1-bromo-3,5-dichloro-2,6-dinitrobenzene | 115423-89-7

• 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: 1-bromo-3,5-dichloro-2,6-dinitrobenzene
• 英文别名: 3-Bromo-1,5-dichloro-2,4-dinitrobenzene
• CAS: 115423-89-7
• 化学式: C₆HBrCl₂N₂O₄
• 分子量: 315.895
• InChiKey: UIXAGNDQHXZADU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-bromo-3,5-dichloro-2,6-dinitrobenzene 在 四(三苯基膦)钯 铜 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 xylene 为溶剂， 反应 32.0h， 生成 3,3',5,5'-tetrakis(4-octyloxyphenyl)-2,2',6,6'-tetranitrobiphenyl
  参考文献：
  名称：

  Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: the effect of heteroatom and substitution pattern on phase stability

  摘要：

  一系列密切相关的四取代苯并[c]吡咯啉（1）、四烯氮（2）、菲（3）和芘（4）衍生物的介质性质通过热学、光学、光谱及粉末XRD分析进行了研究。只有三种3,4-二辛氧基苯衍生物表现出了介质特性。将N替换为CH（3→1和4→2对）以及核心元素尺寸的增加（1→2和3→4对）显著提高了相位稳定性。研究结果及观察到的趋势通过对构象特性的分析进行了合理化，包括平面化能量的计算，以及脂肪链密度和填充分数的建模。分子轨道计算显示，四氮衍生物2c显著缺电子，适合用于电子导电材料。

  DOI：

  10.1039/b615545f
• 作为产物：
  描述：

  1,5-二氯-2,4-二硝基苯 在 双氧水 、 溴 、 铁粉 、 溶剂黄146 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 1-bromo-3,5-dichloro-2,6-dinitrobenzene
  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.
• Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: the effect of heteroatom and substitution pattern on phase stability
  作者：Monika J. Sienkowska、John M. Farrar、Fan Zhang、Sharat Kusuma、Paul A. Heiney、Piotr Kaszynski

  DOI：10.1039/b615545f

  日期：——

  A series of closely related tetrasubstituted derivatives of benzo[c]cinnoline (1), tetraazapyrene (2), phenanthrene (3), and pyrene (4) were investigated for their mesogenic properties using thermal, optical, spectroscopic, and powder XRD analyses. Only three 3,4-dioctyloxyphenyl derivatives exhibited mesogenic properties. Substitution of N for CH (3 → 1 and 4 → 2 pairs) and also increase of the core element size (1 → 2 and 3 → 4 pairs) significantly increases the mesophase stability. The findings and observed trends were rationalized by analysis of conformational properties which included calculation of the planarization energy, and modeling of aliphatic chain density and fill fractions. MO calculations showed that the tetraaza derivative 2c is significantly electron deficient and suitable for electron conductive materials.

  一系列密切相关的四取代苯并[c]吡咯啉（1）、四烯氮（2）、菲（3）和芘（4）衍生物的介质性质通过热学、光学、光谱及粉末XRD分析进行了研究。只有三种3,4-二辛氧基苯衍生物表现出了介质特性。将N替换为CH（3→1和4→2对）以及核心元素尺寸的增加（1→2和3→4对）显著提高了相位稳定性。研究结果及观察到的趋势通过对构象特性的分析进行了合理化，包括平面化能量的计算，以及脂肪链密度和填充分数的建模。分子轨道计算显示，四氮衍生物2c显著缺电子，适合用于电子导电材料。