3,3'-diiodobiphenyl | 31037-00-0

• 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: 3,3'-diiodobiphenyl
• 英文别名: 3,3'-Diiodbiphenyl；1-Iodo-3-(3-iodophenyl)benzene
• CAS: 31037-00-0
• 化学式: C₁₂H₈I₂
• 分子量: 406.005
• InChiKey: XMIAXDFATHZEDR-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77℃ (ethanol )
• 沸点：
  417.1±38.0 °C(Predicted)
• 密度：
  2.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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：

  3,3'-diiodobiphenyl 在 palladium diacetate copper(l) iodide 、 1,10-菲罗啉 、 三叔丁基膦 、 caesium carbonate 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Practical Synthesis of Azobenzenophanes

  摘要：

  We devised a practical synthetic route to azobenzenophanes via successive Cu- and Pd-catalyzed coupling reaction of aryl hydrazide and aryl halide followed by Cu(I)-mediated oxidation reaction.

  DOI：

  10.1021/jo062164p
• 作为产物：
  描述：

  m-Iodbenzol-diazonium 在 1,10-菲罗啉 、 三苯基膦氯金 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.0h， 生成 3,3'-diiodobiphenyl
  参考文献：
  名称：

  可见光驱动、金 (I) 催化通过芳基偶氮磺酮的均偶联制备对称（杂）联芳基化合物

  摘要：

  在PPh 3 AuCl作为催化剂的情况下，在可见光照射下成功地通过芳基偶氮砜制备了对称（杂）联芳基化合物。本方案可以在无光催化剂的条件下在有机水溶剂中有效合成多种目标化合物。

  DOI：

  10.1021/acs.joc.2c00225

文献信息

• Syntheses and physical properties of several octiphenyls containing mixed linkages.
  作者：SHIGERU OZASA、YASUHIRO FUJIOKA、MACHIYO TSUKADA、EIICHI IBUKI

  DOI：10.1248/cpb.29.344

  日期：——

  Eight new linear octiphenyls containing two or three kinds of linkage were synthesized by the Ullmann homo-coupling reaction of iodoquaterphenyl. Among them, five compounds were alternatively synthesized by the Kharash-type Grignard cross-coupling of biphenylylmagnesium bromide and diiodoquaterphenyl or of terphenylylmagnesium iodide and diiodoquaterphenyl in the presence of bis (acetylacetonato) nickel (II). Spectral studies proved that the octiphenyls thus prepared displayed highly characteristic infrared, ultraviolet, and nuclear magnetic resonance spectra. Empirical Huckel molecular orbital calculations of the longest wavelength absorption bands of the octiphenyls were also performed. The calculated and observed wavelengths were in rather good agreement, except for the cases of two compounds.

  通过碘四联苯的Ullmann同系偶联反应合成了8个新型线性八联苯，包含2种或3种连接方式。其中5个化合物是通过双(乙酰丙酮)镍(II)催化的二碘四联苯和联苯基溴化镁或三联苯基碘化镁的Kharash型Grignard交叉偶联反应替代合成的。光谱研究表明，这些合成的八联苯显示出非常有特征的红外、紫外和核磁共振光谱。同时对八联苯最长波长吸收带的实验性Huckel分子轨道计算也进行了研究，除了两种化合物外，计算得到的波长与观测值相当吻合。
• Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles
  作者：Stanisława Tarnowicz、Waleed Alsalahi、Ewa Mieczyńska、Anna M. Trzeciak

  DOI：10.1016/j.tet.2017.03.034

  日期：2017.9

  Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium

  Pd（0）纳米粒子 通过在稳定PVP的聚合物存在下于80°C的水中还原PdCl 2和Pd（OAc）2可获得直径为2 nm的直径。Pd（0）NPs已成功用于烯丙醇与碘代和溴代苯的Heck偶联反应。碘苯在无溶剂条件下或在DMF溶液中反应，生成3-芳基丙醛和2-芳基丙醛作为主要产物。在溴苯在TBAB中作为反应介质的反应中获得了相同的产物。Pd（0）NPs的稳定性在回收实验中得到了证明。在相同条件下，钯化合物PdCl 2（cod）和Pd（OAc）2也获得了相似的Heck偶联结果。
• Polyphenyl synthesis by means of the Kharash-type Grignard cross-coupling reaction.
  作者：EIICHI IBUKI、SHIGERU OZASA、YASUHIRO FUJIOKA、MOTOFUMI OKADA、YOSHIHIKO YANAGIHARA

