三甲氧基硅烷

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）
沸点	81 °C（354 K）
危险性
主要危害	有毒，可造成角膜损伤
	若非注明，所有数据均出自标准状态（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

三甲氧基硅烷可由硅、氯化亚铜和甲醇在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

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]

它可以和烯烃或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酯、醛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。^[9]

参考文献

^ ^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.
^ ^2.0 ^2.1 L. Larson, Gerald; L. Fry, James. Ionic and Organometallic-Catalyzed Organosilane Reductions: 1–737. 2008. doi:10.1002/0471264180.or071.01.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[Sternbach-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.

[Larson-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.

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三甲氧基硅烷

合成

反应

参考文献

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