1-(2-氯乙基)四唑-5-胺 | 15284-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2-氯乙基)四唑-5-胺
• 英文名称: 1-(2-chloroethyl)-5-aminotetrazole
• 英文别名: 1-(2-chloro-ethyl)-1H-tetrazol-5-ylamine；1-(2-Chlor-aethyl)-1H-tetrazol-5-ylamin；1-(2-Chlorethyl)-5-aminotetracol；1-(2-Chlorethyl)-5-aminotetrazol；1-(2-Chloroethyl)-1,4-dihydro-5H-tetraazol-5-imine；1-(2-chloroethyl)tetrazol-5-amine
• CAS: 15284-31-8
• 化学式: C₃H₆ClN₅
• mdl: MFCD19203787
• 分子量: 147.567
• InChiKey: LZAOOQIITLPTRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 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：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-氯乙基)四唑-5-胺 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以1.2 g的产率得到1-乙烯基四唑-5-胺
  参考文献：
  名称：

  通过涉及1乙烯基5氨基四唑的水包油HIPE的聚合制备非常坚韧的polyHIPE材料

  摘要：

  使用高内相乳液（HIPE）方法已经制备了具有出乎意料的高机械强度的互连微孔聚合物整料。1-乙烯基-5-氨基[1,2,3,4]四唑水溶液（1-VAT）的水包油浓缩乳液，与低摩尔比（7％）的N，N'-亚甲基双丙烯酰胺作为交联剂混合使用十二烷作为分散相和亲水性表面活性剂的混合物制备了氯乙烯。在自由基共聚，溶剂萃取和干燥后获得“反向” polyHIPE材料。讨论了它们的形态，化学组成和物理化学行为。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：2942-2947，2010

  DOI：

  10.1002/pola.24075
• 作为产物：
  描述：

  β-氯丙腈 在 三(2-氯乙基)胺 、 硫酸 、 苯 作用下， 生成 1-(2-氯乙基)四唑-5-胺
  参考文献：
  名称：

  THE SYNTHESIS OF 5-AMINOTETRAZOLE DERIVATIVES

  摘要：

  DOI：

  10.1021/jo01141a021

文献信息

• New Synthesis and Nitration of 1,2-Bis(5-aminotetrazol-1-yl)ethane
  作者：Young-Hyuk Joo、Won-Bok Jeong、Soo-Gyeong Cho、Eun-Mee Goh、Yeong-Gweon Lim、Surk-Sik Moon

  DOI：10.5012/bkcs.2012.33.2.373

  日期：2012.2.20

  the utilization of an excellent in situ method that involves reactions of cyanogen azide and ethylene diamine. Nitration of aminotetrazole 2 using 100% nitric acid produced 3. The synthesis of nitroiminotetrazole salts provided a straightforward approach to highly energetic salts, which exhibit attractive physical properties, such as good thermal stabilities, high densities, and good heats of formation

  具有高氮含量的四唑衍生物属于一类有趣的杂环化合物，可应用于各种高能量密度材料 (HEDM)。特别是氨基四唑基含能材料由于其高热稳定性和较大的甲酸正热而引起了人们的极大兴趣。此外，预计它们非常不敏感，非常强大，并且在爆炸时产生的污染物更少。最近，1,2-双（5-硝基亚氨基四唑-1-基）乙烷（3）及其高能盐已经以良好的收率制备（方案1）。1,2-双（5-氨基四唑-1基）乙烷（2）的开发已通过利用涉及叠氮化氰和乙二胺反应的优良原位方法得到扩展。使用 100% 硝酸对氨基四唑 2 进行硝化产生 3。硝基亚氨基四唑盐的合成为高能盐提供了一种直接的方法，该盐具有有吸引力的物理性质，例如良好的热稳定性、高密度和良好的形成热。1-取代的5-氨基四唑衍生物是通过用卤代烷处理5-氨基四唑钾来制备的。文献中有几篇报道描述了通过 5-氨基四唑与烷基卤化物的烷基化原位生成 1-取代的 5-氨基四唑。然而，由于 1 和
• 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。
• Notes. N-Vinyl-tetrazoles
  作者：William Finnegan、Ronald Henry

  DOI：10.1021/jo01092a602

  日期：1959.10
• New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles
  作者：Jörg Stierstorfer、Karina R. Tarantik、Thomas M. Klapötke

  DOI：10.1002/chem.200802203

  日期：2009.6.2

  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‐[diaquabis1‐(2‐hydroxyethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] (14), trans‐[diaquabis1‐(2‐chloroethyl)‐5‐nitriminotetrazolato‐κ2N4,O5}copper(II)] dihydrate (15), and [diaquabis1‐(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.
• THE SYNTHESIS OF 5-AMINOTETRAZOLE DERIVATIVES
  作者：ROBERT M. HERBST、CARLETON W. ROBERTS、EDWARD J. HARVILL

  DOI：10.1021/jo01141a021

  日期：1951.1