3,4-dibromo-o-phenylenediamine | 1380415-19-9

• 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: 3,4-dibromo-o-phenylenediamine
• 英文别名: Dibrom-Ortho-Phenylendiamin；3,4-dibromobenzene-1,2-diamine
• CAS: 1380415-19-9
• 化学式: C₆H₆Br₂N₂
• 分子量: 265.935
• InChiKey: JIVQZEYXNZTAEM-UHFFFAOYSA-N

物化性质

• 沸点：
  327.7±37.0 °C(Predicted)
• 密度：
  2.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dibromo-o-phenylenediamine 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 4,5-dibromobenzotriazole
  参考文献：
  名称：

  Synthesis and Physico-Chemical Properties in Aqueous Medium of All Possible Isomeric Bromo Analogues of Benzo-1H-Triazole, Potential Inhibitors of Protein Kinases

  摘要：

  In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2 alpha, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK(a) values for dissociation of the triazole proton. Experimental data (pK(a), solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2 alpha. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.

  DOI：

  10.1021/jp301561x
• 作为产物：
  描述：

  4,5-dibromo-2,1,3-benzothiadiazole 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 3,4-dibromo-o-phenylenediamine
  参考文献：
  名称：

  Synthesis and Physico-Chemical Properties in Aqueous Medium of All Possible Isomeric Bromo Analogues of Benzo-1H-Triazole, Potential Inhibitors of Protein Kinases

  摘要：

  In ongoing studies on the role of the individual bromine atoms of 4,5,6,7-tetrabromobenzotriazole (TBBt) in its relatively selective inhibition of protein kinase CK2 alpha, we have prepared all the possible two mono-, four di-, and two tri-bromobenzotriazoles and determined their physicochemical properties in aqueous medium. They exhibited a general trend of a decrease in solubility with an increase in the number of bromines on the benzene ring, significantly modulated by the pattern of substitution. For a given number of attached bromines, this was directly related to the electronic effects resulting from different sites of substitution, leading to marked variations of pK(a) values for dissociation of the triazole proton. Experimental data (pK(a), solubility) and ab initio calculations demonstrated that hydration of halogenated benzotriazoles is driven by a subtle balance of hydrophobic and polar interactions. The combination of QM-derived free energies for solvation and proton dissociations was found to be a reasonably good predictor of inhibitory activity of halogenated benzotriazoles vs CK2 alpha. Since the pattern of halogenation of the benzene ring of benzotriazole has also been shown to be one of the determinants of inhibitory potency vs some viruses and viral enzymes, the present comprehensive description of their physicochemical properties should prove helpful in efforts to elucidate reaction mechanisms, including possible halogen bonding, and the search for more selective and potent inhibitors.

  DOI：

  10.1021/jp301561x

文献信息

• Substituted benzazoloporphyrazines for polymerization and surface attachment and articles formed therefrom
  申请人：Youngblood W. Justin

  公开号：US20110015388A1

  公开（公告）日：2011-01-20

  The present invention provides an article of manufacture formed from a substrate and a benzazoloporphyrazine bound to the substrate. The article may take a variety of different forms and may be for example an electrochromic display, a molecular capacitor, a battery, a solar cell, or a molecular memory device. Methods of making such articles, along with compounds, methods and intermediates useful for making such benzazoloporphyrazines, are also described.

  本发明提供了一种由基板和与基板结合的苯并咔唑卟啉制成的制品。该制品可以采用各种不同形式，例如电致变色显示器、分子电容器、电池、太阳能电池或分子存储器件。还描述了制造这种制品的方法，以及用于制造这种苯并咔唑卟啉的化合物、方法和中间体。
• [EN] AZABORININE DERIVATIVES, THEIR SYNTHESIS AND USE IN ORGANIC ELECTRONIC DEVICES<br/>[FR] DÉRIVÉS D'AZABORININE, LEUR SYNTHÈSE ET LEUR UTILISATION DANS DES DISPOSITIFS ÉLECTRONIQUES ORGANIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2015043722A1

  公开（公告）日：2015-04-02

  The present invention relates to azaborinine derivatives of formulae (l-1) or (I-2), their synthesis as well as their use in organic electronic devices, particularly in organic light emitting devices such as OLEDS, organic photovoltaic devices and organic photodetectors. The invention further relates to organic electronic devices comprising the present azaborinine derivatives in devices such as e.g. OFET.

  本发明涉及式（l-1）或（I-2）的氮硼杂环烯衍生物，其合成以及它们在有机电子器件中的应用，特别是在有机发光器件（如OLED）、有机光伏器件和有机光探测器中的应用。该发明还涉及包含本发明氮硼杂环烯衍生物的有机电子器件，例如OFET等器件。
• ORGANIC ELECTROLUMINESCENCE DEVICE AND POLYCYCLIC COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE
  申请人：SAMSUNG DISPLAY CO., LTD.

  公开号：US20200044159A1

  公开（公告）日：2020-02-06

  An organic electroluminescence device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, the emission layer including a condensed polycyclic compound of three or more six-membered rings, at least two six-membered rings among the six-membered rings including an electron donor moiety and an electron acceptor moiety at facing positions, respectively, the at least two six-membered rings not being immediately adjacent to each other, an electron transport region on the emission layer, and a second electrode on the electron transport region.

  一种有机电致发光器件包括第一电极，位于第一电极上的空穴传输区，位于空穴传输区上的发射层，该发射层包括三个或三个以上的六元环的缩合多环化合物，其中至少两个六元环中的六元环包括一个电子给体基团和一个电子受体基团，分别位于对面位置，至少两个六元环不直接相邻，发射层上有一个电子传输区，以及位于电子传输区上的第二电极。
• SUBSTITUTED BENZAZOLOPORPHYRAZINES FOR POLYMERIZATION AND SURFACE ATTACHMENT AND ARTICLES FORMED THEREFROM
  申请人：Youngblood W. Justin

  公开号：US20120101243A1

  公开（公告）日：2012-04-26

  The present invention provides an article of manufacture formed from a substrate and a benzazoloporphyrazine bound to the substrate. The article may take a variety of different forms and may be for example an electrochromic display, a molecular capacitor, a battery, a solar cell, or a molecular memory device. Methods of making such articles, along with compounds, methods and intermediates useful for making such benzazoloporphyrazines, are also described.

  本发明提供了一种由基底和结合在基底上的苯并咪唑卟啉制成的制品。该制品可以采取多种不同的形式，例如电致变色显示器、分子电容器、电池、太阳能电池或分子记忆装置等。还描述了制造这种制品的方法，以及用于制造这种苯并咪唑卟啉的化合物、方法和中间体。
• AZABORININE DERIVATIVES, THEIR SYNTHESIS AND USE IN ORGANIC ELECTRONIC DEVICES
  申请人：MERCK PATENT GMBH

  公开号：US20160248014A1

  公开（公告）日：2016-08-25

  The present invention relates to azaborinine derivatives their synthesis as well as their use in organic electronic devices, particularly in organic light emitting devices, organic photovoltaic devices and organic photodetectors. The invention further relates to organic electronic devices comprising the present azaborinine derivatives

  本发明涉及氮硼杂环衍生物及其合成，以及它们在有机电子器件中的应用，特别是在有机发光器件、有机光伏器件和有机光电探测器中的应用。本发明还涉及包含本发明氮硼杂环衍生物的有机电子器件。