methyl 4-bromo-3-nitro-5-propylthiobenzoate | 642068-75-5

• 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: methyl 4-bromo-3-nitro-5-propylthiobenzoate
• 英文别名: Methyl 4-bromo-3-nitro-5-propylsulfanylbenzoate
• CAS: 642068-75-5
• 化学式: C₁₁H₁₂BrNO₄S
• 分子量: 334.191
• InChiKey: LXIZSWPZJJKNIS-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  389.3±42.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-bromo-3-nitro-5-propylthiobenzoate 以 xylene 为溶剂， 以59%的产率得到dimethyl 2,2'-dinitro-6,6'-bis(propylthio)biphenyl-4,4'-dicarboxylate
  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：

  4-溴-3,5-二硝基苯甲酸 在 五氯化磷 、 氢溴酸 、 铁粉 、 溶剂黄146 作用下， 反应 2.75h， 生成 methyl 4-bromo-3-nitro-5-propylthiobenzoate
  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.