亚老哥尔1016 | 38444-87-0

• 物质功能分类: 分析化学 - 标准品 - 挥发性有机化合物(VOCs)
• 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: 亚老哥尔1016
• 中文别名: 亚老哥尔 116；2,2',3,3',4,5,5'-七氯联苯；亚老哥尔 1016；3,3',5-三氯联苯
• 英文名称: 3,5,3'-trichloro-biphenyl
• 英文别名: 3,3',5-Trichlorobiphenyl；PCB 36；3,3',5-TCB；1,3-dichloro-5-(3-chlorophenyl)benzene
• CAS: 38444-87-0；12674-11-2
• 化学式: C₁₂H₇Cl₃
• 分子量: 257.547
• InChiKey: RIBGNAJQTOXRDK-UHFFFAOYSA-N

物化性质

• 熔点：
  63.91°C (estimate)
• 沸点：
  333.69°C (rough estimate)
• 密度：
  1.3300 (estimate)
• 闪点：
  -26 °C
• 溶解度：
  溶于大多数溶剂 (US EPA, 1985)。
• 暴露限值：
  Potential occupational carcinogen. NIOSH REL: TWA 1.0 μg/m3, IDLH 5 mg/m3.
• 物理描述：
  Pcb-1016 is a viscous oily liquid. (NTP, 1992)
• 颜色/状态：
  ... Colorless mobile oil
• 气味：
  PRACTICALLY ODORLESS
• 蒸汽压力：
  4X10-4 mm Hg at 25 °C
• 亨利常数：
  1.70e-04 atm-m3/mole
• 稳定性/保质期：
  ... PCB's are chemically very inert and are stable to conditions of hydrolysis and oxidation in industrial use. ... /Polychlorinated biphenyls/
• 分解：
  When heated to decomposition they emit toxic fumes of polychlorinated biphenyls and chlorine. /Polychlorinated biphenyls/
• 粘度：
  71-81 Saybolt sec at 37.8 °C
• 折光率：
  Index of refraction = 1.622 - 1.624 at 25 °C
• 保留指数：
  1918;1905.3;1986;1986;1986

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 transported 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

• 危险等级：
  9
• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  亚老哥尔1016 在 potassium tert-butylate 、 重水 作用下， 以 氘代二甲亚砜 为溶剂， 以80 %的产率得到
  参考文献：
  名称：

  多氯联苯的碱催化 H/D 交换

  摘要：

  多氯联苯是目前最普遍、最有害的环境污染物之一。随着基于质谱的分析方法的快速发展，有必要开发多氯联苯同位素体的合成方法。在此，已公开了一种新型的碱催化多氯联苯与 DMSO- d 6 /D 2 O 的 H/D 交换反应。该协议提供了出色的氘掺入和良好的邻位选择性。

  DOI：

  10.1016/j.tetlet.2022.154200
• 作为产物：
  描述：

  三甲基(2,6-二氯苯基)硅 在 四丁基氟化铵 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 亚老哥尔1016
  参考文献：
  名称：

  间位而非邻位定向金属化：支撑效应妨碍从（2,6-二卤苯基）硅烷中提取质子

  摘要：

  (2,6-二氯苯基)三甲基-和-三乙基硅烷对强碱表现出非典型的反应模式。当用 2,2,6,6-四甲基哌啶锂在 -100 摄氏度下处理时，它们会产生两种，仲丁基或叔丁基锂，甚至三种不同的有机金属中间体，它们可以被标准物质截获。亲电试剂。三烷基甲硅烷基在两个方面介入。对相邻的氯原子施加空间压力，它促进其中一个原子对锂的置换置换，这是一种副反应，每当烷基锂化合物时就会发生。受雇。同时，由于空间位阻的中继传输，它阻止了紧邻卤素的碱对氢原子的攻击。作为结果，去质子化优先或仅发生在 5-(qmetaq) 而不是 4-(qorthoq) 位置。4-锂化物种，作为副产品或 sep 产生。通过置换卤素/金属互变，在 -75 摄氏度下消除氯化锂以释放被芳基锂前体捕获的二脱氢苯 (qarynesq)。[在 SciFinder (R) 上]

  DOI：

  10.1002/ejoc.200500553

文献信息

• Instruments for detecting low-molecular weight substance
  申请人：Mizukami Haruki

  公开号：US20090269857A1

  公开（公告）日：2009-10-29

  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，采用免疫层析法能够方便、灵敏地检测低分子量物质，例如环境污染物（例如二恶英），作为试样中所含的目标物质：1.一种仪器，包括1）试样应用部分，用于将试样接触；2）标记产品反应部分，含有能够与试样中所含的目标物质结合的抗体作为其一部分，标记产品未与反应部分结合；3）未结合的标记产品捕获部分，含有能够捕获未结合于目标物质的标记产品的元素，该元素与捕获部分结合；和4）检测部分，含有检测元素，当与结合于标记产品的目标物质接触时，会引起可视的变化；2.一种仪器，其中试样与含有能够与试样中所含的目标物质结合的抗体的标记抗体反应，反应产物用于检测试样中所含的目标物质。
• INSTRUMENTS FOR DETECTING LOW-MOLECULAR WEIGHT SUBSTANCE
  申请人：Enbiotec Laboratories Co., Ltd.

