二苯并-1,3a,4,6a-四氮杂并环戊二烯 | 7120-73-2

• 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: 二苯并-1,3a,4,6a-四氮杂并环戊二烯
• 英文名称: dibenzo<1,3a,4,6a>tetraazapentalene
• 英文别名: 5,6H-Dibenzo-1,3a,4,6a-tetraazapentalen；Dibenzo-1,3a,4,6a-tetra-azapentalen；Dibenzotetraazapentalen；5H-benzo[d]benzo[4,5][1,2,3]triazolo[2,1-a][1,2,3]triazolylium betaine；6H-Benzotriazolo[2,1-a]benzotriazol-5-ium, inner salt；benzotriazolo[2,1-a]benzotriazol-5-ium-6-ide
• CAS: 7120-73-2
• 化学式: C₁₂H₈N₄
• 分子量: 208.222
• InChiKey: GNYDVCSYVQXVGF-UHFFFAOYSA-N

物化性质

• 熔点：
  237-238 °C
• 密度：
  1.425 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二苯并-1,3a,4,6a-四氮杂并环戊二烯 在 sodium azide 、 硝酸 、 氯 作用下， 以 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 3,9-Diazido-4,10-dinitrobenzotriazolo<2,1-a>benzotriazol-6-ium inner salt
  参考文献：
  名称：

  Reactions of Benzotriazolo[2,1-a]benzotriazole Derivatives. 1. Synthesis of New Insensitive High-Density Energetic Compounds

  摘要：

  The sequential preference of electrophilic attack on the dibenzotetraazapentalene ring system 6 has unequivocally been shown to be in the order of position 2(8) > 4(10) much greater than 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to be substrate dependent. Substitution occurred at the 3(9)-position of 9 followed by elimination of hydrogen chloride to give 10 while direct substitution of azide for the 8(10)-nitro group of 2 was found to yield 13. The reactivity of the dibenzotetraazapentalene derivatives toward electrophiles and nucleophiles was exploited for the synthesis of the new heterocyclic system 14H-[1,2,5]oxadiazolo[3,4-e][1,2,5]oxadiazolo[3',4':4,5]benzotriazolo[2,1-alpha]benzotriazol-6-ium inner salt 1,8-dioxide (11). From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2.

  DOI：

  10.1021/jo00124a024
• 作为产物：
  描述：

  2,2'-dinitrenoazobenzene 以 gaseous matrix 为溶剂， 生成 二苯并-1,3a,4,6a-四氮杂并环戊二烯
  参考文献：
  名称：

  Intermediates in photolyses of 2,2′-diazidoazobenzene and 2-azidoazobenzene in low-temperature matrices

  摘要：

  The photolyses of 2,2'-diazidoazobenzene (1) and 2-azidoazobenzene (4) were investigated in argon and 2-methyltetrahydrofuran (MTHF) matrices at cryogenic temperature. Nitrene and dinitrene were observed in the photolysis of 1 in an MTHF matrix by electron spin resonance (ESR). The dinitrene in an argon matrix was also observed by ultraviolet-visible (UV-vis) and Fourier transform infrared (FT-IR) spectroscopies. UV absorption bands at 430 and 460 nm and IR peak at 1263 cm(-1) were assigned to the dinitrene. Furthermore, mononitrene as an intermediate of the photolysis of 4 was confirmed by UV-vis and FT-IR spectroscopies in an argon matrix. An IR band at 1225 cm(-1) of mononitrene was observed. (C) 1998 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1386-1425(97)00231-x

文献信息

• Intermediates in photolyses of 2,2′-diazidoazobenzene and 2-azidoazobenzene in low-temperature matrices
  作者：Tsuguyori Ohana、Yoshinori Koga

  DOI：10.1016/s1386-1425(97)00231-x

  日期：1998.3

  The photolyses of 2,2'-diazidoazobenzene (1) and 2-azidoazobenzene (4) were investigated in argon and 2-methyltetrahydrofuran (MTHF) matrices at cryogenic temperature. Nitrene and dinitrene were observed in the photolysis of 1 in an MTHF matrix by electron spin resonance (ESR). The dinitrene in an argon matrix was also observed by ultraviolet-visible (UV-vis) and Fourier transform infrared (FT-IR) spectroscopies. UV absorption bands at 430 and 460 nm and IR peak at 1263 cm(-1) were assigned to the dinitrene. Furthermore, mononitrene as an intermediate of the photolysis of 4 was confirmed by UV-vis and FT-IR spectroscopies in an argon matrix. An IR band at 1225 cm(-1) of mononitrene was observed. (C) 1998 Elsevier Science B.V. All rights reserved.
• Reactions of Benzotriazolo[2,1-a]benzotriazole Derivatives. 1. Synthesis of New Insensitive High-Density Energetic Compounds
  作者：Ganesan Subramanian、Joseph H. Boyer、Dan Buzatu、Edwin D. Stevens、Mark L. Trudell

  DOI：10.1021/jo00124a024

  日期：1995.9

  The sequential preference of electrophilic attack on the dibenzotetraazapentalene ring system 6 has unequivocally been shown to be in the order of position 2(8) > 4(10) much greater than 1(7) and 3(9). However, nucleophilic substitution reactions with sodium azide were found to be substrate dependent. Substitution occurred at the 3(9)-position of 9 followed by elimination of hydrogen chloride to give 10 while direct substitution of azide for the 8(10)-nitro group of 2 was found to yield 13. The reactivity of the dibenzotetraazapentalene derivatives toward electrophiles and nucleophiles was exploited for the synthesis of the new heterocyclic system 14H-[1,2,5]oxadiazolo[3,4-e][1,2,5]oxadiazolo[3',4':4,5]benzotriazolo[2,1-alpha]benzotriazol-6-ium inner salt 1,8-dioxide (11). From this study the first of a new class of insensitive energetic materials 4 has been synthesized in a straightforward fashion from 2.

表征谱图