2,8-二氯恶蒽 | 38964-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 中文名称: 2,8-二氯恶蒽
• 英文名称: 2,8-dichlorodibenzodioxin
• 英文别名: 2,8-dichlorodibenzo-p-dioxin；2,8-dichlorobenzo-p-dioxin；2,8-dichloro-dibenzo[1,4]dioxine
• CAS: 38964-22-6
• 化学式: C₁₂H₆Cl₂O₂
• 分子量: 253.084
• InChiKey: WMWJCKBJUQDYLM-UHFFFAOYSA-N

物化性质

• 熔点：
  151°C
• 沸点：
  328.83°C (rough estimate)
• 密度：
  1.4710 (estimate)
• 保留指数：
  1976;1985;1985;1985;1996;1996

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

CDDs通过口服、吸入和皮肤暴露途径被吸收。CDDs通过血清脂质和脂蛋白在血浆中运输，主要分布到肝脏和脂肪组织。CDDs通过微粒体单加氧酶系统非常缓慢地被代谢为极性代谢物，这些代谢物可以与葡萄糖醛酸和谷胱甘肽发生结合反应。它们可能通过诱导I相和II相酶来增加自己的代谢速率。CDDs的主要排泄途径是胆汁和粪便，尽管也有少量通过尿液和哺乳排出。

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the faeces, though smaller amounts are excreted in the urine and via lactation. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

CDDs通过结合芳基烃受体并随后改变某些基因的转录来产生其毒性作用。对Ah受体的亲和力取决于特定CDD的结构。基因表达的改变可能是由于Ah受体及其异二聚体形成伙伴芳基烃受体核移位子与基因调控元件的直接相互作用，或者启动磷酸化/去磷酸化级联反应，随后激活其他转录因子。受影响的基因包括几个癌基因、生长因子、受体、激素和药物代谢酶。这些基因的转录/翻译改变被认为是CDD大多数毒性作用的原因。

CDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

3, 无法归类其对人类致癌性的类别。(L135)

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

暴露于大量氯代二苯并二噁烷（CDDs）会引起氯痤疮，这是一种严重的皮肤疾病，其症状类似于粉刺，主要发生在面部和上半身。CDDs还可能引起肝损伤，并导致长期的葡萄糖代谢改变和激素水平的微妙变化。此外，研究表明CDDs可能干扰内分泌系统，削弱免疫系统，以及造成生殖损害和出生缺陷、中枢和周围神经系统病理、甲状腺疾病、子宫内膜异位症和糖尿病。(L177, L178)

Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. (L177, L178)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L177）；吸入（L177）；皮肤（L177）

Oral (L177) ; inhalation(L177) ; dermal (L177)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

除了氯痤疮，CDD暴露还会导致皮肤疹、色素沉着和体毛过度生长。

In addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (L177)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险等级：
  9
• 危险品运输编号：
  UN 3077

反应信息

• 作为反应物：
  描述：

  2,8-二氯恶蒽 在 硝酸铵 、 三氟乙酸酐 作用下， 以 硝基甲烷 为溶剂， 以74%的产率得到2,8-dichloro-3,7-dinitrodibenzodioxin
  参考文献：
  名称：

  A Novel Approach to the Molecular Imprinting of Polychlorinated Aromatic Compounds

  摘要：

  The aim of this investigation was to determine whether relatively weak interactions, such as hydrogen bonds to aromatic chlorine atoms and interactions involving aromatic pi electrons could be exploited within artificial receptors, constructed using the technique of molecular imprinting. For the purposes of this investigation we chose 2,3,7,8-tetrachlorodibenzodioxin (TCDD)as the model target. Imprinted polymers have been prepared with two new templates designed to create recognition sites for TCDD. The first of these, the bis-N-(4-vinylphenyl)urea derivative of 2,8-dichloro-3,7-diaminodibenzodioxin, employed a carbonyl spacer to introduce aromatic amines into the polymer after reductive cleavage of the template. The second, N-(2-(3,7,8-trichlorodibenzodioxinyl))-2-methacryloyloxybenzamide, incorporated a salicylic acid spacer and introduced a methacrylic acid residue into the polymer following hydrolysis. Both amine and acid groups were positioned in such a way as to interact with TCDD through the formation of weak hydrogen bonds to aromatic chlorine atoms. A second recognition element was introduced into the binding sites by the inclusion of a polymerizable, electron-rich, aromatic ether capable of forming pi-pi interactions with the electron-deficient dioxin molecule. Polymers imprinted with either template showed significantly higher uptake of TCDD than the corresponding nonimprinted controls, even at concentrations as low as 2 nM.

