1-butyl-3-methylimidazolium azide | 1031810-49-7

• 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-butyl-3-methylimidazolium azide
• 英文别名: [BMIM]N₃；1-butyl-3-methyl-1H-imidazol-3-ium azide；1-butyl-3-methylimidazol-3-ium;azide
• CAS: 1031810-49-7
• 化学式: C₈H₁₅N₂*N₃
• 分子量: 181.241
• InChiKey: ODTKNLCXDSWDGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  11.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氰基四氮唑 、 1-butyl-3-methylimidazolium azide 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 1-butyl-3-methylimidazolium 5-cyanotetrazolide
  参考文献：
  名称：

  Synthesis and Characterization of 5-Cyanotetrazolide-Based Ionic Liquids

  摘要：

  AbstractNew salts based on imidazolium, pyrrolidinium, phosphonium, guanidinium, and ammonium cations together with the 5‐cyanotetrazolide anion [C2N5]− are reported. Depending on the nature of cation–anion interactions, characterized by XRD, the ionic liquids (ILs) have a low viscosity and are liquid at room temperature or have higher melting temperatures. Thermogravimetric analysis, cyclic voltammetry, viscosimetry, and impedance spectroscopy display a thermal stability up to 230 °C, an electrochemical window of 4.5 V, a viscosity of 25 mPa s at 20 °C, and an ionic conductivity of 5.4 mS cm−1 at 20 °C for the IL 1‐butyl‐1‐methylpyrrolidinium 5‐cyanotetrazolide [BMPyr][C2N5]. On the basis of these results, the synthesized compounds are promising electrolytes for lithium‐ion batteries.

  DOI：

  10.1002/chem.201405264
• 作为产物：
  描述：

  氯化(1-丁基-3-甲基咪唑) 在 sodium azide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-butyl-3-methylimidazolium azide
  参考文献：
  名称：

  A facile and efficient [bmim]N3 catalyzed direct oxidative esterification of arylaldehydes with alcohols

  摘要：

  摘要 特定任务离子液体[bmim]N3被用作芳醛和醇直接氧化酯化反应的有效催化剂及反应介质。多种芳醛与一些初级和次级醇在[bmim]N3中顺利进行氧化酯化反应。对于含有电子吸引基团的芳醛，获得了令人满意的结果。在这些条件下，三级醇未发生反应。

  DOI：

  10.1016/j.crci.2012.08.004
• 作为试剂：
  描述：

  2-硝基苯甲腈 在 phosphotungstic acid 、 1-butyl-3-methylimidazolium azide 作用下， 反应 5.0h， 以89%的产率得到5-P-硝基苯基-1H-四氮唑
  参考文献：
  名称：

  Heteropolyacid catalyzed click synthesis of 5-substituted 1H-tetrazoles from [bmim]N3 and nitriles under solvent-free conditions

  摘要：

  A simple and solvent-free route for the synthesis of 5-substituted 1H-tetrazoles is reported. In this method, 5-substituted 1H-tetrazoles are synthesized from nitriles and [bmim]N-3 with heteropolyacid (H3PW12O40) as a catalyst under solvent-free conditions.

  DOI：

  10.1007/s00706-013-1025-4

文献信息

• Green and Facile Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Click Reaction of α-Bromo Ketones, [bmim]N<sub>3</sub> and Terminal Acetylenes
  作者：Azadeh Fazeli、Hossein Oskooie、Yahya Beheshtiha、Majid Heravi、Hassan Valizadeh

  DOI：10.2174/15701786113109990036

  日期：2013.11

  An efficient and green one pot method is reported for regioselective synthesis of 1,4-disubstituted 1,2,3- triazoles. In this method, β-ketoazides are generated via in situ reaction between α-bromo ketones and 1-butyl-3- methylimidazolium azide [bmim]N3 in aqueous ethanol and reacted with terminal acetylenes using Cu-CuSO4 at room temperature to afford 1,4-disubstituted 1,2,3-triazoles.

