2,2',4,4'-tetrabromodiphenyliodonium chloride | 189084-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2',4,4'-tetrabromodiphenyliodonium chloride
• 英文别名: Bis(2,4-dibromophenyl)iodanium chloride；bis(2,4-dibromophenyl)iodanium;chloride
• CAS: 189084-55-7
• 化学式: C₁₂H₆Br₄I*Cl
• 分子量: 632.153
• InChiKey: OSEJOCMEIURGJS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  18
• 可旋转键数：
  2
• 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：
  1

反应信息

• 作为反应物：
  描述：

  三溴苯酚 、 2,2',4,4'-tetrabromodiphenyliodonium chloride 在 sodium hydroxide 作用下， 以51%的产率得到2,2',4,4',6-五溴联苯醚
  参考文献：
  名称：

  Synthesis of Polybrominated Diphenyl Ethers and Their Capacity to Induce CYP1A by the Ah Receptor Mediated Pathway

  摘要：

  Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyresorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10(-2)-10(-5) times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition Sequence.

  DOI：

  10.1021/es0107475
• 作为产物：
  描述：

  1,3-二溴苯 在 硫酸 、 碘 、 硝酸 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 2,2',4,4'-tetrabromodiphenyliodonium chloride
  参考文献：
  名称：

  多溴联苯醚（BDE）；制备参考标准品和氟化内部分析标准品

  摘要：

  四个新的二氟化四-和五溴用于GC-MS / GC-ECD分析BDE内部标准，2F - BDE 47，2F - BDE 85，2F - BDE 99和2F - BDE 119，已经在纯度98-99.0％制备主要由新tribromodifluorophenols（耦合19 - 21）和对称bromodiphenyliodonium盐（8，22）。四种二氟化BDEs作为定量BDE分析的内标物显示出令人鼓舞的特性。四溴，五溴，六溴和七溴BDE参考标准品，BDE 75，BDE 85，BDE 138和BDE 183的纯度也达到98.4％至99.8％。

  DOI：

  10.1016/j.tet.2006.01.092

文献信息

• Synthesis of Hydroxylated and Methoxylated Polybrominated Diphenyl Ethers − Natural Products and Potential Polybrominated Diphenyl Ether Metabolites
  作者：Göran Marsh、Roland Stenutz、Åke Bergman

  DOI：10.1002/ejoc.200300081

  日期：2003.7

  Hydroxylated and methoxylated polybrominated diphenyl ethers (OH-PBDEs and MeO-PBDEs) may be natural products or they may be formed as metabolites of polybrominated diphenyl ethers (PBDEs), frequently used as flame retardants. The aim of this work was to synthesize authentic OH- and MeO-PBDE reference standards for analytical and toxicological studies. Brominated phenoxybenzaldehydes were prepared

  羟基化和甲氧基化的多溴联苯醚（OH-PBDEs 和 MeO-PBDEs）可能是天然产物，也可能作为多溴化二苯醚 (PBDEs) 的代谢物形成，通常用作阻燃剂。这项工作的目的是为分析和毒理学研究合成真正的 OH- 和 MeO-PBDE 参考标准。溴化苯氧基苯甲醛通过 2,4-二溴苯酚与各种氟苯甲醛的偶联或通过溴化羟基苯甲醛与 2,2',4,4'-四溴二苯基氯化碘的偶联制备。OH-PBDEs 是通过 Baeyer-Villiger 氧化和酸催化水解通过溴化苯氧基苯甲醛合成的。这些 OH-PBDEs 用三溴化苄基三甲基铵进行邻溴化和对溴化（相对于羟基）和/或用溴/叔丁胺邻溴化，并且在一种情况下也用溴溴化。MeO-PBDEs 是通过甲基化制备的 OH-PBDEs 获得的。MeO-PBDEs 也通过溴化甲氧基苯酚与 2,2',4,4'-四溴二苯基碘盐偶联制备，脱甲基后得到相应的 OH-PBDEs。大多数制备的
• Non-polar halogenated natural products bioaccumulated in marine samples. II. Brominated and mixed halogenated compounds
  作者：Walter Vetter、Wu Jun

