六氯二苯并呋喃 | 70648-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 六氯二苯并呋喃
• 中文别名: 1,2,3,4,7,8-六氯二苯并呋喃；5-氯-2-(β-D-呋喃核糖基)-2H-1,2,3-三唑-4-羧酸甲基酯
• 英文名称: 1,2,3,4,7,8-hexachlorodibenzofuran
• 英文别名: 1,2,3,4,7,8-HxCDF；1,2,3,4,7,8-hexachlorodibenzodioxin；1,2,3,4,7,8-hexachlorodibenzo[b,d]furan；1,2,3,4,7,8-hexachlorinated dibenzofuran；1,2,3,4,7,8-hexaCDF；1,2,3,4,7,8-H6CDF
• CAS: 70648-26-9；55684-94-1
• 化学式: C₁₂H₂Cl₆O
• 分子量: 374.865
• InChiKey: LVYBAQIVPKCOEE-UHFFFAOYSA-N

物化性质

• 保留指数：
  2693;2706;2708;2708

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在现有文献中没有找到关于二苯并呋喃在哺乳动物体内的代谢信息。细菌Sphingomonas、Brevibacterium、Terrabacter和Staphylococcus auricularis通过二苯并呋喃4,4a-二加氧酶将二苯并呋喃降解为2,2',3-三羟基联苯。

No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

卤素代二苯并呋喃（PCDFs和PBDFs）与芳基烃受体（AhR）结合，增加了其在XRE（外源化合物响应元件）启动子区域激活转录的能力。具体来说，AhR与PCDF结合，将其转运到细胞核，并与芳烃核转运蛋白（ARNT）和外来化合物响应元件（XRE）一起增加CYP1A1和芳基烃羟化酶（CYP1B1）的表达。AhR信号还通过环氧合酶-2增加花生四烯酸转化为前列腺素，改变Wnt/β-连环蛋白信号，下调Sox9，并改变炎症细胞因子受体的信号传导。AhR信号还改变类固醇激素受体的蛋白体降解，改变细胞的UVB应激反应，并改变某些T细胞亚群的分化。由此产生的AhR介导的激活和改变导致体重减轻、癌症和胸腺萎缩（免疫和内分泌紊乱的特征），这是对PCDFs和相关有毒卤素代芳基烃的常见毒性反应。

Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 其对人类致癌性无法分类。

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

CDFs会导致呕吐和腹泻、贫血、更频繁的肺部感染、麻木以及对神经系统等其他影响，以及肝脏的轻微变化。然而，在摄入CDFs的人群中没有发现永久性的肝脏变化或明确的肝脏损伤。

CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入 (L952) ; 皮肤 (L952) ; 口服 (L952)

Inhalation (L952) ; dermal (L952) ; oral (L952)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

皮肤和眼部刺激，尤其是严重的痤疮、肤色变黑和带有分泌物的肿胀眼睑是CDF中毒最明显的健康影响。

Skin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 包装等级：
  I
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 2811

反应信息

• 作为产物：
  描述：

  一硫化四甲基秋兰姆 在 氧气 作用下， 生成 六氯二苯并呋喃
  参考文献：
  名称：

  Estimation of dioxin emission from fires in chemicals

  摘要：

  The formation of the 17 toxic 2,3,7,8-substituted PCDDs and PCDFs during combustion of selected chemicals were measured by high-resolution GC/MS. The 16 chemicals studied were commonly used chlorinated pesticides, industrial chemicals, and PVC. In a series of experiments carried out in a DIN 53,436 furnace, 2.5 g of these compounds were burned at 500 degrees C and 900 degrees C, respectively. The resultant yields ranged from 740 ng ITEQ/g for pentachlorophenol, to below 0.01 ng ITEQ/g for PVC and dichlobenil. The results show that some chemicals generate PCDD/F in very high possibly dangerous - amounts during burning, whereas others generate insignificant amounts. The influence of scale were studied for chlorobenzene and 4-chloro-3-nitro-benzoic acid in additional experiments, carried out in a cone calorimeter burning 20 g substance, and in ISO 9705 room test burning about 50 kg. A good agreement between the results for large and small scale indicated that formation of PCCD/F during a fire may be estimated from laboratory experiments. This suggest laboratory test may be used to screen for chemicals posing a hazard for release of PCDD/F during fires. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0045-6535(99)00231-3

