1,2,3-trimethyl-imidazolium 5-amino-tetrazolate | 1384103-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,2,3-trimethyl-imidazolium 5-amino-tetrazolate
• 英文别名: 1,2,3-Triaza-4-azanidacyclopenta-2,5-dien-5-amine;1,2,3-trimethylimidazol-1-ium
• CAS: 1384103-83-6
• 化学式: CH₂N₅*C₆H₁₁N₂
• 分子量: 195.227
• InChiKey: GSSNMMDMOWEJKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.43
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  silver 5-amino-1H-tetrazolate 、 1,2,3-三甲基咪唑碘化物 以 甲醇 为溶剂， 反应 24.0h， 以98%的产率得到1,2,3-trimethyl-imidazolium 5-amino-tetrazolate
  参考文献：
  名称：

  Synthesis, Structure and Property of 5‐Aminotetrazolate Room‐Temperature Ionic Liquids

  摘要：

  AbstractEight 5‐aminotetrazolate (AT) salts based on the 1,2,3‐trimethylimidazolium (1), 1,3‐dimethylimidazolium (2), 1‐ethyl‐3‐methylimidazolium (3), 1‐butyl‐3‐methylimidazolium (4), 1‐isobutyl‐3‐methylimidazolium (5), 1‐(3′‐methylbutyl)‐3‐methylimidazolium (6), 1‐hexyl‐3‐methylimidazolium (7) and 1‐methyl‐3‐octylimidazolium (8) cations have been synthesized in high yields and fully characterized by IR and NMR spectroscopy and elemental analysis. White plate crystals of 1 were isolated in methanol/diethyl ether and crystallized. Both the AT anion and the 1,2,3‐trimethylimidazolium cation in 1 were delocalized. Differential scanning calorimetry (DSC) combined with thermogravimetric analysis (TGA) tests were used to assess the thermal stabilities of the AT salts. These salts decomposed within the temperature range 230 °C–262 °C. Salts 3–8 are very fluent room‐temperature ionic liquids, whose glass transition temperatures are low. Their viscosities at 30 °C are in the range from 92 cP to 208 cP. A correlation between the viscosity and temperature was found, and the ionic liquids to do not display an Arrhenius temperature behaviour. In addition, the standard enthalpies of formation of salts 1–8 were investigated and analyzed by the theoretical methods. Salt 2 with the 1,3‐dimethylimidazolium cation gave the highest positive enthalpy of formation. For the assessment of the energetic character of the AT salts, impact sensitivities and friction sensitivities were recorded. These AT salts are insensitive to impact (>40 J) and friction (>360 N) confirmed by UN standards. The reactions of these AT salts with 100 % HNO3 were also determined.

  DOI：

  10.1002/ejic.201200065

文献信息

• Azolium azolates from reactions of neutral azoles with 1,3-dimethyl-imidazolium-2-carboxylate, 1,2,3-trimethyl-imidazolium hydrogen carbonate, and N,N-dimethyl-pyrrolidinium hydrogen carbonate
  作者：Marcin Smiglak、C. Corey Hines、W. Matthew Reichert、Julia L. Shamshina、Preston A. Beasley、Parker D. McCrary、Steven P. Kelley、Robin D. Rogers

  DOI：10.1039/c3nj00147d

  日期：——

  Utilizing previously reported synthetic protocols for the halide- and metal-free synthesis of organic salts, we have prepared a new group of imidazolium and pyrrolidinium azolate anion-based salts demonstrating the general applicability of the methodology and expanding our investigation into non ion exchange routes to potentially energetic ionic liquids. Eighteen salts, out of which six exhibit melting points below 100 °C, were prepared by a simple decarboxylation reaction, which resulted in clean formation of the new compounds without the need for extensive purification. The low stability of the H2CO3 by-product, and its decomposition to CO2 and H2O in aqueous media, allows for purification of the salts by evaporation only.

  利用先前报道的无卤素、无金属有机盐合成协议，我们成功制备了一组以咪唑鎓和吡咯烷鎓氮酸盐为阴离子的新型盐类，展示了该合成方法的普遍适用性，并扩展了我们对非离子交换途径制备潜在高能离子液体的研究。通过简单的脱羧反应，我们合成了十八种新盐，其中六种的熔点低于100°C。这种反应过程简洁，新化合物形成纯净，无需大量纯化。由于副产物碳酸不稳定，在水中分解为二氧化碳和水，使得这些盐可通过仅蒸发方法进行纯化。