2-hydroxy-5-bromotrimethylanilinium iodide | 114960-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-bromotrimethylanilinium iodide
• 英文别名: 5-bromo-2-hydroxy-tri-N-methyl-anilinium; iodide；5-Brom-2-hydroxy-tri-N-methyl-anilinium; Jodid
• CAS: 114960-01-9
• 化学式: C₉H₁₃BrNO*I
• 分子量: 358.017
• InChiKey: OQZYMZBXGMLYIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-bromotrimethylanilinium iodide 在 Amberlyst A-27 resin (chloride form) in H₂O 作用下， 生成 2-hydroxy-5-bromotrimethylanilinium chloride
  参考文献：
  名称：

  Acid-Base Equilibria of Hydrophilic Indicators in Water-in-Oil Microemulsions

  摘要：

  AbstractThe apparent pKa values of the positively charged, hydrophilic indicators 2‐hydroxy‐5‐bromo‐trimethylanilinium chloride (HBTC) and 2‐hydroxy‐5‐nitro‐trimethylanilinium chloride (HNTC) in the presence of water‐in‐oil microemulsion of the surfactants benzylcetyldimethyl ammonium chloride (BCDC) in benzene and polyoxyethylene (4) dodecyl ether (Brij‐30) in heptane were determined spectrophotometrically. The experimental variables were the type of buffer (benzimidazole, phosphate, and tris) and the ratios [water]/[surfactant] and [buffer]/[surfactant]. It is shown that: a) the indicators are confined within the second hydration shell of the nanodroplet, i.e. are not adsorbed at the water/oil interface; b) the use of the starting pH values of the buffer solutions, i.e., those measured outside the micellar domain, to calculate the micellar pKa values of the indicators is inadequate; c) buffer‐independent micellar pKa values can be obtained if the starting pHs of the buffer solutions were corrected for ion exchange with the counter‐ion of the positively charged surfactant, and for the lower polarity of the micelle‐solubilized water (relative to bulk water); d) the micellar ΔpKa (=pKa in the aggregate −pKa in water) ranged from ‐0.45 to ‐0.20 unit for HBTC/BCDC, from ‐0.44 to ‐0.13 unit for HNTC/BCDC, from 0.22 to 0.64 unit for HBTC/Brij‐30, and from 0.27 to 0.59 unit for HNTC/Brij‐30; e) these micelle‐induced pKa shifts can be analyzed in terms of the lower polarity of the micelle‐solubilized water (relative to bulk water) and perturbation of the acid‐base equilibria by the electrostatic effect of the positively charged W/O interface (BCDC); f) the magnitude of latter effect, at the average solubilization site of the indicator was calculated to range from 28 to 67 mV.

  DOI：

  10.1002/bbpc.19900940812
• 作为产物：
  描述：

  4-溴-2-硝基苯酚 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-hydroxy-5-bromotrimethylanilinium iodide
  参考文献：
  名称：

  Acid-Base Equilibria of Hydrophilic Indicators in Water-in-Oil Microemulsions

  摘要：

  AbstractThe apparent pKa values of the positively charged, hydrophilic indicators 2‐hydroxy‐5‐bromo‐trimethylanilinium chloride (HBTC) and 2‐hydroxy‐5‐nitro‐trimethylanilinium chloride (HNTC) in the presence of water‐in‐oil microemulsion of the surfactants benzylcetyldimethyl ammonium chloride (BCDC) in benzene and polyoxyethylene (4) dodecyl ether (Brij‐30) in heptane were determined spectrophotometrically. The experimental variables were the type of buffer (benzimidazole, phosphate, and tris) and the ratios [water]/[surfactant] and [buffer]/[surfactant]. It is shown that: a) the indicators are confined within the second hydration shell of the nanodroplet, i.e. are not adsorbed at the water/oil interface; b) the use of the starting pH values of the buffer solutions, i.e., those measured outside the micellar domain, to calculate the micellar pKa values of the indicators is inadequate; c) buffer‐independent micellar pKa values can be obtained if the starting pHs of the buffer solutions were corrected for ion exchange with the counter‐ion of the positively charged surfactant, and for the lower polarity of the micelle‐solubilized water (relative to bulk water); d) the micellar ΔpKa (=pKa in the aggregate −pKa in water) ranged from ‐0.45 to ‐0.20 unit for HBTC/BCDC, from ‐0.44 to ‐0.13 unit for HNTC/BCDC, from 0.22 to 0.64 unit for HBTC/Brij‐30, and from 0.27 to 0.59 unit for HNTC/Brij‐30; e) these micelle‐induced pKa shifts can be analyzed in terms of the lower polarity of the micelle‐solubilized water (relative to bulk water) and perturbation of the acid‐base equilibria by the electrostatic effect of the positively charged W/O interface (BCDC); f) the magnitude of latter effect, at the average solubilization site of the indicator was calculated to range from 28 to 67 mV.

  DOI：

  10.1002/bbpc.19900940812

文献信息

• Pfleger; Waldmann, Chemische Berichte, 1957, vol. 90, p. 2471,2576
  作者：Pfleger、Waldmann

  DOI：——

  日期：——