三氯(3-氯苯基)硅烷 | 2003-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 三氯(3-氯苯基)硅烷
• 英文名称: trichloro(m-chlorophenyl)silane
• 英文别名: m-chlorophenyltrichlorosilane；trichloro-(3-chloro-phenyl)-silane；Trichlor-(3-chlor-phenyl)-silan；Trichlor-<3-chlor-phenyl>-silan；<3-Chlor-phenyl>-trichlorsilan；-trichlorsilan；trichloro-(3-chlorophenyl)silane
• CAS: 2003-89-6
• 化学式: C₆H₄Cl₄Si
• 分子量: 245.995
• InChiKey: ZIILLBRFKOKOGU-UHFFFAOYSA-N

物化性质

• 沸点：
  230.36°C (estimate)
• 保留指数：
  1313.3

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  三氯(3-氯苯基)硅烷 在 三氯硅烷 作用下， 生成 3-Cl3SiC6H4SiCl3
  参考文献：
  名称：

  Motsarev,G.V.; Inshakova,V.T., Journal of general chemistry of the USSR, 1967, vol. 37, p. 230 - 232

  摘要：

  DOI：
• 作为产物：
  描述：

  (3-chlorophenyl)magnesium bromide 在 四氯化硅 作用下， 生成 三氯(3-氯苯基)硅烷
  参考文献：
  名称：

  Petrow et al., Zhurnal Obshchei Khimii, 1956, vol. 26, p. 1229,1231;engl.Ausg.S.1391,1393

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of Silicon‐Stereogenic Monohydrosilanes by Rhodium‐Catalyzed Intramolecular Hydrosilylation
  作者：Yu‐Hao Huang、Yichen Wu、Zile Zhu、Sujuan Zheng、Zihang Ye、Qian Peng、Peng Wang

  DOI：10.1002/anie.202113052

  日期：2022.1.3

  An intramolecular hydrosilylation strategy was developed for the asymmetric synthesis of chiral monohydrosilanes. This protocol is suitable for the synthesis of dihydrobenzosilole-, tetrahydrobenzosiline- and oxatetrahydrobenzosiline-based monohydrosilanes with excellent diastereo-, regio-, and enantioselectivities. Notably, the catalyst loading could be reduced to 0.1 mol %.

  为手性单氢硅烷的不对称合成开发了一种分子内氢化硅烷化策略。该协议适用于合成具有优异非对映选择性、区域选择性和对映选择性的二氢苯甲硅烷、四氢苯甲硅烷和 oxatetrahydrobenzosiline 基单氢硅烷。值得注意的是，催化剂负载量可以降低到 0.1 mol%。
• Zur synthese von siloxanen
  作者：K. Käppler、A. Porzel、U. Scheim、K. Rühlmann

  DOI：10.1016/0022-328x(91)83059-d

  日期：1991.1

  The reaction of organotrichlorosilanes with acetic acid in acetic anhydride forming organodichloroacetoxysilanes was investigated kinetically by means of 1H-NMR spectroscopy. It was found that the reaction takes place exclusively with the acetic anhydride under the conditions used. The ϱ-value of the reaction was found to be 1.8 and the δ-value to be 1.2. A reaction mechanism is proposed.

  通过1 H-NMR光谱动力学地研究了有机三氯硅烷与乙酸在乙酸酐中形成有机二氯乙酰氧基硅烷的反应。发现该反应仅在所用条件下与乙酸酐发生。发现反应的值是1.8，δ值是1.2。提出了一种反应机理。
• A Study of the Influence of the HCl Concentration on the Composition and Structure of (Hydroxy)Arylsiloxanes from the Hydrolysis–Condensation Reaction of Aryltrichlorosilanes
  作者：Irina M. Petrova、Yury I. Lyakhovetsky、Vladimir V. Chernyshev、Nikolai S. Ikonnikov、Nataliya N. Makarova

  DOI：10.3390/molecules24224195

  日期：——

  The hydrolysis–condensation reactions of m-tolyl, m-chlorophenyl, and α-naphtyl-trichlorsilanes, (1, 2, and 3, respectively) in water-acetone solutions were examined for how they were influenced by the change in the concentration of HCl (CHCl). The composition of the products was monitored by 29Si NMR spectroscopy and atmospheric pressure chemical ionization mass spectrometry (APCI-MS). The acidity of the medium was shown to affect the yields of the products, and so, what products were formed. For 3, e.g., APCI-MS showed peaks of α-naphtyl-T8 and α-naphtyl-T10 as the most abundant in the spectra taken after 48 and 240 h for the reaction conducted at CHCl = 0.037 mol L−1. Unlike this, at CHCl = 0.15 mol L−1, those peaks were of [α-naphtyl(HO)2SiO]2(α-naphtyl)(HO)Si and/or [α-naphtyl(HO)Si]3, [α-naphtyl(HO)Si]4,5, and α-naphtyl-T8 after 192 h. However, at both CHCl values, the main product (and an intermediate) after 24 h was trans-1,1,3,3-tetrahydroxy-1,3-di-α-naphtyldisiloxane. It was isolated and its structure established by 1H-, 29Si-NMR, and X-ray powder diffraction.

  在水-丙酮溶液中，研究了m-甲苯基、m-氯苯基和α-萘基三氯硅烷（分别为1、2和3）的水解-缩合反应对HCl浓度变化的影响。通过29Si NMR光谱和大气压化学电离质谱（APCI-MS）监测产物的组成。结果表明，介质的酸度影响产物的收率和类型。例如，对于3，APCI-MS显示在CHCl = 0.037 mol L−1下反应48和240小时后，α-萘基-T8和α-萘基-T10峰是最丰富的。相反，在CHCl = 0.15 mol L−1下，这些峰是[α-萘基(HO)2SiO]2(α-萘基)(HO)Si和/或[α-萘基(HO)Si]3、[α-萘基(HO)Si]4,5和α-萘基-T8。然而，在这两个CHCl值下，24小时后的主要产物（和中间体）是反-1,1,3,3-四羟基-1,3-二α-萘基二硅氧烷。通过1H-、29Si-NMR和X射线粉末衍射确定了其结构。
• Mironow; Ponomarenko, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 199,204;engl.Ausg.S.211,215
  作者：Mironow、Ponomarenko

  DOI：——

  日期：——
• Voronkov, M. G.; Kuznetsova, G. A.; Baryshok, V. P., Journal of general chemistry of the USSR, 1983, vol. 53, # 7, p. 1512 - 1513
  作者：Voronkov, M. G.、Kuznetsova, G. A.、Baryshok, V. P.

  DOI：——

  日期：——