tert-Butyldimethylsilyl chloride

*tert*-Butyldimethylsilyl chloride
Names
	Preferred IUPAC name tert-Butyl(chloro)di(methyl)silane
Identifiers
CAS Number	18162-48-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:85071;
ChemSpider	26908;
ECHA InfoCard	100.038.206
EC Number	242-042-4;
PubChem CID	28928;
UNII	550OPF5Z9F;
CompTox Dashboard (EPA)	DTXSID4038843 ;
	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
Odor	pungent, grassy
Melting point	86–89 °C (187–192 °F; 359–362 K)
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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

^ Bret E. Huff; Wenming Zhang (2008). "t-Butyldimethylchlorosilane". EROS. doi:10.1002/047084289X.rb373.pub2. ISBN 978-0-471-93623-7.
^ 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.
^ Paquette; Heidelbaugh, Todd M. (1996). "tert-Butyldimethylsiloxy-2-cyclopenten-1-one". Organic Syntheses. 73: 44first1=Leo A. doi:10.15227/orgsyn.073.0044.
^ 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.
^ Dondoni, Alessandro; Perrone, Daniela (2000). "Diastereoselective Synthesis of Protected Vicinal Amino Alcohols: (S)-2-[(4s)-n-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidinyl]-2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde". Organic Syntheses. 77: 78. doi:10.15227/orgsyn.077.0078.
^ "tert-Butyldimethylsilyl ethers".

[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-[(4s)-n-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidinyl]-2-tert-butyldimethylsiloxyethanal from a Serine-Derived Aldehyde". Organic Syntheses. 77: 78. doi:10.15227/orgsyn.077.0078.

[6] "tert-Butyldimethylsilyl ethers".

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