1-n-butyl-3-methylimidazolium borohydride | 1085783-64-7

• 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-n-butyl-3-methylimidazolium borohydride
• 英文别名: 1-allyl-3-methylimidazolium borohydride；3-butyl-1-methylimidazolium borohydride；[bmim]BH₄
• CAS: 1085783-64-7
• 化学式: BH₄*C₈H₁₅N₂
• 分子量: 154.063
• InChiKey: GCGBGCSVERRRMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 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：
  0.62
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-丁基-3-甲基咪唑溴盐 在 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到1-n-butyl-3-methylimidazolium borohydride
  参考文献：
  名称：

  基于双氰基硼酸盐的离子液体作为高齿液体

  摘要：

  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。

  DOI：

  10.1002/anie.201005748
• 作为试剂：
  描述：

  2,4,6-三苯基吡喃鎓高氯酸盐 在 1-n-butyl-3-methylimidazolium borohydride 作用下， 反应 8.0h， 生成 2,4,6-triphenyl-4H-pyran 、 1,3,5-triphenyl-penta-2,4-dien-1-one
  参考文献：
  名称：

  使用任务特定的离子液体/硼氢化物作为稳定和促进的氢释放试剂，可轻松，立体地合成各种二烯

  摘要：

  在这项工作中，首次使用任务特定的离子液体1 - n-丁基-3-甲基咪唑硼氢化物（[bmim] BH 4）作为介质和试剂，将高氯酸三芳基吡啶鎓区域选择性还原为提供芳香二烯酮作为唯一产品​​。具有反应性阴离子的[bmim] BH 4也可以促进所需的反应，从而减少反应时间并显着提高产率。通过简单的提取，可以容易地从反应混合物中分离出产物。

  DOI：

  10.1002/jhet.2983

文献信息

• 3-Butyl-1-methylimidazolinium borohydride ([bmim][BH4])—a novel reducing agent for the selective reduction of carbon–carbon double bonds in activated conjugated alkenes
  作者：Jiayi Wang、Gonghua Song、Yanqing Peng、Yidong Zhu

  DOI：10.1016/j.tetlet.2008.08.110

  日期：2008.11

  A novel ionic reducing reagent, 3-butyl-1-methylimidazolium borohydride ([bmim][BH4]), was synthesized and successfully used for the selective reduction of carbon–carbon double bonds in conjugated alkenes as well as the α,β-carbon–carbon double bonds in highly activated α,β,γ,δ-unsaturated alkenes. The reagent can be regenerated and reused several times without losing its activity.

  合成了一种新型的离子还原剂，3-丁基-1-甲基咪唑硼氢化物（[bmim] [BH 4 ]），并成功地用于选择性还原共轭烯烃中的碳-碳双键以及α，β-高度活化的α，β，γ，δ不饱和烯烃中的碳碳双键。该试剂可以再生并重复使用几次，而不会失去其活性。
• Borohydride Ionic Liquids and Borane/Ionic-Liquid Solutions as Hypergolic Fuels with Superior Low Ignition-Delay Times
  作者：Songqing Li、Haixiang Gao、Jean'ne M. Shreeve

  DOI：10.1002/anie.201309044

  日期：2014.3.10

  could allow the use of these substances as bipropellant fuels under a variety of conditions. A new family of borohydride ionic liquids and borane–ionic‐liquid solutions is described which meets nearly all of the desired important criteria for well‐performing fuels. They exhibit ignition‐delay times that are superior to that of any known hypergolic ionic liquid and may thus be legitimate replacements for

  在推进剂系统中，选择的燃料仍然是肼及其衍生物，即使它们包含一类急性致癌和有毒物质，它们表现出相当高的蒸气压，需要昂贵的处理程序和昂贵的安全预防措施。高分子量离子液体倾向于具有低挥发性以及高的热和化学稳定性，并且通常表现出宽的液体范围，这可以允许在各种条件下将这些物质用作双推进剂燃料。描述了一个新的硼氢化物离子液体和硼烷-离子液体溶液系列，它们满足了性能良好的燃料几乎所有所需的重要标准。它们的点火延迟时间优于任何已知的高离子离子液体，因此可能是肼及其衍生物的合法替代品。
• Effect of imidazolium ionic liquids on the hydrolytic activity of lipase
  作者：Na LI、Weiyan DU、Zhuonan HUANG、Wei ZHAO、Shoujiang WANG

  DOI：10.1016/s1872-2067(11)60521-4

  日期：2013.4

  The effect of 1-alkyl-3-methylimidazolium ionic liquids (ILs) on the hydrolysis activity of Candida rugosa lipase (CRL) toward triacylglycerol was investigated. The critical micelle concentrations (CMC) of ILs with Br-, Cl-, and [BF4](-) anions and the solubility of ILs with [PF6](-) anions were determined in phosphate buffer. Results suggested that the content of the ILs, not kosmotropicity, highly influenced the effects of anions and cations of ILs on CRL activity. As the length of alkyl chain of the cation [CnMIM](+) increased, lower IL content was required to achieve high enzyme activity. Once the concentrations of the ILs with Br-, Cl-, and [BF4](-) anions exceeded the CMC value, enzyme activity was suppressed. The positive promotion effect of anions on enzyme activity was in the order of Br- > Cl- > [BF4]- > [PF6](-). The effect of ionic liquid on enzyme activity was highly dependent on the pH and temperature of the system, with the optimum pH being 7.000. Under optimal conditions of pH 7.000, 30 degrees C, and 47.6 mmol/L of [C8MIM]Br, the highest relative activity of CRL (1734%) was achieved, with a specific activity of 54.4 U/mg protein. (C) 2013, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• Improved intermolecular hydride transfer using task-specific ionic liquid: a reasonable and environmentally benign approach for the synthesis of bioactive 2H-thiopyran derivatives
  作者：Arash Mouradzadegun、Zeynab Najafi、Somayeh Elahi

  DOI：10.1080/17415993.2015.1077388

  日期：2015.11.2

  The present study describes, for the first time, the application of 1-n-butyl-3-methylimidazolium borohydride ([bmim]BH4) as task-specific ionic liquid for highly regioselective reduction of triarylthiopyrylium salts. This method furnished a straightforward route for the synthesis of valuable 2H-thiopyrans derivatives, which are widely present as motifs in an assortment of biologically active molecules, in satisfactory yields, and excellent conversions without any conventional catalyst and organic solvent.[GRAPHICS].