4-chlorononafluoro-1,1′-biphenyl

• 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: 4-chlorononafluoro-1,1′-biphenyl
• 英文别名: 4'-Chloro-2,3,4,5,6,2',3',5',6'-nonafluorobiphenyl；1-chloro-2,3,5,6-tetrafluoro-4-(2,3,4,5,6-pentafluorophenyl)benzene
• 化学式: C₁₂ClF₉
• 分子量: 350.571
• InChiKey: ICCZODPSIIBBNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• 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：
  9

反应信息

• 作为反应物：
  描述：

  4-chlorononafluoro-1,1′-biphenyl 在 potassium hydrosulfide 作用下， 以 乙二醇 、 异丙醇 为溶剂， 反应 4.0h， 以89%的产率得到4′-chlorooctafluoro-1,1′-biphenyl-4-thiol
  参考文献：
  名称：

  4 和 4,4' 位含溴和氯原子的溴氯多氟联苯的合成

  摘要：

  一种由四氟联苯-4-硫醇与Cl2、PCl5和Br2反应合成4-氯九氟-和4-溴一氟联苯的新方法，以及由八氟联苯-4,4'-合成4,4'-二氯八氟联苯的新方法开发了二硫醇、4'-氯八氟联苯-4-硫醇、Cl2和PCl5。首次以4'-氯八氟联苯-4-硫醇和Br2为原料合成了4-溴-4'-氯八氟联苯。4,4'-二氯八氟联苯是4'-溴八氟联苯-4-硫醇与PCl5反应的主要产物。

  DOI：

  10.1134/s1070363221070097
• 作为产物：
  描述：

  十氟联苯 在 potassium hydrosulfide 、 五氯化磷 作用下， 以 乙二醇 、 异丙醇 为溶剂， 反应 7.5h， 生成 4-chlorononafluoro-1,1′-biphenyl
  参考文献：
  名称：

  4 和 4,4' 位含溴和氯原子的溴氯多氟联苯的合成

  摘要：

  一种由四氟联苯-4-硫醇与Cl2、PCl5和Br2反应合成4-氯九氟-和4-溴一氟联苯的新方法，以及由八氟联苯-4,4'-合成4,4'-二氯八氟联苯的新方法开发了二硫醇、4'-氯八氟联苯-4-硫醇、Cl2和PCl5。首次以4'-氯八氟联苯-4-硫醇和Br2为原料合成了4-溴-4'-氯八氟联苯。4,4'-二氯八氟联苯是4'-溴八氟联苯-4-硫醇与PCl5反应的主要产物。

  DOI：

  10.1134/s1070363221070097

文献信息

• Halophilic reactions of pentafluorohalobenzenes with transition-metal carbonyl anions
  作者：V.A. Ivushkin、P.K. Sazonov、G.A. Artamkina、I.P. Beletskaya

  DOI：10.1016/s0022-328x(99)00598-7

  日期：2000.3

  present work we widen the scope of the halophilic mechanism of nucleophilic aromatic substitution, which we found earlier for the reaction of pentafluorochlorobenzene with [CpFe(CO)2]− anion, to reactions of pentafluorohalobenzenes (Hal=Cl, Br, I) with various metal carbonyl anions [Re(CO)5]−, [Mn(CO)5]− and [CpFe(CO)2]−. Nucleophilic aromatic substitution with the [CpFe(CO)2]− anion yields C6F5Fe(CO)2Cp

  在本工作中，我们拓宽了亲核芳族取代的嗜盐机理的范围，我们较早时发现五氟氯苯与[CpFe（CO）2 ] -阴离子的反应与五氟卤代苯的反应（Hal = Cl，Br，I）具有各种金属羰基阴离子[Re（CO）5 ] -，[Mn（CO）5 ] -和[CpFe（CO）2 ] -。用[CpFe（CO）2 ] -阴离子进行亲核芳香族取代生成C 6 F 5 Fe（CO）2 Cp，而用[Re（CO）5 ] -和[Mn（CO）获得5 ] -阴离子的卤代（酰基）金属化物顺式-[C 6 F 5（CO）M（CO）4 Hal] Na（M = Mn，Re）。
• Ivushkin; Sazonov; Artamkina, Russian Journal of Organic Chemistry, 1999, vol. 35, # 11, p. 1640 - 1652
  作者：Ivushkin、Sazonov、Artamkina、Beletskaya

  DOI：——

  日期：——
• The Reaction of the [CpFe(CO)2]− Anion with Pentafluorochlorobenzene: Nucleophilic Aromatic Substitution by Halogen-Metal Exchange
  作者：G. A. Artamkina、P. K. Sazonov、V. A. Ivushkin、I. P. Beletskaya

  DOI：10.1002/(sici)1521-3765(19980710)4:7<1169::aid-chem1169>3.0.co;2-h

  日期：1998.7.10

  In the reaction of the [CpFe(CO)(2)](-) anion with pentafluorochlorobenzene, [CpFe(CO)(2)](2) and p-chloroperfluoropolyphenyls C6F5(C6F4)(n)-C6F4Cl (n=0-3) are formed alongside the expected chlorine substitution product [C6F5Fe(CO)(2)Cp]. The relative yield of these products depends on the ratio of initial reactants, solvent (THF ether, DMSO, MeCN), counterion (K+, K(+)18-crown-6, [(C6H5)(3)P=N=P(C6H5)(3)](+) [PPN+]) and temperature. The highest yield of [C6F5Fe(CO)(2)Cp] (approximate to 50%) was obtained in THF, with a slight excess of pentafluorochlorobenzene added to [CpFe(CO)(2)]K at room temperature. In the presence of proton donors rBuOH or PhCH(Et)CN the reaction does not yield [C6F5Fe(CO)(2)Cp] and p-chloroperfluoropolyphenyls at all; instead C6F5H and [CpFe(CO)(2)](2) are formed. This fact and other data point to the [C6F5](-) anion as the key intermediate in all of the observed transformations, among them the formation of [C6F5Fe(CO)(2)Cp]. The evidence from the use of radical traps (R2PH and PEt3) indicates that free radicals are not involved in the major reaction pathway. Halogen-metal exchange is proposed as the first step of the reaction mechanism. The subsequent competition between the possible reactions of the exchange intermediates, [CpFe(CO)(2)Cl] and [C6F5](-), is discussed to account for the highly variable ratio of the final products.
• US6129863A
  申请人：——

  公开号：US6129863A

  公开（公告）日：2000-10-10
• [EN] CLEAN GENERATION OF A PERFLUOROARYL GRIGNARD REAGENT<br/>[FR] GENERATION D'UN PERFLUOROARYLE REACTIF DE GRIGNARD PUR
  申请人：ALBEMARLE CORP

  公开号：WO2000035923A1

  公开（公告）日：2000-06-22

  Perfluoroaryl Grignard reagents are produced from a hydrocarbyl Grignard reagent and polyhaloaromatic compounds via separate additions of different polyhaloaromatic compounds, such that the conversion of hydrocarbyl Grignard reagent to the desired perfluoroaryl Grignard reagent is essentially complete, and thus the reaction product is free or essentially free of agents that may negatively affect subsequent reactions. The perfluoroaryl Grignard reagents may be further reacted with boron trihalides in order to obtain tris(perfluoroaryl)boranes or tetrakis(perfluoroaryl)borates.