phenyldimethylpentafluorophenylsilane | 23431-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyldimethylpentafluorophenylsilane
• 英文别名: (Pentafluorophenyl)dimethylphenylsilan；1-(Dimethylphenylsilyl)-2,3,4,5,6-pentafluorobenzene；dimethyl-(2,3,4,5,6-pentafluorophenyl)-phenylsilane
• CAS: 23431-49-4
• 化学式: C₁₄H₁₁F₅Si
• 分子量: 302.319
• InChiKey: WKHRLOZVMZKXPG-UHFFFAOYSA-N

物化性质

• 沸点：
  262.4±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyldimethylpentafluorophenylsilane 在 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到fluorodimethylsilylpentafluorobenzene
  参考文献：
  名称：

  Reactions of methyl(pentafluorophenyl)- and methyl(pentafluorophenyl)phenylsilanes with electrophiles. A convenient preparative route to halogeno(methyl)pentafluorophenylsilanes C6F5SiMe2X and C6F5SiMeX2 (X=F, Cl and Br)

  摘要：

  Halogeno(methyl)pentafluorophenylsilanes C6F5SiMenX3-n (n = 1, 2) (X = F, Cl, Br) were prepared in good yields from the corresponding phenylsilanes C6F5SiMenPh3-n by reactions with the electrophiles aHF, HCl-AlCl3, Br-2-AlBr3 or AlX3 (X = Cl, Br) halogenated hydrocarbons. Additionally, reactions of C6F5SiMe3 and (C6F5)(2)SiMe2 with selected electrophiles were studied. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00805-5
• 作为产物：
  描述：

  双(五氟苯基)二甲基硅烷 在 aluminum tri-bromide 、 溴 、 六乙基亚磷酸胺 作用下， 以 苯 为溶剂， 反应 1.25h， 生成 phenyldimethylpentafluorophenylsilane
  参考文献：
  名称：

  Reactions of methyl(pentafluorophenyl)- and methyl(pentafluorophenyl)phenylsilanes with electrophiles. A convenient preparative route to halogeno(methyl)pentafluorophenylsilanes C6F5SiMe2X and C6F5SiMeX2 (X=F, Cl and Br)

  摘要：

  Halogeno(methyl)pentafluorophenylsilanes C6F5SiMenX3-n (n = 1, 2) (X = F, Cl, Br) were prepared in good yields from the corresponding phenylsilanes C6F5SiMenPh3-n by reactions with the electrophiles aHF, HCl-AlCl3, Br-2-AlBr3 or AlX3 (X = Cl, Br) halogenated hydrocarbons. Additionally, reactions of C6F5SiMe3 and (C6F5)(2)SiMe2 with selected electrophiles were studied. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00805-5

文献信息

• A new synthesis of perfluoroaromatic grignard reagents
  作者：W.L. Respess、C. Tamborski

  DOI：10.1016/s0022-328x(00)85394-2

  日期：1969.8

  RhCl3 and AgCl). The yields of the perfluoroarylmagnesium compound vary with the type of perfluoroaryl substrate and metal halide. The perfluoroarylmagnesium compounds thus formed undergo typical Grignard reactions.

  全氟芳基镁化合物是由完全氟化的芳基化合物（例如六氟苯，十氟联苯，八氟甲苯和八氟萘）与乙基镁溴化物和某些过渡金属卤化物（CoCl 2，FeCl 2，NiCl 2，CuI，TiCl 4，PdCl 2，RhCl 3和AgCl）。全氟芳基镁化合物的产率随全氟芳基底物和金属卤化物的类型而变化。由此形成的全氟芳基镁化合物经历典型的格氏反应。
• Kinetic and mechanistic studies of the transformation of the catalyst, tris(pentafluorophenyl)borane, in the presence of silyl and germyl hydrides
  作者：Slawomir Rubinsztajn、Julian Chojnowski、Marek Cypryk、Urszula Mizerska、Witold Fortuniak、Irena I. Bak-Sypien

  DOI：10.1016/j.jcat.2019.09.023

  日期：2019.11

  triethylsilane and triethylgermane were studied by 19F NMR and UV spectroscopy, GC/MS and quantum-mechanical calculations. The observed exchange of pentafluorophenyl group attached to boron to hydrogen results in the formation of bis(pentafluorophenyl)borane, which has a strongly reduced ability to activate the Si-H bond. The substitution kinetics were studied by following the disappearance of absorption of the

  三（五氟苯基）硼烷催化的Si-H键活化为许多无过渡金属的还原方法打开了大门，并广泛用于有机和聚合物化学中。然而，在甲硅烷基氢化物的存在下，B（C 6 F 5）3的化学稳定性受到限制，这会强烈影响其催化活性。通过19研究了在苯基二甲基硅烷，三乙基硅烷和三乙基锗烷存在下B（C 6 F 5）3的转化。F NMR和UV光谱，GC / MS和量子力学计算。观察到附着在硼上的五氟苯基与氢的交换导致形成双（五氟苯基）硼烷，该双（五氟苯基）硼烷的活化Si-H键的能力大大降低。通过追踪B（C 6 F 5）3电荷转移峰在紫外光谱中的吸收消失来研究取代动力学。互补的量子力学计算使我们能够提出配体交换反应的机制，该机制涉及通过四中心过渡态对五氟苯基进行亲电取代。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.4, 2.2.4, page 68 - 115
  作者：

  DOI：——

  日期：——
• Reactions of methyl(pentafluorophenyl)- and methyl(pentafluorophenyl)phenylsilanes with electrophiles. A convenient preparative route to halogeno(methyl)pentafluorophenylsilanes C6F5SiMe2X and C6F5SiMeX2 (X=F, Cl and Br)
  作者：H.-J Frohn、A Lewin、V.V Bardin

  DOI：10.1016/s0022-328x(98)00805-5

  日期：1998.11

  Halogeno(methyl)pentafluorophenylsilanes C6F5SiMenX3-n (n = 1, 2) (X = F, Cl, Br) were prepared in good yields from the corresponding phenylsilanes C6F5SiMenPh3-n by reactions with the electrophiles aHF, HCl-AlCl3, Br-2-AlBr3 or AlX3 (X = Cl, Br) halogenated hydrocarbons. Additionally, reactions of C6F5SiMe3 and (C6F5)(2)SiMe2 with selected electrophiles were studied. (C) 1998 Elsevier Science S.A. All rights reserved.