1，2，3，4，5—五氯联苯 | 18259-05-7

• 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: 1，2，3，4，5—五氯联苯
• 中文别名: 1，2，3，4，5--五氯联苯；3,4,5,3',5'-五氯联苯；五氯联苯；2,3,4,5,6-五氯联苯
• 英文名称: 2,3,4,5,6-pentachlorobiphenyl
• 英文别名: 2,3,4,5,6-PCB；PCB 116；PCB-116；2,3,4,5,6-Pentachlor-biphenyl；2,3,4,5,6-Pentachlor-diphenyl；1,2,3,4,5-pentachloro-6-phenylbenzene
• CAS: 18259-05-7；25429-29-2
• 化学式: C₁₂H₅Cl₅
• 分子量: 326.437
• InChiKey: GGMPTLAAIUQMIE-UHFFFAOYSA-N

物化性质

• 熔点：
  95.86°C (estimate)
• 沸点：
  412.3°C (rough estimate)
• 密度：
  1.5220 (rough estimate)
• 保留指数：
  2081;2081;2110

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  17
• 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

ADMET

代谢

多氯联苯(PCBs)通过吸入、口服和皮肤接触途径被吸收。它们通过血液运输，通常与白蛋白结合。由于它们的亲脂性特性，它们倾向于在富含脂质的组织中积累，如肝脏、脂肪组织和皮肤。多氯联苯的代谢非常缓慢，并且根据氯化的程度和位置而有所不同。多氯联苯通过微粒体单加氧酶系统代谢，该系统由细胞色素P-450酶催化，转化为极性代谢物，这些代谢物可以与谷胱甘肽和葡萄糖醛酸结合。主要代谢物是羟基化产物，通过胆汁和粪便排出。多氯联苯的缓慢代谢意味着它们倾向于在身体组织中积累。(L4, T6)

PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are trasported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

PCB的作用机制因具体类型而异。类二噁烷PCB通过结合芳基烃受体，通过改变基因的转录来扰乱细胞功能，主要是通过诱导肝脏第一阶段和第二阶段酶的表达，特别是细胞色素P450家族。PCB的大多数毒性效应被认为是由Ah受体结合的结果。其他PCB被认为会干扰钙通道和/或改变大脑中的多巴胺水平。PCB还通过改变甲状腺激素的生成和结合到雌激素受体来引起内分泌紊乱，这可以刺激某些癌细胞的生长并产生其他雌激素效应，如生殖功能障碍。它们会通过结合到如uteroglobin等受体蛋白而生物累积。(A3, A4, A30, A66)

The mechanism of action varies with the specific PCB. Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family. Most of the toxic effects of PCBs are believed to be results of Ah receptor binding. Other PBCs are believed to interfere with calcium channels and/or change brain dopamine levels. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. They will bioaccumulate by binding to receptor proteins such as uteroglobin. (A3, A4, A30, A66)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

1, 对人类致癌。

1, carcinogenic to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

PCBs最常见的健康影响是皮肤状况，如氯痤疮和皮疹。长期暴露于PCBs还可能导致肝脏、胃和肾脏损害、黄疸、水肿、贫血、免疫系统变化、行为改变以及生殖能力受损。

The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L4级）；吸入（L4级）；皮肤给药（L4级）

Oral (L4) ; inhalation (L4) ; dermal (L4)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

慢性PCB暴露会导致如下症状：腹痛、恶心、呕吐、腹泻、头痛、眩晕、抑郁、紧张、皮肤和眼睛损伤、疲劳、月经周期不规律以及免疫力下降。

Chronic PCB exposure results in symptoms such as abdominal pain, nausea, vomiting, diarrhea, headache, dizziness, depression, nervousness, dermal and ocular lesions, fatigue, irregular menstrual cycles and a lowered immune response. (A3)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2903999010

制备方法与用途

用途：用于油漆工业。

反应信息

• 作为反应物：
  描述：

  1，2，3，4，5—五氯联苯 在 氧气 作用下， 生成 1,3,6,8-四氯二苯并呋喃
  参考文献：
  名称：

  Synthesis of the 38 tetrachlorodibenzofuran isomers and identification by capillary column gas chromatography mass spectrometry

  摘要：

  DOI：

  10.1021/ac00252a028
• 作为产物：
  描述：

  五氯碘苯 以95%的产率得到
  参考文献：
  名称：

  BRATT J.; IDDON B.; MACK A. G.; SUSCHITZKY H.; TAYLOR J. A.; WAKEFIELD B.+, J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 2, 648-656

  摘要：

  DOI：

文献信息

• A General Method for Copper-Catalyzed Arylation of Arene C−H Bonds
  作者：Hien-Quang Do、Rana M. Kashif Khan、Olafs Daugulis

