2,3-dibromomethyl-pyrazino[2,3-b]phenazine | 256377-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-dibromomethyl-pyrazino[2,3-b]phenazine
• 英文别名: 2,3-bis(bromomethyl)pyrazino[2,3-b]phenazine；2,3-Dibromomethyl-pyrazino[2,3-b]phenazine
• CAS: 256377-46-5
• 化学式: C₁₆H₁₀Br₂N₄
• 分子量: 418.09
• InChiKey: NEOWFZRUADEIGE-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C
• 沸点：
  543.4±45.0 °C(predicted)
• 密度：
  1.869±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 2,3-dibromomethyl-pyrazino[2,3-b]phenazine 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以32%的产率得到2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine
  参考文献：
  名称：

  On the Synthesis of Pyrazino[2,3-b]phenazine and 1H-Imidazo[4,5-b]phenazine Derivatives

  摘要：

  Several pyrazino[2,3-D]phenazine derivatives were prepared by the reaction of 2,3-diaminophenazine with different 1,2-diketones. Nucleophilic substitution of 2,3-dibromomethyl-pyrazino[2,3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 2,3-bis(propoxymethyl)-pyrazino[2,3-b]phenazine 2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine, and 2,3-bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazine. 2-Aryl-1H-imidazo[4,5-b]phenazine derivatives were synthesized by a one-pot reaction of 1,3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2,3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo[4,5-b]phenazine and 2-methyl-1H-imidazo[4,5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds are presented.

  DOI：

  10.1007/pl00010183
• 作为产物：
  描述：

  2,3-二氨基吩嗪 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 29.0h， 生成 2,3-dibromomethyl-pyrazino[2,3-b]phenazine
  参考文献：
  名称：

  On the Synthesis of Pyrazino[2,3-b]phenazine and 1H-Imidazo[4,5-b]phenazine Derivatives

  摘要：

  Several pyrazino[2,3-D]phenazine derivatives were prepared by the reaction of 2,3-diaminophenazine with different 1,2-diketones. Nucleophilic substitution of 2,3-dibromomethyl-pyrazino[2,3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 2,3-bis(propoxymethyl)-pyrazino[2,3-b]phenazine 2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine, and 2,3-bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazine. 2-Aryl-1H-imidazo[4,5-b]phenazine derivatives were synthesized by a one-pot reaction of 1,3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2,3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo[4,5-b]phenazine and 2-methyl-1H-imidazo[4,5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds are presented.

  DOI：

  10.1007/pl00010183

文献信息

• Exploration of the Photodegradation of Naphtho[2,3-<i>g</i> ] quinoxalines and Pyrazino[2,3-<i>b</i> ]phenazines
  作者：Nicole Kolmer-Anderl、Andreas Kolmer、Christina M. Thiele、Matthias Rehahn

  DOI：10.1002/chem.201504453

  日期：2016.4.4

  photostability and the degradation pathways of the naphtho[2,3‐g]quinoxalines and pyrazino[2,3‐b]phenazines are explored by NMR spectroscopy of irradiated samples affirming the large influence of the nitrogen atoms in the acene core on the degradation process during the irradiation. Finally, by identifying the degradations products of 2,3‐dimethylnaphtho[2,3‐g]quinoxaline it is possible to track down the most

  含氮多环芳烃是有机电子应用中非常有吸引力的化合物。它们较低的LUMO能量表明它有可能用作n型半导体。此外，期望它们在环境条件下更稳定，这对于需要高纯度材料的半导体膜的形成非常重要。在这项研究中，萘并[2,3- g ]喹喔啉和吡嗪并[2,3- b ]的合成]吩嗪是通过使用反应条件提供的，该条件可高产率，高纯度且无需耗时的纯化步骤即可提供所需的产物。通过循环伏安法和UV / Vis光谱法研究了化合物的HOMO和LUMO能量，并研究了它们对氮含量和末端取代基的依赖性。核磁共振波谱分析了辐照样品中萘并[2,3- g ]喹喔啉和吡嗪并[2,3- b ]吩嗪的光稳定性和降解途径，确认并苯核心中氮原子对降解的影响很大。辐照过程中。最后，通过确定2,3-二甲基萘的降解产物[2,3- g喹喔啉可以追踪化合物中最活泼的位置，并通过用氮封闭该位置来显着提高光稳定性。
• Semiconductor composition comprising an inorganic semiconducting material and an organic binder
  申请人：Merck Patent GmbH

  公开号：US10326090B2

  公开（公告）日：2019-06-18

  The present invention relates to a semiconductor composition including an inorganic semiconducting material and an organic binder. The present invention further relates to an electronic device comprising a semiconducting layer consisting of such semiconductor composition.

  本发明涉及一种半导体组合物，包括一种无机半导体材料和一种有机粘合剂。本发明还涉及一种电子装置，该装置包括由这种半导体组合物构成的半导体层。
• Semiconductor Composition Comprising an Inorganic Semiconducting Material and an Organic Binder
  申请人：Merck Patent GmbH

  公开号：US20170309848A1

  公开（公告）日：2017-10-26

  The present invention relates to a semiconductor composition comprising an inorganic semiconducting material and an organic binder. The present invention further relates to an electronic device comprising a semiconducting layer consisting of such semiconductor composition.