Me3SiOH

Me3SiOH, or trimethylsilanol, is an organosilicon compound with the formula (CH3)3SiOH. It features a silicon atom bound to three methyl groups and a hydroxyl group, forming a silanol that can undergo condensation to siloxanes. It is a volatile, colorless species encountered as a transient intermediate in silicon chemistry and can appear as a trace impurity in moisture-sensitive reactions.

Me3SiOH is typically generated by hydrolysis of chlorotrimethylsilane (Me3SiCl) with water: Me3SiCl + H2O → Me3SiOH + HCl. It may also arise during hydrolysis of other silicon-containing reagents or on moisture-exposed surfaces. The silanol readily undergoes condensation: 2 Me3SiOH → Me3Si-O-SiMe3 + H2O, and can further polymerize to form higher-order siloxanes. In basic media, it can be deprotonated to the trimethylsilanolate anion, Me3SiO−, which can act as a nucleophile in silicon-centered reactions.

As a silanol, Me3SiOH is a weak acid and participates in hydrogen bonding. Its tendency to condense makes it a key intermediate in the formation of Si–O–Si linkages, useful in the preparation of siloxanes and silica-based materials. It serves as a building block in organosilicon chemistry and can be used to introduce trimethylsilyl groups or to generate silylated surfaces.

Safety and handling: Me3SiOH is moisture sensitive and reacts with water, forming siloxanes and releasing heat. It should be stored and handled under inert conditions or generated in situ, with appropriate protective equipment and in well-ventilated spaces to minimize moisture exposure.