1,2,4,5-tetrabromo-3,6-diethylbenzene | 124654-04-2

• 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: 1,2,4,5-tetrabromo-3,6-diethylbenzene
• 英文别名: 1,4-diethyl-2,3,5,6-tetrabromobenzene；2,3,5,6-tetrabromo-1,4-diethylbenzene；1,4-diethyl-2,3,5,6-tetrabromo-benzene；1,4-Diaethyl-2,3,5,6-tetrabrom-benzol
• CAS: 124654-04-2
• 化学式: C₁₀H₁₀Br₄
• 分子量: 449.805
• InChiKey: DHYPURXYFPOYQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  114.5-115.5 °C
• 沸点：
  397.9±37.0 °C(Predicted)
• 密度：
  2.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrabromo-3,6-diethylbenzene 在 selenium 、 sodium tetrahydroborate 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 4,5-bis(4-nitrophenethylseleno)-3,6-diethylphthalonitrile
  参考文献：
  名称：

  Preparation of Phthalocyanines with Eight Benzylchalcogeno Substituents from 5,6-Dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles

  摘要：

  Benzo[1,2,3]trichalcogenoles with two bromine atoms on the benzene ring, 5,6-dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles (1a) and (1b) (chalcogen: 1a = S; 1b = Se), were first prepared by treating 2,3,5,6-tetrabromo-1,4-diethylbenzene (TBDEB) with elemental sulfur or amorphous selenium in DBU at 140 degreesC (for 1a) and 100 degreesC (for 1b) for 24 h. The structures of 1a and 1b were verified by NMR spectroscopy, mass spectrometry, and elemental analysis. X-ray crystallographic analysis ultimately showed that the substitution reactions of TBDEB proceeded at the two adjacent bromine atoms. To apply 1a and 1b to construction of phthalocyanine derivatives with sulfur or selenium functional groups, 4,5-bis(benzylchalcogeno)-3,6-diethylphthalonitriles (5a) and (5b) as key intermediates were prepared by way of introduction of alkyl groups (2-cyanoethyl or 4-nitrophenethyl groups) on two chalcogen atoms, substitution of two bromine atoms with nitrile groups, and subsequent exchange of alkyl groups with benzyl groups. Compound 5a was treated with lithium in n-pentanol at 100 degreesC for 1 h to produce 2,3,9,10,16,17,23,24-octakis(benzylthio)1,4,8,11,15,18,22,25-octaethylphthalocyanine (6a). A similar treatment of 5b in n-hexanol at 100 degreesC for 2 h gave phthalocyanine 6b. The structures of 6a and 6b were determined by H-1 NMR spectroscopy and MALDI-TOFMS. X-ray crystallographic analysis of 6a was also performed. The Q-band absorptions (lambda(max)) for 6a and 6b in UV-vis spectra were observed at 755 nm (log epsilon = 5.1) and 757 nm (log epsilon = 5.1), respectively, and their electrochemical properties were verified by cyclic voltammetry in dichloromethane with Ag/AgNO3 as a reference electrode. Compounds 6a and 6b were further treated with lithium in THF/NH3 at -78 degreesC and then with dibutyltin dichloride to produce phthalocyanine derivatives 8a and 8b with four dichalcogenastannole rings by way of octachalcogenate phthalocyanines 7a and 7b.

  DOI：

  10.1021/jo030354j
• 作为产物：
  描述：

  1,4-二乙基苯 在 溴 、 铁粉 作用下， 以87%的产率得到1,2,4,5-tetrabromo-3,6-diethylbenzene
  参考文献：
  名称：

