2,4,6-triaminophenol | 609-24-5

• 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: 2,4,6-triaminophenol
• CAS: 609-24-5
• 化学式: C₆H₉N₃O
• mdl: MFCD19203412
• 分子量: 139.157
• InChiKey: SUYLOMATYCPVFT-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±45.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.3
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4,6-triaminophenol 、 苯甲酰氯 在 sodium hydroxide 作用下， 生成 1,3,5-tris-benzoylamino-2-benzoyloxy-benzene
  参考文献：
  名称：

  Hinsberg; v.Udranszky, Justus Liebigs Annalen der Chemie, 1889, vol. 254, p. 256

  摘要：

  DOI：
• 作为产物：
  描述：

  特屈儿 在 盐酸 、 tin 作用下， 生成 2,4,6-triaminophenol
  参考文献：
  名称：

  van Romburgh, Recueil des Travaux Chimiques des Pays-Bas, 1883, vol. 2, p. 111

  摘要：

  DOI：

文献信息

• Switchable Bifunctional Bistate Reusable ZnO–Cu for Selective Oxidation and Reduction Reaction
  作者：Kasturi Sarmah、Subhamoy Mukhopadhyay、Tarun K. Maji、Sanjay Pratihar

  DOI：10.1021/acscatal.8b03785

  日期：2019.1.4

  copper loaded zinc oxide (ZnO–Cu) for its stimuli (O2/light) responsive switchable performance between its reduced (S-1) and oxidized (S-2) state for two antagonistic reactions, namely oxidation of alkyl arenes/heteroarenes to aldehydes/ketones and reduction of nitro arenes/heteroarenes to corresponding amines. The two states of the catalyst showed its switchable performance as highly active and poorly

  在这里，我们公开了利用铜负载的氧化锌（ZnO-Cu）在两个还原反应（即氧化）的还原（S-1）和氧化（S-2）状态之间的刺激（O 2 /光）响应可转换性能。将烷基芳烃/杂芳烃还原为醛/酮，并将硝基芳烃/杂芳烃还原为相应的胺。催化剂的两种状态均显示出其可切换的性能，即用于氧化和还原的高活性和低活性催化剂，并且通过改变刺激（光和O 2 / N 2），两个反应都可以“关闭”和“打开”。）。发现状态之间的转换效率及其相对反应性在各种反应条件下均保持一致，并且无论氧化还原顺序（反之亦然）和反应中使用的底物如何，都保持不变。光催化剂（S-1和S-2）表现出良好的催化活性，多种可重复使用性，广泛的底物范围以及对两种反应均具有合理的官能团耐受性，并在大规模应用中探索了其质量性能。该系统被用于辅助串联催化装置中，用于通过催化状态之间的刺激响应切换而利用氧化和还原反应两者来合成苄胺。
• NaBH₄/Charcoal: A New Synthetic Method for Mild and Convenient Reduction of Nitroarenes
  作者：Behzad Zeynizadeh、Davood Setamdideh

  DOI：10.1080/00397910600764709

  日期：2006.9

  Abstract NaBH4 in the presence of charcoal (0.4–0.8 g) reduces varieties of nitroarenes to their corresponding amines. Reduction reactions were carried out in a mixture of H2O‐THF (1:0.5 mL) at 50–60°C with high to excellent yields of products.

  摘要 NaBH4 在木炭 (0.4–0.8 g) 存在下将各种硝基芳烃还原为相应的胺。还原反应在 H2O-THF (1:0.5 mL) 的混合物中在 50–60°C 下进行，产物的产率很高。
• Catalytic hydrogenation of nitrophenols and nitrotoluenes over a palladium/graphene nanocomposite
  作者：Jingwen Sun、Yongsheng Fu、Guangyu He、Xiaoqiang Sun、Xin Wang

  DOI：10.1039/c4cy00048j

  日期：——

  A plausible mechanism for the reduction of p-nitrophenol catalyzed by a Pd/G catalyst in the presence of sodium borohydride.

  一种可能的机制是在钯/石墨烯催化剂存在的情况下，通过硼氢化钠催化对硝基苯酚的还原。
• In situ formed metal nanoparticle systems for catalytic reduction of nitroaromatic compounds
  作者：Xiao-Qiong Wu、Xing-Wen Wu、Jiang-Shan Shen、Hong-Wu Zhang

  DOI：10.1039/c4ra07494g

  日期：——

  Developing robust and facile catalytic systems for converting nitroaromatic compounds to NH2-containing compounds are of importance to decrease or even eliminate their toxicity or risk in the environment. In view of in situ formed metal nanoparticles, the metal ion (Cu2+, Ag+, AuCl4−, Co2+ and Ni2+)/NaBH4 systems were employed to catalyze the reduction reaction of nitroaromatic compounds. By employing the reduction of 4-nitrophenol (4-NP) to 4-aminophenol (4-AP) as a model reaction, the effects of concentration of NaBH4, 4-NP and metal ions on the rate constants of the catalytic reduction reactions were systematically investigated. Apparent activation energies of these metal ion/NaBH4 catalytic systems were further measured and compared. In situ formed metal NPs could be characterized by X-ray diffraction (XRD) and transmission electron microscopy (TEM). Furthermore, these metal ion/NaBH4 systems were successfully employed to catalyze the reduction reaction of a series of other nitroaromatic compounds. These metal ion/NaBH4 catalytic systems investigated in this protocol are simple and do not require the preparation of metal nanoparticles in advance, compared with previous related reports.

