1,3,7,9-四硝基-6H-苯并三唑并[2,1-a]苯并三唑-5-鎓内盐 | 25243-36-1

• 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: 1,3,7,9-四硝基-6H-苯并三唑并[2,1-a]苯并三唑-5-鎓内盐
• 英文名称: TACOT
• 英文别名: 6H-Benzotriazolo[2,1-a]benzotriazol-5-ium, 1,3,7,9-tetranitro-, inner salt；1,3,7,9-tetranitrobenzotriazolo[2,1-a]benzotriazol-5-ium-6-ide
• CAS: 25243-36-1
• 化学式: C₁₂H₄N₈O₈
• 分子量: 388.213
• InChiKey: MNUJHDPQSAMAAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 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：
  206
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,7,9-四硝基-6H-苯并三唑并[2,1-a]苯并三唑-5-鎓内盐 在 sodium azide 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 49.0h， 生成 4,10-bis(triphenylphosphinimino)-2,8-dinitrobenzotriazolo[2,1-a]benzotriazole
  参考文献：
  名称：

  Chemistry of Tetraazapentalenes

  摘要：

  2,4,8, 10-Tetranitrobenzotriazolo[2, 1-alpha]benzotriazole (TACOT), although thermally very stable and insensitive as an explosive, is susceptible to attack by nucleophiles. Reaction with azide ion results in displacement of nitro groups at the 4,10-positions, treatment with methoxide ion effects displacement of the hydrogen atom at the 1-position and scission of the remote triazole ring, while "vicarious nucleophilic amination" displaces all the aromatic hydrogens. 3,5,7-Trinitro-1,3,3-triazolo[2, 1-alpha]benzotriazole and 3,5,7-trinitro-1,2,3-triazolo[1,2-alpha]benzotriazole are prepared readily by nitration of the parent triazolobenzotriazoles. However they are thermally less stable than TACOT and more sensitive to initiation by impact. Furthermore, attempted further nitration and reaction with nucleophiles such as azide and methoxide ions both effect scission of the triazole ring to leave 4,6-dinitrobenzotriazole.

  DOI：

  10.1021/jo972252x
• 作为产物：
  描述：

  二苯并-1,3a,4,6a-四氮杂并环戊二烯 在 硫酸 、 硝酸 作用下， 以75%的产率得到1,3,7,9-四硝基-6H-苯并三唑并[2,1-a]苯并三唑-5-鎓内盐
  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

文献信息

• Chemistry of Tetraazapentalenes
  作者：Karen L. Altmann、Andrew P. Chafin、Lawrence H. Merwin、William S. Wilson、Richard Gilardi

  DOI：10.1021/jo972252x

  日期：1998.5.1

  2,4,8, 10-Tetranitrobenzotriazolo[2, 1-alpha]benzotriazole (TACOT), although thermally very stable and insensitive as an explosive, is susceptible to attack by nucleophiles. Reaction with azide ion results in displacement of nitro groups at the 4,10-positions, treatment with methoxide ion effects displacement of the hydrogen atom at the 1-position and scission of the remote triazole ring, while "vicarious nucleophilic amination" displaces all the aromatic hydrogens. 3,5,7-Trinitro-1,3,3-triazolo[2, 1-alpha]benzotriazole and 3,5,7-trinitro-1,2,3-triazolo[1,2-alpha]benzotriazole are prepared readily by nitration of the parent triazolobenzotriazoles. However they are thermally less stable than TACOT and more sensitive to initiation by impact. Furthermore, attempted further nitration and reaction with nucleophiles such as azide and methoxide ions both effect scission of the triazole ring to leave 4,6-dinitrobenzotriazole.
• 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.