tetrakis(chloromethyl)silane

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: tetrakis(chloromethyl)silane
• 化学式: C₄H₈Cl₄Si
• 分子量: 226.005
• InChiKey: HAFWBIJMQOHTEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tetrakis(chloromethyl)silane 在 sodium azide 作用下， 以 丙酮 为溶剂， 反应 60.0h， 以61%的产率得到tetrakis(azidomethyl)silane
  参考文献：
  名称：

  The Sila-Explosives Si(CH₂N₃)₄ and Si(CH₂ONO₂)₄:  Silicon Analogues of the Common Explosives Pentaerythrityl Tetraazide, C(CH₂N₃)₄, and Pentaerythritol Tetranitrate, C(CH₂ONO₂)₄

  摘要：

  The reaction of tetrakis(chloromethyl)silane, Si(CH2Cl)(4), with sodium azide afforded tetrakis(azidomethyl)silane (sila-pentaerythrityl tetraazide, Si(CH2N3)(4) (1b)). Nitration of tetrakis(hydroxymethyl)silane, Si(CH2OH)(4), with nitric acid resulted in the formation of tetrakis(nitratomethyl)silane (sila-pentaerythritol tetranitrate, Si(CH2ONO2)(4) (2b)). Compounds 1b and 2b are extremely shock-sensitive materials and very difficult to handle. Spectroscopic data were obtained as good as sensitivity and safety allowed for umambiguous identification. Quantum chemical calculations (DFT) of the C/Si pairs C(CH2OH)(4)/Si(CH2OH)(4), 1a/1b, and 2a/2b regarding the structures and electronic populations were performed.

  DOI：

  10.1021/ja071299p
• 作为产物：
  描述：

  溴氯甲烷 在 正丁基锂 、 四氯化硅 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 tetrakis(chloromethyl)silane
  参考文献：
  名称：

  Energetic Sila-Nitrocarbamates: Silicon Analogues of Neo-Pentane Derivatives

  摘要：

  Four silanes based on the neo-pentane skeleton Me4-xSi(CH2R)(x) containing carbamate groups (x = 14, R = OC(O)NH2) have been prepared via the corresponding alcohols Me4-xSi(CH2OH)(x), starting from the chlorosilanes Me4-xSiClx. Subsequent nitration leads to the corresponding primary nitrocarbamates (R = OC(O)NHNO2), examined for the purpose as potential energetic materials, including the silicon analogue of pentaerythritol tetranitrocarbamate (sila-PETNC) and a siloxane based nitrocarbamate side-product. All compounds were thoroughly characterized by spectroscopic methods including X-ray diffraction. Thermal stabilities and sensitivities toward impact and friction were examined, as well as detonation values by calculating energies of formation using the EXPLO5 V6.02 software.

  DOI：

  10.1021/acs.inorgchem.6b00602

文献信息

• Synthesis and Characterization of {[Tris(trimethylsilyl)silyl]methyl}silanes of the Formula Type Me_4−<i>n</i>Si[CH₂Si(SiMe₃)₃]_<i>n</i> (<i>n</i> = 1−3) and Derivatives
  作者：André Berkefeld、Dennis Troegel、Christian Burschka、Reinhold Tacke

  DOI：10.1021/om100721t

  日期：2010.10.25

  Me4−nSi[CH2Si(SiMe3)3]n [n = 1 (5), n = 2 (6), n = 3 (7)] and Me3−n(TMOP)Si[CH2Si(SiMe3)3]n [TMOP = 2,4,6-trimethoxyphenyl, n = 1 (9), n = 2 (10)] was synthesized by treatment of the corresponding (chloromethyl)silanes with [tris(trimethylsilyl)silyl]potassium−18-crown-6 (12). Reaction of tetrakis(chloromethyl)silane (4) with 12, however, yielded the unexpected disilacyclobutane derivative 1,1-bis(trimethylsilyl)-3

  在对分子式为R 4− n Si（CH 2 X）n的多官能四有机基硅烷进行系统研究的基础上（R =有机基，X =官能团，n = 2-4），一系列新的公式类型Me 4- n Si [CH 2 Si（SiMe 3）3 ] n [ n = 1（5），n = 2（6），n = 3（7）]和Me 3- n（TMOP）Si [ CH 2 Si（SiMe 3）3 ]通过用[三（三甲基甲硅烷基）甲硅烷基]钾-18冠处理相应的（氯甲基）硅烷合成n [TMOP = 2,4,6-三甲氧基苯基， n = 1（ 9）， n = 2（ 10）] -6（ 12）。然而，四（氯甲基）硅烷（ 4）与12的反应产生了出乎意料的二硅环环丁烷衍生物1,1-双（三甲基甲硅烷基）-3,3-双[[三（三甲基甲硅烷基）甲硅烷基]甲基] -1,3-二硅环丁烷（ 11）。化合物5 - 7和9 - 11进行了表征通过元素分析（C，H）和核磁共振光谱中的溶液研究（1
• Energetic Sila-Nitrocarbamates: Silicon Analogues of Neo-Pentane Derivatives
  作者：Quirin J. Axthammer、Thomas M. Klapötke、Burkhard Krumm、Thomas Reith

  DOI：10.1021/acs.inorgchem.6b00602

  日期：2016.5.2

  Four silanes based on the neo-pentane skeleton Me4-xSi(CH2R)(x) containing carbamate groups (x = 14, R = OC(O)NH2) have been prepared via the corresponding alcohols Me4-xSi(CH2OH)(x), starting from the chlorosilanes Me4-xSiClx. Subsequent nitration leads to the corresponding primary nitrocarbamates (R = OC(O)NHNO2), examined for the purpose as potential energetic materials, including the silicon analogue of pentaerythritol tetranitrocarbamate (sila-PETNC) and a siloxane based nitrocarbamate side-product. All compounds were thoroughly characterized by spectroscopic methods including X-ray diffraction. Thermal stabilities and sensitivities toward impact and friction were examined, as well as detonation values by calculating energies of formation using the EXPLO5 V6.02 software.
• The Sila-Explosives Si(CH₂N₃)₄ and Si(CH₂ONO₂)₄:  Silicon Analogues of the Common Explosives Pentaerythrityl Tetraazide, C(CH₂N₃)₄, and Pentaerythritol Tetranitrate, C(CH₂ONO₂)₄
  作者：Thomas M. Klapötke、Burkhard Krumm、Rainer Ilg、Dennis Troegel、Reinhold Tacke

  DOI：10.1021/ja071299p

  日期：2007.5.1

  The reaction of tetrakis(chloromethyl)silane, Si(CH2Cl)(4), with sodium azide afforded tetrakis(azidomethyl)silane (sila-pentaerythrityl tetraazide, Si(CH2N3)(4) (1b)). Nitration of tetrakis(hydroxymethyl)silane, Si(CH2OH)(4), with nitric acid resulted in the formation of tetrakis(nitratomethyl)silane (sila-pentaerythritol tetranitrate, Si(CH2ONO2)(4) (2b)). Compounds 1b and 2b are extremely shock-sensitive materials and very difficult to handle. Spectroscopic data were obtained as good as sensitivity and safety allowed for umambiguous identification. Quantum chemical calculations (DFT) of the C/Si pairs C(CH2OH)(4)/Si(CH2OH)(4), 1a/1b, and 2a/2b regarding the structures and electronic populations were performed.