tert-Butyldimethylsilyl chloride

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 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
Tert-butyldimethylchloorsilaan.png
Names
Preferred IUPAC name
tert-Butyl(chloro)di(methyl)silane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.038.206 Edit this at Wikidata
EC Number
  • 242-042-4
UNII
  • InChI=1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3
    Key: BCNZYOJHNLTNEZ-UHFFFAOYSA-N
  • CC(C)(C)[Si](C)(C)Cl
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:
GHS02: FlammableGHS05: Corrosive
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).

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 reagentsEdit

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

ReferencesEdit

  1. ^ Bret E. Huff, Wenming Zhang (2008). "t‐Butyldimethylchlorosilane". EROS. doi:10.1002/047084289X.rb373.pub2. ISBN 978-0471936237.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  2. ^ "tert-Butyldimethylsilyl ethers".