4-氯-4'-碘-1,1'-联苯 | 60200-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-4'-碘-1,1'-联苯
• 英文名称: 4-chloro-4'-iodobiphenyl
• 英文别名: 4-chloro-4'-iodo-1,1'-biphenyl；1-chloro-4-(4-iodophenyl)benzene
• CAS: 60200-91-1
• 化学式: C₁₂H₈ClI
• mdl: MFCD03931233
• 分子量: 314.553
• InChiKey: HCHAMYGZDLHKMD-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C
• 沸点：
  350.2±25.0 °C(Predicted)
• 密度：
  1.666±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  14
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-氯-4'-碘-1,1'-联苯 在 吡啶 、 palladium diacetate 、 potassium carbonate 作用下， 反应 3.0h， 以87%的产率得到4-氯联苯
  参考文献：
  名称：

  吡啶介导的醋酸钯催化离子液体体系中联芳卤化物的脱卤

  摘要：

  已经在室温离子液体中研究了乙酸钯催化的联芳基卤化物的脱卤，吡啶作为共溶剂。[bmim][PF6] 中吡啶与 Pd(OAc)2 结合的显着效果在联芳基碘和溴化物的脱卤中得到了极好的结果。吡啶将咪唑鎓盐的 C2-H 活化为氢源。所需产物的分离很容易通过乙醚萃取进行，Pd(OAc)2–[bmim][PF6] 系统可以循环使用五次，而活性仅略有下降。该程序代表了一种无需使用复杂配体即可制备联芳基化合物的环保方法。

  DOI：

  10.3184/174751912x13371621157105
• 作为产物：
  描述：

  4-氯联苯 在 iodinating agent 作用下， 以45%的产率得到4-氯-4'-碘-1,1'-联苯
  参考文献：
  名称：

  Haydock; Mulholland; Telford, European Journal of Medicinal Chemistry, 1984, vol. 19, # 3, p. 205 - 214

  摘要：

  DOI：

文献信息

• Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction
  作者：Yongxin Han、Shawn D Walker、Robert N Young

  DOI：10.1016/0040-4039(96)00364-4

  日期：1996.4

  A method for attaching haloarylsilanes to polymer support was developed. The polymer bound arylhalides were reacted with a variety of ArB(OH)2 under the Suzuki cross-coupling reaction conditions and the coupled resins were cleaved by different electrophiles to give ipso-substitution products in good yields.

  开发了一种将卤代芳基硅烷连接到聚合物载体上的方法。在Suzuki交叉偶联反应条件下，使聚合物键合的芳基卤化物与各种ArB（OH）2反应，并通过不同的亲电试剂裂解偶联的树脂，从而以高收率得到ipso取代产物。
• Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups
  作者：Arne Lützen、Ivonne Wallmann、Gregor Schnakenburg

  DOI：10.1055/s-0028-1083260

  日期：2009.1

  Oligo-p-phenylenes have proven to be versatile building blocks for the generation of self-assembled nanoaggregates via vapour deposition on solid supports whose optical properties and morphologies can be influenced by the introduction of functional groups. These aggregates show strong polarized luminescence and they have been demonstrated to have wave-guiding, lasing and even non-linear optical properties (e.g., frequency doubling) when the molecular building blocks are suitably functionalized. Thus, there is a demand for the synthesis of further functionalised p-phenylenes because similar properties can be expected from derivatives incorporating heteroaryl groups in the oligoarylene scaffold such as thiophenes, pyridines or carbazole units. The synthesis of such derivatives using a reliable Suzuki cross-coupling strategy is presented here.

