1,2-二溴-4,5-双(溴甲基)苯 | 6425-67-8

• 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: 1,2-二溴-4,5-双(溴甲基)苯
• 英文名称: 1,2-dibromo-4,5-bis(bromomethyl)benzene
• 英文别名: 1,2-bis(bromomethyl)-4,5-dibromobenzene
• CAS: 6425-67-8
• 化学式: C₈H₆Br₄
• 分子量: 421.752
• InChiKey: QOSUUORMRZRRJA-UHFFFAOYSA-N

物化性质

• 沸点：
  400.6±40.0 °C(Predicted)
• 密度：
  2.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  12
• 可旋转键数：
  2
• 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

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1,2-二溴-4,5-双(溴甲基)苯 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-bis(dodecylsulfanylmethyl)benzene-1,2-dicarbonitrile
  参考文献：
  名称：

  Cho, Iwhan; Lim, Youngsoo, Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 154, p. 9 - 26

  摘要：

  DOI：
• 作为产物：
  描述：

  邻二甲苯 在 溴 作用下， 生成 1,2-二溴-4,5-双(溴甲基)苯
  参考文献：
  名称：

  Kotha, Sambasivarao; Ghosh, Arun Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 1, p. 227 - 231

  摘要：

  DOI：

文献信息

• Chiral Softballs:  Synthesis and Molecular Recognition Properties
  作者：José M. Rivera、Tomás Martín、Julius Rebek

  DOI：10.1021/ja004080i

  日期：2001.6.1

  dimeric softball chiral although the monomer itself is achiral. The dimers represent capsules with dissymmetric cavities with volumes ranging from 190 to 390 A(3). The cavities are distorted spheres, and asymmetric guests, such as naturally occurring terpenes, generally prefer one enantiomer of the capsule to its mirror image. The selectivities are moderate (up to 4:1). The complexation studies show that

  对垒球的不同同源物进行了研究，以探索对映选择性封装的结构变体。尽管单体本身是非手性的，但单体亚基中的两个不同的间隔元件使二聚垒球具有手性。二聚体代表具有不对称腔的胶囊，体积范围为 190 到 390 A(3)。空腔是扭曲的球体，不对称的客体，如天然存在的萜烯，通常更喜欢胶囊的一种对映异构体而不是它的镜像。选择性适中（高达 4:1）。络合研究表明，宿主胶囊足够灵活，可以在客体周围舒适地安排自己，但仍保持足够的刚度，以受到手性客体占用的影响。
• A Columnar Cholesteric Liquid Crystal Based on Phthalocyanine Core
  作者：Iwhan Cho、Youngsoo Lim

  DOI：10.1246/cl.1987.2107

  日期：1987.11.5

  A new columnar cholesterogen based on the octasubstituted phthalocyanine(PcH2), (+)-2,3,9,10,16,17,23,24-octakis[4-(dodecyloxy)-2-oxa-pentyl ]-phthalocyanine (1), is described. The chiral PcH2 1 exhibited classical cholesteric textures in which the transition of platelet to fan-shaped texture was observed (K\xrightarrow23°CM\xrightarrow158°CI). This is the first instance of columnar cholesterogen observed

  基于八取代的酞菁(PcH2), (+)-2,3,9,10,16,17,23,24-octakis[4-(dodecyloxy)-2-oxa-pentyl]-phthalocyanine ( 1), 描述。手性 PcH2 1 表现出经典的胆甾型结构，其中观察到血小板向扇形结构的转变（K\xrightarrow23°CM\xrightarrow158°CI）。这是用盘状液晶系统观察到的柱状胆固醇的第一个实例。
• Novel two-fold-macrocycle-substituted phthalocyanines
  作者：Makbule Koçak、Ali I. Okur、Özer Bekaroglu

  DOI：10.1039/dt9940000323

  日期：——

  or Ni) substituted in peripheral positions with four 14-membered tetraaza macrocycles each attached to a 15-membered crown ether have been prepared in a multi-step reaction sequence. The N-tosylated derivatives are extensively soluble in apolar solvents and form adducts with alkali-metal cations. Detosylation of the macrocyclic aza groups provides donor sites for binding transition-metal ions (e.g.