  公开号：EP1489420A1

  公开（公告）日：2004-12-22

  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，作为一种采用免疫层析技术的低分子量物质检测仪器，能够方便、灵敏地检测作为检测样品中目标物质的低分子量物质，如环境污染物（如二恶英）： 1.仪器，包括：1）测试样品应用部分，测试样品与之接触；2）标签产品反应部分，包含标签产品，作为其一部分，该标签产品含有能够与测试样品中所含目标物质结合的抗体，标签产品未与反应部分结合；3) 非结合标签产品捕获部分，包含能够捕获未与目标物质结合的标签产品的元件，该元件与捕获部分结合；以及 4) 检测部分，包含检测元件，该元件与结合在标签产品上的目标物质接触时，会引起视觉上可观察到的变化，以及 2. 2. 一种仪器，其中测试样品与标记抗体反应，标记抗体的一部分能够与测试样品中的目标物质结合，反应产物用于检测测试样品中的目标物质。
• Physical, spectral and chromatographic properties of all 209 individual PCB congeners
  作者：Michael Bolgar、James Cunningham、Russell Cooper、Richard Kozloski、Jack Hubball、Don P. Miller、Terry Crone、Harry Kimball、Anita Janooby、Barry Miller、Billy Fairless

  DOI：10.1016/0045-6535(95)00140-4

  日期：1995.7

  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.
• Synthesis of polychlorinated biphenyls (PCBs) using the Suzuki-coupling
  作者：Hans-Joachim Lehmler、Larry W Robertson

  DOI：10.1016/s0045-6535(00)00546-4

  日期：2001.10

  An improved synthesis of polychlorinated biphenyls (PCBs) utilizing a palladium-catalyzed cross-coupling reaction (Suzuki-coupling) is described. The coupling of (chlorinated) aryl boronic acids 1-3 with bromochlorobenzenes 4 using the standard conditions of the Suzuki-coupling gave the desired PCB congeners 5-7 in good to excellent yields. The self-coupling product of the aryl boronic acids is the major impurity of this reaction. 3,4,5-trichlorophenyl derivatives such as 10 can be synthesized by coupling of an aryl boronic acid with the corresponding bromochloroaniline 8. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials. (C) 2001 Elsevier Science Ltd. All rights reserved.
• meta- Rather thanortho-Directed Metalations: Buttressing Effects Prejudicing the Proton Abstraction from (2,6-Dihalophenyl)silanes
  作者：Christophe Heiss、Fabrice Cottet、Manfred Schlosser

  DOI：10.1002/ejoc.200500553

  日期：2005.12

  neighboring chlorine atoms, it facilitates the permutational displacement of one of them against lithium, a side reaction which occurs whenever alkylithium compds. are employed. At the same time it impedes the attack of hydrogen atoms by the base in the immediate vicinity of the halogens due to relay transmission of steric hindrance. As a consequence, deprotonation occurs preferentially or exclusively

  (2,6-二氯苯基)三甲基-和-三乙基硅烷对强碱表现出非典型的反应模式。当用 2,2,6,6-四甲基哌啶锂在 -100 摄氏度下处理时，它们会产生两种，仲丁基或叔丁基锂，甚至三种不同的有机金属中间体，它们可以被标准物质截获。亲电试剂。三烷基甲硅烷基在两个方面介入。对相邻的氯原子施加空间压力，它促进其中一个原子对锂的置换置换，这是一种副反应，每当烷基锂化合物时就会发生。受雇。同时，由于空间位阻的中继传输，它阻止了紧邻卤素的碱对氢原子的攻击。作为结果，去质子化优先或仅发生在 5-(qmetaq) 而不是 4-(qorthoq) 位置。4-锂化物种，作为副产品或 sep 产生。通过置换卤素/金属互变，在 -75 摄氏度下消除氯化锂以释放被芳基锂前体捕获的二脱氢苯 (qarynesq)。[在 SciFinder (R) 上]

表征谱图