2,2’,4,4’,5-五溴联苯醚 | 60348-60-9

• 物质功能分类: 分析化学 - 标准品 - 有机污染物标样
• 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: 2,2’,4,4’,5-五溴联苯醚
• 中文别名: 2,2',3,5,6'-五氯联苯；2,2',4,4',5-五溴联苯醚
• 英文名称: 2,2',4,4',5-pentrabromodiphenyl ether
• 英文别名: BDE-99；2,2′,4,4′,5-pentabromodiphenyl ether；2,2',4,4',5-pentabrominated diphenyl ether；2, 2', 4, 4',5-pentabromodiphenyl ether；2,2',4,4',5-Pentabromodiphenyl ether；2,2',4,4',5-pentabromo diphenylether；1,2,4-tribromo-5-(2,4-dibromophenoxy)benzene
• CAS: 60348-60-9
• 化学式: C₁₂H₅Br₅O
• 分子量: 564.691
• InChiKey: WHPVYXDFIXRKLN-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C(Solv: tetrahydrofuran (109-99-9); water (7732-18-5); acetonitrile (75-05-8))
• 沸点：
  416 °C
• 密度：
  2.343±0.06 g/cm3(Predicted)
• 闪点：
  -12 °C
• 溶解度：
  可溶于氯仿（轻微）、乙酸乙酯（轻微）、甲醇（轻微、加热）
• 物理描述：
  Pentabromodiphenyl oxide is an amber solid. (NTP, 1992)
• 颜色/状态：
  White crystalline solid
• 蒸汽压力：
  3.50X10-7 mm Hg at 25 °C
• 分解：
  200-300 °C
• 粘度：
  Highly viscous at room temperature (ca. 2X10+6 cps at 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

多溴联苯可以通过口服、吸入和皮肤途径被吸收。一旦进入人体，它们会分布到全身并在血液、母乳和脂肪组织中生物累积。PBDE的代谢程度取决于溴化的程度。代谢过程被认为涉及脱溴和甲基化，产生酚类代谢物。代谢和未代谢的PBDE化合物主要通过粪便排出体外。(L628, L881)

Polybrominated biphenyls can be absorbed through oral, inhalation, and dermal routes. Once in the body they distribute throughout and bioaccumulate in the blood, breast milk, and adipose tissue. The extent of PBDE metabolism depends on the degree of bromination. Metabolism is believed to involve debromination and methylation, resulting in phenolic metabolites. Metabolized and unmetabolized PDBE compounds are excreted mainly in the faeces. (L628, L881)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

像其他卤代芳烃一样，多溴联苯醚会与细胞中的芳烃受体（AhR）结合，该受体调节多种蛋白质的合成。AhR的激活诱导了许多酶的产生，包括细胞色素P-450依赖性单加氧酶CYP1A和CYP2B家族、UDP-葡萄糖醛酸基转移酶和乙氧基芪素-O-脱乙基酶。PBDEs还被认为是干扰甲状腺激素的产生、运输和处置。一种机制涉及PBDEs的代谢物与甲状腺素竞争结合转甲状腺素，降低血清甲状腺激素水平。甲状腺激素水平的变化与甲状腺毒性和神经行为改变有关。某些PBDEs及其代谢物也是内分泌干扰物，可能作为雌激素受体的激动剂或作为雄激素和孕酮受体的拮抗剂。（L628, A262）

Like other halogenated aromatic hydrocarbons, polybrominated diphenyl ethers bind to the cellular aryl hydrocarbon receptor (AhR), which regulates the synthesis of a variety of proteins. Activation of the AhR induces a number of enzymes, including cytochrome P-450-dependent monooxygenases of the CYP1A and CYP2B families, UDP-glucuronosyltransferase, and ethoxyresorufin-o-deethylase. PBDEs are also believed to disrupt the production, transport, and disposition of thyroid hormones. One mechanism of this involves metabolites ot PDBEs competing with thyroxine to bind to transthyretin, decreasing serum thyroid hormone levels. This change in thyroid hormone levels has been linked to both thyroid toxicity and neurobehavioral alterations. Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors or antagonists at the androgen and progesterone receptors. (L628, A262)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

多溴联苯醚可能会影响甲状腺和肝脏。动物研究也表明，PDBEs可以导致神经行为改变并影响免疫系统。

Polybrominated diphenyl ethers may affect the thyroid gland and liver. Animals studies have also shown that PDBEs can cause neurobehavioral alterations and affect the immune system. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（L628）；吸入（L628）；皮肤给药（L628）

Oral (L628) ; inhalation (L628) ; dermal (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 最低风险水平

中间吸入：0.006 毫克/立方米（L134） 急性口服：0.03 毫克/千克/天（L134） 中间口服：0.007 毫克/千克/天（L134）

Intermediate Inhalation: 0.006 mg/m3 (L134) Acute Oral: 0.03 mg/kg/day (L134) Intermediate Oral: 0.007 mg/kg/day (L134)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 危险品标志：
  Xn,F,N
• 安全说明：
  S60,S61,S62
• 危险类别码：
  R67,R38,R50/53,R11,R65
• WGK Germany：
  2
• 海关编码：
  2909309090
• 危险品运输编号：
  UN 1262 3/PG 2

