1-amino-3-methyl-1,2,3-triazol-3-ium iodide

• 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-amino-3-methyl-1,2,3-triazol-3-ium iodide
• 英文别名: [1-amino-3-methyl-1,2,3-triazolium] iodide；1-amino-3-methyl-1,2,3-triazolium iodide；1-methyl-3-amino-1,2,3-triazolium iodide；3-methyl-1-amino-1,2,3-triazolium iodide；[1-amino-3-Me-1,2,3-triazolium]iodide；[1-amino-3-Me-1,2,3-triazolium][I]；3-methyltriazol-3-ium-1-amine;iodide
• 化学式: C₃H₇N₄*I
• 分子量: 226.02
• InChiKey: BQBYKNQWJXGYCP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.57
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-3-methyl-1,2,3-triazol-3-ium iodide 生成 1-甲基-1,2,3-三氮唑
  参考文献：
  名称：

  Confined rapid thermolysis/FTIR/ToF studies of methyl-amino-triazolium-based energetic ionic liquids

  摘要：

  Thermal decomposition of the energetic ionic liquids 1-methyl-4-amino-1,2,4-triazolium iodide (Me4ATI), 1-methyl-4-amino-1,2,4-triazolium nitrate (Me4ATN), 1-amino-3-methyl-1,2,3-triazolium iodide (Me1ATI), and 1-amino-3-methyl-1,2,3-triazolium nitrate (Me1ATN) was studied by confined rapid thermolysis. Sub-milligram quantities of the compounds were subjected to decomposition under isothermal conditions achieved by initially heating the sample at rates of approximately 2000 K/s. The products formed by decomposition under the afore-mentioned conditions were sampled by rapid scan FTIR spectroscopy and time-of-flight mass spectrometry. Decomposition studies involving the iodide salts were carried out around 270-290 degrees C, whereas the nitrate salts were subjected to 320-340 degrees C. The amino group was found to be involved in the initiation reaction, forming copious quantities of ammonia from the iodide compounds and, N2O and H2O from the nitrate compounds. The extent of decomposition of the triazole ring was minimal at the considered temperatures. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.tca.2010.03.022
• 作为产物：
  描述：

  1H-1,2,3-三唑-1-胺 、 碘甲烷 以 乙醚 、 乙醇 为溶剂， 生成 1-amino-3-methyl-1,2,3-triazol-3-ium iodide
  参考文献：
  名称：

  将杂环阳离子与近二十面体硼烷和碳硼烷阴离子配对，II：具有显着水溶性的二元三唑盐和四唑盐的台式替代合成方法

  摘要：

  摘要 已开发出两种通过一步露天复分解反应合成 12 相对水溶性二元三唑鎓和第一种四唑鎓硼烷 [B12H12] 和碳硼烷 [CB11H12] 盐的有效方法。首先，将两种固体反应物盐与回流的无水乙腈彻底研磨，然后通过硅胶塞进行快速过滤的组合，为广泛系列的水溶性杂环盐提供了极好的回收率。其次，另一种水性复分解，通过沉淀卤化银完成，然后除去水，重新溶解在乙腈中，并通过硅胶塞过滤，也产生了这种杂环硼烷和碳硼烷盐。混合1：1 二阳离子杂环硼烷盐首先使用第二种方法合成，一个例子显示熔点降低行为。图形概要

  DOI：

  10.1080/00397911.2010.520543

文献信息

• Preparation of substituted-1,2,3-triazoles
  申请人：The United States of America as represented by the Secretary of the Air Force

  公开号：US07550601B1

  公开（公告）日：2009-06-23

  The invention provides a high yield/isomerically pure synthesis of new 1-amino-3-substituted-1,2,3-triazolium salts and their subsequent transformation into isomerically pure 1-substituted-1,2,3-triazoles. These new 1-amino-3-substituted-1,2,3-triazolium salts are easily isolated and can be stored at ambient conditions with no degradation or isomerization. These quarternary salts are easily converted with appropriate silver salts to a wide array of new quarternary salts with various anions, with many of these new salts having melting points below 100 C, classifying them as ionic liquids. Subsequent diazotization of these 1-amino-3-substituted-1,2,3-triazolium salts results in high yields of isomerically pure 1-substituted-1,2,3-triazoles, that until this invention were problematic to make pure without tedious reagents or workup procedures. Both classes of materials (1-amino-3-substituted-1,2,3-triazolium salts as well as 1-substituted-1,2,3-triazoles) should be of high interest as these classes of materials are known to be very important pharmaceutical materials for a wide array of medical and agricultural applications as well as possible propellant applications.

