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三甲氧基硅烷

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三甲氧基硅烷
别名 TMS
识别
CAS号 2487-90-3  ✓
PubChem 6327428
性质
化学式 C3H10O3Si
摩尔质量 122.2 g·mol−1
密度 0.860 g·cm−3
熔点 −114.8 °C(158.3 K)[1]
沸点 81 °C(354 K)[1]
危险性
主要危害 有毒,可造成角膜损伤[2]
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

三甲氧基硅烷是一种有机化合物,是化学式为(CH3O)3SiH的无色易燃液体。

合成[编辑]

三甲氧基硅烷可由氯化亚铜甲醇在240 °C反应制得。[3]三氯氢硅和甲醇在二甲苯和石油醚中反应,也能得到三甲氧基硅烷。[4]

反应[编辑]

三甲氧基硅烷和二氢化(P,P,P',P'-四环己基乙二膦)合铂(II)发生配體取代反应,可以得到二(三甲氧基硅基)(P,P,P',P'-四环己基乙二膦)合铂(II)。[5]

它可以和烯烃炔烃发生硅氢化反应,如在三氯化钌的催化下和乙烯反应,生成乙基三甲氧基硅烷[6];和1-己炔反应,得到1-三甲氧基硅基-1-己烯。[7]

它是一种还原剂,在有机合成中可用于将等化合物中的羰基还原。[2]例如,在氯化锌存在下,它可以将4-(4-硝基苯基)-3-丁烯-2-酮还原为1-(4-硝基苯基)-1-丁烯;[8]或将苯乙酮还原为1-苯乙醇英语1-Phenylethanol[9]

三甲氧基硅烷还原羰基化合物

参考文献[编辑]

  1. ^ 1.0 1.1 Sternbach, Burt; MacDiarmid, Alan G. The Preparation of Methoxysilanes by the Interaction of Monosilane and Methanol. Journal of the American Chemical Society. 2002, 81 (19): 5109–5110. ISSN 0002-7863. doi:10.1021/ja01528a023. 
  2. ^ 2.0 2.1 L. Larson, Gerald; L. Fry, James. Ionic and Organometallic-Catalyzed Organosilane Reductions: 1–737. 2008. doi:10.1002/0471264180.or071.01. 
  3. ^ Watanabe, Yoshiyuki; Shibuya, Hiromitsu; Suzuki, Eiichi. Development of the chlorine-​free monosilane production process via methoxysilanes using a fluidized-​bed reactor. Studies in Surface Science and Catalysis, 2003. 145. 547-548. ISSN: 0167-2991. CODEN: SSCTDM.
  4. ^ 吴洪特, 刘侨, 汤艳. 双溶剂法合成三甲氧基硅烷. 精细石油化工, 2006 (06): 62-64.
  5. ^ Mitzenheim, Cathérine; Braun, Thomas. Si-Si and Si-O Bond Activation at Platinum: Stepwise Formation of a SiH3Complex. Angewandte Chemie International Edition. 2013, 52 (33): 8625–8628. ISSN 1433-7851. doi:10.1002/anie.201302459. 
  6. ^ Liu, L.; Li, X.; Ma, Y.; Wu, C.; Han, G. Selective Catalytic Hydrosilylation of Ethylene. Preparation of Ethyltrimethoxysilane by H2O Promoted RuCl3 ⋅ 3H2O Catalyst. Kinetics and Catalysis. 2020, 61 (3): 414–420. ISSN 0023-1584. doi:10.1134/S0023158420030167. 
  7. ^ Ojima, Iwao; Clos, Nuria; Donovan, Robert J.; Ingallina, Patrizia. Hydrosilylation of 1-hexyne catalyzed by rhodium and cobalt-rhodium mixed-metal complexes. Mechanism of apparent trans addition. Organometallics. 2002, 9 (12): 3127–3133. ISSN 0276-7333. doi:10.1021/om00162a026. 
  8. ^ Li, Jiayun; Peng, Jiajian; Bai, Ying; Chen, Lingzhen; Lai, Guoqiao. Rapid Selective Defunctionalization of the Carbonyl Group of α,β-Unsaturated Ketones with Trialkoxylsilane/ZnX2. Phosphorus, Sulfur, and Silicon and the Related Elements. 2011, 186 (8): 1621–1625. ISSN 1042-6507. doi:10.1080/10426507.2010.536188. 
  9. ^ Hosomi, Akira; Hayashida, Hisashi; Kohra, Shinya; Tominaga, Yoshinori. Pentaco-ordinate silicon compounds in synthesis: chemo- and stereo-selective reduction of carbonyl compounds using trialkoxy-substituted silanes and alkali metal alkoxides. Journal of the Chemical Society, Chemical Communications. 1986, (18): 1411. ISSN 0022-4936. doi:10.1039/c39860001411.