5,6-二氰基-1H-苯并三唑 | 355435-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 中文名称: 5,6-二氰基-1H-苯并三唑
• 英文名称: 5,6-dicyano-1H-benzotriazole
• 英文别名: 1H-Benzotriazole-5,6-dicarbonitrile；2H-benzotriazole-5,6-dicarbonitrile
• CAS: 355435-70-0；447411-81-6
• 化学式: C₈H₃N₅
• 分子量: 169.145
• InChiKey: DOBRSOMSFCYWPN-UHFFFAOYSA-N

物化性质

• 沸点：
  596.4±35.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-二氰基-1H-苯并三唑 在 cobalt(II) acetate 、 尿素 作用下， 反应 1.0h， 以37%的产率得到
  参考文献：
  名称：

  摘要：

  Reactions of 4,5-diaminophthalodinitrile with thionyl chloride, sodium nitrite in concentrated sulfuric acid, and phenanthrenequinone gave, respectively, 5,6-dicyano-2,1,3-benzothiadiazole, 5,6-dicyano-1H-benzotriazole, and 6,7-dicyano-2,3-(9,10-phenanthro)quinoxaline, from which the corresponding cobalt porphyrazines were prepared. The effect of the heterocyclic moiety on the physicochemical and spectral properties of porphyrazines was elucidated.

  DOI：

  10.1023/a:1015406625722
• 作为产物：
  描述：

  4,5二胺基邻苯二氰 在 硫酸 、 sodium nitrite 作用下， 反应 2.0h， 以47%的产率得到5,6-二氰基-1H-苯并三唑
  参考文献：
  名称：

  摘要：

  Reactions of 4,5-diaminophthalodinitrile with thionyl chloride, sodium nitrite in concentrated sulfuric acid, and phenanthrenequinone gave, respectively, 5,6-dicyano-2,1,3-benzothiadiazole, 5,6-dicyano-1H-benzotriazole, and 6,7-dicyano-2,3-(9,10-phenanthro)quinoxaline, from which the corresponding cobalt porphyrazines were prepared. The effect of the heterocyclic moiety on the physicochemical and spectral properties of porphyrazines was elucidated.

  DOI：

  10.1023/a:1015406625722

文献信息

• Reactivity of Dehydrometallophthalocyanines and -porphyrazines
  作者：Sergei I. Vagin、Antje Frickenschmidt、Bernd Kammerer、Michael Hanack

  DOI：10.1002/chem.200601056

  日期：2007.1.12

  respectively, by oxidation with Pb(OAc)(4) in different solvents, for example, diethyl ether, tetrahydrofuran, acetic acid, and benzene. The reactivity of 2 and 8 a was studied in detail. These species not only easily undergo Diels-Alder additions with dienes, but also the used solvents can be added. Among the addition products with solvents ethoxy-, acetoxy-, acetoxybutyloxy-substituted and barrelen-fused

  脱氢酞菁锌2和脱氢​​苯并吡嗪锌8a分别由1N-氨基苯并三唑环化的酞菁锌1和苯并吡嗪锌8通过在不同溶剂（例如乙醚，四氢呋喃，乙酸和苯。详细研究了2和8 a的反应性。这些物质不仅容易与二烯进行Diels-Alder加成反应，而且还可以添加用过的溶剂。在具有溶剂的加成产物中，分离出乙氧基，乙酰氧基，乙酰氧基丁氧基取代的和桶状稠合的酞菁和苯并吡嗪。在2 a或8 a中均未观察到由两种脱氢物质的二聚作用产生的产物。
• MATERIALS HAVING ELECTRON DEFICIENT MOIETIES AND METHODS OF SYNTHESIZING THEREOF
  申请人：Georgia Tech Research Corporation

  公开号：US20150218115A1

  公开（公告）日：2015-08-06

  Various materials and polymers having electron deficient moieties and methods of synthesizing thereof are described herein. Specifically, a C—H bond activation method is disclosed wherein an electron deficient group having one or more activated C—H bonds is coupled to one or more aryl groups to afford materials or polymers which may be used in organic electronic and photonic applications.

