2,5-二溴联苯 | 57422-77-2

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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: 2,5-二溴联苯
• 中文别名: 2-乙酰基-6,7-二甲氧基-1-亚甲基-1,2,3,4-四氢异喹啉
• 英文名称: 2,5-dibromo-1,1'-biphenyl
• 英文别名: 2,5-dibromobiphenyl；2,5-dibromo-biphenyl；2,5-Dibrom-biphenyl；2,5-Dibrombiphenyl；1,4-dibromo-2-phenylbenzene
• CAS: 57422-77-2
• 化学式: C₁₂H₈Br₂
• 分子量: 312.004
• InChiKey: MHQCPXUMZCNOSF-UHFFFAOYSA-N

物化性质

• 熔点：
  40-42 °C
• 沸点：
  209 °C(Press: 15 Torr)
• 密度：
  1.667±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  14
• 可旋转键数：
  1
• 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：
  0

ADMET

代谢

多溴联苯（PBBs）可以通过口服、吸入和皮肤途径被吸收。由于它们的亲脂性，尤其是高溴代的多溴联苯，倾向于在富含脂质的组织中积累，如肝脏、脂肪、皮肤和母乳。某些多溴联苯化合物通过由苯巴比妥诱导的细胞色素P-450类型的微粒体单加氧酶系统进行代谢。代谢速率可能取决于溴取代模式。低溴含量的多溴联苯同系物转化为主要在尿液中排出的羟基衍生物。高溴代同系物要么被保留，要么在粪便中不变排出。(L628)

PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

多氯联苯（PBBs）的毒性机制因具体同系物而异。主要的相互作用被认为是涉及芳基烃受体（AhR）。PBBs与AhR结合并激活它，进而启动一系列基因的转录上调，影响生化途径和内分泌途径、细胞周期调节、形态发生、氧化应激反应以及各种其他过程。这导致PBBs特有的多种毒性反应。一些已知的诱导基因包括细胞色素P-450依赖性单加氧酶CYP1A1和CYP1A2。

The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

2A，可能对人类致癌。（L135）

2A, probably carcinogenic to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

PBB暴露可能会导致体重减轻、皮肤问题（如痤疮）、神经和免疫系统的影响，以及对肝脏、肾脏和甲状腺的影响。

PBB exposure may cause weight loss, skin disorders (such as acne), nervous and immune systems effects, and effects on the liver, kidneys, and thyroid gland. (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

• 症状

PBB暴露的症状可能包括恶心、腹痛、食欲不振、关节痛、疲劳和虚弱。

Symptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. (L629)

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 储存条件：
  室温

制备方法与用途

用途：多溴联苯类常用于ROHS项目或POPs中的分析和检测作为标准品。

反应信息

• 作为反应物：
  描述：

  2,5-二溴联苯 在 乙醚 、 magnesium 作用下， 生成 6-bromo-biphenyl-3-carboxylic acid
  参考文献：
  名称：

  The Preparation of 3,4-Dibromodiphenyl

  摘要：

  DOI：

  10.1021/ja01298a047
• 作为产物：
  描述：

  2-硝基联苯 在 盐酸 、 四氯化碳 、 tin 、 溴 作用下， 生成 2,5-二溴联苯
  参考文献：
  名称：

  Scarborough; Waters, Journal of the Chemical Society, 1927, p. 94

  摘要：

  DOI：

文献信息

• Reactivity of alkali and alkaline earth metal tetrafluorobromates towards aromatic compounds and pyridine
  作者：Vasily I. Sobolev、Victor D. Filimonov、Roman V. Ostvald、Vyacheslav B. Radchenko、Ivan I. Zherin

  DOI：10.1016/j.jfluchem.2016.10.022

  日期：2016.12

  The bromination activity of tetrafluorobromates of alkali and alkali-earth metals increases in the order KBrF4, CsBrF4, RbBrF4 and Ba(BrF4)2. The most active tetrafluorobromate—Ba(BrF4)2 is able to selectively brominate the deactivated aromatic compounds nitrobenzene and 4-nitrotoluene, but not the activated compounds benzene and toluene. In all cases bromination of methyl groups of methylbenzenes

  碱金属和碱土金属四氟溴酸盐的溴化活性按KBrF 4，CsBrF 4，RbBrF 4和Ba（BrF 4）2的顺序增加。活性最高的四氟溴酸盐-Ba（BrF 4）2能够选择性地溴化失活的芳族化合物硝基苯和4-硝基甲苯，但不能选择性地溴化活化的苯和甲苯。在所有情况下，都不发生甲基苯的甲基溴化。Ba（BrF 4）2与吡啶反应形成已知的络合物C 6 H 5 N·BrF 3。由于用惰性BaF 2稀释，这种基于吡啶的配合物是空气稳定的，与原始的氟代溴酸盐相比，可以认为是更安全，更方便的试剂；与四氟溴酸盐相比，它可以选择性地溴化苯和甲苯。
• Homolytic aromatic substitution. Part XXXIV. Major products from the reaction of benzoyl peroxide with p-disubstituted benzenes
  作者：D. I. Davies、D. H. Hey、B. Summers

  DOI：10.1039/j39700002653

  日期：——

  p-tolyl sulphide, or methyl p-tolyl sulphoxide. The major reaction is oxidation at the sulphur atom, which leads to the formation of, in addition to benzoic anhydride, arylthiomethyl and arylsulphinylmethyl benzoates from the aryl sulphides and sulphoxides respectively. There is no evidence that free radicals are involved in the reaction of benzoyl peroxide with these sulphur-containing compounds.

