2,2'-diamino-3,3',5,5'-tetrabromobiphenyl | 91331-19-0

• 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: 2,2'-diamino-3,3',5,5'-tetrabromobiphenyl
• 英文别名: 2,2'-Diamino-3,5,3',5'-tetrabrom-biphenyl；2-(2-Amino-3,5-dibromophenyl)-4,6-dibromoaniline
• CAS: 91331-19-0
• 化学式: C₁₂H₈Br₄N₂
• 分子量: 499.825
• InChiKey: RSZIFLVCRFXVFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2'-diamino-3,3',5,5'-tetrabromobiphenyl 在 吡啶 、 双氧水 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 4.0h， 生成 2-amino-3,3',5,5'-tetrabromo-2'-nitrobiphenyl
  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：

  2,2-联苯二胺 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以46%的产率得到2,2'-diamino-3,3',5,5'-tetrabromobiphenyl
  参考文献：
  名称：

  3,5,3?,5?-3H4-2,2?-二亚苯基碘鎓阳离子及其4-硝基衍生物的合成

  摘要：

  3,5,3',5'-3H4-2,2'-二亚苯基碘鎓阳离子 [3H]-1 由冷的 2,2'-二氨基二苯基分三步合成。[3H]-1 的硝化很容易得到 4-硝基衍生物 [3H]-2。这两种含有四个氚标记的化合物具有高比活性，被提议用作研究 2,2'-二亚苯基碘鎓阳离子与氧化还原酶，尤其是黄素蛋白相互作用的工具。版权所有 © 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1344(200004)43:5<515::aid-jlcr337>3.0.co;2-v

文献信息

• 一种联苯类化合物及其在制备1,3,6,8-四溴芘中的应用
  申请人：李现伟

  公开号：CN108059582A

  公开（公告）日：2018-05-22

  本发明公开了一种联苯类化合物及其在制备1,3,6,8‑四溴芘中的应用。
• Synthesis of the 3,5,3?,5?-3H4-2,2?-diphenylene-iodonium cation and of its 4-nitro derivative
  作者：Jean-Luc Berthon、Maryl�ne Dias、Ren� Mornet、Jean-Michel Camadro

  DOI：10.1002/(sici)1099-1344(200004)43:5<515::aid-jlcr337>3.0.co;2-v

  日期：2000.4

  The 3,5,3′,5′-3H4-2,2′-diphenyleneiodonium cation [3H]-1 was synthesized in three steps from cold 2,2′-diaminodiphenyl. The nitration of [3H]-1 gave easily the 4-nitro derivative [3H]-2. These two compounds which contain four tritium labels were obtained with a high specific activity, and are proposed as tools to study the interaction of 2,2′-diphenyleneiodonium cations with redox enzymes, especially

  3,5,3',5'-3H4-2,2'-二亚苯基碘鎓阳离子 [3H]-1 由冷的 2,2'-二氨基二苯基分三步合成。[3H]-1 的硝化很容易得到 4-硝基衍生物 [3H]-2。这两种含有四个氚标记的化合物具有高比活性，被提议用作研究 2,2'-二亚苯基碘鎓阳离子与氧化还原酶，尤其是黄素蛋白相互作用的工具。版权所有 © 2000 John Wiley & Sons, Ltd.
• 989. Polycyclic cinnoline derivatives. Part IX. The bromination of benzo[c]cinnoline and the preparation and ultraviolet absorption spectra of reference compounds
  作者：J. F. Corbett、P. F. Holt

  DOI：10.1039/jr9610005029

  日期：——
• 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。