tert-Butyldimethylsilyl chloride

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tert-Butyldimethylsilyl chloride
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 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]

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]

Related reagents

The triflate derivative (Me3C)Me2SiOTf is used similarly but is more reactive.[5][6]

References

  1. ISBN 978-0-471-93623-7
    .
  2. doi:10.15227/orgsyn.083.0155
    .
  3. doi:10.15227/orgsyn.073.0044
    .
  4. doi:10.15227/orgsyn.081.0157
    .
  5. doi:10.15227/orgsyn.077.0078
    .
  6. ^ "tert-Butyldimethylsilyl ethers".
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