  过氧化苯甲酰与对-二取代苯（不包括具有硫取代基的苯）的反应可导致被苯基和/或苯甲酰氧基自由基取代。产物的形成依赖于取代基的性质，并且可以与哈米特相关联σ p值。在对位取代的甲苯，联苄类的形成与在增加而降低σ p的值对位-取代。在过氧化苯甲酰与甲基苯硫醚，甲基对甲苯硫醚或甲基对苯二酚的反应中，未观察到芳环的苯基化或苯甲酰氧基化。-甲苯基亚砜。主要反应是在硫原子上的氧化，除苯甲酸酐外，还导致分别由芳基硫醚和亚砜形成芳基硫基甲基和芳基亚磺酰基甲基苯甲酸酯。没有证据表明自由基参与过氧化苯甲酰与这些含硫化合物的反应。
• C–H Bond Functionalization of (Hetero)aryl Bromide Enabled Synthesis of Brominated Biaryl Compounds
  作者：Kai-Hui Liu、Guang-Qi Hu、Cai-Xia Wang、Fei-Fei Sheng、Jing-Wen Bai、Jian-Guo Gu、Hong-Hai Zhang

  DOI：10.1021/acs.orglett.1c01613

  日期：2021.8.6

  Aryl bromide is one of the most important compounds in organic chemistry, because it is widely used as synthetic building blocks enabling quick access to a wide array of bioactive molecules, organic materials, and polymers via the versatile cutting-edge transformations of C–Br bond. Direct C–H bond functionalization of aryl bromide is considered to be an efficient way to prepare functionalized aryl

  芳基溴是有机化学中最重要的化合物之一，因为它被广泛用作合成构建块，通过 C-Br 键的多功能尖端转化，可以快速获取各种生物活性分子、有机材料和聚合物. 芳基溴的直接 C-H 键功能化被认为是制备功能化芳基溴的有效方法；然而，由于芳基溴对 C-H 键活化的反应性相对较低，因此很少对其进行探索。我们在此报告了钯催化的芳基碘化物和芳基溴化物之间的偶联反应，用于通过银介导的 C-H 键活化途径制备溴化联芳基化合物。
• COMPOUND HAVING TRIARYLAMINE STRUCTURE AS CORE, AND PREPARATION METHOD THEREFOR
  申请人：JIANGSU SUNERA TECHNOLOGY CO., LTD.

  公开号：US20210163411A1

  公开（公告）日：2021-06-03

  A compound having a triarylamine structure as a core, a preparation method therefor, and an application thereof. The compound has a structure represented by general formula (1). The compound has high glass transition temperature and molecular thermal stability, has suitable HOMO and LIMO energy levels, and has high mobility. By means of device structure optimization, the photoelectric properties of an OLED device can be effectively improved and the life of the OLED device can be effectively prolonged.

  一种具有三芳胺结构作为核心的化合物，其制备方法以及应用。该化合物具有由一般式（1）表示的结构。该化合物具有高玻璃转变温度和分子热稳定性，具有适当的HOMO和LIMO能级，并具有高迁移率。通过器件结构优化，可以有效改善OLED器件的光电特性，并有效延长OLED器件的寿命。
• Polyparaphenylene Hydrocarbon Electrolyte, Manufacture Method Therefor, and Polyparaphenylene as well as Electrolyte Membrane, Catalyst Layer and Solid Polymer Fuel Cell
  申请人：Hoshikawa Naohiro

  公开号：US20100197815A1

  公开（公告）日：2010-08-05

  A polyparaphenylene hydrocarbon electrolyte having a structure represented by a formula (1), a manufacture method therefore, and a polyparaphenylene usable as a raw material for manufacturing the polyparaphenylene hydrocarbon electrolyte, as well as a electrolyte membrane, a catalyst layer and a solid polymer fuel cell that employ the polyparaphenylene hydrocarbon-based electrolyte. In the formula, A is an integer of (1) or greater; B is an integer of 0 or greater; and C is an integer of 1 to 10. X represents a direct bond or an oxygen atom, which is arbitrarily assignable in repetitions. At least one of Y 1 s represents a proton-conducting site, and the rest of Y 1 s each represent a hydrogen atom or a proton-conducting site, which is arbitrarily assignable in repetitions. The proton-conducting site is made up of —SO 3 H, —COOH, —PO 3 H 2 or —SO 2 NHSO 2 R (R is an alkyl chain or a perfluoroalkyl chain).

  一种聚对苯二甲烷氢碳电解质，其结构由式（1）表示，以及其制备方法。还提供一种可用作制备聚对苯二甲烷氢碳电解质的原材料的聚对苯二甲烷，以及使用聚对苯二甲烷氢碳电解质的电解质膜、催化层和固体聚合物燃料电池。在公式中，A是大于等于1的整数；B是大于等于0的整数；C是1到10的整数。X表示直接键或氧原子，可在重复中任意分配。至少一个Y1代表质子导电位点，其余的Y1分别表示氢原子或质子导电位点，可在重复中任意分配。质子导电位点由—SO3H，—COOH，—PO3H2或—SO2NHSO2R（R是烷基或全氟烷基）组成。

表征谱图