1,4,5,8-四氯萘 | 3432-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4,5,8-四氯萘
• 英文名称: 1,4,5,8-tetrachloronaphthalene
• 英文别名: PCN 46；PCN-46；1,4,5,8-tetrachloro-naphthalene；1,4,5,8-Tetrachlor-naphthalin
• CAS: 3432-57-3
• 化学式: C₁₀H₄Cl₄
• 分子量: 265.954
• InChiKey: LITCKAVLJAKHOE-UHFFFAOYSA-N

物化性质

• 保留指数：
  2086.5

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  14
• 可旋转键数：
  0
• 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

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  1,4,5,8-四氯萘 在 selenium 、 sodium methylate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 1,4,5,8-tetraselenonaphthalene
  参考文献：
  名称：

  Process for the preparation of peri-dichalcogeno polycyclic aromatic

  摘要：

  一种制备周二硫族元素多环芳烃化合物的方法，首先在酰胺溶剂中制备碱金属硫化物、硒化物或碲化物，然后在第二步中，将其与周卤代芳烃化合物反应，该方法包括在第一步中，在高温下将碱金属碱基与元素硫、硒或碲反应。

  公开号：

  US05284942A1
• 作为产物：
  描述：

  晕苯 在 copper(l) chloride 氧气 、 甲烷 作用下， 反应 2.0h， 生成 1,4,5,8-四氯萘
  参考文献：
  名称：

  De Novo Synthesis Mechanism of Polychlorinated Dibenzofurans from Polycyclic Aromatic Hydrocarbons and the Characteristic Isomers of Polychlorinated Naphthalenes

  摘要：

  Polychlorinated dibenzofurans (PCDFs) and polychlorinated naphthalenes (PCNs) are known to be emitted from municipal waste incinerators (MWIs) with polychlorinated dibenzo-p-dioxins (PCDDs). Two formation paths for PCDD/Fs could mainly work, which are condensation of the precursors such as chlorophenols and "de novo" formation from carbon. However the correlation between the chemical structure of carbon and the resulting PCDD/Fs still remains unknown. In this study, the PCDD/Fs formation from polycyclic aromatic hydrocarbons (PAHs) and CuCl was examined at 400 under 10% O-2. Coronene among the PAHs characteristically gave 1,2,8,9-T4CDF and the derivatives. These isomers clearly indicate that chlorination causes the cleavage of the C-C bonds in a coronene molecule and also that oxygen is easily incorporated from its outside to form 1,2,8,9-T4CDF. The symmetrical preformed structures in the coronene molecule enabled to amplify the de novo formation of the isomer. PCNs are also formed directly from these PAHs. Since there have been few reports on the formation mechanism of PCNs, this study will be a first step to know the whole formation paths. We also define the de novo synthesis as the breakdown reaction of a carbon matrix, since the word has been used without the precise definition.

  DOI：

  10.1021/es980857k

文献信息

• Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using <i>N</i>-Halosuccinimides
  作者：Yuji Nishii、Mitsuhiro Ikeda、Yoshihiro Hayashi、Susumu Kawauchi、Masahiro Miura

  DOI：10.1021/jacs.9b12672

  日期：2020.1.22

  A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a non-coordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable

  介绍了一种用于使用 N-卤代琥珀酰亚胺 (NXS) 进行亲电芳香卤化的路易斯碱催化剂 Trip-SMe（Trip = triptycenyl）。在合适的活化剂（作为非配位阴离子源）存在下，一系列未活化的芳香族化合物在环境温度下使用 NXS 进行卤化。该催化体系适用于目前除使用 Br2 或 Cl2 之外无法实现的转化：例如萘的多卤化、BINOL 的区域选择性溴化等。 对照实验表明，三烯基取代基对催化活性起着至关重要的作用，和动力学实验暗示锍盐 [Trip-S(Me)Br][SbF6] 作为活性物质的存在。与简单的二烷基硫醚相比，Trip-SMe 在卤络合物中表现出显着的电荷分离离子对特征，其结构信息是通过单晶 X 射线分析获得的。一项初步的计算研究表明，三烯基官能团的 π 系统是巩固亲电性增强的关键基序。
• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• Methyl and dimethyl derivatives of tetrathionaphthalene and tetraselenonaphthalene as novel electron donors
  作者：Takashi Kodama、Mie Kodani、Kazuo Takimiya、Yoshio Aso、Tetsuo Otsubo

  DOI：10.1002/hc.1046

  日期：——

  the introduced methyl groups. They all are able to form charge-transfer complexes with tetracyanoquinodimethane. Irrespective of the chalcogen kind of the donor, the complexes of the dimethyl derivatives are conductive, while those of the monomethyl derivatives are insulating. The different conductivities are explained by the difference of their crystal structures, which are studied by infrared spectroscopy

  单甲基和二甲基四硫代萘和四硒萘已被开发为改性电子给体。甲基的引入非常有助于提高母体化合物固有的低溶解度。在循环伏安图中，它们显示出两个可逆的氧化还原波，其第一和第二氧化电位随着引入的甲基数量的增加而逐渐降低。它们都能够与四氰基醌二甲烷形成电荷转移络合物。与供体的硫属元素种类无关，二甲基衍生物的配合物是导电的，而单甲基衍生物的配合物是绝缘的。不同的电导率是由它们的晶体结构的差异来解释的，这是通过红外光谱研究的。© 2001 约翰威利父子公司。
• Naphtho[1,8-cd:4,5-c′d′]bis[1,2]diselenole
  作者：Atsushi Yamahira、Takashi Nogami、Hiroshi Mikawa

  DOI：10.1039/c39830000904

  日期：——

  The title compound was synthesized was synthesized for the preparation of highly conductive organic materials.

  合成了标题化合物，用于制备高导电性有机材料。
• Aromatic halogenation using carborane catalyst
  作者：Chandrababu Naidu Kona、Rikuto Oku、Shotaro Nakamura、Masahiro Miura、Koji Hirano、Yuji Nishii

  DOI：10.1016/j.chempr.2023.10.006

  日期：2024.1

  transformations. Classical electrophilic aromatic halogenation using molecular halogens and Lewis/Brønsted acid activators is still a promising synthetic tool; however, it suffers from handling difficulties, low selectivity, and limited functional group tolerance. We herein introduce carborane-based Lewis base catalysts for aromatic halogenation using -halosuccinimides. The developed reaction system

  卤代芳烃一直是现代有机化学领域中的一类重要化学品，因为卤化物官能团提供了许多可能的转化。使用分子卤素和路易斯/布朗斯台德酸活化剂的经典亲电芳香族卤化仍然是一种有前途的合成工具；然而，它存在操作困难、选择性低和官能团耐受性有限的问题。我们在此介绍基于碳硼烷的路易斯碱催化剂，用于使用卤代琥珀酰亚胺进行芳族卤化。所开发的反应体系易于应用于药物分子的后期功能化和多卤代芳烃的高效合成。 β-碳硼烷支架最适合催化，并且通过装饰簇顶点进行可能的微调对于调节卤物种的电子性质以最大化催化性能非常重要。