azoxybenzene-4,4'-dicarboxylic acid | 115325-88-7

• 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: azoxybenzene-4,4'-dicarboxylic acid
• 英文别名: 4,4'-dicarboxyazoxybenzene；4,4′-azoxydibenzoic acid；4,4’-azoxydibenzoic acid；Azoxybenzol-4,4'-dicarbonsaeure；4,4'-Dicarboxy-azoxy-benzol；Benzoic acid, 4,4'-azoxybis-；(4-carboxyphenyl)-(4-carboxyphenyl)imino-oxidoazanium
• CAS: 115325-88-7
• 化学式: C₁₄H₁₀N₂O₅
• 分子量: 286.244
• InChiKey: ZYVHVGJGLOEEKD-UHFFFAOYSA-N

物化性质

• 沸点：
  562.5±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  azoxybenzene-4,4'-dicarboxylic acid 在 硫酸 作用下， 反应 0.33h， 以0.18 g的产率得到4-(4-羟基苯偶氮基)苯甲酸
  参考文献：
  名称：

  一些 4,4'-二取代偶氮苯的 Wallach 重排

  摘要：

  用硫酸处理在 4,4'-位带有吸电子取代基的偶氮苯得到相应的 2-羟基偶氮苯和 4'-取代的 4-羟基偶氮苯。用对甲苯磺酸和乙酸酐处理 4,4'-二甲氧基偶氮苯，得到 4,4'-二甲氧基-3-乙酰氧基偶氮苯和 4,4'-二甲氧基-2-甲苯磺酰氧基偶氮苯作为主要重排产物。

  DOI：

  10.1246/bcsj.56.643
• 作为产物：
  描述：

  对硝基苯甲酸乙酯 在 sodium n-propoxide 、 苯 作用下， 生成 azoxybenzene-4,4'-dicarboxylic acid
  参考文献：
  名称：

  THE REDUCTION OF AROMATIC NITRO AND NITROSO COMPOUNDS WITH SODIUM ALCOHOLATES. II.

  摘要：

  DOI：

  10.1021/ja01357a050

文献信息

• A functionalized metal–organic framework decorated with O⁻ groups showing excellent performance for lead(<scp>ii</scp>) removal from aqueous solution
  作者：Caixia Yu、Zhichao Shao、Hongwei Hou

  DOI：10.1039/c7sc03308g

  日期：——

  A novel MOF decorated with O⁻ groups was elaborately constructed and showed excellent performance for Pb²⁺ removal.

  一种新型MOF被精心构建并点缀了O−基团，显示出对Pb2+移除的卓越性能。
• Ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives with trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane catalyzed by Preyssler acid-mediated nano-TiO2
  作者：Davood Azarifar、Seyed-Mola Khatami、Zohreh Najminejad

  DOI：10.1007/s13738-013-0328-z

  日期：2014.4

  Preyssler-type heteropolyacid supported on TiO2 nanoparticles has been explored as an efficient catalyst in selective oxidation of primary aromatic amines to azoxy derivatives using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as oxidant. The reactions proceeded smoothly under mild and green ultrasound-accelerated conditions to afford the products in high yields. The catalyst recovered from the reaction mixture exhibits long-term stability with no significant drop in its catalytic activity. .

  以TiO2纳米粒子为载体的Preyssler型杂多酸已被探索作为高效催化剂，用于在温和且环保的超声加速条件下，使用反式3,5-二氢过氧-3,5-二甲基-1,2-二恶烷作为氧化剂，将伯芳香胺选择性氧化为偶氮氧衍生物。反应在温和条件下顺利进行，产率极高。从反应混合物中回收的催化剂显示出长期的稳定性，其催化活性没有显著下降。
• Nb₂O₅ supported on mixed oxides catalyzed oxidative and photochemical conversion of anilines to azoxybenzenes
  作者：Gustavo Senra Gonçalves De Carvalho、Luciano Honorato Chagas、Carla Grijó Fonseca、Pedro Pôssa de Castro、Antônio Carlos Sant’Ana、Alexandre Amaral Leitão、Giovanni Wilson Amarante

  DOI：10.1039/c9nj00625g

  日期：——

  The synthesis of novel supported niobium oxide catalysts and their application for aniline conversion to azoxybenzenes is described. The catalysts were successfully prepared by thermal decomposition of layered double hydroxides (LDHs), containing M2+ (M = Mg2+ and/or Zn2+) and Al3+ as layer cations, followed by niobium oxide incorporation employing the wetness impregnation method. These catalysts were

  描述了新型的负载型氧化铌催化剂的合成及其在苯胺转化为a氧基苯中的应用。通过热分解含M 2+（M = Mg 2+和/或Zn 2+）和Al 3+的层状双氢氧化物（LDHs），成功制备了催化剂。作为层阳离子，然后采用湿法浸渍法掺入氧化铌。这些催化剂通过实验技术和理论计算均得到了充分表征，然后成功地用于将苯胺选择性转化为a氧基苯衍生物，在紫光存在下，转化率高达98％，分离产率为92％。对照实验和DFT计算表明，该催化剂在该转化中具有双重作用，在氧化步骤中既充当路易斯酸，又在亚硝基苯中间体的二聚作用中充当光催化剂。
• An Easy Access to Aromatic Azo Compounds under Ultrasound/Microwave Irradiation
  作者：Giancarlo Cravotto、Luisa Boffa、Marco Bia、Werner Bonrath、Massimo Curini、Georgios Heropoulos

  DOI：10.1055/s-2006-951481

  日期：2006.9

  Chemoselective reduction of nitroarenes to azo and azoxy compounds was easily achieved using zinc powder and ­ammonium chloride in DMF or DMF-water (95:5) under high intensity ultrasound (US) or microwave (MW) irradiation, separately or combined. When carried out under conventional heating the reaction required much higher temperatures and gave lower yields. The addition of a small amount of water caused a dramatic increase in the reactivity, permitting the reduction of hindered nitroarenes at the expense of selectivity. A novel reactor for combined US/MW ­irradiation was employed which demonstrated additional beneficial effects.

  利用锌粉和氯化铵在DMF或DMF-水（95:5）中，在高强度超声（US）或微波（MW）辐照下，分别或结合地很容易实现对硝基芳烃的化学选择性还原成偶氮和偶氮氧化物。当在常规加热下进行反应时，需要更高的温度且产率较低。添加少量水显著提高了反应性，使得在牺牲选择性的情况下可以还原受阻的硝基芳烃。采用了一种新型反应器用于联合US/MW辐照，显示出额外的有益效果。
• Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water
  作者：Yufang Liu、Bo Liu、Ailing Guo、Zhenming Dong、Shuo Jin、Yun Lu

  DOI：10.3390/molecules16053563

  日期：——

  The synthesis of the azoxybenzenes by the reduction of nitroarenes with reducing agent potassium borohydride in water was reported for the first time. PEG-400 was used as a phase transfer catalyst and could effectively catalyze the reduction. The electronic effects of substituent groups play an important role in determining the reduction efficiencies. Electron-withdrawing substituents promote the formation

  首次报道了还原剂硼氢化钾在水中还原硝基芳烃合成偶氮苯类化合物。PEG-400 用作相转移催化剂，可以有效地催化还原。取代基的电子效应在决定还原效率方面起着重要作用。吸电子取代基促进氧化偶氮苯产物的形成，而放电子基团根据其给电子能力的程度不同程度地阻止还原。