2,2'-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline | 68090-59-5

• 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: 2,2'-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline
• 英文别名: 1,4-bis (o-aminophenoxy)tetrafluorobenzene；1,4-bis(o-aminophenoxy)-tetrafluorobenzene；1,4-bis(o-aminophenoxy)tetrafluorobenzene；1.4-Bis(o-Aminophenoxy)tetrafluorbenzol；2-[4-(2-Aminophenoxy)-2,3,5,6-tetrafluorophenoxy]aniline
• CAS: 68090-59-5
• 化学式: C₁₈H₁₂F₄N₂O₂
• 分子量: 364.299
• InChiKey: CTYJQBYSUKSJHE-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C(Solv: benzene (71-43-2))
• 沸点：
  349.3±42.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-乙基-N-羟乙基苯胺 、 2,2'-[(2,3,5,6-tetrafluoro-1,4-phenylene)-bis-(oxy)]dianiline 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 4.0h， 以82%的产率得到2,2'-{(2,3,5,6-tetrafluoro-1,4-phenylene)bis[oxy-1,2-phenylene(E)diazene-1,2-diyl-1,4-phenylene(ethylimino)]}diethanol
  参考文献：
  名称：

  Synthesis and properties of hydroxylated core-fluorinated diamines and polyurethanes based on them with azobenzene nonlinear optical chromophores in the backbone

  摘要：

  We report on the synthesis of core-fluorinated phenylene- and biphenyldianilines, which was accomplished by diazotization reaction of diamines followed by coupling of the obtained diazonium salts with 2-[ethyl(phenyl)aminol-ethanol. Two types of core-fluorinated aromatic units were used in a molecular design of azo-chromophore monomers with enhanced second order nonlinear optical (NLO) properties: octafluorobiphenyl (OFB) and tetrafluorobenzene (TFB) ones. Polymerization of the monomers was performed to obtain polyurethanes with azo-chromophores in the main chain. Comparison of physical and optical properties of these polymers reveals that the main factor influencing the observed NLO activity of the latter is the inherent isomery of the macromolecular chains rather than a variation of the structure of electron-accepting groups. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.09.053
• 作为产物：
  描述：

  六氟苯 、 2-氨基苯酚 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以73%的产率得到2-(2,3,4,5,6-五氟苯氧基)苯胺
  参考文献：
  名称：

  多氟芳族化合物与邻氨基苯酚的相互作用。多氟芳烃系列中的Smiles重排

  摘要：

  在芳环中含有除氟以外的吸引电子的取代基的多氟芳族化合物与邻氨基苯酚的反应在氨基或羟基上进行，并导致形成相应的羟基二芳基胺（在中性介质中）或氨基二芳基醚（在碱性介质中）。与2,3,4,5,6-五氟-2'-氨基二苯醚不同，后一种化合物在二甲基甲酰胺（DMFA）中转化为异构的多氟-2-羟基二芳基胺（Smiles重排）。取代基的电子吸引能力的提高导致活化能的降低和重排速率常数的提高。

  DOI：

  10.1016/s0022-1139(00)81035-0

文献信息

• Reaction of polyfluoroaromatics with o- and p- aminophenols in DMF
  作者：T. N. Gerasimova、E. F. Kolchina、I. Yu. Kargapolova

  DOI：10.1007/bf00957246

  日期：1987.12
• KOLCHINA, E. F.;GERASIMOVA, T. N., J. FLUOR. CHEM., 41,(1988) N, C. 345-356
  作者：KOLCHINA, E. F.、GERASIMOVA, T. N.

  DOI：——

  日期：——
• GERASIMOVA, T. N.;KOLCHINA, E. F.;KARGAPOLOVA, N. YU., IZV. AN CCCP. CEP. XIM.,(1987) N 12, 2814-2819
  作者：GERASIMOVA, T. N.、KOLCHINA, E. F.、KARGAPOLOVA, N. YU.

  DOI：——

  日期：——
• Interaction of polyfluoroaromatic compounds with o-aminophenol. The Smiles rearrangement in the polyfluoroaromatic series
  作者：E.F. Kolchina、T.N. Gerasimova

  DOI：10.1016/s0022-1139(00)81035-0

  日期：1988.12

  The reactions of polyfluoroaromatic compounds containing an electron-attracting substituent other than fluorine in the aromatic ring with o-aminophenol proceed at the amino or hydroxy group and lead to the corresponding hydroxydiarylamines (in neutral media) or aminodiaryl ethers (in alkaline media). The latter compounds, unlike 2,3,4,5,6-pentafluoro- 2'-aminodiphenyl ether, are transformed in dimethylformamide

  在芳环中含有除氟以外的吸引电子的取代基的多氟芳族化合物与邻氨基苯酚的反应在氨基或羟基上进行，并导致形成相应的羟基二芳基胺（在中性介质中）或氨基二芳基醚（在碱性介质中）。与2,3,4,5,6-五氟-2'-氨基二苯醚不同，后一种化合物在二甲基甲酰胺（DMFA）中转化为异构的多氟-2-羟基二芳基胺（Smiles重排）。取代基的电子吸引能力的提高导致活化能的降低和重排速率常数的提高。
• Synthesis and properties of hydroxylated core-fluorinated diamines and polyurethanes based on them with azobenzene nonlinear optical chromophores in the backbone
  作者：V.V. Shevchenko、A.V. Sidorenko、V.N. Bliznyuk、I.M. Tkachenko、O.V. Shekera、N.N. Smirnov、I.A. Maslyanitsyn、V.D. Shigorin、A.V. Yakimansky、V.V. Tsukruk

  DOI：10.1016/j.polymer.2013.09.053

  日期：2013.11

  We report on the synthesis of core-fluorinated phenylene- and biphenyldianilines, which was accomplished by diazotization reaction of diamines followed by coupling of the obtained diazonium salts with 2-[ethyl(phenyl)aminol-ethanol. Two types of core-fluorinated aromatic units were used in a molecular design of azo-chromophore monomers with enhanced second order nonlinear optical (NLO) properties: octafluorobiphenyl (OFB) and tetrafluorobenzene (TFB) ones. Polymerization of the monomers was performed to obtain polyurethanes with azo-chromophores in the main chain. Comparison of physical and optical properties of these polymers reveals that the main factor influencing the observed NLO activity of the latter is the inherent isomery of the macromolecular chains rather than a variation of the structure of electron-accepting groups. (C) 2013 Elsevier Ltd. All rights reserved.