1-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole | 13417-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole
• 英文别名: 1-(benzotriazol-1-yl)-2,4-dinitrobenzene；1-(2,4-dinitrophenyl)-1H-benzotriazole；1-(2,4-dinitro-phenyl)-1H-benzotriazole；1-(2,4-Dinitro-phenyl)-1H-benzotriazol；1-<2,4-Dinitro-phenyl>-1H-benzotriazol；1-<2.4-Dinitro-phenyl>-benzotriazol；1-(2,4-dinitrophenyl)benzotriazole
• CAS: 13417-39-5
• 化学式: C₁₂H₇N₅O₄
• mdl: MFCD00412732
• 分子量: 285.219
• InChiKey: KJTTXOXWFXOPHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C
• 沸点：
  506.9±60.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole 生成 9-乙酰基-1,3-二硝基-咔唑
  参考文献：
  名称：

  Starkova et al., Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 1019,1021

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole 以 N,N-二甲基甲酰胺-d7 为溶剂， 反应 2616.0h， 生成 1-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  Synthesis, structure, and isomerism of N-2,4-dinitrophenylbenzotriazoles

  摘要：

  Both isomers of N-(2,4'-dinitrophenyl)benzotriazole, the 1(3)- and the 2-substituted, have been characterized and their reciprocal isomerism was studied. Cross-experiments in the presence of 5(6)-nitro-1H-benzotriazole proved that the isomerization of 2-(2',4'-dinitrophenyl)-2H-benzotriazole into the 1-isomer occurs by an intermolecular mechanism. The reported reaction of 5 (6) -nitro-1H-benzotriazole with 1-chloro-2,4-dinitrobenzene has been reexamined discovering that there is an error in the proportions of N-substituted isomers. A possible explanation for the observed isomerizations was proposed. Identification of all compounds by multinuclear magnetic resonance, including solid-state studies, has been achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.083

文献信息

• A Simple, Versatile Synthetic Route to<i>N</i>-1-Aryl-, -Heteroaryl-, - Acylmethyl-, -Carboxymethyl-and -Alkyl-benzotriazoles via Regiospecific or Highly Regioselective Substitutions of Benzotriazole
  作者：Alan R. Katritzky、Jing Wu

  DOI：10.1055/s-1994-25530

  日期：——

  In the absence of any added base in refluxing benzene or toluene, benzotriazole replaces the halogen atom of an α-halogenated ketone or a carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer. 2-Bromopyridine and 1-chloro-2,4-dinitrobenzene reacted similarly with benzotriazole to afford the corresponding N-1-substituted benzotriazole derivatives in quantitative yields. Alkyl halides reacted regioselectively to afford the N-1-alkylbenzotriazoles in ratios of more than 10 to 1 over the N-2 isomers. An α-(benzotriazol-1-yl)carboxylic ester was hydrolyzed into the corresponding carboxylic acid, which upon heating under-went smooth decarboxylation into the corresponding 1-alkylbenzotriazole.

  在没有加入任何碱的回流苯或甲苯中，苯并三唑取代了α-卤代酮或羧酸酯中的卤原子，生成唯一的异构体，即相应的N-1-取代苯并三唑。2-溴吡啶和1-氯-2,4-二硝基苯与苯并三唑反应类似，以定量产率得到相应的N-1-取代苯并三唑衍生物。烷基卤化物反应时具有区域选择性，生成N-1-烷基苯并三唑的比率超过N-2异构体的10比1。一个α-(苯并三唑-1-基)羧酸酯被水解为相应的羧酸，在加热下经历平滑的脱羧反应，生成相应的1-烷基苯并三唑。
• SelectiveN(1)-arylation of benzotriazole with activated aryl halides under conditions of phase transfer catalysis
  作者：I. P. Beletskaya、D. V. Davydov、M. S. Gorovoi、S. V. Kardashov

  DOI：10.1007/bf02496407

  日期：1999.8

  3-benzotriazole, with activated aryl halides in a medium of aromatic hydrocarbons under conditions of phase transfer catalysis with the use of inorganic bases and cetyltrimethylammonium bromide as a phase-transfer catalyst was studied. Arylation affords bothN(1)- andN(2)-arylation products. Their ratio depends on the nature of the base and the reactivity of the arylating agent. In the presence of catalytic

  1H-1,2,3-苯并三唑与活化的卤代芳烃在相转移催化条件下，使用无机碱和十六烷基三甲基溴化铵作为相转移催化剂进行了芳基化研究。芳基化提供N(1)-和N(2)-芳基化产物。它们的比例取决于碱的性质和芳基化剂的反应性。在催化量的苯基环丙烷羧酸铜存在下，芳基化在 N(1) 原子上区域选择性地进行。
• 硝基或二硝基苯基-苯并[1,2,3]三唑、衍生物 及制备方法
  申请人：中国工程物理研究院化工材料研究所

  公开号：CN106866561B

  公开（公告）日：2019-04-23

  本发明公开了硝基苯基‑苯并[1,2,3]三唑、二硝基苯基‑苯并[1,2,3]三唑、二硝基苯基‑苯并[1,2,3]三唑衍生物的结构，以及他们的质谱信息。另外，本发明还公开了硝基苯基‑苯并[1,2,3]三唑、二硝基苯基‑苯并[1,2,3]三唑、二硝基苯基‑苯并[1,2,3]三唑衍生物的制备方法。本发明制备出新型化合物硝基苯基‑苯并[1,2,3]三唑及二硝基苯基‑苯并[1,2,3]三唑衍生物结构。可应用于含能材料、石油开采、太空探索等领域用新型材料。本发明的合成方法具有原料易得、操作简便、安全性高、工艺可控等特点。
• Process for the arylation of aza-heterocycles with activated aromatics in presence of caesium carbonate
  申请人：——

  公开号：US20040249185A1

  公开（公告）日：2004-12-09

  The invention concerns a process for the preparation of N-aryl-aza-heterocycles of the general formula I 1 by reaction of aza-heterocycles with activated aryl halides with use of caesium carbonate without addition of further catalysts at room temperature.

  本发明涉及通式 I 的 N-芳基氮杂环的制备工艺 1 在不添加其他催化剂的情况下，使用碳酸铯在室温下使氮杂环与活化的芳基卤化物反应。
• Organic Reactions in Ionic Liquids: A Simple Highly Regioselective or Regiospecific Substitutions of Benzotriazole
  作者：Zhen-Chu Chen、Zhang-Gao Le、Yi Hu、Qin-Guo Zheng

  DOI：10.3987/com-04-10010

  日期：——