  DOI：10.1016/s0045-6535(03)00200-5

  日期：2003.7

  BDE-99, BDE-100, BDE-154) were detected in a sample of human milk. The sample was from a woman from the Faeroe Islands who frequently consumed fish as well as whale blubber and meat. The most abundant compound originated from the natural tetrabromo phenoxyanisole BC-3 which may have a 3:1 distribution of bromine on the two phenyl units. This sample also accumulated a dibromochloroanisole, as well as a

  在这项工作中研究了几种已确定的和潜在的天然溴化生物富集化合物。合成了先前在澳大利亚海洋哺乳动物中检出并从海绵中分离出来的4,6-二溴-2-（2（'），4（'）-二溴）苯氧基苯甲醚（BC-2）。还研究了两种副产物（四溴异构体和三溴同类物）。在所研究的环境样品中未鉴定出合成的副产物。先前描述的天然溴化化合物（BC-1，BC-2，BC-3，BC-10，BC-11，MHC-1）和人为溴化二苯醚（BDE-47，BDE-99，BDE-100，BDE- 154）在人乳样品中检测到。样本来自法罗群岛的一名妇女，该妇女经常食用鱼，鲸脂和肉。最丰富的化合物源自天然的四溴苯氧基茴香醚BC-3，其在两个苯基单元上的溴分布比例为3：1。该样品还积聚了二溴氯茴香醚，以及以前未知的混合卤代化合物（MHC-X）和未知的，最可能是芳族溴化的化合物。在DB-5色谱柱上发现了BDE-99和BC-11以及BDE-154和未知溴代
• Synthesis and Characterization of 32 Polybrominated Diphenyl Ethers
  作者：Göran Marsh、Jiwei Hu、Eva Jakobsson、Sara Rahm、Ȧke Bergman

  DOI：10.1021/es9902266

  日期：1999.9.1
• Polybrominated diphenyl ethers (BDEs); preparation of reference standards and fluorinated internal analytical standards
  作者：Huiling Liu、Monica Bernhardsen、Anne Fiksdahl

  DOI：10.1016/j.tet.2006.01.092

  日期：2006.4

  difluorinated tetra- and pentabromo BDE internal standards for GC–MS/GC–ECD analysis, 2F-BDE47, 2F-BDE85, 2F-BDE99 and 2F-BDE119, have been prepared in 98–99.0% purity, mainly by coupling of the new tribromodifluorophenols (19–21) and symmetrical bromodiphenyliodonium salts (8, 22). The four difluorinated BDEs showed promising properties as internal standards for quantitative BDE analysis. Tetra-, penta-, hexa-

  四个新的二氟化四-和五溴用于GC-MS / GC-ECD分析BDE内部标准，2F - BDE 47，2F - BDE 85，2F - BDE 99和2F - BDE 119，已经在纯度98-99.0％制备主要由新tribromodifluorophenols（耦合19 - 21）和对称bromodiphenyliodonium盐（8，22）。四种二氟化BDEs作为定量BDE分析的内标物显示出令人鼓舞的特性。四溴，五溴，六溴和七溴BDE参考标准品，BDE 75，BDE 85，BDE 138和BDE 183的纯度也达到98.4％至99.8％。
• Synthesis of Polybrominated Diphenyl Ethers and Their Capacity to Induce CYP1A by the Ah Receptor Mediated Pathway
  作者：Guosheng Chen、Alexandre D. Konstantinov、Brock G. Chittim、Elizabeth M. Joyce、Niels C. Bols、Nigel J. Bunce

  DOI：10.1021/es0107475

  日期：2001.9.1

  Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyresorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10(-2)-10(-5) times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition Sequence.