tert-Butyldimethylsilyl chloride

tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me₃C)Me₂SiCl (Me = CH₃). 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. Examples can be found in the Nicolaou taxol total synthesis.

tert-Butyldimethylsilyl chloride

Identifiers
CAS Number	18162-48-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:85071
ChemSpider	26908
EC Number	242-042-4
PubChem CID	28928
UNII	550OPF5Z9F
InChI InChI=1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3 Key: BCNZYOJHNLTNEZ-UHFFFAOYSA-N
SMILES CC(C)(C)[Si](C)(C)Cl
Properties
Chemical formula	C6H15ClSi
Molar mass	150.72 g·mol^−1
Appearance	white solid
Melting point	86–89 °C (187–192 °F; 359–362 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H228, H314
GHS precautionary statements	P210, P240, P241, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ethers:[1]

(Me₃C)Me₂SiCl + ROH → (Me₃C)Me₂SiOR + HCl

These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers.

Related reagents

The triflate derivative (Me₃C)Me₂SiOTf is used similarly but is more difficult to handle.[2]

References

1. Bret E. Huff, Wenming Zhang (2008). "t‐Butyldimethylchlorosilane". EROS. doi:10.1002/047084289X.rb373.pub2.CS1 maint: uses authors parameter (link)
2. "tert-Butyldimethylsilyl ethers".