2-(トリメチルシリル)エタンスルホニルクロリド

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H225：引火性の高い液体および蒸気

  H315：皮膚刺激

  H319：強い眼刺激

  H335：呼吸器への刺激のおそれ

• 注意書き

  P210：熱/火花/裸火/高温のもののような着火源から遠ざ けること。－禁煙。

  P302+P352：皮膚に付着した場合：多量の水と石鹸で洗うこと。

  P305+P351+P338：眼に入った場合：水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

2-(トリメチルシリル)エタンスルホニルクロリド 価格

2-(トリメチルシリル)エタンスルホニルクロリド 化学特性,用途語,生産方法

• 物理的性質

  bp 60 °C/0.1 mmHg; yellow oil.

• 使用

  β-Trimethylsilylethanesulfonyl Chloride is used in the protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion. It participates in the reations of Protection of Amines, SESCl in Synthesis, N-Alkylation, Deprotection Conditions, Formation of 2-Trimethylsilylethanesulfonylimines, the (N-SES-Imino) Phenyliodinane or SESN=IPh Reagent, SES-N3, etc.

• 製造方法

  |?-Trimethylsilylethanesulfonyl Chloride can be most conveniently synthesized from commercially available vinyltrimethylsilane (eq 1). Radical addition of sodium bisulfite to the vinyl group catalyzed by t-butyl perbenzoate yields the sulfonate salt which can be directly converted to SESCl with phosphorus(V) chloride. The chloride can then be purified by distillation. The intermediate sulfonate salt is commercially available. The chloride can also be prepared in 62% yield from the salt using sulfuryl chloride and triphenylphosphine (eq 2). A less convenient procedure to synthesize SESCl using |?-trimethylsilylethylmagnesium chloride and sulfuryl chloride has also been developed (eq 3).

  

• 純化方法

  Check IR; if the bands at ~3200 (OH) cm-1 are strong, then much of the SES-Cl had hydrolysed, and it should be treated with POCl3 (with cooling) and stirred at ~25o for about 1hour, poured into ice cold H2O, extracted with CH2Cl2, washed with NaHCO3, dried (Na2SO4), evaporated , and it distils as a yellow oil in a vacuum. This procedure is used for converting the Na salt to SES-Cl. It reacts with amines to form amides, e.g. SES-NRR’, which on heating with CsF (i.e. F-ions) in DMF at 95o provide the amine (NHRR’), SO2 and CH2=CH2 [Weinreb et al. Tetrahedron Lett 27 2099 1986]. [Ribiere et al. Chem Rev 106 2249 2006.]

2-(トリメチルシリル)エタンスルホニルクロリド 生産企業

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