多氯联苯(Aroclor1248)标样 | 33284-52-5

• 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: 多氯联苯(Aroclor1248)标样
• 中文别名: 甲基乙酯1248；亚老哥尔1248；多氯联苯1248标准品；氯联苯1248；多氯联苯1248；3,3',5,5'-四氯联苯；多氯联苯
• 英文名称: 3,5,3',5'-tetrachlorobiphenyl
• 英文别名: 3,3',5,5'-tetrachlorobiphenyl；PCB 80；3,3',5,5'-Tetrachlorbiphenyl；3,3',5,5'-tetrachloro-1,1'-biphenyl；3,5,3',5'-Tetrachlor-biphenyl；1,3-dichloro-5-(3,5-dichlorophenyl)benzene
• CAS: 33284-52-5；12737-87-0；12672-29-6
• 化学式: C₁₂H₆Cl₄
• 分子量: 291.992
• InChiKey: UTMWFJSRHLYRPY-UHFFFAOYSA-N

物化性质

• 物理描述：
  Pcb-1248 is a viscous oily liquid. (NTP, 1992)
• 颜色/状态：
  Colorless mobile oil
• 气味：
  Practically odorless; mild aromatic odor
• 沸点：
  644 to 707 °F at 760 mm Hg (NTP, 1992)
• 熔点：
  340-375 °C
• 闪点：
  193-196 °C (Cleveland open cup)
• 溶解度：
  In water, 54 ug/L at 25 °C
• 密度：
  1.405-1.415 at 15.5 °C
• 蒸汽压力：
  4.94X10-4 mm Hg at 25 °C (avg)
• 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 chlorine. /Polychlorinated biphenyls/
• 粘度：
  36-37 Saybolt sec at 98.9 °C
• 折光率：
  Index of refraction at 20 °C = 1.630 - 1.631
• 相对蒸发率：
  Evaporation loss at 100 °C/6 hr= 0-0.3%

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  16
• 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

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  多氯联苯(Aroclor1248)标样 在 三氯化铝 、 五羰基铁 作用下， 以 苯 为溶剂， 反应 11.0h， 生成 1,1',3,3',6,6',8,8'-octachloro-9,9'-bifluorenylidene
  参考文献：
  名称：

  1,1‘,3,3‘,6,6‘,8,8‘-Octachloro-9,9‘-bifluorenylidene and Perchloro-9,9‘-bifluorenylidene, Two Exceedingly Twisted Ethylenes

  摘要：

  The syntheses of 1,1',3,3',6,6',8,8'-octachloro-9,9'-bifluorenylidene (1), its precursors, and the byproduct 3,3',5,5'-tetrachloro-4-(trichloromethyl)biphenyl (5) are described. Accurate structural X-ray data on 1 and on perchloro-9,9'-bifluorenylidene (2) are reported and discussed. Because of chlorine overcrowding, the dihedral angles between their two identical fluorenylidene moieties are abnormally large, the central-ethylene twist angles being 55 and 66degrees, respectively. Significant out-of-plane carbon-chlorine bond bending is likewise exhibited. Their ESR spectra and magnetic measurements prove that they are singlet species. The exceptionally large bathochromic displacements of their UV-vis absorption spectrum with respect to that of their parent hydrocarbon are mainly attributed to bond bending and molecular warping.

  DOI：

  10.1021/jo010979m
• 作为产物：
  描述：

  1,3-二氯苯 在 1,10-菲罗啉 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 copper diacetate 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 多氯联苯(Aroclor1248)标样
  参考文献：
  名称：

  经由CH硼化的芳烃立体控制CH / CH均偶联。

  摘要：

  描述了一种温和的一锅法方案，该方案通过顺序的Ir催化的CH硼酸酯化和Cu催化的芳烃均偶联合成对称的联芳基。所形成的联芳基的区域化学空间上受CH硼酸酯化步骤的控制。该方法还成功地扩展到了杂芳烃。通过这种方法获得的某些产品无法通过Ullmann或Suzuki耦合协议获得。最后，我们显示了一锅序列描述了CH硼化/ Cu催化的均偶联/ Pd催化的Suzuki偶联以获得π扩展的芳烃骨架。

  DOI：

  10.1039/c9ob00995g

文献信息

• Copper-Mediated C–N Coupling of Arylsilanes with Nitrogen Nucleophiles
  作者：Johannes Morstein、Eric D. Kalkman、Chen Cheng、John F. Hartwig

  DOI：10.1021/acs.orglett.6b02543

  日期：2016.10.21

  A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C–H silylation generates arylamines from unactivated arenes

