2,3,7,8-tetrafluorodibenzodioxin | 100231-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 英文名称: 2,3,7,8-tetrafluorodibenzodioxin
• 英文别名: 2,3,7,8-Tetrafluoro DBD；2,3,7,8-tetrafluorodibenzo-p-dioxin
• CAS: 100231-56-9
• 化学式: C₁₂H₄F₄O₂
• 分子量: 256.156
• InChiKey: NOZDVIWMUAUYAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 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：
  6

反应信息

• 作为产物：
  描述：

  2,4,5-三氟苯酚 在 potassium tert-butylate 作用下， 以 环丁砜 为溶剂， 反应 24.0h， 以21.1%的产率得到2,3,7,8-tetrafluorodibenzodioxin
  参考文献：
  名称：

  一种多氟代二苯并对二噁英的制备方法

  摘要：

  本发明公开一种多氟代二苯并对二噁英的制备方法，属于含氟化合物的合成技术领域，以邻位有氟原子取代的氟酚(FP)和叔丁醇钾(t‑BuOK)为反应原料，环丁砜(C4H8O2S)作溶剂，在惰性气体保护下，反应温度为180~220℃，反应24~32 h，分离提纯，得偶数个氟原子取代的多氟代二苯并对二噁英。本发明为一种合成具有偶数个氟原子的PFDDs的通用方法，且反应条件温和、操作方便、产率较高，获得的PFDDs纯度较高。

  公开号：

  CN108358885A

文献信息

• 一种多氟代二苯并对二噁英的制备方法
  申请人：信阳师范学院

  公开号：CN108358885A

  公开（公告）日：2018-08-03

  本发明公开一种多氟代二苯并对二噁英的制备方法，属于含氟化合物的合成技术领域，以邻位有氟原子取代的氟酚(FP)和叔丁醇钾(t‑BuOK)为反应原料，环丁砜(C4H8O2S)作溶剂，在惰性气体保护下，反应温度为180~220℃，反应24~32 h，分离提纯，得偶数个氟原子取代的多氟代二苯并对二噁英。本发明为一种合成具有偶数个氟原子的PFDDs的通用方法，且反应条件温和、操作方便、产率较高，获得的PFDDs纯度较高。
• Synthesis of polyfluorinated dibenzo-p-dioxins
  作者：U. Haffer、W. Rotard、W. Mailahn

  DOI：10.1016/0045-6535(94)90346-8

  日期：1994.11

  Fluorinated dibenzo-p-dioxins (PFDD) have been selectively synthesized from fluorophenols and isolated by liquid-column- and thin layer chromatography. The structures were confirmed by IR, MS, HR-MS, H-1-NMR and F-19-NMR-spectroscopy. Reaction times, melting points and the IR-absorption bands are presented for several PFDD's as well as H-1- and (19)-F-NMR-spectra for two PFDD's and the mass-spectrum for 2,3,7,8-T4FDD.
• Polyfluorinated dibenzodioxins and dibenzofurans — synthesis, analysis, formation and toxicology
  作者：R. Weber、D. Schrenk、H.-J. Schmitz、A. Hagenmaier、H. Hagemnaier

  DOI：10.1016/0045-6535(94)00429-x

  日期：1995.2

  The 75 congeners of the polyfluorinated dibenzodioxins (PFDDs) and about half of the 135 polyfluorinated dibenzofurans (PFDFs) have been synthesized by pyrolysis of fluorophenols and fluorobenzenes. The individual congeners were characterized by GC/MS. 2,3,7,8-TFDD was also characterized by H-1-, C-13- and F-19-NMR spectroscopy. The retention behavior of PFDDs and PFDFs during gaschromatographic separation is entirely different from that of PCDDs/PCDFs or PBDDs/PBDFs. The PFDDs/PFDFs elute earlier than the PCDDs/PCDFs and the order of the elution is not governed by the degree of substituion, O8FDD eluting e.g. much earlier than the M(1)FDDs.A preliminary toxicological evaluation of 2,3,7,8-TFDD was carried out. The elimination of 2,3,7,8-TFDD from mice after a single i.p. injection is biphasic with a very rapid elimination half-live of 5 minutes and a slower phase of 165 minutes. This means a dramatically reduced half-live compared to 2,3,7,8-TCDD with 8.5 d. In liver the TFDD level reaches a maximum 30 minutes after injection and also declined in a biphasic manner. In rat hepatocytes a primary culture induction of CYP4501A1-catalyzed EROD activity could be demonstrated, indicating that 2,3,7,8-TFDD activates the dioxin receptor. In rat hepatocyte cultures similar EC(50) values were found for 2,3,7,8-TCDD and 2,3,7,8-TFDD.So far no de novo synthesis of PFDD/PFDF could be detected under conditions were PCDDs/PCDFs are formed Also, formation of PFDDs/PFDFs could not be detected during thermal treatment of fluorotrichloromethane or Teflon.