1,2-bis(1H-tetrazol-5-yl)benzene | 73096-43-2

• 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-bis(1H-tetrazol-5-yl)benzene
• 英文别名: 1,2-bis(5-tetrazolyl)benzene；5-[2-(2H-tetrazol-5-yl)phenyl]-2H-tetrazole
• CAS: 73096-43-2
• 化学式: C₈H₆N₈
• 分子量: 214.189
• InChiKey: OQTRDGZKQAZJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• 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

反应信息

• 作为反应物：
  描述：

  1,2-bis(1H-tetrazol-5-yl)benzene 、 苯甲酰氯 在 吡啶 作用下， 反应 24.0h， 以58%的产率得到1,2-bis(5-phenyl-1,3,4-oxadiazol-2-yl)benzene
  参考文献：
  名称：

  Excited State Luminescence of Multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes in an Electron-Donating Matrix: Exciplex or Electroplex?

  摘要：

  Multi-(5-phenyl-1,3,4-oxadiazo-2-yl)benzenes show emission in organic solvents from ultraviolet to blue (339-447 nm). The reduction potentials E-1/2(red) cover a large range of -2.11 V for 2,5-diphenyl-1,3,4-oxadiazole to -0.76 V for l,2,3,4,5,6-hexa(5-phenyl-1,3,4-oxadiazo-2-yl)benzene. An unexpectedly wide spectral range of the oxadiazole (OXD) exciplex emissions in PVK is observed, ranging from 406 to 603 nm. The OXDs also exhibit similar electroluminescence (EL) when blended into polyvinylcarbazole (PVK). A linear correlation between the lambda(max) of the electroluminescence and photoluminescence is observed, implying that the emission mechanisms in both processes are similar. In addition, the linear correlation between the E-1/2(red) versus of lambda(max) of EL (eV) reflected that the term of the charge-transfer configuration of the contact electron-hole pair plays a major role in the exciplex emission. The exciplex EL of 1,2,5-tri(5-phenyl- 1,3,4-oxadiazo-2-yl)benzene (5) could be as high as 1.0 cd/A. Since the exciplex emission usually has a large Stokes shift, this provides a window for us to generate duo emissions for near white light EL with high efficiency. Among the devices we tried, the device of PVK/2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole/5/2,5,8,11-tetra-tert-butylperylene (100: 40:40:4) gave EL with good current efficiency of 1.63 cd/A.

  DOI：

  10.1021/jp9093063
• 作为产物：
  描述：

  1,2-二氰基苯 在 sodium azide 、 zinc(II) chloride 作用下， 以 乙二醇 为溶剂， 反应 0.33h， 以83%的产率得到1,2-bis(1H-tetrazol-5-yl)benzene
  参考文献：
  名称：

  锌催化叠氮化物离子加成至不饱和化合物的机理：由腈合成5取代的1Н-四唑和由异硫氰酸酯合成1取代的1Н-四唑-5-硫醇

  摘要：

  研究了NaN 3和ZnCl 2在脂肪醇中由有机腈和硫氰酸盐形成5-取代的1 H-四唑的机理。这项研究的结果允许提出从腈，硫氰酸盐和异硫氰酸盐合成取代四唑的有效方法。

  DOI：

  10.1134/s1070363217040119
• 作为试剂：
  描述：

  4-溴苯乙酮 、 potassium hexacyanoferrate(III) 在 1,2-bis(1H-tetrazol-5-yl)benzene 、 copper(I) iodide 、 caesium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以92%的产率得到对氰基苯乙酮
  参考文献：
  名称：

  在 1,2-双（5-四唑基）苯作为有效配体存在下，使用无毒 K 4 [Fe(CN) 6 ]碘化铜纳米粒子催化芳基卤化氰化

  摘要：

  在催化量的铜盐和1,2-双(5-四唑基)苯作为配体的存在下，在热条件下用K4[Fe(CN)6]进行芳基溴化物的氰化。该方法具有收率高、方法简单、易操作等优点。

  DOI：

  10.3184/174751914x13966206828910

文献信息

• Mechanism of the zinc-catalyzed addition of azide ion to unsaturated compounds: Synthesis of 5-substituted 1Н-tetrazoles from nitriles and of 1-substituted 1Н-tetrazole-5-thiols from isothiocyanates
  作者：L. V. Myznikov、S. V. Vorona、T. V. Artamonova、Yu. E. Zevatskii

  DOI：10.1134/s1070363217040119

  日期：2017.4

  The mechanism of the formation of 5-substituted 1H-tetrazoles from organic nitriles and thiocyanates in the presence of NaN3 and ZnCl2 in aliphatic alcohols was studied. The results of this study allowed efficient methods of synthesis of substituted tetrazoles from nitriles, thiocyanates, and isothiocyanates to be proposed.