  这项发明提供了新的1-氨基-3-取代-1,2,3-三唑盐的高产率/异构纯合成，以及它们随后转化为异构纯的1-取代-1,2,3-三唑。这些新的1-氨基-3-取代-1,2,3-三唑盐易于分离，并且可以在常温条件下存储而不会发生降解或异构化。这些季铵盐可以很容易地与适当的银盐转化为各种带有不同阴离子的新的季铵盐，其中许多这些新盐的熔点低于100摄氏度，可归类为离子液体。随后对这些1-氨基-3-取代-1,2,3-三唑盐进行重氮化反应，可以高产率地得到异构纯的1-取代-1,2,3-三唑，这在这项发明之前是难以纯净制备的，需要繁琐的试剂或工作程序。这两类材料（1-氨基-3-取代-1,2,3-三唑盐以及1-取代-1,2,3-三唑）应该具有很高的研究兴趣，因为这些材料类别被认为是非常重要的药用材料，可用于广泛的医药和农业应用，以及可能的推进剂应用。
• Synthesis, characterization, and structural investigations of 1-amino-3-substituted-1,2,3-triazolium salts, and a new route to 1-substituted-1,2,3-triazoles
  作者：Greg Kaplan、Greg Drake、Kerri Tollison、Leslie Hall、Tommy Hawkins

  DOI：10.1002/jhet.5570420104

  日期：2005.1

  Quarternary salts based upon 3-alkyl substituted 1-amino-1,2,3-triazolium cations (alkyl = methyl, ethyl, nypropyl, 2-propenyl, and n-butyl) have been synthesized and characterized by vibrational spectra, multinuclear NMR, elemental analysis, and DSC studies. Subsequent diazotization of these salts results in the exclusive formation of 1-alkyl-1,2,3-triazoles. Single crystal X-ray studies were carried

  基于3-烷基取代的1-氨基-1,2,3-三唑鎓阳离子（烷基=甲基，乙基，正丙基，2-丙烯基和正丁基）的季铵盐已合成并通过振动光谱，多核NMR表征，元素分析和DSC研究。这些盐的随后重氮化导致1-烷基-1,2,3-三唑的排他性形成。对1-氨基-3-甲基-1,2,3-碘化三唑鎓，1-氨基-3-乙基-1,2,3-溴化三唑鎓，1-氨基-3-碘化物进行了单晶X射线研究正丙基1,2,3-三唑鎓溴化物和1-氨基-3-正丁基1,2,3-三唑鎓溴化物以及起始杂环1-氨基1,2,3-三唑，并讨论了所有结构。
• Pairing Heterocyclic Cations with <i>closo-</i>Icosahedral Borane and Carborane Anions. I. Benchtop Aqueous Synthesis of Binary Triazolium and Imidazolium Salts with Limited Water Solubility
  作者：Scott A. Shackelford、John L. Belletire、Jerry A. Boatz、Stefan Schneider、Amanda K. Wheaton、Brett A. Wight、Leslie M. Hudgens、Herman L. Ammon、Steven H. Strauss

  DOI：10.1021/ol900550v

  日期：2009.6.18

  Ten new salts that pair triazolium and imidazolium cations with closo-icosahedral anions [B12H12]2− and [CB11H12]− were synthesized in water solvent using an open-air, benchtop method. These unreported [Heterocyclium]2[B12H12] and [Heterocyclium][CB11H12] salts extend reports of [Imidazolium][CB11H12] and [Pyridinium][CB11H12] salts that were synthesized in anhydrous organic solvents under an inert