  DOI：10.1021/ja805688p

  日期：2008.11.12

  A general method for copper-catalyzed arylation of sp (2) C-H bonds with p K a's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K 3PO 4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can

  已经开发出一种铜催化 pKa 低于 35 的 sp (2) CH 键芳基化的通用方法。该方法采用芳基卤作为偶联配偶体、锂醇盐或K 3PO 4 碱以及DMF、DMPU或混合DMF/二甲苯溶剂。多种富电子和缺电子杂环，例如唑类、咖啡因、噻吩、苯并呋喃、氧化吡啶、哒嗪和嘧啶可以芳基化。此外，在苯环上具有至少两个吸电子基团的贫电子芳烃也可以被芳基化。独立合成了两种芳基铜-菲咯啉络合物中间体。
• COPPER-CATALYZED C-H BOND ARYLATION
  申请人：Daugulis Olafs

  公开号：US20090076266A1

  公开（公告）日：2009-03-19

  The present invention is a one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using a combination of aryl halides, a substrate, and a copper salt as catalyst. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores and explosives.

  本发明是一种一步法，通过使用芳基卤化物、底物和铜盐作为催化剂，高效地将碳氢键转化为碳碳键的方法。该方法允许更快地引入复杂的分子实体，否则这个过程需要更多步骤。该发明特别适用于有机合成中复杂分子的合成，例如药用分子和爆炸物等。
• Cross-coupling of polychlorobenzenes with phenylboronic acid in the presence of [Pd]-imidazolium salts as catalytic systems
  作者：A. S. Burukin、A. A. Vasil’ev、N. L. Merkulova、A. O. Chizhov、E. A. Mistryukov、S. G. Zlotin

  DOI：10.1007/s11172-007-0224-8

  日期：2007.7

  The reactions of di-, tetra-, and hexachlorobenzenes with phenylboronic acid in the presence of [Pd]-imidazolium salt-base as catalytic systems afford cross-coupling products in moderate yields. The highest conversions are attained when imidazolium salts bearing bulky aromatic substituents are used and the reaction is carried out in the presence of alkali alkoxides containing Hα atoms. Cross-coupling is accompanied by hydrodechlorination of aromatic C-Cl bonds.

  二氯、四氯和六氯苯与苯基硼酸在[钯]-咪唑盐碱性催化体系的存在下反应，生成交叉偶联产物，产率适中。当使用带有大体积芳香取代基的咪唑盐，并且反应在含有Hα原子的碱性烷氧基的环境中进行时，可以达到最高转化率。交叉偶联伴随着芳香C-Cl键的氢脱氯反应。
• Bis(tetrazolyl)benzenes as ligands in the Suzuki reaction: Promoters or inhibitors?
  作者：A. S. Burukin、A. A. Vasil’ev、N. L. Merkulova、M. I. Struchkova、S. G. Zlotin

  DOI：10.1007/s11172-006-0224-0

  日期：2006.1

  The Suzuki cross-coupling with phenylboronic acid in the presence of the Pd(OAc)2/K3PO4/DMF catalytic system was successful for aryl bromides and somewhat poorer for aryl chlorides. Addition of 1,3-bis(tetrazol-1-yl)benzene or its analogs lowered the yields of biaryls.

  在Pd(OAc)2/K3PO4/DMF催化体系中，铃木交叉偶联与苯基硼酸的反应对芳基溴化物成功，而对芳基氯化物的反应效果稍差。添加1,3-双(四氮唑-1-基)苯或其类似物会降低双芳烃的产率。
• Pd-catalyzed direct arylation of electron-deficient polyfluoroarenes with aryliodine(III) diacetates
  作者：Zhengjiang Fu、Qiheng Xiong、Wenbiao Zhang、Zhaojie Li、Hu Cai

  DOI：10.1016/j.tetlet.2014.11.033

  日期：2015.1

  polyfluoroarenes with readily available aryliodine(III) diacetates was developed with moderate to good yields. The process exhibited good functional tolerance with respect to methyl, methoxy, bromo, chloro, trifluoromethyl, cyano, and aldehyde groups. Mechanistic studies revealed this coupling involved in situ generation of aryl iodide from heating-promoted decomposition of aryliodine(III) diacetate, followed by

  现已开发出Pd催化的缺电子多氟芳烃与易于获得的芳基碘（III）二乙酸酯的直接芳基化反应，产率中等至良好。该方法对于甲基，甲氧基，溴，氯，三氟甲基，氰基和醛基表现出良好的功能耐受性。机理研究表明，这种偶联涉及加热促进的二乙酸芳基碘（III）的分解，原位生成芳基碘化物，然后与多氟芳烃底物偶联，得到所需的产物。

表征谱图