三甲氧基矽烷

化合物

三甲氧基矽烷是一種有機化合物,是化學式為(CH3O)3SiH的無色易燃液體。

三甲氧基矽烷
別名 TMS
識別
CAS編號 2487-90-3  checkY
PubChem 6327428
性質
化學式 C3H10O3Si
摩爾質量 122.2 g·mol−1
密度 0.860 g·cm−3
熔點 −114.8 °C(158.3 K)[1]
沸點 81 °C(354 K)[1]
危險性
主要危害 有毒,可造成角膜損傷[2]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

合成

編輯

三甲氧基矽烷可由氯化亞銅甲醇在240 °C反應製得。[3]三氯氫矽和甲醇在二甲苯和石油醚中反應,也能得到三甲氧基矽烷。[4]

反應

編輯

三甲氧基矽烷和二氫化(P,P,P',P'-四環己基乙二膦)合鉑(II)發生配體取代反應,可以得到二(三甲氧基矽基)(P,P,P',P'-四環己基乙二膦)合鉑(II)。[5]

它可以和烯烴炔烴發生矽氫化反應,如在三氯化釕的催化下和乙烯反應,生成乙基三甲氧基矽烷[6];和1-己炔反應,得到1-三甲氧基矽基-1-己烯。[7]

它是一種還原劑,在有機合成中可用於將等化合物中的羰基還原。[2]例如,在氯化鋅存在下,它可以將4-(4-硝基苯基)-3-丁烯-2-酮還原為1-(4-硝基苯基)-1-丁烯;[8]或將苯乙酮還原為1-苯乙醇[9]

 

參考文獻

編輯
  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. ^ 吳洪特, 劉僑, 湯艷. 雙溶劑法合成三甲氧基矽烷. 精細石油化工, 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.