  报道了一种高效绿色的合成1,4-二取代1,2,3-三氮唑的一锅法。在该方法中，通过α-溴酮与1-丁基-3-甲基咪唑锍叠氮[bmim]N3在乙醇水溶液中的原位反应生成β-酮叠氮，再与末端炔烃在室温下使用Cu-CuSO4反应，得到1,4-二取代的1,2,3-三氮唑。
• Expanded perlite: an inexpensive natural efficient heterogeneous catalyst for the green and highly accelerated solvent-free synthesis of 5-substituted-1H-tetrazoles using [bmim]N₃ and nitriles
  作者：Roya Jahanshahi、Batool Akhlaghinia

  DOI：10.1039/c5ra21481e

  日期：——

  A versatile, green and highly accelerated protocol for preparing 5-substituted-1H-tetrazoles is reported using expanded perlite as a heterogeneous catalyst.

  报道了一种多功能、绿色且高度加速的协议，用于使用膨胀珍珠岩作为非均相催化剂制备5-取代-1H-四唑。
• Magnetically separable Fe₃O₄@chitin as an eco-friendly nanocatalyst with high efficiency for green synthesis of 5-substituted-1H-tetrazoles under solvent-free conditions
  作者：Monireh Zarghani、Batool Akhlaghinia

  DOI：10.1039/c6ra07252f

  日期：——

  application of this new nanocatalyst allows the synthesis of a variety of tetrazoles through the reaction of nitriles with 1-butyl-3-methylimidazolium azide ([bmim][N3]) under solvent-free conditions. This synthetic pathway is a green protocol offering significant advantages, such as excellent yield of products in short reaction times, mild reaction conditions, minimization of chemical waste, easy preparation

  本研究描述了一种高效，环保且简单的方法，该方法可合成磁铁矿-甲壳质（Fe 3 O 4 @甲壳质）作为绿色可回收催化剂，催化合成5-取代-1 H-四唑。Fe 3 O 4几丁质最初是使用水热合成法制备的。随后，使用诸如FT-IR，XRD，SEM，TEM，VSM和TGA等不同的光谱，显微镜和热重技术研究了制备的纳米催化剂的结构，形态和磁性。获得的结果表明，Fe 3 O 4几丁质纳米颗粒表现出均匀的立方体形状并且被良好地单分散。而且，磁测量显示合成的纳米催化剂具有超顺磁性特征。这种新型纳米催化剂的应用使得腈在无溶剂条件下通过腈与1-丁基-3-甲基咪唑鎓叠氮化物（[bmim] [N 3 ]）的反应可以合成多种四唑。该合成途径是绿色的方法，具有显着的优势，例如在短的反应时间内获得优异的产品收率，温和的反应条件，化学废物的最小化，催化剂的易于制备及其在不影响效率的情况下最多可循环使用六个循环。
• A facile and efficient [bmim]N3 catalyzed direct oxidative esterification of arylaldehydes with alcohols
  作者：Hassan Valizadeh、Mina Ahmadi

  DOI：10.1016/j.crci.2012.08.004

  日期：2012.11

  Résumé Task-specific ionic liquid, [bmim]N3 was used as an effective catalyst and reaction medium for the direct oxidative esterification of arylaldehydes with alcohols. The oxidative esterification reaction of a variety of arylaldehydes took place smoothly with some primary and secondary alcohols in [bmim]N3. Satisfactory results were obtained with arylaldehydes containing electron withdrawing groups. Tertiary alcohols did not react under these conditions.

  摘要 特定任务离子液体[bmim]N3被用作芳醛和醇直接氧化酯化反应的有效催化剂及反应介质。多种芳醛与一些初级和次级醇在[bmim]N3中顺利进行氧化酯化反应。对于含有电子吸引基团的芳醛，获得了令人满意的结果。在这些条件下，三级醇未发生反应。
• Pyridine based ionic fluoride for catalyzing indole and tetrazole formation
  申请人：King Abdulaziz University

  公开号：US10577327B2

  公开（公告）日：2020-03-03

  A pyridine based ionic liquid with a fluoride counter anion which catalyzes Fischer indole reaction and click chemistry. Methods of preparing the ionic liquid, and methods of utilizing the ionic liquid as a catalyst to synthesize indoles/indolenines and tetrazoles are also provided.

  一种含有氟化反阴离子的吡啶基离子液体，可催化费舍尔吲哚反应和点击化学。此外，还提供了制备该离子液体的方法，以及利用该离子液体作为催化剂合成吲哚/吲哚啉和四唑的方法。