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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