  本文描述了具有电子亏损基团的各种材料和聚合物，以及它们的合成方法。具体来说，披露了一种C-H键活化方法，其中具有一个或多个活化的C-H键的电子亏损基团与一个或多个芳基偶联，以获得可用于有机电子和光子应用的材料或聚合物。
• Synthesis and Properties of an Unsymmetrical Triazole-Functionalized (Phthalocyaninato)zinc Complex
  作者：Sergej Vagin、Antje Frickenschmidt、Bernd Kammerer、Michael Hanack

  DOI：10.1002/ejoc.200500105

  日期：2005.8

  condensation of 2 and 4,5-bis(3,5-di-tert-butylphenoxy)phthalonitrile (3) with subsequent separation by column chromatography. The triazole-functionalized (phthalocyanine)zinc complex 5 shows interesting spectral properties in solutions depending on the chemical medium because of the reactions which are typical for the triazole fragment. These are acid ionization of NH, coordination to metal ions, N-alkylation

  5,6-二氰基-1H-1,2,3-苯并三唑(2)的合成得到显着简化，并提高了其总收率。这为 2 作为三唑官能化酞菁的前体的扩展用途开辟了可能性。其中之一，不对称的9,10,16,17,23,24-六(3,5-二叔丁基苯氧基)[1,2,3]三唑并[4,5-b]酞菁}-锌(5) 在 2 和 4,5-双(3,5-二-叔丁基苯氧基)邻苯二甲腈 (3) 的统计缩合中制备，随后通过柱色谱分离。由于三唑片段的典型反应，三唑官能化（酞菁）锌配合物 5 在溶液中显示出有趣的光谱特性，具体取决于化学介质。这些是 NH 的酸电离、与金属离子的配位、N-烷基化和 N-酰化等。使用 UV/Vis、1H 和 13C NMR 光谱、质谱 (MALDI-TOF) 和元素分析对化合物 5 进行了详细表征。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany
• Materials having electron deficient moieties and methods of synthesizing thereof
  申请人：Georgia Tech Research Corporation

  公开号：US09315477B2

  公开（公告）日：2016-04-19

  Various materials and polymers having electron deficient moieties and methods of synthesizing thereof are described herein. Specifically, a C—H bond activation method is disclosed wherein an electron deficient group having one or more activated C—H bonds is coupled to one or more aryl groups to afford materials or polymers which may be used in organic electronic and photonic applications.

  本文介绍了具有电子不足官能团和聚合物的各种材料及其合成方法。具体而言，本文揭示了一种C-H键活化方法，其中将具有一个或多个活性C-H键的电子不足基团与一个或多个芳基团偶联，以得到可用于有机电子和光子应用的材料或聚合物。
• C–H-Activated Direct Arylation of Strong Benzothiadiazole and Quinoxaline-Based Electron Acceptors
  作者：Junxiang Zhang、Timothy C. Parker、Wayne Chen、LaRita Williams、Victor N. Khrustalev、Evgheni V. Jucov、Stephen Barlow、Tatiana V. Timofeeva、Seth R. Marder

  DOI：10.1021/acs.joc.5b02551

  日期：2016.1.15

  Electron acceptors are important components of p-conjugated materials, but the strong electron-withdrawing properties of the required synthetic intermediates often make them poor substrates in synthetic schemes designed around conventional organometallic cross-coupling. Here, strong benzodiimine-based acceptors, including 5,6-difluoro[2,1,3]benzothiadiazole, 5,6-dicyano[2,1,3]benzothiadiazole, 5,6-dicyanobenzo[d][1,2,3]triazole, 6,7-dicyanoquinoxaline, and 6,7-dinitroquinoxaline, are shown to undergo facile palladium-catalyzed C-H direct arylation with a variety of bromoarenes in moderate to high yields. The electrochemical characteristics of di-2-thienyl derivatives synthesized using this methodology are compared and suggest that, in an electron-transfer sense, 5,6-dicyano[2,1,3]benzothiadiazole is a comparably strong acceptor to benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole. The synthetic results suggest that high electron-withdrawing ability, which has traditionally limited reaction yields and structural variety in organic electronic materials, may be advantageous when employing C-H activated direct arylation in certain circumstances.