3-amino-6-(3,5-diamino-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine | 1612764-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四嗪
• 英文名称: 3-amino-6-(3,5-diamino-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine
• 英文别名: 3-amino-6-(3,5-diamino-1H-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine；1-(6-Amino-1,2,4,5-tetrazin-3-yl)-1,2,4-triazole-3,5-diamine
• CAS: 1612764-69-8
• 化学式: C₄H₆N₁₀
• 分子量: 194.159
• InChiKey: DCCQLTJQLRXKQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-amino-6-(3,5-diamino-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine 在 双氧水 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到3-amino-6-(5-amino-3-nitro-1H-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine-2,4-di-N-oxide
  参考文献：
  名称：

  N-Oxide 1,2,4,5-Tetrazine-Based High-Performance Energetic Materials

  摘要：

  AbstractOne route to high density and high performance energetic materials based on 1,2,4,5‐tetrazine is the introduction of 2,4‐di‐N‐oxide functionalities. Based on several examples and through theoretical analysis, the strategy of regioselective introduction of these moieties into 1,2,4,5‐tetrazines has been developed. Using this methodology, various new tetrazine structures containing the N‐oxide functionality were synthesized and fully characterized using IR, NMR, and mass spectroscopy, elemental analysis, and single‐crystal X‐ray analysis. Hydrogen peroxide (50 %) was used very effectively in lieu of the usual 90 % peroxide in this system to generate N‐oxide tetrazine compounds successfully. Comparison of the experimental densities of N‐oxide 1,2,4,5‐tetrazine compounds with their 1,2,4,5‐tetrazine precursors shows that introducing the N‐oxide functionality is a highly effective and feasible method to enhance the density of these materials. The heats of formation for all compounds were calculated with Gaussian 03 (revision D.01) and these values were combined with measured densities to calculate detonation pressures (P) and velocities (νD) of these energetic materials (Explo 5.0 v. 6.01). The new oxygen‐containing tetrazines exhibit high density, good thermal stability, acceptable oxygen balance, positive heat of formation, and excellent detonation properties, which, in some cases, are superior to those of 1,3,5‐tritnitrotoluene (TNT), 1,3,5‐trinitrotriazacyclohexane (RDX), and octahydro‐1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocine (HMX).

  DOI：

  10.1002/chem.201405122
• 作为产物：
  描述：

  3,5-二氨基-1,2,4-三氮唑 、 3-amino-6-chloro-1,2,4,5-tetrazine 以 水 、 乙腈 为溶剂， 反应 16.0h， 以76%的产率得到3-amino-6-(3,5-diamino-1,2,4-triazol-1-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Thermally Stable 3,6-Disubstituted 1,2,4,5-Tetrazines

  摘要：

  以 3,6-双-(3,5-二甲基吡唑-1-基)-1,2,4,5-四嗪和 3,6-二氯-1,2,4,5-四嗪为亲电体，通过亲核取代反应合成了几种 3,6-二取代的 1,2,4,5-四嗪。所有新化合物都通过 1H NMR、13C NMR 和振动光谱、质谱和元素分析（C、H、N）进行了表征。为了分析热稳定性，使用了差示扫描量热法（DSC）。尤其是对称的双-3,5-二氨基-1,2,4-三唑基取代衍生物显示出极高的热稳定性，最高温度可达 370 ℃。因此，我们测定了它的能量特性，并将其与己酮二苯乙烯（HNS）的能量特性进行了比较。低温 X 射线衍射测定了 3,6-双肼基-1,2,4,5-四嗪、3,6-二氯-1,2,4,5-四嗪和 3-氨基-6-(3,5-二氨基-1,2,4-三唑-1-基)-1,2,4,5-四嗪二水合物的晶体结构。

  DOI：

  10.5560/znb.2013-3237