  以多步反应顺序制备了在外围位置被四个14元四氮杂大环取代的新金属酞菁（M = Cu或Ni），每个大环连接到15元冠醚上。所述Ñ -tosylated衍生物在非极性溶剂和形成加合物与碱金属阳离子广泛可溶。大环氮杂基团的脱甲苯磺酸化为结合过渡金属离子（例如Ni II）提供了供体位点，从而导致了五核水溶性复合物。
• Synthesis, spectroscopy and electrochemistry of phthalocyanine derivatives functionalised with four and eight peripheral tetrathiafulvalene units
  作者：Changsheng Wang、Martin R. Bryce、Andrei S. Batsanov、Claire F. Stanley、Andrew Beeby、Judith A. K. Howard

  DOI：10.1039/a701703k

  日期：——

  Metal-free phthalocyanine derivatives 2 and 14 bearing eight and four peripheral tetrathiafulvalene (TTF) units, respectively, have been synthesised, and their solution electrochemistry and optical spectroscopy have been studied. The compounds display redox properties arising from the TTF and from the phthalocyanine groups. 1H NMR and UV–VIS spectroscopic studies in solution show that aggregation is strongly solvent dependent. Quenching of the fluorescence of the phthalocyanine core by the TTF units was observed. The X-ray crystal structure of 4,5-bis(hexylthio)-4′,5′-bis(hydroxymethyl)-TTF 11, which was synthesised during the course of this work, has been determined. The hydroxy groups of 11 engage in intermolecular (and interstack) hydrogen bonds. Computer modelling studies on phthalocyanine derivatives 2 and 14 are reported.

  无金属酞菁衍生物2和14分别带有八个和四个外围的四硫富瓦烯（TTF）单元，已被合成，并研究了它们的溶液电化学和光学光谱。这些化合物表现出源自TTF和酞菁基团的氧化还原特性。溶液中的1H核磁共振和紫外-可见光谱研究显示，聚集强烈依赖于溶剂。观察到TTF单元对酞菁核心的荧光淬灭效应。在此工作中合成的4,5-双(己硫基)-4',5'-双(羟甲基)-TTF 11的X射线晶体结构已被测定。11的羟基参与了分子间（及堆叠间）的氢键。报告了关于酞菁衍生物2和14的计算机模拟研究。
• The Synthesis and Reactivity of 5H-Cycloprop[f]isobenzofuran and Related Compounds. A Kinetic Probe for the Mills-Nixon Effect
  作者：IJ Anthony、D Wege

  DOI：10.1071/ch9961263

  日期：——

  5H-Cycloprop[f]isobenzofuran (6) and the sulfur analogue 5H-cyclopropa[f][2] benzothiophen (18) have been prepared by a sequence of reactions involving trapping of 1,2-dibromocyclopropene with 3,4-dimethylidenetetrahydrofuran and 3,4-dimethylidenetetrahydrothiophen followed by sequential dehydrogenation and di-dehydrobromination. Both cyclopropa -fused heterocycles, like their parents, have limited stability. Several other 5,6-methylene-bridged and 5,6-disubstituted isobenzofurans (32) have been generated and characterized as their adducts with dimethyl fumarate . Second-order rate constants for the reaction of dimethyl fumarate with isobenzofuran, 5H-cycloprop[f] isobenzofuran as well as the series of substituted derivatives have been measured. The reactivity span is only one order of magnitude suggesting that π-bond fixation (the Mills-Nixon effect) does not play a significant role in determining the reactivity of (6).

  5H- 环丙[f]异苯并呋喃（6）和硫类似物 5H- 环丙[f][2] 苯并噻吩（18）是通过一系列反应制备的，这些反应包括 1,2-二溴环丙烯与 3,4-二亚甲基四氢呋喃和 3,4-二亚甲基四氢噻吩的捕获反应，然后依次进行脱氢和二脱氢溴化反应。这两种环丙融合杂环与它们的母体一样，稳定性有限。其他几种 5,6-亚甲基桥式和 5,6-二取代异苯并呋喃（32）已经生成，并以它们与富马酸二甲酯的加合物进行了表征。测量了富马酸二甲酯与异苯并呋喃、5H-环丙[f]异苯并呋喃以及一系列取代衍生物反应的二阶速率常数。反应性跨度仅为一个数量级，这表明 π 键固定（米尔斯-尼克松效应）在决定 (6) 的反应性方面不起重要作用。