safer alternative to diazomethane, which is highly toxic and potentially explosive. TMSD can be used in a variety of reactions, including the methylation of carboxylic acids, phenols, and alcohols.

Safety

While trimethylsilyldiazomethane is less hazardous than diazomethane, it is still a potentially dangerous compound. It is flammable and can react violently with strong oxidizing agents. Proper safety precautions should be taken when handling this compound.