3-methyl-1-sulfonic acid imidazolium hydrogen sulfate | 1343478-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate
• 英文别名: Hydrogen sulfate;3-methylimidazol-3-ium-1-sulfonic acid
• CAS: 1343478-60-3
• 化学式: C₄H₇N₂O₃S*HO₄S
• 分子量: 260.249
• InChiKey: CSZTWVCOYPXXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.03
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-methyl-1-sulfonic acid imidazolium chloride 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.05h， 以1.691 g的产率得到3-methyl-1-sulfonic acid imidazolium hydrogen sulfate
  参考文献：
  名称：

  Preparation, characterization and use of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an eco-benign, efficient and reusable ionic liquid catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups

  摘要：

  New and novel ionic liquid (3-methyl-1-sulfonic acid imidazolium hydrogen sulfate) is a recyclable and eco-benign catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups under solvent-free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-8 min). The catalyst was characterized by FT-IR, H-1 NMR and C-13 NMR studies. All the products were extensively characterized by H-1 NMR, IR, GC-MS and melting point analyses. A mechanism for the catalytic activity is proposed. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.08.021
• 作为试剂：
  描述：

  环戊醇 、 六甲基二硅氮烷 在 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate 作用下， 反应 0.08h， 以92%的产率得到环戊氧基(三甲基)硅烷
  参考文献：
  名称：

  Preparation, characterization and use of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an eco-benign, efficient and reusable ionic liquid catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups

  摘要：

  New and novel ionic liquid (3-methyl-1-sulfonic acid imidazolium hydrogen sulfate) is a recyclable and eco-benign catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups under solvent-free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-8 min). The catalyst was characterized by FT-IR, H-1 NMR and C-13 NMR studies. All the products were extensively characterized by H-1 NMR, IR, GC-MS and melting point analyses. A mechanism for the catalytic activity is proposed. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.08.021

文献信息

• Selective monoalkylation of hydroquinone in the presence of SO3H-functionalized ionic liquids as catalysts
  作者：Priyanka V. Bhongale、Sunil S. Joshi、Nilesh A. Mali

  DOI：10.1007/s11696-020-01230-1

  日期：2020.12

  A process aiming at O -alkylation of hydroquinone (HQ), where ionic liquids (ILs) act as catalyst is objectively described. Five SO3H-functionalized ILs having different cations were prepared and characterized by NMR and FTIR techniques. The acidity and thermal stability of ILs were determined by Hammett function and thermogravimetric analysis (TGA), respectively. The catalytic activity of these ILs

  瞄准的方法 Ô 烷基化氢醌（HQ），其中离子液体（离子液体）作为催化剂客观描述。制备了五种具有不同阳离子的SO 3 H官能化IL，并通过NMR和FTIR技术对其进行了表征。IL的酸度和热稳定性分别通过Hammett函数和热重分析（TGA）确定。测试了这些IL的催化活性以测定 O 在少量苯醌（BQ）存在下，用甲醇在4-甲氧基苯酚（4MP）中对HQ进行烷基化。使用1,3-二磺酸咪唑硫酸氢盐（IL2）催化剂检查并优化了反应参数（如温度，时间，催化剂负载和底物浓度）对HQ转化率和产物分布的影响，以使4MP的收率最大化。在338 K温度，5.45×10 –2  mol HQ，8.33×10 –3的条件下，所需产物4MP的最大产率为93.79％ 摩尔BQ和120分钟反应时间内的催化剂负载量为10.37摩尔％。在高达338 K的温度下观察到单一产物的形成，但较高的温度（338 K以上）和更长的反应时间导致形成副产物2
• 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.