4-butyl-1-methyl-4H-1,2,4-triazol-1-ium bromide | 1268852-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-butyl-1-methyl-4H-1,2,4-triazol-1-ium bromide
• 英文别名: 1-n-butyl-3-methyltriazolium bromide
• CAS: 1268852-02-3
• 化学式: Br*C₇H₁₄N₃
• 分子量: 220.112
• InChiKey: ZJXTZLGHLKAWEE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.49
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-butyl-1-methyl-4H-1,2,4-triazol-1-ium bromide 、 sodium cyanoborohydride 以 二氯甲烷 为溶剂， 以91 %的产率得到4-butyl-1-methyl-1H-1,2,4-triazol-4-ium cyanotrihydroborate
  参考文献：
  名称：

  Achieving short ignition delay and high specific impulse with cyanoborohydride-based hypergolic ionic liquids

  摘要：

  介绍了一种基于取代的 1H-1,2,4-三唑-4-鎓、吡咯烷鎓、铵和吡啶鎓阳离子以及氰硼氢化阴离子的新型 HIL 系列，与二甲基肼相比，其形成热、燃烧热和比冲都更高。

  DOI：

  10.1039/d2nj03372k
• 作为产物：
  描述：

  1-甲基-1,2,4-三唑 、 正溴丁烷 反应 24.0h， 生成 4-butyl-1-methyl-4H-1,2,4-triazol-1-ium bromide
  参考文献：
  名称：

  烷基和芳基取代基对基于1,2,4-三唑鎓的离子液体的二氧化碳分离和捕获作用†

  摘要：

  已经合成了一系列基于1,2,4-三唑鎓的离子液体，并对其在基于支持的离子液体膜的CO 2分离中的用途进行了评估。这些基于三唑鎓的化合物的性质已证明对异构取代（例如异丙基和丙基）以及芳基衍生物化合物中的邻位和对位取代敏感。虽然结构异构体之间的物理特性（如粘度）没有显着变化，但CO 2渗透性，选择性和溶解度表现出显着变化，从而允许开发用于分离应用的任务特定的三唑基离子液体。还完成了COSMOtherm研究，以更好地了解离子液体，这证明了含烷基离子液体的实验值与计算值之间存在很强的相关性。因此，基于1,2,4-三唑鎓的液体包括一类化合物，这些化合物提供了独特的机会来研究结构变化如何影响物化化学性质，这对于离子液体的连续开发具有增强的吸附能力和分离的选择性是必需的。

  DOI：

  10.1039/c2ra22646d

文献信息

• Dicyanoborate-Based Ionic Liquids as Hypergolic Fluids
  作者：Yanqiang Zhang、Jean'ne M. Shreeve

  DOI：10.1002/anie.201005748

  日期：2011.1.24

  Explosive though stable: Dicyanoborate‐based ionic liquids are hypergolic fuels in the presence of white fuming nitric acid as oxidizer (see high‐speed picture of the ignition process). With long liquid ranges, low viscosities, and short ignition delay times, these thermally and hydrolytically stable ionic liquids appear to be very promising substitutes for hydrazine and its derivatives as bipropellants

  爆炸性但稳定：在存在白色发烟硝酸作为氧化剂的情况下，基于双氰基硼酸盐的离子液体是高混合燃料（请参见点火过程的高速图片）。具有长的液体范围，低的粘度和短的点火延迟时间，这些热和水解稳定的离子液体似乎是肼及其衍生物作为双推进剂的非常有希望的替代品。
• Pd-PEPPSI complexes based on 1,2,4-triazol-3-ylidene ligands as efficient catalysts in the Suzuki—Miyaura reaction
  作者：A. Yu. Chernenko、A. V. Astakhov、D. V. Pasyukov、P. V. Dorovatovskii、Ya. V. Zubavichus、V. N. Khrustalev、V. M. Chernyshev

  DOI：10.1007/s11172-018-2040-8

  日期：2018.1

  The palladium complexes of the Pd-PEPPSI type with N-heterocyclic carbenes of the 1,2,4-triazole series were synthesized in 76—99% yields by the reactions of PdCl2 with 1,4-di- alkyl-1,2,4-triazolium salts in pyridine in the presence of KBr or KI as sources of halide ions and tetrabutylammonium salts as phase-transfer catalysts. The obtained complexes can be used as efficient catalysts for the Suzuki—Miyaura

  通过 PdCl2 与 1,4-二烷基-1,2 的反应，合成了 Pd-PEPPSI 型与 1,2,4-三唑系列的 N-杂环卡宾的钯配合物，产率为 76-99%，在作为卤离子源的 KBr 或 KI 和作为相转移催化剂的四丁基铵盐存在下，吡啶中的 4-三唑鎓盐。所得配合物可作为Suzuki-Miyaura交叉偶联的高效催化剂，其活性不逊于市售的Pd-PEPPSI催化剂。
• A New Mode of Operation of Pd-NHC Systems Studied in a Catalytic Mizoroki–Heck Reaction
  作者：Alexander V. Astakhov、Oleg V. Khazipov、Andrey Yu. Chernenko、Dmitry V. Pasyukov、Alexey S. Kashin、Evgeniy G. Gordeev、Victor N. Khrustalev、Victor M. Chernyshev、Valentine P. Ananikov

  DOI：10.1021/acs.organomet.7b00184

  日期：2017.5.22

  Metal complexes bearing N-heterocyclic carbene (NHC) ligands are typically considered the system of choice for homogeneous catalysis with well-defined molecular active species due to their stable metal ligand framework. A detailed study involving 19 different Pd-NHC complexes with imidazolium, benzimidazolium, and triazolium ligands has been carried out in the present work and revealed a new mode of operation of metal-NHC systems. The catalytic activity of the studied Pd-NHC systems is predominantly determined by the cleavage of the metal NHC bond, while the catalyst performance is strongly affected by the stabilization of in situ formed metal clusters. In the present study, the formation of Pd nanopartides was observed from a broad range of metal complexes with NHC ligands under standard Mizoroki-Heck reaction conditions. A mechanistic analysis revealed two different pathways to connect Pd-NHC complexes to "cocktail"-type catalysis: (i) reductive elimination from a Pd(II) intermediate and the release of NHC-containing byproducts and (ii) dissociation of NHC ligands from Pd intermediates. Metal-NHC systems are ubiquitously applied in modern organic synthesis and catalysis, while the new mode of operation revealed in the present study guides catalyst design and opens a variety of novel opportunities. As shown by experimental studies and theoretical calculations, metal dusters and nanopartides can be readily formed from M-NHC complexes after formation of new M-C or M-H bonds followed by C-NHC or H-NHC coupling. Thus, a combination of a classical molecular mode of operation and a novel cocktail-type mode of operation, described in the present study, may be anticipated as an intrinsic feature of M-NHC catalytic systems.