1-甲基-4-(溴亚甲基)-2,5-二溴苯 | 188403-43-2

• 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: 1-甲基-4-(溴亚甲基)-2,5-二溴苯
• 英文名称: 1,4-dibromo-2-(bromomethyl)-5-methylbenzene
• CAS: 188403-43-2
• 化学式: C₈H₇Br₃
• 分子量: 342.856
• InChiKey: AABWZPJIKSPIEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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-甲基-4-(溴亚甲基)-2,5-二溴苯 在 咪唑 、 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 1-{3,5-Bis[dimethyl(1,1-dimethylethyl)silyloxy]phenoxymethyl}-4-methyl-2,5-dibromobenzene
  参考文献：
  名称：

  Entering a New Level of Use for Suzuki Cross-Coupling: Poly(para-phenylene)s with Fourth-Generation Dendrons

  摘要：

  Three different synthetic routes to the fourth-generation (G4) macromonomers 4, 6, and 9 for Suzuki polycondensation (SPC) are described and compared in their efficiency. Monomer 9 was selected the best as judged by the number and feasibility of synthetic steps and purification behavior and could be prepared in a 15 g scare. SPC of the monomers 4, 6, and 9 gave the novel poly(para-phenylene)s 17, 18, and 19 with pendant G4 dendrons at every other repeat unit. SPC was optimized for 9 and the diboronic acid ester counterpart 16 which led to polymer 19 with a molecular weight of up to M-n=76000, M-w=639000 (GPC versus polystyrene). High molecular weight is most likely to be obtained for the attempted stoichiometry 9:16=1.000:(0.995-1.005).

  DOI：

  10.1002/1521-3765(20000901)6:17<3235::aid-chem3235>3.0.co;2-4
• 作为产物：
  描述：

  2,5-二溴-1,4-二甲基苯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 1-甲基-4-(溴亚甲基)-2,5-二溴苯
  参考文献：
  名称：

  X-Ray Structure Determinations of Bromo- and/or Bromomethylsubstituted Benzenes: C–H···Br, C–Br···Br, and C–Br···π Interactions

  摘要：

  七种苯衍生物[1,2,3-三(溴甲基)苯，(1)；3,5-二(溴甲基)溴苯，(2)；2,5-二(溴甲基)溴苯，(3)；4-(溴甲基)-2,5-二溴甲苯，(4)；4-(溴甲基)溴苯，(5)；(6) 和 (溴甲基)-p-二溴苯，(7)]，并分析了它们与溴和溴甲基（以及一种情况下的甲基）取代基之间高达 4.还发现了一些 Br---π 和 π---π 类型的相互作用，它们在填料中起次要作用。尽管这些化合物的化学性质非常相似，其中一些还是取代基位置颠倒的异构体，但其填料结构却千变万化。化合物 2-5 基于具有 Brn（n=3，4）和/或混合 Br/C 环的层状结构。化合物 1、6 和 7 显示了不同复杂程度的三维填料，但具有可解释的子结构；化合物 1 可以从相连的 Br3 和 Br4 环带的角度进行分析；化合物 6 显示了相连的 Br3 三角形链；化合物 7 由相连的 Br4 四边形带组成。

  DOI：

  10.5560/znb.2012-0249

文献信息

• Synthesis of Optically Active, X-Shaped, Conjugated Compounds and Dendrimers Based on Planar Chiral [2.2]Paracyclophane, Leading to Highly Emissive Circularly Polarized Luminescence
  作者：Masayuki Gon、Yasuhiro Morisaki、Risa Sawada、Yoshiki Chujo

  DOI：10.1002/chem.201504270

  日期：2016.2.12

  Gram‐scale optical resolution and transformations of 4,7,12,15‐tetrasubstituted [2.2]paracyclophanes were also carried out. The high‐generation dendrons effectively absorbed UV light and transferred energy to the core, resulting in high photoluminescence (PL) from the core. In addition, the dendrons sufficiently isolated the emissive X‐shaped conjugated core and bright emission was observed from both thin films

  合成了具有发射性X形π电子系统为核心单元的光学活性Fréchet型树状聚合物。还进行了克级光学拆分和4,7,12,15-四取代[2.2]对环环烷烃的转化。新一代树突有效吸收紫外线并将能量转移至核心，从而导致核心产生高光致发光（PL）。此外，树突充分隔离了发射的X形共轭核，并且从薄膜和溶液中都观察到了明亮的发射。从薄膜观察到强烈的圆偏振发光（CPL）。树枝状聚合物膜表现出优异的光学性质，例如大的摩尔消光系数，高的荧光量子效率，强烈的PL和CPL以及大的CPL不对称因素。
• An Improved Method for the Regiospecific Synthesis of Polysubstituted [2.2]Paracyclophanes
  作者：Hak-Fun Chow、Kam-Hung Low、King Y. Wong

  DOI：10.1055/s-2005-872270

  日期：——

  4,16-Disubstituted, 4,7,12,15-tetrasubstituted, 4,8,12,16-tetrasubstituted and 4,5,7,8,12,13,15,16-octasubstituted [2.2]paracyclophanes can be prepared in significantly improved yields and excellent regiospecificities via the Winberg 1,6-elimination-dimerization reaction from substituted (4-methylbenzyl)tri­methylammonium hydroxides. Using 2-chloro-phenothiazine instead of phenothiazine as a polymerization inhibitor results in a doubling of product yields.

