3,5-dibromo-6-propylthiophenylboronic acid | 642068-41-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,5-dibromo-6-propylthiophenylboronic acid
• 英文别名: (3,5-Dibromo-2-propylsulfanylphenyl)boronic acid
• CAS: 642068-41-5
• 化学式: C₉H₁₁BBr₂O₂S
• 分子量: 353.87
• InChiKey: MALGZWILQDSAHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-三溴-2-硝基苯 、 3,5-dibromo-6-propylthiophenylboronic acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以60%的产率得到3,3',5,5'-tetrabromo-4-nitro-2'-propylthiobiphenyl
  参考文献：
  名称：

  Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals

  摘要：

  A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the formation of the Ar-Ar bond except for the synthesis of 1b. All tetra-ortho-substituted biphenyls were prepared via Ullmann coupling reactions. The halogens were introduced after formation of the biphenyl by utilizing the directing properties of the amino group(s). In the case of 3b, a polyhalogenated benzene substrate was used for biphenyl formation via Ullmann coupling.

  DOI：

  10.1021/jo030212p
• 作为产物：
  描述：

  2,4,6-三溴苯胺 在 盐酸 、 sodium hydroxide 、 正丁基锂 作用下， 以 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 29.75h， 生成 3,5-dibromo-6-propylthiophenylboronic acid
  参考文献：
  名称：

  Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals

  摘要：

  A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the formation of the Ar-Ar bond except for the synthesis of 1b. All tetra-ortho-substituted biphenyls were prepared via Ullmann coupling reactions. The halogens were introduced after formation of the biphenyl by utilizing the directing properties of the amino group(s). In the case of 3b, a polyhalogenated benzene substrate was used for biphenyl formation via Ullmann coupling.

  DOI：

  10.1021/jo030212p

文献信息

• Synthesis of Polyfunctionalized Biphenyls as Intermediates for a New Class of Liquid Crystals
  作者：Jason T. Manka、Fengli Guo、Jianping Huang、Huiyong Yin、John M. Farrar、Monika Sienkowska、Vladimir Benin、Piotr Kaszynski

  DOI：10.1021/jo030212p

  日期：2003.12.1

  A series of hexa- and octasubstituted biphenyls containing halogen, amino, nitro, and propylthio substituents were prepared by metal-mediated convergent synthesis from halobenzene precursors. The Pd-assisted C-C coupling methods were ineffective in the formation of the Ar-Ar bond except for the synthesis of 1b. All tetra-ortho-substituted biphenyls were prepared via Ullmann coupling reactions. The halogens were introduced after formation of the biphenyl by utilizing the directing properties of the amino group(s). In the case of 3b, a polyhalogenated benzene substrate was used for biphenyl formation via Ullmann coupling.