2,4',5-三氯联苯醚 | 16606-02-3

• 物质功能分类: 分析化学 - 食品安全 - 二噁英，多氯联苯，呋喃
• 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: 2,4',5-三氯联苯醚
• 中文别名: 2,4,5-三氯联苯醚；2,4',5-三氯联苯；2,4’,5-三氯联苯醚；2,4,5-三氯联苯醚PCBNo31
• 英文名称: 2,4',5-Trichlorobiphenyl
• 英文别名: 1,4-dichloro-2-(4-chlorophenyl)benzene
• CAS: 16606-02-3
• 化学式: C₁₂H₇Cl₃
• mdl: MFCD00078742
• 分子量: 257.547
• InChiKey: VAHKBZSAUKPEOV-UHFFFAOYSA-N

物化性质

• 熔点：
  67℃
• 沸点：
  334.36°C (rough estimate)
• 密度：
  1.3510 (rough estimate)
• 溶解度：
  5.55e-07 M
• 蒸汽压力：
  4.00e-04 mmHg
• 亨利常数：
  1.90e-04 atm-m3/mole
• 大气OH速率常数：
  1.20e-12 cm3/molecule*sec
• 保留指数：
  1829;1818;1846;1819;1820;1839.2;1848.8;1858;1858.1;1819

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  15
• 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。它们通过血液传输，通常与白蛋白结合。由于其亲脂性，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。主要的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。

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

多氯联苯最常见的健康影响是皮肤状况，如氯痤疮和皮疹。长期暴露于多氯联苯还会导致肝脏、胃和肾脏损伤、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、神经紧张、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

• 危险品标志：
  N
• 安全说明：
  S35
• 危险类别码：
  R33
• 海关编码：
  2903999090
• 危险品运输编号：
  UN 3432 9/PG 2
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 2,4',5-三氯联苯醚 在 dicobalt octacarbonyl 作用下， 生成 4’,5-dichloro[1,1'-biphenyl]-2-carboxylic acid
  参考文献：
  名称：

  环氧改性钴羰基催化剂催化芳基卤化物羰基化合成芳族羧酸

  摘要：

  开发了一种新方法，用于通过相应的芳基卤化物的羰基化合成芳族和杂芳族酸及其衍生物（酯，盐）。在非常温和的条件下可以高产率选择性地形成酸。高活性的催化体系（用环氧化物改性的含羰基钴钴的含碱醇溶液）用于活化芳基卤化物。

  DOI：

  10.1007/s11167-005-0619-y
• 作为产物：
  描述：

  2,4'-Diacetamino-biphenyl 在 盐酸 、 氯 、 溶剂黄146 作用下， 生成 2,4',5-三氯联苯醚
  参考文献：
  名称：

  Bellavita, Gazzetta Chimica Italiana, 1935, vol. 65, p. 632,643

  摘要：

  DOI：

文献信息

• Experimental and theoretical studies on synthesis and structure elucidation of some polychlorinated biphenyl derivatives
  作者：Vadim P. Boyarskiy、Irina А. Boyarskaya、Elisaveta A. Savicheva、Maria Gdaniec、Marina S. Fonari、Yurii A. Simonov

  DOI：10.1016/j.molstruc.2010.04.019

  日期：2010.6

  4-chloro-2-(4-chlorophenyl)benzoate 2 . The substitution of methoxycarbonyl group for chlorine in ortho -position of trichlorobiphenyls seems not to affect the twist angle of the biphenyl unit. However, the twist angle of the methoxycarbonyl group relative to the phenyl ring was found to be significantly larger in the meta -derivative 1 than the ortho -derivative 2 . To rationalize conformational differences

  摘要 多氯联苯 (PCB)、2,3,4'-三氯联苯 (РСВ22) 和 2,5,4'-三氯联苯 (PCB31) 的区域选择性甲氧基羰基化，在改性 Co 2 (CO) 8 钴存在下进行羰基催化剂在 РСВ22 的 3 位取代氯原子并产生 2-氯-3-(4-氯苯基)苯甲酸甲酯 1 ，而对于 PCB31 产生 4-氯-2-(4-氯苯基)苯甲酸甲酯 2 . 三氯联苯邻位氯的甲氧基羰基取代似乎不影响联苯单元的扭曲角。然而，发现甲氧基羰基相对于苯环的扭曲角在间位衍生物1中显着大于邻位衍生物2。
• Synthesis of polychlorinated biphenyls and their metabolites with a modified Suzuki-coupling
  作者：Izabela Kania-Korwel、Sean Parkin、Larry W Robertson、Hans-Joachim Lehmler

  DOI：10.1016/j.chemosphere.2004.04.035

  日期：2004.8

  A modified procedure for the synthesis of polychlorinated biphenyls (PCBs) utilizing the Suzuki-coupling, a palladium-catalyzed cross-coupling reaction, is described. The coupling of (chlorinated) benzene boronic acids with bromochlorobenzenes, using Pd(dppf)(2)Cl(2) (dppf = 1,1'-bis(diphenylphosphino)ferrocene) as the catalyst and aqueous sodium carbonate as the base, gave the desired PCB congeners