  报道了芳基硅烷与氮亲核试剂的氧化偶联的方法。该方法可与多种七甲基三甲硅烷氧基芳烃和氮亲核试剂一起使用，并以芳基硅烷作为限制试剂进行，并且不需要具有电子贫乏的芳基硅烷的氟化物活化剂。该方法与C–H甲硅烷基化相结合，可从未活化的芳烃中生成芳胺，其位点选择性受空间效应控制。通过这些步骤的组合，可以直接访问许多无法通过替代的C–H功能化方法访问的化合物，包括直接的C–H胺化或C–H硼化和胺化的组合。
• Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N-Heterocyclic Carbene-Palladium Complex
  作者：Sharanabasappa Khanapure、Dattaprasad Pore、Megha Jagadale、Vaishali Patil、Gajanan Rashinkar

  DOI：10.1007/s10562-020-03480-w

  日期：——

  carbene-palladium complex (SilFemBenzNHC@Pd) has been prepared and characterized by using fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). This novel complex served as a robust heterogeneous catalyst for the synthesis of biaryls via homocoupling

  摘要 采用傅里叶变换红外（FT-IR）、傅里叶变换拉曼（FT-Raman）、X射线光电子能谱（ XPS)、扫描电子显微镜 (SEM)、热重分析 (TGA) 和能量色散 X 射线分析 (EDX)。这种新型复合物可作为一种强大的多相催化剂，用于在水中无碱条件下通过芳基硼酸的均偶联合成联芳基化合物。连续六次运行成功地执行了可回收性实验。图形摘要
• Homocoupling of Iodoarenes and Bromoalkanes Using Photoredox Gold Catalysis: A Light Enabled Au(III) Reductive Elimination
  作者：Huy Tran、Terry McCallum、Mathieu Morin、Louis Barriault

  DOI：10.1021/acs.orglett.6b02021

  日期：2016.9.2

  formation of homocoupled alkane byproducts have been identified in the reduction of bromoalkanes via photoredox gold catalysis with dimeric Au(I) complexes. This prompted further investigation into the mechanism of formation of these byproducts and the diversity of C–X bonds amenable to this transformation. Examples were found when considering bromoalkanes while a wide variety of iodoarenes underwent this

  通过二聚Au（I）配合物通过光氧化还原金催化还原溴代烷烃，已经确定了均相偶联烷烃副产物的形成。这促使人们进一步研究这些副产物的形成机理以及适合这种转化的C–X键的多样性。当考虑使用溴代烷烃时，发现了许多实例，而各种各样的碘代芳烃以良好至优异的收率进行了该过程。据报道，通过光氧化还原金催化，碘代芳烃的光均质偶联成为可能。
• Homocoupling of Arylboronic Acids with a Catalyst System Consisting of a Palladium(II) N-Heterocyclic Carbene Complex and <i>p</i>-Benzoquinone
  作者：Yoshihiko Yamamoto

  DOI：10.1055/s-2007-984531

  日期：2007.7

  In the presence of 1-3 mol% SIPr-ligated Pd(OAc)2 and 0.6 equivalent of p-benzoquinone, various arylboronic acids underwent homocoupling in MeOH at ambient temperature to produce symmetrical biaryls in 38-96% yields.

  在1-3摩尔% SIPr配位的Pd(OAc)2和0.6当量的对苯醌存在下，各种芳基硼酸在常温的甲醇中发生自偶联，生成对称的双芳烃，产率在38-96%之间。
• Homocoupling reactions of terminal alkynes and arylboronic compounds catalyzed by in situ formed Al(OH) 3 -supported palladium nanoparticles
  作者：Xing Li、Dongjun Li、Yana Bai、Congxia Zhang、Honghong Chang、Wenchao Gao、Wenlong Wei

  DOI：10.1016/j.tet.2016.09.035

  日期：2016.11

  Palladium nanoparticles supported on newly generated Al(OH)3 was found to be a highly efficient catalyst in oxidative homo-couplings of (Het)aryl alkynes, (Het)arylboronic acids and potassium (Het)aryltrifluoroborates, respectively. Moderate to excellent yields of symmetrical 1,3-diynes and biaryls were obtained under mild conditions.

  发现负载在新生成的Al（OH）3上的钯纳米粒子分别是（Het）芳基炔烃，（Het）芳基硼酸和（Het）芳基三氟硼酸钾的氧化均偶联剂中的高效催化剂。在温和条件下获得中等至极好的对称1,3-二炔和联芳基收率。

表征谱图