Tetraethyl (2,5-dihydroxy-1,4-phenylene)bis(phosphonate) | 91633-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Tetraethyl (2,5-dihydroxy-1,4-phenylene)bis(phosphonate)
• 英文别名: tetraethyl(2,5-dihydroxy-1,4-phenylene)diphosphonate；2,5-bis(diethoxyphosphoryl)hydroquinone；2,5-Bis(diethoxyphosphoryl)benzene-1,4-diol
• CAS: 91633-15-7
• 化学式: C₁₄H₂₄O₈P₂
• 分子量: 382.287
• InChiKey: GRGBMHYVALEYJC-UHFFFAOYSA-N

物化性质

• 沸点：
  498.9±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  Tetraethyl (2,5-dihydroxy-1,4-phenylene)bis(phosphonate) 在 盐酸 、 水 作用下， 反应 24.0h， 以90%的产率得到2,5-二羟基-1,4-苯二磷酸
  参考文献：
  名称：

  用于PEMFC的磷化全芳族聚醚

  摘要：

  已经合成了基于带有侧二膦酸酯基和二膦酸酯基的芳族聚醚的新均聚物和共聚物。这些合成的努力导致了热稳定性高但分子量适中的均聚物和共聚物。为了评估固定化的膦酸酯和膦酸部分对燃料电池应用的聚合物电解质膜的影响，制备了新合成的均聚物和共聚物与吡啶基芳香族聚醚的共混物。这些混合物可与高玻璃化转变温度和高热稳定性混溶。此外，与净基质相比，将这些基团引入聚合物主链显着提高了磷酸中的掺杂能力以及高掺杂水平的离子电导率。分级为4 +©2010 Wiley Periodicals，Inc.

  DOI：

  10.1002/pola.24055
• 作为产物：
  描述：

  四乙基1,4-亚苯基双(磷酸盐) 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以68%的产率得到Tetraethyl (2,5-dihydroxy-1,4-phenylene)bis(phosphonate)
  参考文献：
  名称：

  Phosphonated poly(arylene ether)s as potential high temperature proton conducting materials

  摘要：

  The preparation and characterization of new phosphonated polymeric ionomers based on a fully aromatic poly(arylene ether) backbone with applications as proton exchange membranes for fuel cell is reported. The high-molecular-weight polymers were obtained by the polycondensation of the phosphonated monomers with decafluorobiphenyl in high yields with inherent viscosities up to 0.58 dL g(-1). The hydrolysis of the phosphonated ester into phosphonic acid groups was carried out quantitatively under acidic conditions. The polymers were studied by TGA after hydrolysis and showed10% weight loss above 430 degrees C. Membranes with total ion-exchange capacities above 6 meq/g showed proton conductivities of approximately92 mS/cm at 25 degrees C and 100% relative humidity increasing to ca.150 mS/cm at 140 degrees C. Their conductivity under dry condition showed values over 2 mS/cm at 120 degrees C which upon doping with phosphoric acid jumped to nearly 100 mS/cm. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.08.020

文献信息

• Highly Selective 1,4- and 1,6-Addition of P(O)H Compounds to<i>p</i>-Quinones: A Divergent Method for the Synthesis of<i>C</i>- and<i>O</i>-Phosphoryl Hydroquinone Derivatives
  作者：Biquan Xiong、Ruwei Shen、Midori Goto、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1002/chem.201202074

  日期：2012.12.21

  functionality. Further studies on these reactions by using optically active H‐phosphinates showed that all addition reactions took place stereospecifically with retention of configuration at the phosphorus center. The findings lead to the establishment of a divergent method for the synthesis of C‐ and O‐phosphoryl hydroquinone derivatives from easily available P(O)H compounds.

  P的反应（O） H的化合物与p -quinones可以继续通过任1,4-或通过使用不同的添加剂，以1,6-加成途径选择性地得到良好的收率相应C-和O-磷酰基氢醌衍生物。P（O）H化合物向p的氧化双1,4-加成还可以通过调节溶剂来获得对苯二酚，从而轻松合成具有磷官能团的双取代对苯二酚。通过使用旋光性H-次膦酸酯对这些反应的进一步研究表明，所有加成反应均发生立体定向，并且在磷中心保留了构型。这些发现导致建立了一种从容易获得的P（O）H化合物合成C-和O-磷酰基氢醌衍生物的方法。
• Synthesis and Characterization of New Ortho-Acetyl or Ortho-bis- p -aminophenoxy Phosphonate Monomers
  作者：G. A. Consiglio、S. Failla、P. Finocchiaro、V. Siracusa

  DOI：10.1080/10426500214564

  日期：2002.11.1

  Some new aryl phosphonic acid ethyl ester analogs of acetyl salicylic acids, and bis- p -aminophenoxy-benzo-phosphonic acid ethyl esters have been prepared in good yield. Characterization by spectroscopic techniques indicates that in the phosphorus NMR spectra a significant change in chemical shift values between the starting phenolic phosphonate and both the corresponding derivative is observed; thus

  一些新的乙酰水杨酸的芳基膦酸乙酯类似物和双-对-氨基苯氧基-苯并-膦酸乙酯已经以良好的收率制备。光谱技术表征表明，在磷 NMR 光谱中，观察到起始酚膦酸酯和相应衍生物之间的化学位移值发生显着变化；因此，这种场上移对于此类化合物非常具有诊断意义。
• Copper‐Catalyzed Cross‐Dehydrogenative Phosphorylation of 2‐Amino‐1,4‐naphthoquinones with <i>H</i> ‐Phosphonates
  作者：Fang Yang、Qiuju Zhou、Heyan Wang、Lin Tang

  DOI：10.1002/ejoc.202100870

  日期：2021.11.8

  AbstractAs a simple and efficient system, Cu(OAc)2 ⋅ H2O and K2S2O8 can activate H‐phosphonates to produce the corresponding dialkyl phosphoryl radicals. The obtained dialkyl phosphoryl radicals react smoothly with 2‐amino‐1,4‐naphthoquinones, affording accurate preparation of various phosphoryl‐functionalized 2‐amino‐1,4‐naphthoquinones. The developed copper‐catalyzed cross‐dehydrogenative phosphorylation features broad substrate scope, easily available reagents, high atom economy and operational simplicity, which enables a practical avenue for C−P bond formation.
• Phosphorus Can Also Be a “Photocopy”
  作者：Marlena P. Washington、Vittal B. Gudimetla、Feng L. Laughlin、Nihal Deligonul、Susan He、John L. Payton、M. Cather Simpson、John D. Protasiewicz

  DOI：10.1021/ja1009426

  日期：2010.4.7

  The syntheses of benzoxaphospholes and new benzobisoxaphospholes that display blue fluorescence are presented. The latter compounds were accessed by the use of a new precursor, 2,5-diphosphinohydroquinone. The new compounds were fully characterized, including a structural study of 2,6-tert-butylbenzo[1,2-d;4,5-d']bisoxaphosphole. Quantum yields for photoluminescence were determined for a series of compounds. These materials feature bona fide P=C p-p pi bonds suitable for conjugated materials having phosphorus as a participatory atom and can thus "photocopy" the properties of other conjugated organic molecules.
• o-Hydroxyaryl diphosphonic acids
  作者：Balram Dhawan、Derek Redmore

  DOI：10.1021/jo00195a029

  日期：1984.10