''tert''-Butyldimethylsilyl chloride is an

organosilicon compound Organosilicon chemistry is the study of organometallic compounds containing carbon–silicon bonds, to which they are called organosilicon compounds. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, f ...

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 Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula , often abbreviated or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely u ...

. 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 ether Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R1R2R3Si−O−R4 where R4 is an alkyl group or an aryl group. Silyl ethers are usually used as protectin ...

s: :(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 In organic chemistry, triflate (Preferred IUPAC name, systematic name: trifluoromethanesulfonate), is a functional group with the Chemical formula, formula and Chemical structure, structure . The triflate group is often represented by , as opp ...

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

References

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