''tert''-Butyldimethylsilyl chloride is an

organosilicon compound Organosilicon compounds are organometallic compounds containing carbon–silicon bonds. Organosilicon chemistry is the corresponding science of their preparation and properties. Most organosilicon compounds are similar to the ordinary organic c ...

with the formula (Me₃C)Me₂SiCl (Me = CH₃). It is commonly abbreviated as TBSCl or TBDMSCl. It is a silane containing two methyl groups, a ''tert''-butyl group, and a reactive 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 special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

. Examples can be found in the Nicolaou taxol total synthesis. ''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 protecting g ...

s: :(Me₃C)Me₂SiCl + ROH → (Me₃C)Me₂SiOR + HCl These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers.

Related reagents

The

triflate In organic chemistry, triflate (systematic name: trifluoromethanesulfonate), is a functional group with the formula and structure . The triflate group is often represented by , as opposed to −Tf, which is the triflyl group, . For example, ' ...

derivative (Me₃C)Me₂SiOTf is used similarly but is more difficult to handle.

References

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