  DOI：

  10.1021/ja9818295
• 作为产物：
  描述：

  2,3,7-三氯二苯并-对-二恶英 生成 2,8-二氯恶蒽
  参考文献：
  名称：

  KOSHIOKA, MASAJI;YAMADA, TADAO;KANAZAWA, JUN;MURAI, TOSHINOBU, NIXON NOYAKU GAKKAJSI, 14,(1989) N, S. 175-179

  摘要：

  DOI：

文献信息

• 一种二噁英类有机化合物及其应用
  申请人：烟台九目化学制品有限公司

  公开号：CN109535168A

  公开（公告）日：2019-03-29

  本发明公开了一种二噁英类有机化合物及其应用，本发明以含有二噁英的有机化合物作为发光层或电子传输层材料，制作的OLED器件，较现有的OLED发光器件，具有较高的热稳定性、较低的驱动电压和较高的效率，寿命较长，具有良好的产业化前景。
• Formation of chlorinated phenols, dibenzo-p-dioxins, dibenzofurans, benzenes, benzoquinnones and perchloroethylenes from phenols in oxidative and copper (II) chloride-catalyzed thermal process
  作者：Jae-Yong Ryu

  DOI：10.1016/j.chemosphere.2007.10.036

  日期：2008.4

  CuCl(2). Chlorination preferentially occurred on ortho-(2, 6) and para-(4) positions. Chlorination increased up to 200 degrees C, and thereafter decreased as temperature increased. Chlorination of phenols plays an important role in the formation of the more chlorinated PCDD/Fs. Chlorinated benzenes are formed possibly from both chlorination of benzene and chlorodehydroxylation of phenols. Chlorinated phenols

  在100-425℃的温度范围内，在流式反应器中研究了CuCl（2）上由未取代苯酚和三种一氯酚形成多氯二苯对恶二恶英（PCDDs），多氯二苯并呋喃（PCDFs）和氯化苯酚。含8.0％氧气的氮气流用作载气。将0.00024摩尔未取代的苯酚和0.00039摩尔每种一氯苯酚通过1g和1cm的SiO（2）颗粒，其中包含0.5％（Cu质量）CuCl（2）。氯化反应优先发生在邻位（2，6）和对位（4）位置。氯化增加到200摄氏度，然后随温度升高而降低。苯酚的氯化在氯化程度更高的PCDD / Fs的形成中起着重要作用。氯化苯可能是由苯的氯化和苯酚的氯脱羟基化而形成的。带有邻氯的氯化苯酚形成PCDD产物，而主要的PCDD产物是通过损失一个氯而生产的。对于PCDF的形成，至少需要一种未氯化的原碳。
• Verfahren zur Herstellung einer sehr reinen Handelsform von 4,2',4'-Trichlor-2-hydroxydiphenyläther
  申请人：CIBA-GEIGY AG

