Misplaced Pages

tert-Butyldimethylsilyl chloride

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from Tert-Butyldimethylchlorosilane)
tert-Butyldimethylsilyl chloride
Names
Preferred IUPAC name tert-Butyl(chloro)di(methyl)silane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.038.206 Edit this at Wikidata
EC Number
  • 242-042-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3Key: BCNZYOJHNLTNEZ-UHFFFAOYSA-N
SMILES
  • CC(C)(C)(C)(C)Cl
Properties
Chemical formula C6H15ClSi
Molar mass 150.72 g·mol
Appearance white solid
Odor pungent, grassy
Melting point 86–89 °C (187–192 °F; 359–362 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Danger
Hazard statements H228, H314
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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.

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

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

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

It also can silylate terminal alkynes.

Related reagents

The triflate derivative (Me3C)Me2SiOTf is used similarly but is more reactive.

References

  1. Bret E. Huff; Wenming Zhang (2008). "t-Butyldimethylchlorosilane". EROS. doi:10.1002/047084289X.rb373.pub2. ISBN 978-0-471-93623-7.
  2. Bajwa, Joginder S.; Prasad, Kapa; Repic, Oljan (2006). "2-(2',2'-Dimethylpropoxy)-2,3-Dihydro-1H-Indene". Organic Syntheses. 83: 155. doi:10.15227/orgsyn.083.0155.
  3. Paquette; Heidelbaugh, Todd M. (1996). "tert-Butyldimethylsiloxy-2-cyclopenten-1-one". Organic Syntheses. 73: 44first1=Leo A. doi:10.15227/orgsyn.073.0044.
  4. Marshall, James A.; Yanik, Mathew M.; Adams, Nicholas D.; Ellis, Keith C.; Chobanian, Harry R. (2005). "Generation of Nonracemic 2-(t-Butyldimethylsilyloxy)-3-butynyllithium from (S)-Ethyl Lactate". Organic Syntheses. 81: 157. doi:10.15227/orgsyn.081.0157.
  5. Dondoni, Alessandro; Perrone, Daniela (2000). "Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)-2--2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde". Organic Syntheses. 77: 78. doi:10.15227/orgsyn.077.0078.
  6. "tert-Butyldimethylsilyl ethers".
Categories: