2-(5-氨基四唑-1-基)乙醇 | 15284-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(5-氨基四唑-1-基)乙醇
• 英文名称: 1-(2-hydroxyethyl)-5-aminotetrazole
• 英文别名: 5-amino-1-(2-hydroxyethyl)tetrazole；5-amino-1-hydroxyethyl-1H-tetrazole；2-(5-amino-tetrazol-1-yl)-ethanol；2-(5-Amino-tetrazol-1-yl)-aethanol；1-(2-Hydroxyethyl)-5-aminotetrazol；1H-Tetrazole-1-ethanol, 5-amino-；2-(5-aminotetrazol-1-yl)ethanol
• CAS: 15284-29-4
• 化学式: C₃H₇N₅O
• mdl: MFCD00186455
• 分子量: 129.121
• InChiKey: MDLBOPYCJZSTMS-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  391.3±44.0 °C(Predicted)
• 密度：
  1.511 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(5-氨基四唑-1-基)乙醇 在 氯化亚砜 作用下， 以75%的产率得到1-(2-氯乙基)四唑-5-胺
  参考文献：
  名称：

  New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles

  摘要：

  AbstractA new way to make a bang: Several functionalized 1‐ethyl‐5‐aminotetrazoles, 1‐ethyl‐5‐nitrimino‐tetrazoles, and copper complexes have been synthesized and their chemical and energetic properties have been comprehensively characterized. The compounds belong to all classes of “energetic materials”: explosives, propellants, and pyrotechnics.magnified imageAlkylation of 5‐aminotetrazole (1) with 2‐chloroethanol leads to a mixture of the N‐1 and N‐2 isomers of (2‐hydroxyethyl)‐5‐aminotetrazole. Treatment of 1‐(2‐hydroxyethyl)‐5‐aminotetrazole (2) with SOCl2 yielded 1‐(2‐chlorethyl)‐5‐aminotetrazole (3). 1‐(2‐Azidoethyl)‐5‐aminotetrazole (4) was generated by the reaction of 3 with sodium azide. Nitration of 2, 3, and 4 with HNO3 (100 %) yielded in the case of 2 and 3 1‐(2‐hydroxyethyl)‐5‐nitriminotetrazole (5) and 1‐(2‐chloroethyl)‐5‐nitriminotetrazole (6). In the case of 4, 1‐(2‐nitratoethyl)‐5‐nitriminotetrazole monohydrate (7) was obtained. 1‐(2‐Azidoethyl)‐5‐nitriminotetrazole (8) could be obtained by nitration of 4 with NO2BF4 via the formation of potassium 1‐(2‐azidoethyl)‐5‐nitriminotetrazolate (9). The reaction of 6 with NaN3 resulted in the formation of the salt sodium 1‐(2‐chloroethyl)‐5‐nitriminotetrazolate (10 a). The deprotonation reaction of 6 was further investigated by the formation of the ammonium salt (10 b). The protonation of 2 and 4 with dilute nitric acid led to 1‐(2‐hydroxyethyl)‐5‐aminotetrazolium nitrate (11) and 1‐(2‐azidoethyl)‐5‐aminotetrazolium nitrate (12), respectively. Similarly, protonation of 4 with perchloric acid led to 1‐(2‐azidoethyl)‐5‐aminotetrazolium perchlorate monohydrate (13). Since 5‐nitrimino‐tetrazoles can be used as bidentate ligands, the coordination abilities of 5, 6, and 8 were tested by the reaction with copper nitrate trihydrate, yielding the copper complexes trans‐[diaquabis{1‐(2‐hydroxyethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] (14), trans‐[diaquabis{1‐(2‐chloroethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] dihydrate (15), and [diaquabis{1‐(2‐azidoethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] (16). All compounds were characterized by low‐temperature single‐crystal X‐ray diffraction. In addition, comprehensive characterization (IR, Raman, and multinuclear NMR spectroscopy (1H, 13C), elemental analysis, mass spectrometry, DSC) was performed. The heats of formation of selected compounds were computed by using heats of combustion obtained by bomb calorimetry or calculated by the atomization method. With these values and the densities determined from X‐ray crystallography, several detonation parameter were calculated by the EXPLO5 program. Finally, the sensitivities towards impact and friction were determined using a BAM drop hammer and friction tester.

  DOI：

  10.1002/chem.200802203
• 作为产物：
  描述：

  1-Diazo-2-(2-hydroxyethyl)guanidine 以 水 、 乙腈 为溶剂， 生成 2-(5-氨基四唑-1-基)乙醇
  参考文献：
  名称：

  1-Substituted 5-Aminotetrazoles: Syntheses from CNN₃ with Primary Amines

  摘要：

  1-Substituted 5-aminotetrazoles were prepared in situ by an excellent reaction of cyanogen azide and primary amines to generate an imidoyl azide as an intermediate in acetonitrile/water. After cyclization, the intermediate gave 1-substituted aminotetrazole in good yield. This protocol also was utilized in the syntheses of bis- and tris(1-substituted 5-aminotetrazole) derivatives.

  DOI：

  10.1021/ol8019742

文献信息

• Energetic<i>N</i>-Trinitroethyl-Substituted Mono-, Di-, and Triaminotetrazoles
  作者：Qinghua Zhang、Jiaheng Zhang、Damon A. Parrish、Jean'ne M. Shreeve

  DOI：10.1002/chem.201300994

  日期：2013.8.12

  A series of dense energetic N‐trinitroethyl‐substituted mono‐, bis‐, and tri‐5‐aminotetrazoles were obtained by reacting primary amines with in situ generated cyanogen azide, followed by the trinitroethyl functionalization that involves a condensation of a hydroxymethyl intermediate (prepared by a reaction with formaldehyde) with trinitromethane. These compounds were fully characterized by using multinuclear

  通过使伯胺与原位生成的叠氮化氰反应，然后进行三硝基乙基官能化（涉及羟甲基中间体的缩合反应，制得了一系列致密的高能N-三硝基乙基取代的单，双和三-5-氨基四唑）通过与甲醛反应）与三硝基甲烷反应。这些化合物通过多核NMR光谱，IR，元素分析，差示扫描量热法（DSC）进行了充分表征，并且在一种情况下（使用9进行单晶XRD分析）得到了充分表征。用高斯03计算所有化合物的形成热，然后与实验密度结合确定爆轰压力（P）和速度（D v）的高能材料。有趣的是，它们大多数都表现出高密度，良好的热稳定性，可接受的氧平衡，正形成热，低冲击敏感性和出色的爆震性能，这突出了它们作为令人着迷的高能材料一类的实际应用潜力。
• Energetic Nitrogen‐Rich Salts of 1‐(2‐Hydroxyethyl)‐5‐nitriminotetrazole
  作者：Niko Fischer、Thomas M. Klapötke、Jörg Stierstorfer

  DOI：10.1002/ejic.201100535

  日期：2011.10

  1-(2-Hydroxyethyl)-5-nitriminotetrazole (2) was formed by the reaction of 5-amino-1-(2-hydroxyethyl)tetrazole (1) and 100 % HNO3. Compound 1 was obtained by alkylation of 5-amino-1H-tetrazole with 2-chloroethanol. Nitrogen-rich salts such as the ammonium (3), hydroxylammonium (4), guanidinium (5), aminoguanidinium (6), diaminoguanidinium (7), triaminoguanidinium (8), azidoformamidinium (9), and diaminouronium

  1-(2-羟乙基)-5-硝基四唑(2)是由5-氨基-1-(2-羟乙基)四唑(1)和100％HNO3反应形成的。通过用2-氯乙醇将5-氨基-1H-四唑烷基化得到化合物1。富氮盐，例如铵 (3)、羟铵 (4)、胍 (5)、氨基胍 (6)、二氨基胍 (7)、三氨基胍 (8)、叠氮甲脒 (9) 和二氨基脲 (10) 1-( 2-羟乙基)-5-硝基四唑酸盐通过去质子化或复分解反应制备。通过单晶 X 射线衍射（9 和 10 除外）、振动光谱（IR 和拉曼）、多核 NMR 光谱、元素分析和差示扫描量热法 (DSC) 测量对化合物 3-10 进行了全面表征。4-10 的形成热是通过基于 CBS-4M 焓的雾化方法计算的。利用这些值和 X 射线密度，使用 EXPLO5 代码计算了几个爆震参数，例如爆震压力、速度、能量和温度。此外，还使用 ​​BAM 落锤、摩擦测试仪和小型放电装置测试了它们对冲击、摩擦和放电的敏感性。
• Energetic Mono-, Di-, and Trisubstituted Nitroiminotetrazoles
  作者：Young-Hyuk Joo、Jean'ne M. Shreeve

  DOI：10.1002/anie.200804755

  日期：2009.1.5

  with 100 % nitric acid and were fully characterized by spectroscopic methods, elemental analysis, and in some cases X‐ray diffraction (see example; N blue, O red). The heats of formation of these energetic materials were calculated, as well as their detonation pressures and velocities.

  大量能量：标题化合物是由氨基四唑（由叠氮化氰与伯胺反应制得）通过用100％硝酸处理而以高收率合成的，并通过光谱法，元素分析和在某些情况下X进行了全面表征射线衍射（请参见示例； N蓝色，O红色）。计算了这些高能材料的形成热，以及它们的爆炸压力和速度。
• Synthesis and Investigation of Energetic Boron Compounds for Pyrotechnics
  作者：Thomas M. Klapötke、Magdalena Rusan、Véronique Sproll

  DOI：10.1002/zaac.201400218

  日期：2014.8

  4-triazolyl)borate and potassium bis(4, 4′,5, 5′-tetranitro-2, 2′-bisimidazolyl)borate were synthesized and fully characterized as well. Moreover, the energetic and thermal properties of the energetic boron esters and tetracoordinate borates were determined. The 11B NMR chemical shifts of potassium tetrakis(3-nitro-1, 2,4-triazolyl)borate and potassium bis(4, 4′,5, 5′-tetranitro-2, 2′-bisimidazolyl)borate were calculated

  含能硼酯三(1-乙基-5-氨基四唑基)硼酸酯、三(2-乙基-5-氨基四唑基)硼酸酯、三(1-乙基四唑基)硼酸酯、三(2-乙基四唑基)硼酸酯和三(2-(合成了 3-nitro-1, 2,4-triazolyl)ethyl) borate 并通过 NMR 和 IR 光谱、元素分析和质谱分析。合成并充分表征了两种四配位硼酸盐四(3-硝基-1, 2,4-三唑基)硼酸钾和双(4, 4',5, 5'-四硝基-2, 2'-双咪唑基)硼酸钾. 此外，还测定了含能硼酯和四配位硼酸盐的能量和热性能。计算并比较了四(3-硝基-1, 2,4-三唑基)硼酸钾和双(4, 4',5, 5'-四硝基-2, 2'-双咪唑基)硼酸钾的11B NMR化学位移到实验值。
• Evolving the Scope of 5,5’‐Azobistetrazoles in the Search for High Performing Green Energetic Materials
  作者：Maximilian Benz、Michael S. Gruhne、Thomas M. Klapötke、Nina Krüger、Tobias Lenz、Marcus Lommel、Jörg Stierstorfer

  DOI：10.1002/ejoc.202100747

  日期：2021.8.13

  great platform for energetic materials, it offers a planar and nitrogen-rich backbone, combined with a high heat of formation, which easily can be functionalized and tuned. Herein, we start from sodium 5-aminotetrazolate and obtain two isomers by substitution reaction with 2-chloroethanol. Azidoethyl and nitratoethyl substituted azo- tetrazoles were finally synthesized by oxidative azo coupling of the

  偶氮四唑部分代表了高能材料的一个很好的平台，它提供了一个平面和富含氮的骨架，结合了高形成热，很容易被功能化和调整。在此，我们从5-氨基四唑钠开始，通过与2-氯乙醇的取代反应得到两种异构体。叠氮乙基和硝基乙基取代的偶氮四唑最终通过各自的 N-乙基官能化 5-氨基四唑前体的氧化偶氮偶联合成，使用次氯酸叔丁酯作为试剂。通过多核核磁共振和红外光谱以及质谱分析所有化合物。使用低温 X 射线晶体学进一步研究了所有固体化合物。通过 CHNO 元素分析验证纯度，并确定分解温度 (DTA) 和对冲击、摩擦和静电放电的敏感性。基于CBS-4M计算结果，使用EXPLO5代码计算能量特性。