  用于改善ROMP胶粘剂高温性能的交联剂

  摘要：

  开环易位聚合（ROMP）已被证明是一种在各种基材之间进行粘合的有效方法。在各种基材（包括硫化后的弹性体，聚烯烃和金属）上均表现出优异的附着力。当一个基材表面涂有复分解催化剂，而另一基材表面涂有ROMPable单体时，则具有很强的附着力。对于在粘结线可能经受高于环境温度的动态应用中使用基于ROMP的胶粘剂的担忧促使了这项研究。在本报告中，使用了多种双降冰片二烯交联剂，以各种自粘合和交联配置粘合轮胎胎体，轮胎胎面，硫化后的EPDM和喷砂钢。然后，在各种交联剂浓度下，在−40°C至66°C的温度范围内使用180°剥离测试评估所得粘合组件。在高温下观察到粘结强度的显着改善，即使在高交联剂浓度下，对低温强度的有害影响也很小。还研究了聚烯烃组件的自粘合。还发现在初始ROMP配方中添加过氧化物自由基引发剂并在后固化反应中使键合组件交联可提高高温键合强度。报道了制备几种交联剂的合成细节。在高温下观察到粘结

  DOI：

  10.1002/adsc.200600455

文献信息

• Preparation and Electrochemical Properties of 1,4,8,11,15,18,22,25-Octalkylphthalocyanines Containing Four Trithiole Rings
  作者：Takeshi Kimura、Takahiro Suzuki、Yutaka Takaguchi、Akinori Yomogita、Takatsugu Wakahara、Takeshi Akasaka

  DOI：10.1002/ejoc.200500654

  日期：2006.3

  5-(o-xylylenedithio)phthalonitriles 3a–d with lithium in n-pentanol. Reductive removal of the four o-xylylene groups from 4b and 4c was performed with lithium/THF/ammonia, and the octathiolate anions generated were then treated with elemental sulfur to give the new phthalocyanines 6b and 6c, respectively, each containing four trithiole rings, after partial desulfurization and ring-contraction reactions of the corresponding

  1,4,8,11,15,18,22,25-Octalkyl-2,3;9,10;16,17;23,24-tetrakis(o-xylylenedithio)phthalocyanines 4a–d（烷基 = 乙基，丁基通过在正戊醇中用锂处理 3,6-二烷基-4,5-（邻苯二甲硫基）邻苯二甲腈 3a-d，以中等产率制备 ((、辛基和十二烷基)。用锂/四氢呋喃/氨从 4b 和 4c 中还原去除四个邻二甲苯基团，然后用元素硫处理产生的八硫醇阴离子，分别得到新的酞菁 6b 和 6c，每个都含有四个三硫醇环，在相应的酞菁5b和5c部分脱硫和缩环反应后。酞菁的结构由1H NMR光谱和MALDI-TOF质谱确定。在紫外/可见光谱的 λmax ≈ 770 nm 处观察到 4a-d 的 Q 带的吸收，而在一个区域中发现 4b-Ni、5b、5c 和 6c 的吸收，相对于 4a 发生蓝移-d。当在浓硫酸中测量 6c
• Cross-Linkers for Improved High Temperature Performance of ROMP Adhesives
  作者：Christopher G. Keck、Jonathan L. Kendall、Kenneth C. Caster

  DOI：10.1002/adsc.200600455

  日期：2007.1.8

  observed at elevated temperature with little detrimental affect on low temperature strengths even at high cross-linker concentration. Self-bonding of polyolefins assemblies was also investigated. Addition of a peroxide radical initiator to the initial ROMP formulation and cross-linking the bonded assembly in a post-cure reaction was also found to lead to improved high temperature bond strength. Synthetic

  开环易位聚合（ROMP）已被证明是一种在各种基材之间进行粘合的有效方法。在各种基材（包括硫化后的弹性体，聚烯烃和金属）上均表现出优异的附着力。当一个基材表面涂有复分解催化剂，而另一基材表面涂有ROMPable单体时，则具有很强的附着力。对于在粘结线可能经受高于环境温度的动态应用中使用基于ROMP的胶粘剂的担忧促使了这项研究。在本报告中，使用了多种双降冰片二烯交联剂，以各种自粘合和交联配置粘合轮胎胎体，轮胎胎面，硫化后的EPDM和喷砂钢。然后，在各种交联剂浓度下，在−40°C至66°C的温度范围内使用180°剥离测试评估所得粘合组件。在高温下观察到粘结强度的显着改善，即使在高交联剂浓度下，对低温强度的有害影响也很小。还研究了聚烯烃组件的自粘合。还发现在初始ROMP配方中添加过氧化物自由基引发剂并在后固化反应中使键合组件交联可提高高温键合强度。报道了制备几种交联剂的合成细节。在高温下观察到粘结
• Preparation of bromine-containing polymers useful as flame retardants
  申请人：Bromine Compounds Ltd.

