''tert''-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me₃C)Me₂SiCl (Me = CH₃). It is commonly abbreviated as TBSCl or TBDMSCl. It is a chlorosilane containing two methyl groups and a ''tert''-butyl group. As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

. ''tert''-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give ''tert''-butyldimethyl silyl ethers: :(Me₃C)Me₂SiCl + ROH → (Me₃C)Me₂SiOR + HCl These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers. It also can silylate terminal alkynes.

Related reagents

The triflate derivative (Me₃C)Me₂SiOTf is used similarly but is more reactive.

References

{{DEFAULTSORT:Butyldimethylsilyl chloride, tert- Reagents for organic chemistry Organochlorosilanes