  描述了使用铃木偶联（钯催化的交叉偶联反应）合成多氯联苯（PCB）的改进方法。以Pd（dppf）（2）Cl（2）（dppf = 1,1'-双（二苯基膦基）二茂铁）为催化剂，碳酸钠水溶液为碱，将（氯化）苯硼酸与溴氯苯偶合所需的PCB同类产品，产量适中至良好。使用此修改程序合成了11种PCB同类物，包括对环境重要的PCB同类物和代谢物。与Pd（PPh（4））（4）相比，这种新的催化剂Pd（dppf）（2）Cl（2）具有空气敏感性较低的优点，并且具有更长的保存期限。通过将氯化苯硼酸与溴（二）甲氧基苯偶联或通过将（二）甲氧基苯硼酸与氯化溴苯偶联，使用相同的步骤合成了三个新的（二）甲氧基化PCB同类物。使用三溴化硼的二氯甲烷溶液可以轻松地将二甲氧基化的PCB同类物转化为相应的二羟基化的PCB衍生物。与常规方法（例如Cadogan反应）相比，该方法具有高选择性和中等至良好收率的优势，并允许使用毒性较小的原料。
• Photochemical behaviour of 1,4-dichlorobenzene in aqueous solution
  作者：Laurence Meunier、Jean-François Pilichowski、Pierre Boule

  DOI：10.1139/v01-091

  日期：2001.7.1

  Several photoproducts were identified in the direct photolysis of 1,4-dichlorobenzene (1,4-DCB) in air-saturated aqueous solution, namely 4-chlorophenol, hydroquinone, hydroxybenzoquinone, and 2,5-dichlorophenol. In the absence of oxygen the latter is not formed and phenol was detected, but the unexpected formations of 4,4'-dichlorobiphenyl, 2,4',5-trichlorobiphenyl, and a terphenyl derivative are observed. Mechanisms are proposed to explain the formations of identified photoproducts. The phototransformation of 1,4-DCB may be photoinduced by NO^–₃ or Fe^III salts. The main primary product is 2,5-dichlorophenol, which results from a hydroxylation without dechlorination. Some other products have been identified in particular 4-chlorophenol and 2,5-dichlorobenzoquinone in the case of Fe^III salts.Key words: 1,4-dichlorobenzene, photolysis, aqueous solution, induced phototransformation.

  在饱和空气的水溶液中，直接光解1,4-二氯苯（1,4-DCB）识别出了几种光产物，包括4-氯苯酚、羟基苯醌、羟基苯醌和2,5-二氯苯酚。在没有氧气的情况下，不会形成后者，而会检测到苯酚，但观察到了出乎意料的4,4'-二氯联苯、2,4',5-三氯联苯和一个三苯基衍生物的形成。提出了机制来解释已识别的光产物的形成。1,4-DCB的光转化可能是由NO^–₃或Fe^III盐诱导的光诱导。主要的初级产物是2,5-二氯苯酚，它是通过羟基化而不是去氯化而形成的。在Fe^III盐的情况下，还发现了其他一些产物，特别是4-氯苯酚和2,5-二氯苯醌。关键词：1,4-二氯苯，光解，水溶液，诱导光转化。
• Instruments for detecting low-molecular weight substance
  申请人：Mizukami Haruki

  公开号：US20050148097A1

  公开（公告）日：2005-07-07

  To provide the following instruments 1 and 2 as a low-molecular-weight substance detection instrument employing immunochromatography capable of detecting conveniently and sensitively detecting a low-molecular weight substance such as an environmental pollutant (e.g., a dioxin), as a target substance contained in a test sample: 1. an instrument, which comprises 1) a test sample application section with which a test sample is brought into contact; 2) a label product reaction section containing a label product containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, the label product being not bound to the reaction section; 3) an unbound label product capturing section containing an element capable of capturing the label product which is not bound to the target substance, the element being bound to the capturing section; and 4) a detection section containing a detection element which, when coming into contact with the target substance bound to the label product, causes a visually observable change, and 2. an instrument wherein a test sample is reacted with a labeled antibody containing, as a portion thereof, an antibody capable of binding to a target substance contained in the test sample, and the resultant reaction product is employed for detecting the target substance contained in the test sample.

  提供以下仪器1和2作为低分子量物质检测仪器，采用免疫层析技术，能够方便敏感地检测低分子量物质，例如环境污染物（例如二恶英），作为测试样品中包含的目标物质：1. 仪器，包括1）测试样品应用部分，用于将测试样品接触；2）标签产物反应部分，包含一种标签产物，其中包含一种能够结合到测试样品中的目标物质的抗体，标签产物未结合到反应部分；3）未结合标签产物捕获部分，包含一种能够捕获未结合到目标物质的标签产物的元素，该元素与捕获部分结合；以及4）检测部分，包含一种检测元素，当与结合到标签产物的目标物质接触时，会引起可视的变化；2. 仪器，其中测试样品与标记抗体反应，其中一部分包含能够结合到测试样品中的目标物质的抗体，产生的反应产物用于检测测试样品中包含的目标物质。
• Generation of aryl radicals from <i>in situ</i> activated homolytic scission: driving radical reactions by ball milling
  作者：Xinjie Yang、Hao Wang、Yanhua Zhang、Weike Su、Jingbo Yu

  DOI：10.1039/d2gc00910b

  日期：——

  The need for an operationally straightforward application of radical chemistry has led researchers to explore practical strategies to obtain and trap radicals. Herein, we report a mechanoradical generation method by direct C–N bond breaking of aryldiazonium salts using NaCl as an activator. This method opens a new pathway to radical reactions ranging from (hetero)arylation, cascade addition, and hydrogen

  自由基化学在操作上直接应用的需求促使研究人员探索获得和捕获自由基的实用策略。在此，我们报告了一种机械自由​​基生成方法，该方法通过使用 NaCl 作为活化剂直接断裂芳基重氮盐的 C-N 键。该方法为自由基反应开辟了一条新途径，范围从（杂）芳基化、级联加成和氢原子转移（HAT）加成到交叉偶联。自由基生成过程的机制涉及 NaCl 和芳基重氮四氟硼酸盐之间的离子交换和原位的机械“均裂”（由抗衡离子诱导）形成反应性氯化物。放大实验、药剂后期修饰、生物活性化合物和药物的合成进一步证明了该方法的实用性和实用性。

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