2-bromo-5-diisopropylphosphinothiophene | 1594710-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-bromo-5-diisopropylphosphinothiophene
• CAS: 1594710-61-8
• 化学式: C₁₀H₁₆BrPS
• 分子量: 279.181
• InChiKey: XSYQYUBNKABVOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-bromo-5-diisopropylphosphinothiophene 在 sulfur 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis and characterization of thienyl phosphines and thienyl phosphine chalcogenides

  摘要：

  Functionalized phosphine and phosphine chalcogenide ligands have the potential for applications in organometallic, inorganic and polymer chemistry. They serve as traditionally versatile donor ligands but also as handles for further chemical modification. The synthesis of 2-diisopropylphosphinothiophene (1), 2-bromo-5-diisopropylphosphinothiophene (2) and 5-diisopropylphosphino-2,2'-bithiophene (3) were performed. Compounds 1, 2 and 3 were isolated via lithium halogen exchange of 2-bromothiophene, 2,5-dibromothiophene, or 2,2'-bithiophene followed by addition of chlorodiisopropylphosphine, respectively. Compounds 1, 2, and 3 were then converted to the phosphine chalcogenides by reaction with elemental sulfur or selenium in toluene to yield 2-diisopropylphosphinothiophene sulfide (4), 2diisopropylphosphinothiophene selenide (5), 2-bromo-5-diisopropylphosphinothiophene sulfide (6), 2bromo-5-diisopropylphosphinothiophene selenide (7), 5-diisopropylphosphino-2,2'-bithiophene sulfide (8) and 5-diisopropylphosphino-2,2'-bithiophene selenide (9). All compounds 1-9 were isolated in excellent yields (85%-quantitative). H-1, C-13, and P-31 NMR, elemental analysis and gas chromatography mass spectrometry, were used to characterize the new phosphines and phosphine chalcogenides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.02.030
• 作为产物：
  描述：

  2,5-二溴噻吩 、 氯二异丙基膦 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以89%的产率得到2-bromo-5-diisopropylphosphinothiophene
  参考文献：
  名称：

  Synthesis and characterization of thienyl phosphines and thienyl phosphine chalcogenides

  摘要：

  Functionalized phosphine and phosphine chalcogenide ligands have the potential for applications in organometallic, inorganic and polymer chemistry. They serve as traditionally versatile donor ligands but also as handles for further chemical modification. The synthesis of 2-diisopropylphosphinothiophene (1), 2-bromo-5-diisopropylphosphinothiophene (2) and 5-diisopropylphosphino-2,2'-bithiophene (3) were performed. Compounds 1, 2 and 3 were isolated via lithium halogen exchange of 2-bromothiophene, 2,5-dibromothiophene, or 2,2'-bithiophene followed by addition of chlorodiisopropylphosphine, respectively. Compounds 1, 2, and 3 were then converted to the phosphine chalcogenides by reaction with elemental sulfur or selenium in toluene to yield 2-diisopropylphosphinothiophene sulfide (4), 2diisopropylphosphinothiophene selenide (5), 2-bromo-5-diisopropylphosphinothiophene sulfide (6), 2bromo-5-diisopropylphosphinothiophene selenide (7), 5-diisopropylphosphino-2,2'-bithiophene sulfide (8) and 5-diisopropylphosphino-2,2'-bithiophene selenide (9). All compounds 1-9 were isolated in excellent yields (85%-quantitative). H-1, C-13, and P-31 NMR, elemental analysis and gas chromatography mass spectrometry, were used to characterize the new phosphines and phosphine chalcogenides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.02.030