2,4'-二氯联苯 | 34883-43-7

• 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'-二氯联苯
• 中文别名: 2,4’-二氯联苯；2,4ˊ-二氯联苯
• 英文名称: 2,4'-dichlorobiphenyl
• 英文别名: PCB 8；CB 8；1-chloro-2-(4-chlorophenyl)benzene
• CAS: 34883-43-7
• 化学式: C₁₂H₈Cl₂
• mdl: MFCD00152399
• 分子量: 223.102
• InChiKey: UFNIBRDIUNVOMX-UHFFFAOYSA-N

物化性质

• 熔点：
  46°C
• 沸点：
  289.78°C (rough estimate)
• 密度：
  1.2490 (rough estimate)
• 溶解度：
  5.24e-06 M
• 蒸汽压力：
  0.00 mmHg
• 亨利常数：
  2.30e-04 atm-m3/mole
• 保留指数：
  1660;1660;1700;1665;1665;1700.9;1654

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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

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进行代谢，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。

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。类似于二噁烷的PCB会与芳基烃受体结合，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。人们认为PCB的大多数毒性效应是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与雌激素受体结合来引起内分泌紊乱，这可能会刺激某些癌细胞的生长并产生其他类雌激素效应，如生殖功能障碍。它们还会通过结合如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、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,S60,S61
• 危险类别码：
  R50/53,R33
• WGK Germany：
  3
• 海关编码：
  2903999010
• 危险品运输编号：
  UN 3432 9/PG 2
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2,4'-二氯联苯 在 potassium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 20.0h， 以98%的产率得到联苯
  参考文献：
  名称：

  Significant stabilization of palladium by gold in the bimetallic nanocatalyst leading to an enhanced activity in the hydrodechlorination of aryl chlorides

  摘要：

  Au对Pd的稳定作用增强了Au/Pd双金属纳米团簇中Pd的反应性，并改变了反应机制。

  DOI：

  10.1039/c5cc04432d
• 作为产物：
  描述：

  2-氯-联苯-4-胺盐酸盐 在 copper(I) chloride 、 亚硝酸 作用下， 生成 2,4'-二氯联苯
  参考文献：
  名称：

  Physical, spectral and chromatographic properties of all 209 individual PCB congeners

  摘要：

  Physical, spectral and chromatographic data for all 209 individual PCB congeners is presented. The individual congeners were synthesized and then isolated and purified. Recent emphasis on the source of the toxicity of commercial PCB formulations has increased the need for a complete set of the PCB congeners. Through the use of two capillary GC columns: 40% octadecyl/ 15% phenyl methyl siloxane and 50% phenyl methyl siloxane, it was possible to separate 201 PCB congeners with only four unresolved pairs. The data compiled in this study for all 209 congeners will aid in the identification of selected individual components of these environmental pollutants. The use of this data also presents the opportunity for the improved quantification of the commercial PCB formulations.

  DOI：

  10.1016/0045-6535(95)00140-4

文献信息

• Highly Chemoselective Mono-Suzuki Arylation Reactions on All Three Dichlorobenzene Isomers and Applications Development
  作者：Ehsan Ullah、James McNulty、Al Robertson

  DOI：10.1002/ejoc.201200160

  日期：2012.4

  A Pd catalyst system is described that allows very high chemoselective monoarylation on all three isomers of dichlorobenzene. Direct application of these commodity chemicals to high-value ligands, anilines, azides, and carbazoles was achieved through this process discovery.

  描述了一种 Pd 催化剂体系，其允许对二氯苯的所有三种异构体进行非常高的化学选择性单芳基化。通过这一过程发现，将这些商品化学品直接应用于高价值的配体、苯胺、叠氮化物和咔唑。
• Pd-Catalysed Suzuki–Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides
  作者：Patrizio Orecchia、Desislava Slavcheva Petkova、Roland Goetz、Frank Rominger、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1039/d1gc02602j

  日期：——

  The Suzuki–Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling

  公开了缺电子芳基氯化物在水中合成作物保护相关活性成分中的 Suzuki-Miyaura 偶联反应。反应条件的优化允许在较短的反应时间内在交叉偶联反应步骤中以 50 ppm 的 Pd 催化剂负载量进行反应，而无需额外的有机溶剂。该系统针对大规模生产的杀菌剂啶酰菌胺、氟吡菌胺和联苯吡菌胺的初始交叉偶联步骤进行了优化，产率高达 97%。还表明，在后处理中使用对环境无害的溶剂进行简单的产物分离和纯化，可以轻松地将 Suzuki-Miyaura 反应放大到 50 g。为了展示这种方法的可用性，它被额外应用于所需活性成分的三步合成。
• Silylated polycarbonate polymers, method of making, and articles
  申请人：Lens Jan Pleun

  公开号：US20080306294A1

  公开（公告）日：2008-12-11

  A silylated dihydroxy aromatic compound of the formula (1a); wherein G a and G b are each independently C 1-12 alkyl, —OSi(C 1-12 alkyl) 3 , C 1-12 arylalkyl, or —OSi(C 1-12 arylalkyl) 3 ; Z a and Z b are each independently a straight or branched C 2-18 alkylene, a C 8-18 arylalkylene, or a C 8-18 alkylarylene, X a is a direct bond, a heteroatom-containing group, or a C 1-18 organic group, and r and s are each independently 1 or 2 is disclosed.

  一种具有式(1a)的硅烷化二羟基芳香族化合物；其中Ga和Gb各自独立地为C1-12烷基、—OSi(C1-12烷基)3、C1-12芳基烷基或—OSi(C1-12芳基烷基)3；Za和Zb各自独立地为直链或支链的C2-18亚烷基、C8-18芳基亚烷基或C8-18烷基芳基亚烷基，Xa为直接键、含杂原子基团或C1-18有机基团，且r和s各自独立地为1或2。
• Visible-Light-Promoted, Catalyst-Free Gomberg–Bachmann Reaction: Synthesis of Biaryls
  作者：Juyoung Lee、Boseok Hong、Anna Lee

  DOI：10.1021/acs.joc.9b00557

  日期：2019.7.19

  Biaryls were synthesized via a novel visible-light-promoted Gomberg–Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor–acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.

  联芳基是通过不需要光敏剂或任何金属试剂的新型可见光促进的Gomberg-Bachmann反应合成的。在芳基重氮盐和吡啶之间形成电子供体-受体配合物，可以在可见光照射下以中等至高收率合成联芳基。
• Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles
  作者：Aiichiro Nagaki、Daisuke Ichinari、Jun-ichi Yoshida

  DOI：10.1021/ja5071762

  日期：2014.9.3

  carbolithiation of benzyne with the aryllithium took place spontaneously. The resulting functionalized biaryllithium was reacted with an electrophile in the subsequent reactor to give the corresponding three-component coupling product. The precise optimization of reaction conditions using the temperature-residence time mapping is responsible for the success of the present transformation. The present method

  建立了一种基于闪速化学的苯三组分偶联流动微反应器方法。由 1-溴-2-碘苯产生的邻溴苯基锂和由相应芳基卤化物产生的官能化芳基锂在 -70 °C 下混合。在随后的反应器中，邻溴苯基锂在 -30°C 下分解生成苄基而不影响官能化的芳基锂，并且苄基与芳基锂的碳锂化反应自发发生。所得官能化联芳基锂在随后的反应器中与亲电试剂反应，得到相应的三组分偶联产物。使用温度-停留时间映射对反应条件进行精确优化是目前转化成功的原因。

表征谱图