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Bis(trimethylsilyl)acetamide : ウィキペディア英語版 | Bis(trimethylsilyl)acetamide
|Section2= |Section7= |Section8= }} Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula Me3SiNC(OSiMe3)Me (Me = CH3). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with compounds, including solvents and moisture, containing OH and NH functional groups. It is used in analytical chemistry for the derivatisation of compounds in analysis to increase their volatility, e.g. for gas chromatography. It is also used to introduce the trimethylsilyl protecting group in organic synthesis.〔Harry Heaney, Jian Cui, “N,O-Bis(trimethylsilyl)acetamide” Encyclopedia of Reagents for Organic Synthesis Copyright © 2007 John Wiley & Sons. .〕 A related reagent is N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA). ==Synthesis and reactions== BSA is prepared by treating acetamide with trimethylsilyl chloride in the presence of a base:〔 : 2 Me3SiCl + H2NC(O)Me + 2 Et3N → Me3SiNC(OSiMe3)Me + 2 Et3NHCl The reaction of BSA with alcohols gives the corresponding trimethylsilyl ether, together with N-(trimethylsilyl)acetamide as a byproduct: :ROH + Me3SiNC(OSiMe3)Me → Me3SiN(H)C(O)Me + ROSiMe3
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