  公开号：EP0086745A1

  公开（公告）日：1983-08-24

  Verfahren zur Herstellung einer sehr reinen, staubfreien und gerucharmen Handelsform von 4,2',4'-Trichlor-2-hydroxydiphenyläther durch Diazotieren von 4,2',4'-Trichlor-2-ami- nodiphenyläther, Verkochen des Diazoniumsalzes und Reinigung des Reaktionsproduktes. Die reine, staubfreie und geruchfreie Handelsform wird dadurch erhalten, dass die nach Abtrennen der sauren wässrigen Phase des Reaktionsgemisches alkalisch gestellte, 4,2',4'-Trichler-2-hydroxydiphenyläther und 2,4,8-Trichlordibenzofuran enthaltende Mischung entweder nach Entfernung des organischen Lösungsmittels durch Wasserdampfdestillation und Abscheidung des Nebenproduktes 2,4,8-Trichlordibenzofuran oder direkt mehrmals mit einem inerten, mit Wasser nicht mischbaren Lösungsmittel extrahiert und anschliessend auf pH 3 bis 10 eingestellt wird; hierauf die ausgefallene Schmelze von 4,2',4'-Trichlor-2-hydroxydiphenyläther, nach Entfernung der leichtflüchtigen Anteile, einer Kurzwegdestillation unterworfen und die destillierte Schmelze in eine wässrige Dispersin von kristallinem 4,2',4'-Trichlor-2-hydroxydiphenyläther eingeleitet wird, wobei diese Dispersion gleichzeitig einer Nassmahlung unterzogen wird. Nach Filtration und Trocknung wird eine granulatartige, gebrauchsfertige Handelsform erhalten.

  通过对 4,2',4'-三氯-2-氨基二苯醚进行重氮化，沸腾重氮盐并提纯反应产物，制备纯度极高、无尘、低气味的 4,2',4'-三氯-2-羟基二苯醚商用产品的工艺。通过将 4,2',4'-三氯-2-羟基二苯醚和 2,4,8-三氯二苯并呋喃制成 4,2',4'-三氯-2-羟基二苯醚，可以得到纯净、无尘、无味的商用产品、4,2',4'-trichloro-2hydroxydiphenyl ether 和 2,4,8-trichlorodibenzofuran，通过蒸汽蒸馏去除有机溶剂并分离副产物 2,4,8-trichlorodibenzofuran，或直接用惰性、不溶于水的溶剂多次萃取，然后调节 pH 值至 3 至 10；然后，析出的 4,2',4'-三氯-2-羟基二苯醚熔体在去除高挥发性成分后，进行短程蒸馏，并将蒸馏后的熔体引入结晶的 4,2',4'-三氯-2-羟基二苯醚水分散液中，同时对分散液进行湿法研磨。经过过滤和干燥后，就得到了颗粒状的即用型商品。
• A Novel Approach to the Molecular Imprinting of Polychlorinated Aromatic Compounds
  作者：Markus Lübke、Michael J. Whitcombe、Evgeny N. Vulfson

  DOI：10.1021/ja9818295

  日期：1998.12.1

  The aim of this investigation was to determine whether relatively weak interactions, such as hydrogen bonds to aromatic chlorine atoms and interactions involving aromatic pi electrons could be exploited within artificial receptors, constructed using the technique of molecular imprinting. For the purposes of this investigation we chose 2,3,7,8-tetrachlorodibenzodioxin (TCDD)as the model target. Imprinted polymers have been prepared with two new templates designed to create recognition sites for TCDD. The first of these, the bis-N-(4-vinylphenyl)urea derivative of 2,8-dichloro-3,7-diaminodibenzodioxin, employed a carbonyl spacer to introduce aromatic amines into the polymer after reductive cleavage of the template. The second, N-(2-(3,7,8-trichlorodibenzodioxinyl))-2-methacryloyloxybenzamide, incorporated a salicylic acid spacer and introduced a methacrylic acid residue into the polymer following hydrolysis. Both amine and acid groups were positioned in such a way as to interact with TCDD through the formation of weak hydrogen bonds to aromatic chlorine atoms. A second recognition element was introduced into the binding sites by the inclusion of a polymerizable, electron-rich, aromatic ether capable of forming pi-pi interactions with the electron-deficient dioxin molecule. Polymers imprinted with either template showed significantly higher uptake of TCDD than the corresponding nonimprinted controls, even at concentrations as low as 2 nM.
• KOSHIOKA, MASAJI;YAMADA, TADAO;KANAZAWA, JUN;MURAI, TOSHINOBU, NIXON NOYAKU GAKKAJSI, 14,(1989) N, S. 175-179
  作者：KOSHIOKA, MASAJI、YAMADA, TADAO、KANAZAWA, JUN、MURAI, TOSHINOBU

  DOI：——

  日期：——