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Synlett 2011(5): 732-733  
DOI: 10.1055/s-0030-1259594
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© Georg Thieme Verlag Stuttgart ˙ New York

Lithium Bis(trimethylsilyl)amide

Yong-Hui Liu*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
e-Mail: liu_yonghui1986@163.com;
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Publication History

Publication Date:
25 February 2011 (online)

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Introduction

Lithium bis(trimethylsilyl)amide (LiHMDS) is a colorless solid, which is soluble in a variety of organic solvents suitable for reactive compounds, such as organometallic substances or substituted metal amides. The compound melts at 71-72 ˚C. [¹] It is unstable in air and catches fire when compressed, but it is stable in an atmosphere of nitrogen. Reactions with a variety of nonmetallic halides give lithium halides and hexamethyldisilazyl derivatives. The preparation of lithium bis(trimethylsilyl)amid must be performed in an atmosphere of dry nitrogen. The pentane containing n-butyllithium is added slowly to a stirred solution of hexamethyldisilazane (Scheme [¹] ). The reaction mixture is boiled for 30 minutes, and evaporate the solvents. LiHMDS is obtained as colorless crystals.

Scheme 1