5-(2H-四唑-5-基)-2H-四唑 | 2783-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(2H-四唑-5-基)-2H-四唑
• 英文名称: 5,5'-bi-1H-tetrazole
• 英文别名: 5,5'-bistetrazole；5,5'-Bitetrazole；5,5’-bistetrazole；5,5′-bistetrazole；5-(2H-tetrazol-5-yl)-2H-tetrazole
• CAS: 2783-98-4
• 化学式: C₂H₂N₈
• mdl: MFCD00603746
• 分子量: 138.091
• InChiKey: MTAYYBKXNAEQOK-UHFFFAOYSA-N

物化性质

• 沸点：
  545.0±33.0 °C(Predicted)
• 密度：
  1.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-(2H-四唑-5-基)-2H-四唑 在 oxone 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 15.0h， 以39%的产率得到5,5'-bis(2-hydroxytetrazole)
  参考文献：
  名称：

  Energetic salts of 5,5′-bis(tetrazole-2-oxide) in a comparison to 5,5′-bis(tetrazole-1-oxide) derivatives

  摘要：

  xcThe preparation and isolation of 5,5'-bis(2-hydroxytetrazole) by oxidation of 5,5'-bistetrazole using commercially available oxone is described. The nitrogen-rich salts including ammonium, hydroxylammonium, guanidinium, aminoguanidinium, triaminoguanidinium, 5-aminotetrazolium and aminonitroguanidinium have been prepared, characterized (XRD, NMR and vibrational spectroscopy, DSC, mass spectrometry) and compared to their 5,5'-bis(tetrazole-1-oxide) analogues. The impact, friction and electrical spark sensitivities of all compounds were measured and several detonation parameters such as the detonation velocities and detonation pressures were also calculated with the EXPLO5 code based on calculated heats of formation (CBS-4M) and the X-ray densities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.12.015
• 作为产物：
  描述：

  氰 在 迭氮酸 、 水 作用下， 生成 5-(2H-四唑-5-基)-2H-四唑
  参考文献：
  名称：

  Oliveri-Mandala; Passalacqua, Gazzetta Chimica Italiana, 1913, vol. 43 II, p. 473

  摘要：

  DOI：

文献信息

• New lithium borates with bistetrazolato²⁻ and pyrazinediolato²⁻ ligands – potentially interesting lithium electrolyte additives
  作者：Lars H. Finger、Alexander Venker、Fabian G. Schröder、Jörg Sundermeyer

  DOI：10.1039/c7dt00308k

  日期：——

  We present a convenient synthesis of the first silylated bistetrazole via a catalyzed twin [2 + 3] cycloaddition of TMS-azide at cyanogen and its application to access bistetrazolatoborates, structurally characterized by a unique unsaturated ten-membered B2N4C4 heterocyclic system. Furthermore, new borate anions with two pyrazine-2,3-diolato ligands were synthesized from tetrafluoroborate salts and

  我们提出了一种方便的合成方法，通过在氰根上催化TMS-叠氮化物的双[2 + 3]环加成反应合成第一个甲硅烷基联苯二唑，并应用它来访问双四唑硼酸酯，其结构特征是独特的不饱和十元B 2 N 4 C 4杂环系统。此外，由四氟硼酸盐合成了具有两个吡嗪-2，3-二醇基配体的新硼酸根阴离子，并对其结构进行了表征。它们的有机阳离子可以通过阳离子交换被Li +交换。讨论了这些新盐与锂离子电池双草酸酯硼酸酯添加剂LiBOB（一种显着的固体电解质界面（SEI）发生器）的概念关系。
• Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction
  作者：Zeinab Noorpoor、Saeed Tavangar

  DOI：10.1080/00958972.2021.1914333

  日期：2021.5.19

  heterogeneous catalyst was characterized by FT-IR, 13C NMR, XRD, SEM, EDX, BET, BJH, and ICP-AES analysis. The catalytic activity of the catalyst was probed through the Ullmann reaction for synthesis of diaryl ether derivatives from two component reactions of aromatic arylhalides and phenol derivatives in DMSO. Simple procedure, high yields, short reaction time, and environmentally benign methods are advantages

  摘要 Cu基于5,5'-双四唑（[Cu 2 BT·2H 2 O] n）作为可回收的金属有机骨架（MOF）多相催化剂通过FT-IR、13 C NMR、XRD、SEM、EDX、 BET、BJH 和 ICP-AES 分析。该催化剂的催化活性是通过乌尔曼反应从芳香芳基卤化物和苯酚衍生物在 DMSO 中的两组分反应合成二芳基醚衍生物来探测的。该协议的优点是程序简单、产量高、反应时间短和环境友好。催化剂很容易通过简单的过滤分离并可重复使用，而不会显着降低其催化效率。
• Amination of energetic anions: high-performing energetic materials
  作者：Thomas M. Klapötke、Davin G. Piercey、Jörg Stierstorfer

  DOI：10.1039/c2dt30684k

  日期：——

  The new energetic materials 2-amino-5-nitrotetrazole (ANT, 1), 1-amino-3,4-dinitro-1,2,4-triazole (ADNT, 2), and both 1,1′-diamino-5,5′-bistetrazole and 1,2′-diamino-5,5′-bistetrazole (11DABT, 3 and 12DABT, 4) have been prepared by the amination of the parent anion with O-tosylhydroxylamine. The 5-H-tetrazolate anion has also been aminated using hydroxylamine O-sulfonic acid to both 1-aminotetrazole and 2-aminotetrazole (1AT, 5 and 2AT, 6). The prepared materials have been characterized chemically (XRD (1–4, 6·AtNO222, 8), multinuclear NMR, IR, Raman) and as explosives (mechanical and electrostatic sensitivity) and their explosive performances calculated using the EXPLO5 computer code. The prepared N-amino energetic materials, which can also be used as new ligands for high energy-capacity transition metal complexes, exhibit high explosive performances (in the range of hexogen and octogen) and a range of sensitivities from low to extremely high.