  开发强健且简便的催化体系，将硝基芳香化合物转化为含NH2的化合物，对于降低甚至消除它们在环境中的毒性或风险具有重要意义。鉴于原位形成的金属纳米颗粒，采用了金属离子（Cu2+、Ag+、AuCl4−、Co2+和Ni2+）/NaBH4体系来催化硝基芳香化合物的还原反应。通过以4-硝基苯酚（4-NP）还原为4-氨基苯酚（4-AP）为模型反应，系统地研究了NaBH4、4-NP和金属离子浓度对催化还原反应速率常数的影响。进一步测量并比较了这些金属离子/NaBH4催化体系的表观活化能。原位形成的金属NPs可以通过X射线衍射（XRD）和透射电子显微镜（TEM）进行表征。此外，这些金属离子/NaBH4体系成功地用于催化一系列其他硝基芳香化合物的还原反应。与之前的相关报道相比，本研究所调查的这些金属离子/NaBH4催化体系简单，不需要提前制备金属纳米颗粒。
• One pot green synthesis of polyaniline coated gold nanorods and its applications
  作者：Sanjoy Mondal、Utpal Rana、Rama Ranjan Bhattacharjee、Sudip Malik

  DOI：10.1039/c4ra12080a

  日期：——

  Morphology controlled high aspect ratio worm-like polyaniline (PANI) layer coated Au-nanostructures (Au/PANI) have been successively synthesized by in situ polymerisation techniques using aniline as a monomer with HAuCl4 as an oxidising agent in the absence and presence of citric acid (CA). Synthesized composites were characterized by HRTEM, FESEM, XRD, XPS, UV-vis and FTIR study. Spherical morphologies are seen in the absence of CA and Au nanoparticles are coated by a PANI thin layer with ∼30 nm thickness. In the presence of CA, as well as depending upon the CA to aniline molar ratio, morphology varies from irregular assembly to regular fiber to spherical-like nanostructures. The nanostructures show fibrous morphology with an average diameter of ∼100 nm and lengths of more than 5 μm when CA to aniline molar ratios are 1.0 and 0.2. When the ratios are 2.0 and 0.1, the nanostructure represents the granular-like morphology. Nanofiber formation takes place by the assembly of the CA capped tiny Au-nanorods in the presence of aniline during the polymerisation, and all Au-nanorods are finely coated by a PANI thin layer of ∼5 nm thickness. Importantly, fibrous Au/PANI nanostructures show superior catalytic activity compared to spherical/irregular Au/PANI nanostructures towards the reduction of toxic aromatic nitro compounds like 4-nitrophenol (4-NP), 4-nitroaniline (4-NA), 2,4-dinitrophenol (2,4-DNP) and 2,4,6-trinitrophenol (2,4,6-TNP). This is because of the coating thickness of PANI over Au-nanoparticles in fibrous Au/PANI nanostructures as well as enhanced surface area.

  通过原位聚合技术，利用苯胺作为单体，HAuCl4作为氧化剂，在柠檬酸（CA）存在或不存在的情况下，成功合成了形态学调控的具有高纵横比蠕虫状聚苯胺（PANI）层包覆的金纳米结构（Au/PANI）。合成的复合材料通过HRTEM、FESEM、XRD、XPS、UV-vis和FTIR进行了表征。在无CA存在时，观察到球形形态，金纳米粒子被厚度约为30 nm的PANI薄层包覆。在CA存在的情况下，以及根据CA与苯胺的摩尔比，形态从无规则集合体变为规则纤维，再到类球形纳米结构。当CA与苯胺的摩尔比为1.0和0.2时，纳米结构呈现纤维状形态，平均直径约为100 nm，长度超过5 μm。当摩尔比为2.0和0.1时，纳米结构呈现颗粒状形态。纳米纤维的形成是通过CA包覆的微小金纳米棒在苯胺存在的聚合过程中组装而成的，所有金纳米棒都被厚度约为5 nm的PANI薄层精细包覆。重要的是，与球形/不规则的Au/PANI纳米结构相比，纤维状Au/PANI纳米结构对有毒芳香族硝基化合物如4-硝基酚（4-NP）、4-硝基苯胺（4-NA）、2,4-二硝基酚（2,4-DNP）和2,4,6-三硝基酚（2,4,6-TNP）的还原表现出更优越的催化活性。这是因为纤维状Au/PANI纳米结构中PANI在金纳米粒子上的包覆厚度以及增强的表面积所致。