亚老哥尔1221 | 2051-61-8

• 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: 亚老哥尔1221
• 中文别名: 多氯联苯(Aroclor1221)标样；氯联苯1221；间氯联苯；氯代对甲氧基苯基1221；亚老哥儿1221；多氯联苯，2,3,3',4,4',5-六氯联苯；3-氯二苯酚；多氯联苯1221标准品；多氯联苯1221；芳氯1221；3-氯联苯PCBNo2；3-氯联苯
• 英文名称: m-chlorobiphenyl
• 英文别名: 3-chlorobiphenyl；3-Chloro[1,1'-biphenyl]；PCB 2；3-monochlorobiphenyl；3-chloro-1,1′-biphenyl；2-chlorobiphenyl；1-chloro-3-phenylbenzene
• CAS: 2051-61-8；11104-28-2
• 化学式: C₁₂H₉Cl
• mdl: MFCD00013633
• 分子量: 188.656
• InChiKey: NMWSKOLWZZWHPL-UHFFFAOYSA-N

物化性质

• 熔点：
  89℃
• 沸点：
  285℃
• 密度：
  1.1320 (estimate)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）
• 物理描述：
  Pcb-1221 is a viscous oily liquid. (NTP, 1992)
• 颜色/状态：
  ... Colorless mobile oil
• 气味：
  PRACTICALLY ODORLESS
• 闪点：
  141-150 °C (Cleveland open cup)
• 蒸汽压力：
  Average vapor pressure of most volatile components: 6.7X10-3 mm Hg, 25 °C
• 亨利常数：
  6.13e-04 atm-m3/mole
• 大气OH速率常数：
  5.28e-12 cm3/molecule*sec
• 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/
• 自燃温度：
  Fire point= 176 °C (Cleveland open cup)
• 分解：
  When heated to decomposition they emit highly toxic fumes of chlorine. /Polychlorinated biphenyls/
• 粘度：
  38-41 Saybolt sec at 37.8 °C; 30-31 Saybolt sec at 54.4 °C; 30-32 Saybolt sec at 98.9 °C
• 折光率：
  Index of refraction = 1.617-1.618 at 20 °C
• 相对蒸发率：
  Evaporation loss at 100 °C/6 hr = 1.0-1.5%
• 保留指数：
  1535;1575;1567.1;1571.4;1575.7;1548;1535

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 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)

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I相和II相酶的表达，特别是细胞色素P450家族。人们认为PCB的大部分毒性效应是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结合到雌激素受体来造成内分泌干扰，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等受体蛋白上而生物累积。(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

• 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

• 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)

安全信息

• 危险等级：
  9
• 危险品标志：
  N,Xn
• 安全说明：
  S35,S60,S61
• 危险类别码：
  R50/53
• WGK Germany：
  3
• RTECS号：
  DV2072000
• 海关编码：
  2903999090
• 包装等级：
  III
• 危险类别：
  9
• 危险品运输编号：
  UN 3077

制备方法与用途

类别：农药
毒性分级：中毒
急性毒性：腹腔-大鼠 LD50: 160 毫克/公斤
可燃性危险特性：可燃；火场分解产生有毒氯化物气体
储运特性：库房低温、通风、干燥
灭火剂：水、二氧化碳、干粉、砂土

反应信息

• 作为反应物：
  描述：

  亚老哥尔1221 以 丙酮 为溶剂， 反应 0.25h， 生成 联苯
  参考文献：
  名称：

  用紫外线照射脱氯多氯联苯。九。一氯联苯在 2-丙醇溶液中的反应

  摘要：

  在 2-丙醇中测定了导致一氯联苯脱氯反应的光激发态的多重性。通过使用 1,3- 环己二烯进行 2- 和 3- 氯联苯的脱氯反应获得线性 Stern-Volmer 图；斜率分别为 35.7 和 11.0 dm3 mol-1。荧光发射也被淬灭，2-和 3-氯联苯的淬灭常数与从反应的 Stern-Volmer 图中获得的斜率的各自值一致。4-氯联苯的反应被顺式1,3-戊二烯猝灭，但被1,3-环己二烯加速。一氯联苯的光敏脱氯发生在几种酮类中，例如丙酮和苯乙酮。然而，这些敏感的反应是 与直接激发中的反应相比，效率非常低，4-氯联苯除外。然后得出结论，2-和3-氯联苯的脱氯仅发生在...

