5-Bromo-2-fluorotoluene | 2050-16-0

• 物质功能分类: 有机原料 - 重氮、偶氮或氧化偶氮化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 5-Bromo-2-fluorotoluene
• 英文别名: 4-[(4-hydroxyphenyl)hydrazinylidene]cyclohexa-2,5-dien-1-one；(E)-4,4'-dihydroxyazobenzene；4,4'-dihydroxy-azobenzene；(E)-(4-(2,6-diisopropylphenyl)diazenyl)phenoll；(E)-4,4′-(diazene-1,2-diyl)diphenol；(E)-4,4'-(diazene-1,2-diyl)diphenol；4,4’-bis(hydroxyl)azobenzene；(E)-4,4-(diazene-1,2-diyl)diphenol
• CAS: 2050-16-0；51437-66-2
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: WKODVHZBYIBMOC-BUHFOSPRSA-N

物化性质

• 熔点：
  204 °C
• 沸点：
  449.7±30.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)
• 最大波长(λmax)：
  360nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

安全信息

• 海关编码：
  2927000090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-fluorotoluene 在 sodium hydroxide 、 potassium carbonate 、 lithium bromide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 120.0h， 生成 4,4'-bis<2-<2-<2-(2-tosyloxyethoxy)ethoxy>ethoxy>ethoxy>azobenzene
  参考文献：
  名称：

  Photoactive Azobenzene-Containing Supramolecular Complexes and Related Interlocked Molecular Compounds

  摘要：

  Two acyclic and three macrocyclic polyethers, three [2]catenanes, and one [2]rotaxane, each containing one 4,4'-azobiphenoxy unit, have been synthesized. In solution, the azobenzene-based acyclic polyethers are bound by cyclobis(paraquat-p-phenylene)-a tetracationic cyclophane-in their trans forms only. On irradiation (lambda = 360 nm) of an equimolar solution of the tetracationic cyclophane host and one of the guests containing a trans-4,4'-azobiphenoxy unit, the trans double bond isomerizes to its cis form and the supramolecular complex dissociates into its molecular components. The trans isomer of the guest and, as a result, the complex are reformed, either by irradiation (lambda = 440 nm) or by warming the solution in the dark. Variable temperature H-1 NMR spectroscopic investigations of the [2]catenanes and the [2]rotaxane revealed that, in all cases, the 4,4'-azobiphenoxy unit resides preferentially alongside the cavities of their tetracationic cyclophane components, which are occupied either by a 1,4-dioxybenzene or by a 1,5-dioxynaphthalene unit. In the acyclic and macrocyclic polyethers containing 1,4-dioxybenzene or 1,5-dioxynaphthalene chromophoric groups and a 4,4'-azobiphenoxy moiety, the fluorescence of the former units is quenched by the latter. Fluorescence quenching is accompanied by photosensitization of the isomerization. The rate of the energy-transfer process is different for trans and cis isomers. In the [2]rotaxane and the [2]catenanes, the photoisomerization is quenched to an extent that depends on the specific structure of the compound. Only in one of the three [2]catenanes and in the [2]rotaxane was an efficient photoisomerization (lambda=360 nm) from the trans to the cis isomer of the 4,4'-azobiphenoxy unit observed. Single crystal X-ray structural analysis of one of the [2]catenanes showed that, in the solid state, the 4,4'-azobiphenoxy unit in the macrocyclic polyether component also resides exclusively alongside. The cavity of the tetracationic cyclophane component of the [2]catenane is filled by a 1,5-dioxynaphthalene unit, and infinite donor-acceptor stacks between adjacent [2]catenanes are formed in the crystal. These supramolecular complexes and their mechanically interlocked molecular counterparts can be regarded as potential photoactive nanoscale devices.

  DOI：

  10.1002/(sici)1521-3765(19990301)5:3<860::aid-chem860>3.0.co;2-k
• 作为产物：
  描述：

  对氨基苯酚 在 双氧水 作用下， 反应 24.0h， 以70%的产率得到5-Bromo-2-fluorotoluene
  参考文献：
  名称：

  均相磺酸催化剂对苯胺的氧化二聚作用

  摘要：

  我们在本文中报道，使用过氧化氢作为清洁氧化剂，适当负载的全氟磺酸可以催化苯胺的氧化二聚作用。该反应不需要使用有机溶剂，并提供所需的偶氮苯和水作为产物，使废物的形成最小化。不含金属的固体催化剂对反应显示出显着的活性和选择性，这在非常温和的条件下发生，并且具有宽泛的官能团耐受性。

