Tert-Butyldimethylsilyl chloride explained

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