  DOI：

  10.1246/bcsj.55.3569
• 作为产物：
  描述：

  1,2,3,5-四氯苯 反应 120.0h， 生成 亚老哥尔1221
  参考文献：
  名称：

  多卤苯在苯中的光反应。三联苯的形成

  摘要：

  多氯苯、多溴苯和多氯多溴苯（C6H6−nXn）在苯溶液中光解；产物采用 GC/MS 方法分析。脱卤和苯基化都显示出竞争性，产生少一个卤素原子的（多）卤代苯（C6H7-nXn-1）和（多）卤代联苯（C6H6-nXn-1-C6H5）作为主要产品。除了这些产品之外，三联苯是通过形成的卤代联苯的连续苯基化产生的。只有当通过 2-氯联苯的途径成为可能时，多氯苯才会形成相应的三联苯；然而，多溴苯可以通过中间形成的任何异构溴联苯产生三联苯。还显示通过氯原子的间迁移发生异构化的程度要小得多。

  DOI：

  10.1246/bcsj.62.3122

文献信息

• Palladium salt and functional reduced graphene oxide complex: in situ preparation of a generally applicable catalyst for C–C coupling reactions
  作者：Sheng Wang、Donghua Hu、Wenwen Hua、Jiangjiang Gu、Qiuhong Zhang、Xudong Jia、Kai Xi

  DOI：10.1039/c5ra10585d

  日期：——

  A novel Pd catalyst was designed by affording Pd2+ salt on the surface of functional reduced graphene oxide (FRGO), providing a new cheap and stable in situ prepared palladium catalyst for C–C coupling reactions, including the Heck reaction, Suzuki reaction, C–H bond functionalization reactions of thiophenes, and terminal alkyne C–H activation and homocoupling.

  一种新颖的钯催化剂是通过得到的Pd设计2+官能还原的石墨烯氧化物（FRGO）的表面上的盐，提供了一个新的廉价和稳定在原位对C-C偶联反应，包括Heck反应制备的钯催化剂，Suzuki反应，噻吩的C–H键官能化反应以及末端炔烃C–H活化和均偶联。
• Cross-Coupling of Triallyl(aryl)silanes with Aryl Bromides and Chlorides: An Alternative Convenient Biaryl Synthesis
  作者：Akhila K. Sahoo、Takuro Oda、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1002/adsc.200404188

  日期：2004.12

  give various biaryls in good yields. It is worthwhile to note that the all-carbon-substituted arylsilanes, stable towards moisture, acid, and base and easily accessible, serve as a highly practical alternative to their aryl(halo)silane counterparts. A catalyst system consisting of [(η3-C3H5)PdCl]2 and 2-[2,4,6-(i-Pr)3C6H2]-C6H4PCy2 and use of TBAF⋅3 H2O in THF-H2O are effective especially for the cross-coupling

  在DMSO-H 2 O中存在PdCl 2 / PCy 3和氟化四丁基铵（TBAF）的情况下，多种芳基溴化物与三烯丙基（芳基）硅烷的交叉偶联是有效的，以高收率得到各种联芳基。值得一提的是，全碳取代的芳基硅烷对水分，酸和碱稳定，易于获得，可作为其芳基（卤代）硅烷对应物的高度实用替代品。由[（η的催化剂体系3 -C 3 H ^ 5）的PdCl] 2和2- [2,4,6-（我-Pr）3 c ^ 6 ħ 2 ] -C 6 H ^ 4 PCY2和在THF-H 2 O中使用TBAF·3 H 2 O对于与芳基氯的交叉偶联特别有效。两种催化剂体系均能耐受多种常见的官能团。推测反应的高效率归因于用TBAF·3 H 2 O和适量的水处理后烯丙基的易裂解。二烯丙基（二苯基）硅烷还可以与各种芳基溴化物和氯化物交联，收率很高，而烯丙基（三苯基）硅烷只能以中等收率得到交联产物。通过溴氯苯与不同芳基硅烷的顺序交叉偶联，可
• Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: direct access to biaryls
  作者：Ren-Jin Tang、Qing He、Luo Yang