反应信息

• 作为反应物：
  描述：

  2,2’,4,4’,5-五溴联苯醚 生成 1,2,3-三溴二苯并二恶因
  参考文献：
  名称：

  DUMLER, R.;TEUFL, C.;LENOIR, D.;HUTZINGER, O., VDI-BER.,(1987) N34, C. 287-292

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,5-三溴苯胺 在 sodium hydroxide 、 三氟乙酸 、 sodium nitrite 作用下， 反应 0.83h， 生成 2,2’,4,4’,5-五溴联苯醚
  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

文献信息

• 一种多溴联苯醚单体的微波合成方法
  申请人：山东省分析测试中心

  公开号：CN104860799B

  公开（公告）日：2016-10-12

  本发明公开了一种多溴联苯醚单体的微波合成方法，溴代苯在蒙脱土的催化下与溴代苯酚反应，反应产物经提纯分离后，即得多溴联苯醚。其设备简单，化学反应彻底且安全无污染。避免使用强碱强酸性试剂，安全性高且清洁环保；本发明为一步反应，合成时间为20～60分钟，较“碘鎓盐‑偶联两步反应法”反应反应时间大大缩短；微波功率在130～300瓦，其能耗较低。
• Purification of brominated organic products
  申请人：Great Lakes Chemical Corporation

  公开号：US04214103A1

  公开（公告）日：1980-07-22

  Crude halogenated organic products, especially products consisting of partially halogenated diphenyl ethers alone or in admixture with other materials may be purified by contacting the crude brominated product with a finely divided basic solid such as a carbonate or bicarbonate of an alkali metal or ammonia for a time and at a temperature sufficient to enhance the purity thereof. The purification step may be performed in the presence of an organic solvent or by adding the basic solid directly to molten crude products in the presence of a small amount of water.

  粗卤代有机产品，特别是由部分卤代二苯醚单独或与其他物质混合而成的产品，可以通过将粗溴化产物与碱金属的碳酸盐或碱性氢氧化物或氨等细分碱性固体接触一段时间并在足够的温度下提高其纯度。纯化步骤可以在有机溶剂的存在下进行，或者通过在少量水的存在下将碱性固体直接加入熔融的粗产品中进行。
• SCORCH RETARDANT HALOGENATED FLAME RETARDANT COMPOUNDS AND ARTICLES MADE THEREFROM
  申请人：PolyOne Corporation

  公开号：EP3699224A1

  公开（公告）日：2020-08-26

  A halogenated flame retardant polyethylene compound is disclosed containing at least one organic additive which presents in its molecular structure at least one nitrogen atom to serve as a scorch retardant to forestall premature crosslinking during manufacture of wire and cable insulation and/or jacketing, in order to obtain a flame retardant crosslinked polyethylene (XLPE), and especially when the XLPE material is obtained via an alkoxysilane condensation-hydrolysis step.

  本发明公开了一种卤化阻燃聚乙烯化合物，其中含有至少一种有机添加剂，该添加剂在其分子结构中至少含有一个氮原子，可作为阻燃剂防止电线电缆绝缘层和/或护套层在制造过程中过早交联，从而获得阻燃交联聚乙烯（XLPE），特别是当 XLPE 材料是通过烷氧基硅烷缩合-水解步骤获得时。
• Highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester with reduced environmental pollutants, and method for producing same
  申请人：NIPPON SUISAN KAISHA, LTD.

  公开号：US10399922B2

  公开（公告）日：2019-09-03

  A highly unsaturated fatty acid or a highly unsaturated fatty acid ethyl ester that has been produced using as a feedstock oil a fat or oil that contains highly unsaturated fatty acids as constituent fatty acids and which has been reduced in the contents of environmental pollutants, wherein among the dioxins contained, polychlorinated dibenzoparadioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs) are contained in amounts of less than 0.05 pg-TEQ/g and coplanar PCBs (Co-PCBs) in amounts of less than 0.03 pg-TEQ/g. Also disclosed is a method for producing the highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester by the steps of removing free fatty acids and environmental pollutants by thin-film distillation from a feedstock oil, ethyl esterifying the resulting fat or oil, and refining the same by rectification and column chromatography.

  一种高度不饱和脂肪酸或高度不饱和脂肪酸乙酯，它是以含有高度不饱和脂肪酸作为组成脂肪酸的脂肪或油作为原料油生产的，其环境污染物含量已经降低，其中所含的二恶英中，多氯二苯并对二恶英（PCDD）和多氯二苯并呋喃（PCDF）的含量低于 0.05 pg-TEQ/g，共面多氯联苯（Co-PCB）的含量低于 0.03 pg-TEQ/g。05 pg-TEQ/g，共面多氯联苯（Co-PCBs）含量低于 0.03 pg-TEQ/g。本发明还公开了一种生产高度不饱和脂肪酸或高度不饱和脂肪酸乙酯的方法，其步骤是通过薄膜蒸馏法从原料油中去除游离脂肪酸和环境污染物，对所得脂肪或油进行乙酯化，并通过精馏和柱层析法对其进行精制。
• Oern, Ulrika; Eriksson, Lars; Jakobsson, Eva, Acta Chemica Scandinavica, 1996, vol. 50, p. 802 - 807
  作者：Oern, Ulrika、Eriksson, Lars、Jakobsson, Eva、Bergman, Ake

  DOI：——

  日期：——