  研究了NaN 3和ZnCl 2在脂肪醇中由有机腈和硫氰酸盐形成5-取代的1 H-四唑的机理。这项研究的结果允许提出从腈，硫氰酸盐和异硫氰酸盐合成取代四唑的有效方法。
• Highly Efficient Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by Cu-Zn Alloy Nanopowder, Conversion into 1,5- and 2,5-Disubstituted Tetrazoles, and Synthesis and NMR Studies of New Tetrazolium Ionic Liquids
  作者：Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1002/ejoc.201100957

  日期：2011.11

  synthesize several novel tetrazolium ionic liquids (ILs) with EtSO4–, OTf–, and NTf2– counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approximately 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and ethyl sulfate salts are room-temperature ILs that are hydrophilic, whereas

  在Cu-Zn合金纳米粉体作为催化剂存在下，通过腈类RCN和NaN3之间的[3+2]环加成反应合成了一系列5-取代的1H-四唑。然后将 1,5-二丁基、1-丁基-5-己基、2,5-二丁基和 2-丁基-5-己基衍生物用作结构单元，用 EtSO4– 合成几种新型四唑鎓离子液体 (IL)， OTf– 和 NTf2– 反离子。而 2,5-二烷基四唑的烷基化选择性地产生 N-4 烷基化鎓盐，而 1,5-二烷基衍生物通过在 N-3 和 N-4 处烷基化形成大约 1:1 的两种四唑盐混合物。三氟甲磺酸盐和乙基硫酸盐是亲水的室温离子液体，而 NTf2 盐是低熔点离子液体并且是疏水的。
• An Improved Protocol for the Preparation of 5-Substituted Tetrazoles from Organic Thiocyanates and Nitriles
  作者：Leonid Myznikov、Svetlana Vorona、Tatiana Artamonova、Yuri Zevatskii

  DOI：10.1055/s-0033-1340616

  日期：——

  unstable thiocyanates. Organic thiocyanates and nitriles are converted efficiently into the corresponding 5-substituted 1H-tetrazoles by treatment with zinc(II) chloride and sodium azide in aliphatic alcohols. The presented procedure provides mild reaction conditions, short reaction times, and good to excellent yields for a wide range of substrates, including deactivated aliphatic nitriles and thermally unstable

  摘要 通过在脂肪醇中用氯化锌（II）和叠氮化钠处理，将有机硫氰酸盐和腈有效地转化为相应的5-取代的1 H-四唑。所提出的方法为各种底物（包括失活的脂族腈和热不稳定的硫氰酸盐）提供了温和的反应条件，较短的反应时间以及良好的优良收率。 通过在脂肪醇中用氯化锌（II）和叠氮化钠处理，将有机硫氰酸盐和腈有效地转化为相应的5-取代的1 H-四唑。所提出的方法为各种底物（包括失活的脂族腈和热不稳定的硫氰酸盐）提供了温和的反应条件，较短的反应时间以及良好的优良收率。
• Preparation of 5-Substituted 1<i>H</i>-Tetrazoles from Nitriles in Water
  作者：Zachary P. Demko、K. Barry Sharpless

  DOI：10.1021/jo010635w

  日期：2001.11.1

  The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.

  已显示将叠氮化钠添加至腈中以生成1H-四唑在水中以锌盐为催化剂容易进行。反应范围很广。各种芳族腈，活化和未活化的烷基腈，取代的乙烯基腈，硫氰酸酯和氰胺均已证明是该反应的可行底物。
• Thallium(I)- and organothallium(III)-substituted mono-, bis- and tris-tetrazoles: synthesis and supramolecular structures
  作者：Sonali Bhandari、Mary F. Mahon、Kieran C. Molloy、Julie S. Palmer、Stephen F. Sayers

  DOI：10.1039/a910235n

  日期：——

  Six thallium(I) tetrazolates have been synthesized by either the addition of an alcoholic solution of the appropriate tetrazole to an ethanolic solution of thallium ethoxide, or from the sodium salt of the tetrazole with Tl2SO4. Seven diphenylthallium-substituted mono- and bis-tetrazoles have been synthesized by a condensation route involving the appropriate tetrazole and diphenylthallium hydroxide

  通过添加适当浓度的乙醇溶液，已经合成了六种四唑al（I）四唑 到乙醇th的乙醇溶液中，或从 钠盐 的 四唑用Tl 2 SO 4。通过缩合反应合成了七个二苯基th取代的单-和双-四唑四唑 和 氢氧化二苯th。1-二苯基噻烯基-5-苯基四唑也可以通过之间的环加成反应制得叠氮化二苯th 和 苄腈。[Tl（18-crown-6）+ ] 2 [C 2 N 10 2− ]，Ph 2 TlN 4 CPh·MeOH，1,4-（Ph 2 TlN 4 C）2 C 4 H 8 ·2MeOH的结构和1,2-（PH 2 TLN 4 C）2 C ^ 6 ħ 4 ·博士2 TLCL·2MeOH·2H 2 ö已被确定。后三种化合物产生掺入六元Tl 2 N 4环的超分子结构。最后两个包含第一个示例四唑 利用所有四个可用环 氮 进行协调。

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