  4,16-二取代、4,7,12,15-四取代、4,8,12,16-四取代及4,5,7,8,12,13,15,16-八取代[2.2]对环聚醌可通过Winberg 1,6-消除-聚合反应，从取代的（4-甲基苄基）三甲胺氢氧化物中显著提高产率和优良的区域特异性。使用2-氯苯噻嗪代替苯噻嗪作为聚合抑制剂可使产品产率翻倍。
• X-Ray Structure Determinations of Bromo- and/or Bromomethylsubstituted Benzenes: C–H···Br, C–Br···Br, and C–Br···π Interactions
  作者：Peter G. Jones、Piotr Kuś、Ina Dix

  DOI：10.5560/znb.2012-0249

  日期：2012.12.1

  The structures of seven benzene derivatives [1,2,3-tri(bromomethyl)benzene, (1); 3,5- di(bromomethyl)bromobenzene, (2); 2,5-di(bromomethyl)bromobenzene, (3); 4-(bromomethyl)-2,5- dibromotoluene, (4); 4-(bromomethyl)bromobenzene, (5); 2,3-di(bromomethyl)bromobenzene, (6) and (bromomethyl)-p-dibromobenzene, (7)] with bromo and bromomethyl (and in one case methyl) substituents are presented and analysed in terms of Br···Br interactions up to 4.0 A° , supported by hydrogen bonds H···Br. Some interactions of the type Br···π and π···π are encountered and play a subordinate role in the packing. Despite the close chemical similarity of the compounds, some of which are isomers with permuted substituent positions, the packing motifs are highly variable. Compounds 2-5 are based on layer structures with Br_n (n=3, 4) and/or mixed Br/C rings. Compounds 1, 6 and 7 display three-dimensional packings of differing complexity, but with interpretable substructures; 1 can be analysed in terms of ribbons of linked Br₃ and Br₄ rings; 6 displays chains of linked Br₃ triangles; 7 consists of ribbons of linked Br₄ quadrilaterals.

  七种苯衍生物[1,2,3-三(溴甲基)苯，(1)；3,5-二(溴甲基)溴苯，(2)；2,5-二(溴甲基)溴苯，(3)；4-(溴甲基)-2,5-二溴甲苯，(4)；4-(溴甲基)溴苯，(5)；(6) 和 (溴甲基)-p-二溴苯，(7)]，并分析了它们与溴和溴甲基（以及一种情况下的甲基）取代基之间高达 4.还发现了一些 Br---π 和 π---π 类型的相互作用，它们在填料中起次要作用。尽管这些化合物的化学性质非常相似，其中一些还是取代基位置颠倒的异构体，但其填料结构却千变万化。化合物 2-5 基于具有 Brn（n=3，4）和/或混合 Br/C 环的层状结构。化合物 1、6 和 7 显示了不同复杂程度的三维填料，但具有可解释的子结构；化合物 1 可以从相连的 Br3 和 Br4 环带的角度进行分析；化合物 6 显示了相连的 Br3 三角形链；化合物 7 由相连的 Br4 四边形带组成。
• Immobilization of quaternized polymers on bacterial cellulose by different grafting techniques
  作者：P. Ramar、Sourita Jana、Sandipan Chatterjee、Sellamuthu N. Jaisankar、Debasis Samanta

  DOI：10.1039/c9nj02199j

  日期：——

  Different polymers were immobilized on bacterial cellulose surfaces using grafting techniques to improve their mechanical properties and surface hydrophobicity.

  使用嫁接技术将不同的高分子物质固定在细菌纤维素表面，以提高其机械性能和表面亲水性。
• Toward Dendrimers with Cylindrical Shape in Solution
  作者：Birol Karakaya、Wilhelm Claussen、Katrin Gessler、Wolfram Saenger、A.-Dieter Schlüter

  DOI：10.1021/ja963943y

  日期：1997.4.1

  Three approaches for the synthesis of dendrimers with poly(p-phenylene)-PPP derived cores are described. The respective limitations of these approaches are assessed in view of the goal of this research: to make available structurally perfect, high molecular weight polymers with a dense sequence of sterically demanding dendrons.