4,7-bis(phenylamino)-2,1,3-benzothiadiazole | 507236-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis(phenylamino)-2,1,3-benzothiadiazole
• 英文别名: 4-N,7-N-diphenyl-2,1,3-benzothiadiazole-4,7-diamine
• CAS: 507236-61-5
• 化学式: C₁₈H₁₄N₄S
• 分子量: 318.402
• InChiKey: BEFZOPGOCSYNJD-UHFFFAOYSA-N

物化性质

• 沸点：
  535.8±30.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-bis(phenylamino)-2,1,3-benzothiadiazole 在 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 12.0h， 生成 N,N'''-Diphenyl-benzene-1,2,3,4-tetraamine
  参考文献：
  名称：

  Synthesis and Characterization of p-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit

  摘要：

  Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles 1-3 were synthesized by palladium-catalyzed amination. Quinoxalines 4-6 were prepared by palladium-catalyzed amination or transformation from the benzothiadiazoles. These compounds showed a HOMO-LUMO gap smaller than those of their analogues such as thiophene-substituted BT/QXs. Cyclic voltammetry revealed that the electrochemical behavior is dependent on the position of the acceptor heterocycle. Chemical oxidation with Ag2O afforded the corresponding 1,4-quinonediimine derivatives as an E,E-isomer, stereoselectively. As for the BT pentamer analogues 2 and 3, the first oxidation selectively occurred at the amino group adjacent to the benzothiadiazole unit, giving the regiospecific half-oxidized derivatives. Furthermore, the fully oxidized derivative 24 was isolated and characterized.

  DOI：

  10.1021/jo048324j
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 苯胺 在 palladium diacetate 双(2-二苯基磷苯基)醚 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 27.0h， 以91%的产率得到4,7-bis(phenylamino)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Synthesis and Characterization of p-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit

  摘要：

  Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles 1-3 were synthesized by palladium-catalyzed amination. Quinoxalines 4-6 were prepared by palladium-catalyzed amination or transformation from the benzothiadiazoles. These compounds showed a HOMO-LUMO gap smaller than those of their analogues such as thiophene-substituted BT/QXs. Cyclic voltammetry revealed that the electrochemical behavior is dependent on the position of the acceptor heterocycle. Chemical oxidation with Ag2O afforded the corresponding 1,4-quinonediimine derivatives as an E,E-isomer, stereoselectively. As for the BT pentamer analogues 2 and 3, the first oxidation selectively occurred at the amino group adjacent to the benzothiadiazole unit, giving the regiospecific half-oxidized derivatives. Furthermore, the fully oxidized derivative 24 was isolated and characterized.

  DOI：

  10.1021/jo048324j

文献信息

• Substituent Effect on the Structure and Photophysical Properties of Phenylamino- and Pyridylamino-2,1,3-Benzothiadiazoles
  作者：T. S. Sukhikh、R. M. Khisamov、D. A. Bashirov、L. M. Kovtunova、N. V. Kuratieva、S. N. Konchenko

  DOI：10.1134/s0022476619100135

  日期：2019.10

  4-Bromo-7-phenylamino-2,1,3-benzothiadiazole (1) and 4-bromo-7-(3-pyridylamino)-2,1,3-benzo thiadiazole (2) are synthesized. Their crystal structure and photophysical properties are studied in comparison with the known phenylamino- and pyridylamino-derivatives of 2,1,3-benzothiadiazole. It is found that the aryl substituent and noncovalent interactions affect the absorption band positions and emission

  合成了 4-溴-7-苯基氨基-2,1,3-苯并噻二唑 (1) 和 4-溴-7-(3-吡啶氨基)-2,1,3-苯并噻二唑 (2)。将它们的晶体结构和光物理性质与已知的 2,1,3-苯并噻二唑的苯基氨基和吡啶氨基衍生物进行比较研究。发现芳基取代基和非共价相互作用影响固体和溶液中的吸收带位置和发射。结果表明，在化合物 1 和 2 的多晶样品的机械作用下，发射带发生了低色移，这表明非共价分子间相互作用减弱。
• Synthesis and characterization of p-phenylenediamine derivatives bearing a thiadiazole unit
  作者：Mendra T.S. Ritonga、Hidehiro Sakurai、Toshikazu Hirao

  DOI：10.1016/s0040-4039(02)02315-8

  日期：2002.12

  New p-phenylenediamine derivatives bearing a thiadiazole unit were synthesized by palladium-catalyzed amination. Cyclic voltammetry revealed that the electrochemical properties depend on the position of the benzothiadiazole ring. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and Characterization of <i>p</i>-Phenylenediamine Derivatives Bearing an Electron-Acceptor Unit
  作者：Hidehiro Sakurai、Mendra T. S. Ritonga、Harumi Shibatani、Toshikazu Hirao

  DOI：10.1021/jo048324j

  日期：2005.4.1

  Two series of aniline oligomers bearing fused heterocycles as an electron-acceptor unit were synthesized. They consist of aniline or its derivatives as an electron donor and benzothiadiazole (BT) or quinoxaline (QX) as an electron-acceptor unit. Benzothiadiazoles 1-3 were synthesized by palladium-catalyzed amination. Quinoxalines 4-6 were prepared by palladium-catalyzed amination or transformation from the benzothiadiazoles. These compounds showed a HOMO-LUMO gap smaller than those of their analogues such as thiophene-substituted BT/QXs. Cyclic voltammetry revealed that the electrochemical behavior is dependent on the position of the acceptor heterocycle. Chemical oxidation with Ag2O afforded the corresponding 1,4-quinonediimine derivatives as an E,E-isomer, stereoselectively. As for the BT pentamer analogues 2 and 3, the first oxidation selectively occurred at the amino group adjacent to the benzothiadiazole unit, giving the regiospecific half-oxidized derivatives. Furthermore, the fully oxidized derivative 24 was isolated and characterized.