文献信息

• On Dioxin Formation in Iron Ore Sintering
  作者：Mariusz K. Cieplik、Jose Pastor Carbonell、Christina Muñoz、Sarah Baker、Sophie Krüger、Per Liljelind、Stellan Marklund、Robert Louw

  DOI：10.1021/es026292g

  日期：2003.8.1

  sintering facility could satisfactorily imitate the large-scale process, in part or as a whole. Results obtained with realistic feed mixtures point at dioxin formation in the sinter bed at levels significant enough to explain a major part of the outputs observed in the real-life process. With approximately 8 ppm (wt) of chloride added as NaCl, the PCDD/F output doubled, but with the same proportion of

  铁矿石烧结是“二恶英”，多氯二苯并对二恶英和二苯并呋喃（PCDD / Fs）的重要来源。本文报道了尝试确定造成PCDD / F形成的材料，条件和机理的尝试（i）通过研究矿石的显着特性（即关于模型有机物的氧化，冷凝和氯化），以及（ii）使用现实生活的材料在微观尺度上模拟工业过程。采用实验设计原理（DOE）。铁矿石的反应性差异很大。褐铁矿/针铁矿“软”矿石是一种非常活泼的氧化催化剂（例如，用于苯和苯酚），该特性可用于清除粗烧结工艺废气，而赤铁矿/磁铁矿“硬”矿石则不是。后者，但是强烈促进苯酚缩合为二苯并呋喃。新建的实验室级微型烧结设备可以部分或整体令人满意地模仿大规模过程。用实际的进料混合物获得的结果表明，在烧结床中二恶英的形成水平足以说明在现实生活中观察到的大部分产出。通过添加约8 ppm（wt）的氯化物作为NaCl，PCDD / F的产量增加了一倍，但是在氯的施用比例与C2Cl4相同的情况
• PCDD/DF formations by the heterogeneous thermal reactions of phenols and their TiO2 photocatalytic degradation by batch-recycle system
  作者：Hajime Muto、Koki Saitoh、Hitoshi Funayama

  DOI：10.1016/s0045-6535(00)00552-x

  日期：2001.10

  and dibenzofurans (PCDD/DFs) formation by the thermal reactions of phenols with CuCl2 under oxygen flux were carried out in relation to their formation mechanisms. To evaluate the effect of photocatalytic degradation of titanium dioxide (TiO2) thin film prepared by the sol-gel method, the photocatalysis of PCDD/DFs in acetonitrile/water solution by batch-recycle system was conducted. For the thermal reaction

  就酚类与CuCl2在氧通量下的热反应，进行了多氯代二苯并二恶英和二苯并呋喃（PCDD / DFs）的形成机理的研究。为了评价溶胶-凝胶法制备的二氧化钛（TiO2）薄膜的光催化降解效果，采用间歇循环系统对PCDD / DFs在乙腈/水溶液中的光催化性能进行了研究。对于2,4,5-三氯苯酚（2,4,5-TCP）和CuCl2的粉末混合物的热反应系统，总PCDD /的形成速率为8.1 microg / g-2,4,5-TCP / min PCDDs的DFs和6.9 microg / g-2,4,5-TCP / min，与苯酚蒸气/氧气/ CuCl2粉末系统相比，PCDD / DF的总速率高出约40倍。对于2,4,5-TCP的系统，PCDDs主要是通过邻苯氧酚（POP）中间体通过2,4,5-三氯苯酚的缩合反应形成的。对于PCDD / DF光催化降解，大多数PCDD同系物会快速分解，并且在辐照后24小时使用由2
• Emissions of polychlorinated dibenzo-p-dioxins and dibenzofurans from catalytic and thermal oxidizers burning dilute chlorinated vapors
  作者：John R. Hart

