1-benzyl-3-methylimidazolium p-toluenesulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyl-3-methylimidazolium p-toluenesulfonate
• 英文别名: 1-benzyl-3-methylimidazolium tosylate；[BnMim]TsO；1-Benzyl-3-methylimidazolium tosylate；1-benzyl-3-methylimidazol-3-ium;4-methylbenzenesulfonate
• 化学式: C₇H₇O₃S*C₁₁H₁₃N₂
• 分子量: 344.434
• InChiKey: UDTMKPOKOKZLFT-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-methylimidazolium p-toluenesulfonate 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到1-methyl-3-(4-sulfobenzyl)-1H-imidazol-3-ium 4-methylbenzenesulfonate
  参考文献：
  名称：

  Hydration of alkynes using Brönsted acidic ionic liquids in the absence of Nobel metal catalyst/H2SO4

  摘要：

  In this study, a variety of imidazole based sulfonic acid group functionalized Bronsted acidic ionic liquids (BAILs) were synthesized. BAILs have been successfully developed as task specific ionic liquids for hydration of alkynes under mild conditions to give high yields of ketones as a selective product. Acidity of BAILs was determined using volumetric titration and UV-visible spectroscopic methods. The Hammett acidity order and acid value of BAILS correlate well with the activity order observed for most of the BAILs in the hydration reaction of phenylacetylene. Theoretical studies demonstrate that hydrogen bonding plays a key role in tuning the acidity of BAILs. Density function theory calculations are also able to explain the difference in activity observed in these BAILS. The activity of ionic liquids was theoretically studied by computing the activation energy for the hydration reaction. Recycling experiments suggest that these novel BAILS can be reused without significant loss in activity. BAILS are simple and easy to prepare and exhibit excellent activity toward the hydration of a variety of alkynes to ketones. Moreover, the reaction involving BAILS does not involve heavy metal catalysts or H2SO4. Novel BAILs offer several attractive features such as sustainable synthetic route, low cost, moisture stability, high yields, and recyclability. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.04.010
• 作为产物：
  描述：

  对甲苯磺酸 、 1-苄基-3-甲基咪唑氯盐 以 二氯甲烷 为溶剂， 以94%的产率得到1-benzyl-3-methylimidazolium p-toluenesulfonate
  参考文献：
  名称：

  Hydration of alkynes using Brönsted acidic ionic liquids in the absence of Nobel metal catalyst/H2SO4

  摘要：

  In this study, a variety of imidazole based sulfonic acid group functionalized Bronsted acidic ionic liquids (BAILs) were synthesized. BAILs have been successfully developed as task specific ionic liquids for hydration of alkynes under mild conditions to give high yields of ketones as a selective product. Acidity of BAILs was determined using volumetric titration and UV-visible spectroscopic methods. The Hammett acidity order and acid value of BAILS correlate well with the activity order observed for most of the BAILs in the hydration reaction of phenylacetylene. Theoretical studies demonstrate that hydrogen bonding plays a key role in tuning the acidity of BAILs. Density function theory calculations are also able to explain the difference in activity observed in these BAILS. The activity of ionic liquids was theoretically studied by computing the activation energy for the hydration reaction. Recycling experiments suggest that these novel BAILS can be reused without significant loss in activity. BAILS are simple and easy to prepare and exhibit excellent activity toward the hydration of a variety of alkynes to ketones. Moreover, the reaction involving BAILS does not involve heavy metal catalysts or H2SO4. Novel BAILs offer several attractive features such as sustainable synthetic route, low cost, moisture stability, high yields, and recyclability. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.04.010

文献信息

• Redox Reaction: A New Route for the Synthesis of Water-Miscible Imidazolium Ionic Liquids
  作者：Zhigang Zhang、Wenxiu Li、Shangwu Dai、Dong Li、Qinqin Zhang、Hongtao Fan、Tao Zhang

  DOI：10.1055/s-0036-1589402

  日期：——

  but also simplifies the reaction conditions in comparison with previous routes. A novel chemical redox route was developed for the preparation of water-miscible imidazolium ionic liquids (ILs). In this method, the reaction between 1-alkyl-3-methylimidazolium bromides or 3-butyl-1-phenylimidazolium bromide and the appropriate acid reactant was promoted by the redox reaction between the bromide ion and

  摘要 开发了一种新颖的化学氧化还原路线，用于制备与水混溶的咪唑鎓离子液体（ILs）。在该方法中，通过溴化物离子与过氧化氢水溶液之间的氧化还原反应，与己烯-1-烯之间的氧化还原反应，促进了1-烷基-3-甲基咪唑鎓溴化物或3-丁基-1-苯基咪唑鎓溴化物与适当的酸反应物之间的反应。作为溶剂和溴清除剂。制备的IL的残留溴离子和水含量分别通过离子色谱法和Karl-Fischer试验确定。该方法不仅以高纯度和高产率产生与水混溶的IL，而且与以前的路线相比简化了反应条件。 开发了一种新颖的化学氧化还原路线，用于制备与水混溶的咪唑鎓离子液体（ILs）。在该方法中，通过溴化物离子与过氧化氢水溶液之间的氧化还原反应，与己烯-1-烯之间的氧化还原反应，促进了1-烷基-3-甲基咪唑鎓溴化物或3-丁基-1-苯基咪唑鎓溴化物与适当的酸反应物之间的反应。作为溶剂和溴清除剂。制备的IL的残留溴离子和水含量分别通过离子色谱
• Hydration of alkynes using Brönsted acidic ionic liquids in the absence of Nobel metal catalyst/H2SO4
  作者：Rajkumar Kore、T.J. Dhilip Kumar、Rajendra Srivastava

  DOI：10.1016/j.molcata.2012.04.010

  日期：2012.8

  In this study, a variety of imidazole based sulfonic acid group functionalized Bronsted acidic ionic liquids (BAILs) were synthesized. BAILs have been successfully developed as task specific ionic liquids for hydration of alkynes under mild conditions to give high yields of ketones as a selective product. Acidity of BAILs was determined using volumetric titration and UV-visible spectroscopic methods. The Hammett acidity order and acid value of BAILS correlate well with the activity order observed for most of the BAILs in the hydration reaction of phenylacetylene. Theoretical studies demonstrate that hydrogen bonding plays a key role in tuning the acidity of BAILs. Density function theory calculations are also able to explain the difference in activity observed in these BAILS. The activity of ionic liquids was theoretically studied by computing the activation energy for the hydration reaction. Recycling experiments suggest that these novel BAILS can be reused without significant loss in activity. BAILS are simple and easy to prepare and exhibit excellent activity toward the hydration of a variety of alkynes to ketones. Moreover, the reaction involving BAILS does not involve heavy metal catalysts or H2SO4. Novel BAILs offer several attractive features such as sustainable synthetic route, low cost, moisture stability, high yields, and recyclability. (c) 2012 Elsevier B.V. All rights reserved.