  十个新的盐，与对三唑和咪唑鎓阳离子闭合碳-icosahedral阴离子[B 12 ħ 12 ] 2-和[CB 11 H ^ 12 ] -在水中的溶剂中使用露天合成，台式方法。这些未报告[Heterocyclium] 2 [B 12 ħ 12 ]和[Heterocyclium] [CB 11 H ^ 12 ]的盐延伸[咪唑] [CB的报告11 ħ 12 ]和[吡啶鎓] [CB 11 H ^ 12]盐，是在惰性气氛下通过手套箱或Schlenk技术在无水有机溶剂中合成的。报告了每种盐的光谱数据，熔点和密度。提供了五种新的[B 12 H 12 ] 2-盐的单晶X射线结构。
• Pairing Heterocyclic Cations with <i>closo</i>-Icosahedral Borane and Carborane Anions, II: Benchtop Alternative Synthetic Methodologies for Binary Triazolium and Tetrazolium Salts with Significant Water Solubility
  作者：John L. Belletire、Stefan Schneider、Brett A. Wight、Steven L. Strauss、Scott A. Shackelford

  DOI：10.1080/00397911.2010.520543

  日期：2012.1.15

  series of otherwise water-soluble heterocyclium salts. Second, an alternative aqueous metathesis, driven to completion by precipitation of silver halides, followed by removal of water, redissolution in acetonitrile, and filtration through a silica-gel plug, also yielded such heterocyclium borane and carborane salts. Mixed 1:1 dication heterocyclium borane salts were first synthesized using this second procedure

  摘要 已开发出两种通过一步露天复分解反应合成 12 相对水溶性二元三唑鎓和第一种四唑鎓硼烷 [B12H12] 和碳硼烷 [CB11H12] 盐的有效方法。首先，将两种固体反应物盐与回流的无水乙腈彻底研磨，然后通过硅胶塞进行快速过滤的组合，为广泛系列的水溶性杂环盐提供了极好的回收率。其次，另一种水性复分解，通过沉淀卤化银完成，然后除去水，重新溶解在乙腈中，并通过硅胶塞过滤，也产生了这种杂环硼烷和碳硼烷盐。混合1：1 二阳离子杂环硼烷盐首先使用第二种方法合成，一个例子显示熔点降低行为。图形概要
• Energetic Salts Based on Dipicrylamine and Its Amino Derivative
  作者：Haifeng Huang、Zhiming Zhou、Jinhong Song、Lixuan Liang、Kai Wang、Dan Cao、Wenwen Sun、Xuemin Dong、Min Xue

  DOI：10.1002/chem.201101411

  日期：2011.11.25

  Energetic salts based on dipicrylamine and its amino derivative were synthesized. All salts were fully characterized by multinuclear NMR spectroscopy (1H, 13C), vibrational spectroscopy (IR), and elemental analysis. Ethylenediammonium di‐DPA (DPA=dipicrylamine) and 1,3‐diaminoguanidinium DPA were further confirmed by single‐crystal X‐ray diffraction. These salts exhibit reasonable physical properties

  合成了基于二吡啶胺及其氨基衍生物的高能盐。所有盐均通过多核NMR光谱（1 H，13 C），振动光谱（IR）和元素分析进行了全面表征。单晶X射线衍射进一步证实了乙二铵二-DPA（DPA = dipicrylamine）和1,3-二氨基胍鎓DPA。这些盐表现出合理的物理性质，例如高密度（1.71–1.81 g cm -3），良好的热稳定性（T d= 155–285°C），并且在水中的溶解度低。1-甲基-3,4,5-三氨基-1,2,4-三唑鎓DPA的撞击敏感性低于2,4,6-三硝基甲苯（TNT），对于其他一些高能盐，其撞击敏感性为与TNT相当。根据实验密度和使用高斯03程序套件进行的理论计算，所有盐的爆震压力（22.5–27.8 GPa）和速度（7226–7917 m s -1）均超过了常规TNT。通过发光细菌毒性测试测得的这些盐的毒性远低于TNT，并鉴定出两种熔点在70至100°C之间的二元共晶混合物。