N,O-ビス(トリメチルシリル)アセトアミド

外観

無色澄明の液体

溶解性

水, エタノールで分解, エーテル, ベンゼンに易溶。ジエチルエーテル及びベンゼンに極めて溶けやすく、エタノール及び水で分解する。

用途

ガスクロマトシリル化用。

用途

糖、ステロイド核のOH基のTMS化剤。

使用上の注意

不活性ガス封入

物理的性質

bp 71–73°C/35 mmHg.

使用

N,O-Bis(trimethylsilyl)acetamide is a powerful silylating agent; reacts with a wide range of functional groups.
BSA was used to trimethylsilylate the hydroxyl group of 12 selectively to form in almost quantitative yield (eq 32).The presence of catalytic amounts (～0.02 equiv) of tetrabutylammonium fluoride (TBAF) significantly promoted the silylation of alcohols under mild conditions with high chemoselectivity, i.e., TBAF plays a role as a smooth silyl transfer catalyst from nitrogen to the hydroxyl group.

製造方法

made by the reaction of acetamide with a large excess of chlorotrimethylsilane in the presence of triethylamine.

一般的な説明

N,O-Bis(trimethylsilyl)acetamide is an excellent silylation reagent. For some sterically hindered primary or secondary nitro compounds, N,O-bis(trimethylsilyl)acetamide and BSTFA achieve better results than normal silylation conditions.

純化方法

Fractionate it through a spinning band column and collect liquid b 71-73o/35mm, and not higher because the main impurity MeCONHSiMe3 distils at b 105-107o/35mm. It is used for derivatising alcohols and sugars [Klebe et al. J Am Chem Soc 88 3390 1966, see Matsuo et al. Carbohydr Res 241 209 1993, Johnson Carbohydr Res 237 313 1992]. Itis FLAMMABLE and TOXIC.