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
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 242-042-4
UNII
Properties
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
H228, H314
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.

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".
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