  新的高能材料 2-氨基-5-硝基四氮唑（ANT，1）、1-氨基-3,4-二硝基-1,2,4-三氮唑（ADNT，2）以及 1,1′-二氨基-5,5′-双四唑和 1、2′-二氨基-5,5′-双四唑（11DABT, 3 和 12DABT, 4）都是通过母阴离子与 O-对甲苯磺酸羟胺胺化制备的。5-H 四氮唑阴离子也用羟胺 O-磺酸胺化成了 1-氨基四氮唑和 2-氨基四氮唑（1AT, 5 和 2AT,6）。已对制备的材料进行了化学表征（XRD（1-4、6-AtNO222、8）、多核 NMR、IR、Raman）和爆炸表征（机械和静电敏感性），并使用 EXPLO5 计算机代码计算了它们的爆炸性能。所制备的 N-氨基高能材料也可用作高能量过渡金属配合物的新配体，具有很高的爆炸性能（在六原和八原范围内）和从低到极高的灵敏度。
• New Rare Earth Metal Complexes with Nitrogen-Rich Ligands: 5,5′-Bitetrazolate and 1,3-Bis(tetrazol-5-yl)triazenate—On the Borderline between Coordination and the Formation of Salt-Like Compounds
  作者：Patrick J. Eulgem、Axel Klein、Nicola Maggiarosa、Dieter Naumann、Roland W. H. Pohl

  DOI：10.1002/chem.200702006

  日期：2008.4.18

  two nitrogen-rich ligands BT(2-) (BT=5,5'-bitetrazole) and BTT(3-) (BTT=1,3-bis(1H-tetrazol-5-yl)triazene), a series of novel rare earth metal complexes were synthesised. For the BT ligand, a vast number of these complexes could be structurally characterised by single-crystal XRD, revealing structures ranging from discrete molecular aggregates to salt-like compounds. The isomorphous complexes [La2(BT)3]14

  从两个富含氮的配体BT（2-）（BT = 5,5'-bitetrazole）和BTT（3-）（BTT = 1,3-bis（1H-tetrazol-5-yl）triazene）中获得一系列合成了新颖的稀土金属配合物。对于BT配体，大量的这些络合物可以通过单晶XRD进行结构表征，揭示的结构范围从离散的分子聚集体到盐样化合物。同构配合物[La2（BT）3] 14 H2O（1）和[Ce2（BT）3] 14 （2）显示离散的分子，其中一个BT（2-）充当桥连配体，两个BT基团作为螯合剂配体。配合物[M（BT）（ ）7] 2 [BT] x（x） （3-5），（M = Nd（3），Sm（4）和Eu（5））也是是同构的，由[M（BT）（ ）7] +离子组成，其中每个金属中心只有一个BT（2-）充当螯合配体。[Tb（ ）8] 2 [BT] 3 x （6）和[Er（ ）8]（2）[BT]（3）x
• Synthesis and Characterisation of 5, 5'-Bistetrazolate Salts with Alkali Metal, Ammonium and Imidazolium Cations
  作者：Lars H. Finger、Fabian G. Schröder、Jörg Sundermeyer

  DOI：10.1002/zaac.201300150

  日期：2013.6

  metal 5, 5'-bistetrazolate (BT2–) salts Li2BT (1), Na2BT (2), K2BT (3), Rb2BT (4) and Cs2BT (5) as well as the mono ammonium (9) and the mono (10) and bis(1-ethyl-3-methylimidazolium) (11) salts of 5, 5'-bistetrazole. The crystal structures of the hydrates of the alkali metal salts (1h–4h) and hydrate free (9) to (11) are presented. Additionally we present structures of the monocaesium 5, 5'-bistetrazolate

  我们报告了碱金属 5, 5'-双四唑 (BT2-) 盐 Li2BT (1)、Na2BT (2)、K2BT (3)、Rb2BT (4) 和 Cs2BT (5) 的合成和表征以及单铵(9)和5,5'-双四唑的单(10)和双(1-乙基-3-甲基咪唑鎓)(11)盐。给出了碱金属盐 (1h–4h) 和无水合物 (9) 到 (11) 的水合物的晶体结构。此外，我们还介绍了 5, 5'-双四唑酸单铯 (6) 的结构以及已知盐钡 (7h) 和二铵 (8) 5, 5'-双四唑酸的替代修饰。在所提出的化合物中是第一个可逆熔融的 5, 5'-双四唑盐 (10, 11) 以及第一个基于 5, 5'-双四唑 (11) 的离子液体。所有物质均通过核磁共振和红外光谱研究，元素分析和组合 TGA/DSC 测量。对应于我们的主要动机，评估 5, 5'-双四唑的配位行为，我们简要总结了迄今为止结构表征的金属 5, 5'-双四唑盐。