  DOI：10.1016/j.chemosphere.2003.10.017

  日期：2004.3

  (ng/dscm)=8.4 exp(-0.0084T degrees C); (2) dioxin/furan production occurs at the combustion catalyst; (3) small variations in temperature cause large changes in the congener distribution of the dioxin and furan isomers; (4) molar TEQ yields from the parent compounds fed to the oxidizers are very small (10(-9)-10(-13)); (5) catalytic and thermal oxidizers may destroy dioxins fed from the ambient air; and (6)

  通过对低（几至几百）百万分之一的氯化和非氯化挥发性有机化合物（VOC）的氧化进行的57次现场测试，发现了多氯二苯并对二恶英和二苯并呋喃（二恶英）的排放。在使用铂，铂/钯或铬（IV）氧化物燃烧催化剂的催化氧化剂中，或在热氧化剂（无催化剂）中发生氧化。催化剂入口温度为293至573摄氏度。热氧化剂的运行温度（火焰后）为773至927摄氏度。报告了有毒的二恶英和呋喃异构体的数据，并进行了加权和表示为国际有毒当量（ 2,3,7,8-四氯二苯并-对-二恶英的TEQ）。最大烟囱排放为1.07 ng / m3 TEQ，发生在293摄氏度。该现场研究的主要结果是：（1）堆中的TEQ水平随工作温度的降低而呈指数增长，经验公式为TEQ（ng / dscm）= 8.4 exp（-0.0084T摄氏度）; （2）在燃烧催化剂处产生二恶英/呋喃；（3）温度的微小变化会导致二恶英和呋喃异构体的同类物分布发生较大变化；
• Emission Factors and Importance of PCDD/Fs, PCBs, PCNs, PAHs and PM₁₀ from the Domestic Burning of Coal and Wood in the U.K.
  作者：Robert G. M. Lee、Peter Coleman、Joanne L. Jones、Kevin C. Jones、Rainer Lohmann

  DOI：10.1021/es048745i

  日期：2005.3.1

  fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-sigmaTEQ to total U.K. emissions was minor.

  本文介绍了当煤和木材经过受控燃烧实验时针对一系列持久性有机污染物（POPs）得出的排放因子（EFs），旨在模拟空间供暖的家庭燃烧。排放了各种各样的持久性有机污染物，煤炭的排放量高于木材的排放量。对于颗粒物，PM10（大约10 g / kg燃料）和多环芳烃（对于sigmaPAHs大约100 mg / kg燃料）获得了最高的EF。对于氯化物，多氯联苯（PCB）的EF最高，而多氯萘（PCN），二苯并-对-二恶英（PCDD）和二苯并呋喃（PCDF）的丰度较低。对于sigmaPCB，EF大约为1000 ng / kg燃料，对于sigmaPCNs大约为100s ng / kg燃料，对于sigmaPCDD / Fs大约为100 ng / kg燃料。该研究证实，一氯化至三氯化二苯并呋喃Cl1,2,3DFs是低温燃烧过程（如煤炭和木材的国内燃烧）的有力指标。结论是，在固体燃料燃烧期间通常形成许多PCB和PC
• Superacid-promoted synthesis of polychlorinated dibenzofurans
  作者：Ahmad Qarah、Makafui Gasonoo、Dat Do、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2016.06.100

  日期：2016.8

  Polychlorinated dibenzofurans have been prepared in one step by the condensations of o-chloranil with arenes in triflic acid. A mechanism is proposed involving formation of a monoprotonated quinone (carboxonium ion), electrophilic attack at the arene, and cyclization of a carbocation intermediate. The chemistry is further examined by spectroscopic and theoretical studies.

  多氯二苯并呋喃是一步制备的，其方法是邻氯苯腈与芳烃在三氟甲磺酸中缩合。提出了一种机制，该机制涉及单质子化醌（碳鎓离子）的形成，对芳烃的亲电攻击以及碳正离子中间体的环化。通过光谱学和理论研究进一步检查了化学反应。