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tert-Butyldimethylsilyl chloride
Chemical compound / From Wikipedia, the free encyclopedia
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.[1]
Quick Facts Names, Identifiers ...
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Names | |
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Preferred IUPAC name
tert-Butyl(chloro)di(methyl)silane | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.038.206 ![]() |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C6H15ClSi | |
Molar mass | 150.72 g·mol−1 |
Appearance | white solid |
Odor | pungent, grassy |
Melting point | 86–89 °C (187–192 °F; 359–362 K) |
Hazards | |
GHS labelling: | |
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Danger | |
H228, H314 | |
P210, P240, P241, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ethers:[2][3]
- (Me3C)Me2SiCl + ROH → (Me3C)Me2SiOR + HCl
These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers.
It also can silylate terminal alkynes.[4]