2-iodo-4-nitrobiphenyl | 91330-20-0

• 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-iodo-4-nitrobiphenyl
• 英文别名: 2-Iodo-4-nitro-1-phenylbenzene
• CAS: 91330-20-0
• 化学式: C₁₂H₈INO₂
• 分子量: 325.106
• InChiKey: RBNOGTZDRHXWPK-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±33.0 °C(Predicted)
• 密度：
  1.723±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-iodo-4-nitrobiphenyl 在 三氯化铁 、 甲烷 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 3-Iodo-4-phenylaniline
  参考文献：
  名称：

  Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls

  摘要：

  A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.

  DOI：

  10.1021/ja069238z
• 作为产物：
  描述：

  2-碘-4-硝基苯胺 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 2-iodo-4-nitrobiphenyl
  参考文献：
  名称：

  Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of o-Halobiaryls

  摘要：

  A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.

  DOI：

  10.1021/ja069238z

文献信息

• 420. Mesomorphism and chemical constitution. Part XI. The preparation and mesomorphic properties of substituted 4-p-n-alkoxybenzylideneaminobiphenyls
  作者：D. J. Byron、G. W. Gray、A. Ibbotson、B. M. Worrall

  DOI：10.1039/jr9630002246

  日期：——
• Synthesis of Polycyclic Aromatics and Heteroaromatics via Electrophilic Cyclization
  作者：Tuanli Yao、Marino A. Campo、Richard C. Larock

  DOI：10.1021/jo050104y

  日期：2005.4.1

  A variety of substituted polycyclic aromatics are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of 2-(1-alkynyl)biphenyls with ICl, I-2, NBS, and p-O2NC6H4SCl. This methodology readily accommodates various functional groups and has been successfully extended to systems containing a variety of polycyclic and heterocyclic rings.