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Silylation reaction and use of organic synthesis of trimethylchlorosilane
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Silylation reaction and use of organic synthesis of trimethylchlorosilane   Classification:Industry News Release:2016-05-24 10:39:16   Read:(1290)

Trimethyl chlorosilane, trimethylchlorosilane also called an organic silicon compound (silyl halide) with the formula (CH 3) SiCl 3, usually abbreviated I SiCl or TMSCl 3 of the. It is a colorless, volatile liquid that is stable in the absence of water. It is widely used in organic chemistry. NICPBP reference
TMSCl prepared directly by the process of large-scale preparations, the reaction of methyl chloride with silicon - copper alloy. The main objective of this process is dimethyldichlorosilane, but also received a significant amount of trimethyl and methyl products. 1] is related to the reaction (ME = CH 3):
MeCl + silicon of x → My SiCl 3, I SiCl 2 of 2, MeSiCl 3, other products
Usually about 2-4%, or product stream is a chloride, which forms an azeotrope with MeSiCl 3.
The reaction towards the use and TMSCl nucleophile reactivity, resulting in the replacement of chloride. TMSCl particularity reaction, the nucleophile is water, resulting in hydrolysis, resulting hexamethyldisiloxane: 2 I 3 SiCl + H 2 O → I Si-O-SIME 3 +2 HCl 3
Trimethylchlorosilane reacted with an alcohol-related can be used to produce anhydrous solution of hydrochloric acid alcohols, carboxylic acids and it was found in the use of nitrile mild synthetic esters, as well as, acetals from ketones. Similarly, trimethylchlorosilane silanize also be used for laboratory glassware, making the surface more lipophilic. 2]
Silylated organic synthesis
By the process of the silylation, a polar functional group, such as an alcohol, an amine, and readily reacted with trimethylsilyl chloride to give the trimethylsilyl ether and trimethylsilyl amine. These new groups "protected" S original functional groups by eliminating the instability of the proton and lower alkalinity hetero atoms. Instability after my 3 Si-O and Me Si-N 3 group can be removed ( "deprotection"). Trimethylsilyl, it can also be used to increase the volatility of the compound, so that the generally non-volatile substances gas chromatography, such as glucose. Reaction of trimethylchlorosilane, also with a metal acetylide to give trimethylsilyl alkynes, such as bis (trimethylsilyl) acetylene. These derivatives are useful alkyne forms of protection.
In the presence of triethylamine and lithium diisopropylamide, enolizable aldehydes, ketones and esters are converted to the trimethylsilyl enol ether. 3] although their hydrolytic instability, these compounds have been found widely in organic chemistry; double bond is epoxidized oxidation or hydroxylation may be used to return to the original alcohol group with a carbonyl group in the α carbon. The trimethylsilyl enol ether, can also be used as a masking alcohol equivalent to the mountain aldol addition. NICPBP
Other reactions: trimethylsilyl chloride was used in the preparation of other trimethylsilyl halides and pseudo halides include trimethylsilyl fluoride, trimethylsilyl bromide, trimethylsilyl iodide, trimethyl silane cyanide, trimethylsilyl azide, 4] and trimethylsilyl trifluoromethanesulfonate (TMSOTf). These salt compounds produced by the metathesis reaction between trimethyl chlorosilane and (quasi-) halide (MX) of the formula:
MX + I 3-chloro → MCL + silicon my Si 3-X
The TMSCl, lithium and nitrogen molecules to give tris (trimethylsilyl) amine, catalyzed by a chromium or nickel-chromium alloy wire trichloride:
3 My SiCl Li + 1/2 N2 → 3 + 3 (the I 3 Si) of the LiCl 3 N +3
Using this method, atmospheric nitrogen can be introduced into the organic substrate. For example, tris (trimethylsilyl) amine with α, δ, ω- trione, gives the tricyclic pyrrole. 4]
Restore trimethylchlorosilane hexamethyldisilazane administration:

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