  DOI：10.1248/cpb.30.2369

  日期：——

  A series of twenty-seven polyphenyls, including quater-to sexiphenyls, was synthesized by the cross-coupling reaction of aryl Grignard reagents with arylene diiodides in the presence of bis (acetylacetonato) nickel (II). Twenty of them were obtained in fairly good yields (50-95%) under mild conditions at temperatures below ca. 60°C in ether-benzene solution within a few hours. In the cases of the remaining seven polyphenyls, however, lower yields (1-34%) were inevitable owing to the sterically crowded geometry of the reactant (s). Thus, the Kharash-type Grignard cross-coupling reaction was proved to be an efficient and convenient method for synthesizing a variety of polyphenyls, except in the cases of reactants with remarkably crowded geometry. The infrared, ultraviolet, and proton magnetic resonance spectral properties of several polyphenyls including three new compounds, 3-(2-biphenylyl)-o-quaterphenyl, 6'-(3-biphenylyl)-m-quaterphenyl, and 3, 4'-di (2-biphenylyl) biphenyl, are presented and discussed.

  合成了一系列二十七种多酚类化合物，包括四苯到六苯，通过芳基格氏试剂与芳烃二碘化物在双（乙酰丙酮）镍（II）的存在下进行交叉偶联反应。在温度低于约60°C的醚-苯溶液中，在温和条件下，这二十种化合物的产率相当不错（50-95%），反应时间为几小时。然而，在另外七种多酚类化合物的情况下，由于反应物的立体拥挤几何结构，不可避免地产率较低（1-34%）。因此，Kharash型格氏交叉偶联反应被证明是一种高效且便利的方法用于合成各种多酚类化合物，但在具有显著拥挤几何形状的反应物情况下例外。文中介绍并讨论了包括三个新化合物（3-(2-联苯基)-o-四苯、6'-(3-联苯基)-m-四苯、和3,4'-二（2-联苯基）联苯）在内的几种多酚类化合物的红外、紫外及质子磁共振光谱特性。
• Studies of Polyphenyls and Polyphenylenes. I. The Syntheses and Infrared and Electronic Spectra of Several Sexiphenyls
  作者：Eiichi Ibuki、Shigeru Ozasa、Kazue Murai

  DOI：10.1246/bcsj.48.1868

  日期：1975.6

  Ullmann reaction of iodobiphenyl and diiodobiphenyl. Infrared studies indicated that the fine structure in the 780–810 cm−1 region suggests the presence of consecutive m-phenylene units, and that the positions of the strong or medium bands in the 820–840 cm−1 region indicate approximately the number of continuous p-phenylene units. The electronic spectra commonly displayed a prominent E-band in the narrow

  通过碘联苯和二碘联苯的乌尔曼反应合成了七种线性六联苯。红外研究表明，780-810 cm-1 区域的精细结构表明存在连续的间亚苯基单元，820-840 cm-1 区域中强或中带的位置表明大约有连续对亚苯基单元。电子光谱通常在 192-207 nm 的狭窄区域显示出突出的 E 带。260 nm 以上的强 K 带被认为表明存在一个或多个对亚苯基单元。
• Syntheses and physical properties of several deuterium-labelled polyphenyls.
  作者：SHIGERU OZASA、YASUHIRO FUJIOKA、MOTOFUMI OKADA、HIROMI IZUMI、EIICHI IBUKI

  DOI：10.1248/cpb.29.370

  日期：——

  A Kharash-type Grignard cross-coupling reaction of phenyl-d5-magnesium bromide and an appropriate diiodo compound in the presence of bis (acetylacetonato) nickel (II) was successfully employed for the syntheses of twelve new decadeuterated polyphenyls, each of which has phenyl-d5 rings at both termini. On the basis of the nuclear magnetic resonance spectra of the deuterated and normal polyphenyls, close correlations between the apparent signal patterns of phenylene groups and the structures of the adjacent groups became apparent. The mass spectral studies revealed that the deuterated polyphenyls containing o-linkage (s) were less stable to electron bombardment than those containing no o-linkage. Inspection of the ultraviolet spectra of the deuterated polyphenyls showed that the isotope effect in their K-bands was hardly detectable.

  在双（乙酰丙酮）镍（II）存在下，苯基-d5-溴化镁和适当的二碘化合物的卡拉什型格氏交叉偶联反应成功地用于合成十二种新的十氘代多苯基，每种都含有苯基-d5 在两个末端均响铃。根据氘代和正态聚苯的核磁共振谱，亚苯基的表观信号模式与相邻基团的结构之间的密切相关性变得明显。质谱研究表明，含有o-键的氘代多苯对电子轰击的稳定性低于不含o-键的氘代多苯。对氘代聚苯的紫外光谱的检查表明，其K带中的同位素效应几乎检测不到。