3,4,4'-三氯联苯 | 38444-90-5

• 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: 3,4,4'-三氯联苯
• 中文别名: 三氯联苯
• 英文名称: 3,4,4'-trichlorobiphenyl
• 英文别名: 3,4,4'-trichloro-1,1'-biphenyl；PCB 37；PCB-37；3.4.4'-Trichlor-biphenyl；1,2-dichloro-4-(4-chlorophenyl)benzene
• CAS: 38444-90-5
• 化学式: C₁₂H₇Cl₃
• 分子量: 257.547
• InChiKey: YZANRISAORXTHU-UHFFFAOYSA-N

物化性质

• 熔点：
  87°C
• 沸点：
  334.36°C (rough estimate)
• 密度：
  1.3510 (rough estimate)
• 保留指数：
  1980;1957.3;1969.5;1981.8;1973.2;2005

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 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、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

反应信息

• 作为反应物：
  描述：

  3,4,4'-三氯联苯 在 ammonia borane 作用下， 以 水 、 异丙醇 为溶剂， 反应 5.0h， 以99%的产率得到联苯
  参考文献：
  名称：

  氮掺杂石墨烯负载的NiPd纳米颗粒催化多卤代芳烃的加氢脱卤

  摘要：

  镍30 Pd 70负载在氮掺杂石墨烯（NG）上的纳米颗粒在温和的反应条件下充当卤代芳烃加氢脱卤的催化剂。在10 h或低于50°C的温度下5小时内，它将10％异丙醇水溶液中的单氯或二氯芳烃还原为相应的脱卤芳烃，其收率> 90％。对包含各种官能团的多种底物的测试表明，该催化剂对还原C-Cl和C-Br键具有选择性。此外，该催化剂可在12小时内将高浓度的二恶英，多氯联苯，脱叶剂橙的氯代芳族成分和多溴代二苯醚完全加氢脱卤。该催化剂是可重复使用的，并且在5个循环后无形态或组成变化。这种方法可提供功能强大，成本低廉，

  DOI：

  10.1002/cssc.201800289
• 作为产物：
  描述：

  3,4-二氯碘苯 、 4-氯苯硼酸 在 C₂₀H₂₉Cl₂N₅O₂Pd 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 3,4,4'-三氯联苯
  参考文献：
  名称：

  Regularities of Pd/C-catalyzed reduction of trichlorobiphenyls with 2-propanol in basic medium

  摘要：

  Reduction of a series of trichlorobiphenyls with 2-propanol in basic medium catalyzed by Pd/C has been studied. Regioselectivity of the reduction has been determined. In the studied cases, the chlorine atom in para or meta positions of the more substituted ring has been more reactive. Using isotope labeling, it has been demonstrated that the reaction occurs via the stage of 2-propanol dehydration on palladium catalyst, followed by catalytic hydrogenation of the polychlorinated biphenyls.

  DOI：

  10.1134/s1070363217080023

文献信息

• Copper-Catalyzed Cross-Coupling of Boronic Esters with Aryl Iodides and Application to the Carboboration of Alkynes and Allenes
  作者：Yiqing Zhou、Wei You、Kevin B. Smith、M. Kevin Brown

  DOI：10.1002/anie.201310275

  日期：2014.3.24

  Copper‐catalyzed Suzuki–Miyaura‐type cross‐coupling and carboboration processes are reported. The cross‐couplings function well with a variety of substituted aryl iodides and aryl boronic esters and allows for orthogonal reactivity compared to palladium‐catalyzed processes. The carboboration method includes both alkynes and allenes and provides access to highly substituted and stereodefined vinyl boronic

  据报道，铜催化的铃木-宫浦型交叉偶联和碳硼化过程。与各种取代的芳基碘化物和芳基硼​​酸酯的交叉偶联作用很好，并且与钯催化的方法相比，具有正交的反应性。碳硼化方法包括炔烃和丙二烯，并提供了高度取代的和立体定义的乙烯基硼酸酯的途径。简单的一锅合成他莫昔芬强调了炔烃的碳硼化方法。
• Congener-Specific Dechlorination of Dissolved PCBs by Microscale and Nanoscale Zerovalent Iron in a Water/Methanol Solution
  作者：Gregory V. Lowry、Kathleen M. Johnson

  DOI：10.1021/es049835q

  日期：2004.10.1

  between PCB isomers, and compares the reactivity of nanoscale ZVI to that of palladized microscale ZVI. Six PCB congeners were studied (22', 34', 234, 22'35', 22'45', and 33'44') to compare the initial rate of dechlorination of each and to monitor the order in which chlorines are removed. Using 200 g/L of nanoscale ZVI in a 30% MeOH/water mixture, observed surface-area-normalized pseudo-first-order PCB dechlorination

  受多氯联苯（PCB）污染的沉积物仍然对人类和水生生态系统构成重大威胁。疏ed和处置成本很高，因此需要可行的现场技术对PCB进行脱氯。这项研究表明，在环境条件下，纳米级零价铁（ZVI）将PCBs脱氯成低氯产品，深入了解PCB异构体之间的构效关系，并比较纳米级ZVI和钯制微级ZVI的反应性。研究了六种多氯联苯同源物（22'，34'，234、22'35'，22'45'和33'44'），以比较每一种的初始脱氯速率并监测去除氯的顺序。在30％的MeOH /水混合物中使用200 g / L的纳米级ZVI，观察到的表面积标准化伪一阶PCB脱氯速率常数介于1 x 10（-6）到5.5 x 10（-4）L yr（-1）m（-2）之间，具体取决于测试的PCB同类物。使用200 g / L的钯制（0.05 wt％）微型ZVI，表面积标准化的伪一阶PCB脱氯速率常数显着加快，范围从3.8 x 10（-2）到1.7
• 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。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• 4-HETEROARYL-SUBSTITUTED PHENOXYPHENYLACETIC ACID DERIVATIVES
  申请人：Doherty George A.

  公开号：US20100273850A1

  公开（公告）日：2010-10-28

  Compounds of Formula I: I in which D 1 , D 2 , R 1 , R 2 , R 7 , R 8 and A have the meanings given in the specification, are DP2 receptor modulators useful in the treatment of immunologic diseases.

  公式I的化合物：其中D1，D2，R1，R2，R7，R8和A具有规范中给出的含义，是DP2受体调节剂，可用于治疗免疫性疾病。

表征谱图