  DOI：10.1039/c4cc10155c

  日期：——

  A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the

  开发了芳香醛与富电子或缺电子的芳烃的无金属氧化脱羰基偶联剂，以生产联芳基化合物。基于底物范围，邻位区域选择性，自由基捕获实验和DFT计算研究，提出了通过非链自由基均相芳香族取代（HAS）类型的机理进行这种新型偶联。随着芳香醛和芳烃的现成可用，无金属条件应使这种偶联对于联芳基合成具有吸引力。
• Cobalt‐Catalyzed Direct Arylation of Unactivated Arenes with Aryl Halides
  作者：Wei Liu、Hao Cao、Jie Xin、Liqun Jin、Aiwen Lei

  DOI：10.1002/chem.201002290

  日期：2011.3.21

  and simple: The direct arylation of unactivated arenes with aryl halides has been carried out with [Co(acac)3] as the catalyst and LiHMDS as the base. The corresponding biaryl compounds have been prepared in good to excellent yields and at a relatively low reaction temperature (see scheme; acac=acetylacetonate, LiHMDS=lithium bis(trimethylsilyl)amide). An intramolecular direct arylation has also been

  廉价和简单：未活化的芳烃与芳基卤化物的直接芳基化反应已经以[Co（acac）3 ]为催化剂，LiHMDS为基础进行。相应的联芳基化合物已经以良好的产率和优异的产率在相对较低的反应温度下制备（参见方案； acac =乙酰丙酮酸酯，LiHMDS =双（三甲基甲硅烷基）酰胺锂）。在相同条件下也已经实现了分子内直接芳基化。
• Magnetically recoverable graphene oxide supported Co@Fe3O4/L-dopa for C-C cross-coupling and oxidation reactions in aqueous medium
  作者：Harsha Sharma、Shally Sharma、Chandan Sharma、Satya Paul、James H. Clark

  DOI：10.1016/j.mcat.2019.02.023

  日期：2019.5

  properties. In order to avoid the cumbersome process of separation, magnetite nanoparticles were coated over the graphene oxide. After the successful preparation of graphene oxide based magnetic nanoparticles, L-dopa was grafted over Fe3O4 nanoparticles so as to provide firm anchoring agent for cobalt nanoparticles. Finally, cobalt(0) nanoparticles were immobilized on the developed magnetic support. The catalytic

  我们报告了廉价和对环境无害的钴（0）纳米粒子在L -3,4-二羟基苯丙氨酸（L-多巴）官能化和磁铁矿（Fe 3 O 4）接枝的氧化石墨烯（[受电子邮件保护] / Fe 3 O 4的合成）上的合成。/ L-多巴），使用扫描电子显微镜（SEM），高分辨率透射电子显微镜（HR-TEM），X射线光电子能谱（XPS），X射线粉末衍射（XRD），热重分析（TGA），傅立叶变换红外光谱（FTIR），振动样品磁强计（VSM），碳氢氮（CHN）分析，能量色散X射线（EDX）和电感耦合等离子体原子发射光谱（ICP-AES）。氧化石墨烯由于其机械，电学和热学性质而被用作核心材料。为了避免繁琐的分离过程，将磁铁矿纳米颗粒涂覆在氧化石墨烯上。成功制备基于氧化石墨烯的磁性纳米粒子后，L-dopa接枝到Fe 3 O 4纳米粒子上，从而为钴纳米粒子提供牢固的锚固剂。最后，将钴（0）纳米颗粒固定在已开发的磁性载体上。测试了

表征谱图