ヨードトリメチルシラン

解説trimethylsilyl iodide．C3H9ISi(200.10)．(CH3)3SiI．ヘキサメチルジシロキサンとヨウ化アルミニウムとの反応，あるいはヘキサメチルジシランのヨウ素による切断で得られる．無色の液体．沸点106～107 ℃．d204 1.470．n20D 1.474．ヨードトリメチルシランは，加水分解を受けやすく，光に不安定である．窒素雰囲気中で銅粉を入れて貯蔵する．エステルやほかのハロゲン化アルキルのヨウ化アルキルへの変換，エーテル結合の切断など有機試薬として用いられる．森北出版「化学辞典（第2版）

使用Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.Iodotrimethylsilane is a highly efficient reagent for the cleavage of ethers, esters, carbamates, ketals, and lactones. It is also used for the introduction of TMS groups, such as TMS enol ethers, and is a key reagent for the selective removal of N-Cbz groups in the presence of a trimethyltin moiety.This reagent has recently been reported to convert allyl and benzyl phosphotriesters to the corresponding iodides.

一般的な説明Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.

製造方法Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.

純化方法Add a little antimony powder and fractionate with this powder in the still. 20 1.470. Stabilise the distillate with 1% wt of Cu powder. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4009.]