  寡聚对苯基已被证明是通过在固体载体上进行蒸汽沉积生成自组装纳米聚集体的多功能构建模块，其光学性质和形态可以通过引入功能团来影响。这些聚集体显示出强烈的偏振光发光，并且已经证明，当分子建筑块经过适当功能化时，具有波导、激光和甚至非线性光学性质（如频率倍增）。因此，对进一步合成功能化对苯基的需求日益增加，因为可以预期，结合异芳基团的衍生物在寡聚芳烃骨架中，如噻吩、吡啶或咔唑单元，也会展现出类似的特性。这里展示了一种使用可靠的铃木交叉耦合策略合成此类衍生物的方法。
• Aryl radicals from hexazadienes and tetrazenes
  作者：Donald Mackay、Deane Douglas McIntyre

  DOI：10.1139/v82-148

  日期：1982.4.15

  Aryl radicals are produced from both ends of the hexazadienes 1 and 2 and from the tetrazene 3, either thermally or photolytically. They attack aromatic compounds in the nucleus, the yield of biaryl being in the range 40–70%, though it can be made nearly quantitative by using m-dinitrobenzene as an additive. The aryl radicals also oxidize 2-propanol to acetone, the reduction products being the halogenobenzene and 1,2-diacetylhydrazine.Photolysis of 1 goes mainly by way of the tetrazene 3, and this may also be a significant pathway in the thermal reaction. Azodiacetyl is an intermediate in the thermal reaction of 1 with 2-propanol and may be generally so in all its reactions.Radical induced decomposition is believed to be important in the reactions of 1, 2, and 3, and it is probably responsible for the formation of 1-acetyl-1-arylhydrazines, routinely produced in yields of up to 25%.

  芳基自由基可以通过热力或光解产生自六氮烯1和2的两端以及四氮烯3。它们攻击芳香化合物的核，生成的双芳基产率在40-70%范围内，但通过使用m-二硝基苯作为添加剂几乎可以达到定量。芳基自由基还可以将异丙醇氧化为丙酮，还原产物为卤代苯和1,2-二乙酰肼。光解1主要经过四氮烯3进行，这在热反应中也可能是一个重要途径。三氮乙酰基是1与异丙醇热反应的中间体，可能在所有反应中普遍存在。自由基诱导分解被认为在1、2和3的反应中很重要，可能是产生1-乙酰基-1-芳基肼的原因，通常产率高达25%。
• Synthesis of functionalized thiophene/phenyl co-oligomers by direct arylation of thiophenes
  作者：Andreas Osadnik、Arne Lützen

  DOI：10.3998/ark.5550190.p008.833

  日期：——

  well-defined nanostructures with interesting optica l and optoelectrical properties. Their synthesis, however, turns out to be rather complex in some cases. Here, we have optimized the synthesis of oligomers consisting of thiophene and phenylene groups with three or four aromatic units using a direct arylation approach, which allo ws us to use cheap starting materials and to minimize the number of reaction

  π-共轭棒状分子已被证明是生成具有有趣光学和光电特性的明确纳米结构的有力候选者。然而，在某些情况下，它们的合成结果是相当复杂的。在这里，我们使用直接芳基化方法优化了由具有三个或四个芳族单元的噻吩和亚苯基组成的低聚物的合成，这使我们能够使用廉价的起始材料并显着减少反应步骤的数量。
• Synthesis of Monofunctionalized p-Quaterphenyls
  作者：Arne Lützen、Ivonne Wallmann、Manuela Schiek、Rainer Koch

  DOI：10.1055/s-2008-1067163

  日期：2008.8

  Abstract: p -Oligophenyls have proven to be versatile buildingblocks for the generation of self-assembled nanoaggregates via va-por deposition on solid supports whose optical properties and mor-phologies can be influenced by the introduction of functionalgroups. Nonsymmetrically functionalized p , p ¢-disubstituted deriva-tives could even be demonstrated to form nanoaggregates that canact as frequency

  摘要： 对低聚苯已被证明是一种通用的结构单元，可通过气相沉积在固体载体上产生自组装纳米聚集体，其光学性质和形态会受到官能团的引入的影响。非对称功能化的 p , p ¢-二取代衍生物甚至可以被证明可以形成纳米聚集体，由于它们的非线性光学特性，可以作为倍频器。单功能化衍生物也可以预期类似的性质。因此，我们通过应用可靠的 Suzuki 交叉偶联策略开发了一种合成单官能化 1,1¢:4¢,1¢¢:4¢¢,1¢¢¢ - 四联苯 ( p -quaterphenines) 的通用方法. 关键词: 交叉偶联反应, 对低聚苯, 棒状分子,