1,2-二碘-4-硝基苯 | 1608-46-4

• 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: 1,2-二碘-4-硝基苯
• 英文名称: 1,2-Diiodo-4-nitrobenzene
• 英文别名: 1,2-Diiod-4-nitro-benzol
• CAS: 1608-46-4
• 化学式: C₆H₃I₂NO₂
• 分子量: 374.904
• InChiKey: FBLUCIWMGHTPJO-UHFFFAOYSA-N

物化性质

• 熔点：
  108-110 °C(Solv: ethanol (64-17-5))
• 沸点：
  347.6±32.0 °C(Predicted)
• 密度：
  2.578±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-二碘-4-硝基苯 在 碲化氢 、 copper(l) iodide 、 disodium telluride 作用下， 以 various solvent(s) 为溶剂， 以12%的产率得到2,7-Dinitro-9,10-ditelluranthracene
  参考文献：
  名称：

  A Convenient Synthesis of Functionalized Dibenzotellurophenes and Related Compounds via the Intramolecular Telluro Coupling Reaction. The Positive Effect of Heavy Chalcogen Atoms on the Molecular Hyperpolarizability of a Captodative Conjugation System

  摘要：

  Nitro-containing dibenzotellurophenes and related compounds, which are otherwise laborious to obtain, were prepared by the reaction of 2,2'-diiodobiphenyl derivatives with an in situ prepared tellurium-copper slurry. Partial reduction of 3,7-dinitrodibenzotellurophene using hydrazine hydrate/palladium on charcoal led to 3-amino-7-nitrodibenzotellurophene, which was found to exhibit a relatively large third-order molecular hyperpolarizability gamma (1.4 x 10(-31) esu) in the measurement of degenerated four-wave mixing (DFWM) as compared with 4-amino-4'-nitrobiphenyl and other previously reported compounds, confirming the positive effect of tellurium atom on the nonlinear optical property of a captodative conjugation system.

  DOI：

  10.1021/jo00121a053
• 作为产物：
  描述：

  2-氨基-4-硝基苯甲酸 在 碘 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 氘代氯仿 为溶剂， 以32%的产率得到1,2-二碘-4-硝基苯
  参考文献：
  名称：

  Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines

  摘要：

  A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115-degrees-C, 90 psi of CO, 3% PdCl2L2, and 2.4 equiv of DBU. This process is tolerant of a wide variety of functional groups and gives good yields of the desired products. Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction. The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.

  DOI：

  10.1021/jo00023a023

文献信息

• A New, One-Step, Effective Protocol for the Iodination of Aromatic and Heterocyclic Compounds via Aprotic Diazotization of Amines
  作者：Elena Krasnokutskaya、Nadya Semenischeva、Victor Filimonov、Paul Knochel

  DOI：10.1055/s-2006-958936

  日期：2007.1

  We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotiza- tion-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor sub- stituents in various positions to be obtained from the corresponding amines in

  我们开发了一种方便的一步制备芳香族和一些杂环碘化物的方法，方法是在室温下用 KI/NaNO2/p-TsOH 体系在乙腈中对芳香胺进行连续重氮化碘化。该方法具有一般特征，允许从相应的胺中以 50-90% 的收率获得在不同位置具有供体或受体取代基的芳基碘化物。
• Iodination of nitroarenes by a superactive reagent based on iodine chloride
  作者：V. K. Chaikovskii、T. S. Kharlova、V. D. Filimnov

  DOI：10.1007/bf02495292

  日期：1999.7

  Iodine chloride reacts with Ag2SO3 in H2SO4 to give a new superelectrophilic reagent capable of iodinating nitrobenzene, halogenated nitrobenzenes, nitrotoluenes, and aromatic compounds with two nitro groups in the ring. Mononitroarenes are easily iodinated at 0–20°C, while dinitroarenes require heating to 100–170°C.

  氯化碘在 H2SO4 中与 Ag2SO3 反应生成一种新的超亲电试剂，能够碘化硝基苯、卤代硝基苯、硝基甲苯和环中带有两个硝基的芳香族化合物。单硝基芳烃在 0-20°C 下很容易被碘化，而二硝基芳烃需要加热到 100-170°C。
• Formation of Arenesvia Diallylarenes: Strategic Utilization of Suzuki–Miyaura Cross-Coupling, Claisen Rearrangement and Ring-Closing Metathesis
  作者：Sambasivarao Kotha、Vrajesh R. Shah、Kalyaneswar Mandal

  DOI：10.1002/adsc.200600469

  日期：2007.5.7

  benzoannulation are reported. The first strategy is based on the Suzuki–Miyaura cross-coupling reaction. To this end, various ortho-diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring-closing metathesis (RCM) and one-pot dichlorodicyanoquinone (DDQ) oxidation

  报道了两种新的苯并环合合成策略。第一个策略是基于Suzuki-Miyaura交叉耦合反应。为此，使用烯丙基硼酸酯作为偶联伙伴，通过烯丙基化策略从相应的二碘代衍生物制备了各种邻二烯丙基苯衍生物。对这些二烯丙基衍生物进行闭环复分解（RCM）和一锅法二氯二氰基醌（DDQ）氧化，以生成2-取代的萘。在第二种策略中，使用双重Claisen重排和RCM协议作为关键步骤，以生成高度官能化的苯并苯基醌衍生物。
• Stepwise Assembly of Site Specifically Functionalized Dehydrobenzo[18]annulenes
  作者：Joshua J. Pak、Timothy J. R. Weakley、Michael M. Haley

  DOI：10.1021/ja991749g

  日期：1999.9.1

  Site specifically functionalized dehydrobenzo[18]annulenes (DBAs) with previously inaccessible topologies (C2v and Cs symmetry) were prepared by utilizing an in situ protiodesilylation/alkynylation reaction. By application of a stepwise synthetic route, donor and/or acceptor functional groups were introduced to the annulenic core in a designed manner. The electronic absorption spectra of the DBAs revealed

  通过利用原位蛋白脱甲硅烷基化/炔化反应制备了具有以前无法获得的拓扑结构（C2v 和 Cs 对称性）的位点特异性功能化脱氢苯并 [18] 环烯 (DBA)。通过应用逐步合成路线，以设计的方式将供体和/或受体官能团引入到环核中。DBA 的电子吸收光谱显示，当取代模式和/或官能团发生细微变化时，[18] 轮烯核的电子结构发生了中度至剧烈的变化。包含 C2v 对称性的大环表现出从 20 到 80 nm 的渐进和可预测的红移，以及增加的分子内激发态变化转移 (CT) 行为。不对称（Cs）分子呈现出更有趣的吸收行为，例如可见区域中带的加重。[18]DBA 20、22、23 和 25 的 X 射线晶体结构在平面环内显示出正常的键长和键角。
• NOVEL DIAMINOPHENOTHIAZINE COMPOUNDS, A METHOD FOR PREPARING SAME AND USES THEREOF
  申请人：Galey Laurent

  公开号：US20100204215A1

  公开（公告）日：2010-08-12

  Novel 2,8-diaminophenothiazine compounds, a method for preparing the same, and uses of the novel 2,8-diaminophenothiazine compounds in the field of treating liquid or gaseous fluids, especially influents and industrial or domestic effluents.

  小说2,8-二氨基苯并噻嗪化合物，其制备方法，以及在治疗液体或气态流体，特别是流入物和工业或家庭废水中使用新型2,8-二氨基苯并噻嗪化合物的用途。