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When attached to certain functional groups in a reactant molecule, trimethylsilyl groups may also be used as temporary protecting groups during chemical synthesis or some other chemical reactions. In chromatography, derivitization of accessible silanol groups in a bonded stationary phase with trimethylsilyl groups is referred to as endcapping.
TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in hydrolysis to give the hexamethyldisiloxane: + + The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce anhydrous solutions of hydrochloric acid in alcohols, which find use in the mild synthesis of ...
The most important esters with common protecting-group use are the acetate, benzoate, and pivalate esters, for these exhibit differential removal. Sterically hindered esters are less susceptible to nucleophilic attack: Chloroacetyl > acetyl > benzoyl > pivaloyl Trimethylsilyl chloride, activated with imidazole, protects a secondary alcohol
Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group. The general structure is R 1 R 2 R 3 Si−O−R 4 where R 4 is an alkyl group or an aryl group. Silyl ethers are usually used as protecting groups for alcohols in organic synthesis.
An early example is CpFe(CO) 2 Si(CH 3) 3, prepared by silylation of CpFe(CO) 2 Na with trimethylsilyl chloride. Typical routes include oxidative addition of Si-H bonds to low-valent metals. Metal silyl complexes are intermediates in hydrosilation , a process used to make organosilicon compounds on both laboratory and commercial scales.
The methylchlorosilanes react with water to produce hydrogen chloride, giving siloxanes. In the case of trimethylsilyl chloride, the hydrolyzed product is hexamethyldisiloxane: 2 ((CH 3) 3 SiCl + H 2 O → [(CH 3) 3 Si] 2 O + 2 HCl. The analogous reaction of dimethyldichlorosilane gives siloxane polymers or rings: n (CH 3) 2 SiCl 2 + n H 2 O ...
These chlorides are produced by the "Direct process", which entails the reaction of methyl chloride with a silicon-copper alloy. The main and most sought-after product is dimethyldichlorosilane: 2 CH 3 Cl + Si → (CH 3) 2 SiCl 2. A variety of other products are obtained, including trimethylsilyl chloride and methyltrichlorosilane. About 1 ...
tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me 3 C)Me 2 SiCl (Me = CH 3). 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 ...