  公开号：US10336858B2

  公开（公告）日：2019-07-02

  The invention relates to a process for preparing bromine-containing polymer, comprising a Friedel-Crafts alkylation reaction of tetrabromoxylylene dihalide, or tetrabromoxylylene dihalide in combination with pentabromobenzyl halide, with a reactant having one or more six-membered aromatic rings, wherein the reaction takes place in a solvent in the presence of a Friedel-Crafts catalyst, and isolating from the reaction mixture the bromine-containing polymer. The so-formed polymers and their use as flame retardants form additional aspects of the invention.

  本发明涉及一种制备含溴聚合物的工艺，包括四溴氧二甲苯二卤化物或四溴氧二甲苯二卤化物与五溴苄基卤化物的弗里德尔-卡夫斯烷基化反应，反应物具有一个或多个六元芳香环，反应在弗里德尔-卡夫斯催化剂存在下于溶剂中进行，并从反应混合物中分离出含溴聚合物。由此形成的聚合物及其作为阻燃剂的用途构成了本发明的其他方面。
• Bromine-containing polymers useful as flame retardants
  申请人：Bromine Compounds Ltd.

  公开号：US10472462B2

  公开（公告）日：2019-11-12

  The invention relates to a process for preparing bromine-containing polymer, comprising a Friedel-Crafts alkylation reaction of tetrabromoxylylene dihalide, or tetrabromoxylylene dihalide in combination with pentabromobenzyl halide, with a reactant having one or more six-membered aromatic rings, wherein the reaction takes place in a solvent in the presence of a Friedel-Crafts catalyst, and isolating from the reaction mixture the bromine-containing polymer. The so-formed polymers and their use as flame retardants form additional aspects of the invention.

  本发明涉及一种制备含溴聚合物的工艺，包括四溴氧二甲苯二卤化物或四溴氧二甲苯二卤化物与五溴苄基卤化物的弗里德尔-卡夫斯烷基化反应，反应物具有一个或多个六元芳香环，反应在弗里德尔-卡夫斯催化剂存在下于溶剂中进行，并从反应混合物中分离出含溴聚合物。由此形成的聚合物及其作为阻燃剂的用途构成了本发明的其他方面。
• Contact metathesis polymerization
  申请人：Lord Corporation

  公开号：US20020166629A1

  公开（公告）日：2002-11-14

  A method for bonding a material to a first substrate surface that includes providing a catalyst at the first substrate surface and then contacting that surface with a material that undergoes a metathesis reaction to bond the material to the first substrate surface. There are two embodiments of this method—a coating process and an adhesive process. In the coating embodiment, the metathesizable material is contacted with the catalyst on the substrate surface so that it undergoes metathesis polymerization to form the coating. The adhesive process includes (a) providing a catalyst at the first substrate surface, (b) providing a metathesizable material between the first substrate surface and the second substrate surface, and (c) contacting the catalyst on the first substrate surface with the metathesizable material so that the metathesizable material undergoes a metathesis reaction and bonds the first substrate surface to the second substrate surface.

  一种将材料粘合到第一基底表面的方法，包括在第一基底表面提供催化剂，然后将该表面与发生偏析反应的材料接触，从而将材料粘合到第一基底表面。这种方法有两种实施方式--涂层工艺和粘合工艺。在涂层工艺中，可偏析材料与基底表面上的催化剂接触，使其发生偏析聚合反应形成涂层。粘合工艺包括：(a) 在第一基底表面提供催化剂；(b) 在第一基底表面和第二基底表面之间提供可偏析材料；(c) 第一基底表面的催化剂与可偏析材料接触，使可偏析材料发生偏析反应，将第一基底表面粘合到第二基底表面。