  DOI：

  10.1039/c7gc03060f

文献信息

• [EN] ENCAPSULATES<br/>[FR] PRODUITS ENCAPSULÉS
  申请人：PROCTER & GAMBLE

  公开号：WO2013022949A1

  公开（公告）日：2013-02-14

  The present application relates to encapsulates, compositions, products comprising such encapsulates, and processes for making and using such encapsulates. Such encapsulates comprise a core comprising a perfume and a shell that encapsulates said core, such encapsulates may optionally comprise a parametric balancing agent, such shell comprising one or more azobenzene moieties.

  本申请涉及封装体、组合物、包含这种封装体的产品，以及制备和使用这种封装体的方法。这种封装体包括一个包含香水的核心和封装该核心的壳，这种封装体可以选择性地包含一个参数平衡剂，该壳包括一个或多个偶氮苯基团。
• Cage Encapsulated Gold Nanoparticles as Heterogeneous Photocatalyst for Facile and Selective Reduction of Nitroarenes to Azo Compounds
  作者：Bijnaneswar Mondal、Partha Sarathi Mukherjee

  DOI：10.1021/jacs.8b07767

  日期：2018.10.3

  fine-dispersed cage anchored AuNPs (Au@OC1R) have been finally used as potential heterogeneous photocatalyst for very facile and selective conversion of nitroarenes to respective azo compounds at ambient temperature in just 2 h reaction time. Exceptional chemical stability and reusability without any agglomeration of AuNPs even after several cycles of use are the potential features of this material. The composite

  离散的纳米级有机笼 (OC1R) 由基于吩噻嗪的三醛通过动态亚胺键形成和还原胺化处理与手性 1,2-环己二胺结构单元处理合成。笼状化合物已通过几种光谱方法进行表征，这些方法主张OC1R具有通过[2 + 3]自组装亚胺缩合然后亚胺还原形成的三棱柱形状。这种新设计的笼子具有芳香壁和多孔内部，装饰有两个环状硫醚和三个邻二胺部分，适合结合金离子以设计超细金纳米粒子 (AuNPs) 的受控成核和稳定化。笼子的功能化受限口袋已用于通过封装 Au(III) 离子来控制合成具有窄尺寸分布的 AuNP。电感耦合等离子体质谱 (ICP-MS) 分析表明，复合 Au@OC1R 具有非常高的金负载量（~68 wt%）。不同的是，在没有笼子的情况下金盐的还原产生无结构的附聚物。精细分散的笼状锚定金纳米粒子（Au@OC1R）最终被用作潜在的多相光催化剂，用于在环境温度下在仅 2 小时的反应时间内非常容易和选择性地将硝
• Monodispersive Unsymmetrical Tetramers Exhibiting a Columnar Phase
  作者：C. V. Yelamaggad、S. Anitha Nagamani、Uma S. Hiremath、D. S. Shankar Rao、S. Krishna Prasad

  DOI：10.1080/714965611

  日期：2003.1

  fluidity, viscosity etc. associated with those of low molar mass liquid crystals. The synthesis and evaluation of mesomorphic behavior of two novel monodispersive unsymmetrical tetramesogens have been presented here in detail. The molecular design of these tetramesogens incorporates the cholesteryl ester (as a chiral entity), biphenyl (as a supportive entity for mesomorphism), azobenzene (as a photoactive

  通过柔性间隔物（或多个间隔物）轴向连接两个或多个介晶段而形成的低聚液晶，从基础研究和实际应用的角度来看，似乎都是有趣的材料，因为它们的多功能特性和性质类似于那些聚合物，同时保持与低摩尔质量液晶相关的流动性、粘度等。此处详细介绍了两种新型单分散不对称四晶胞的介晶行为的合成和评估。这些四甲基原的分子设计包含胆固醇酯（作为手性实体）、联苯（作为介晶的支持实体）、偶氮苯（作为光敏介晶）、和 tolan（作为半圆盘）段通过偶-偶-奇和奇-偶-奇亚烷基间隔物相互连接。目标液晶四聚体已通过采用方便的合成策略实现，包括制备两个重要的不对称二聚体，最后将它们缩合。所有中间体和不对称四聚体的分子结构已通过光谱分析表征。两种不对称四聚体的介晶性质已通过光学显微、量热和 X 射线衍射研究进行评估。我们的研究表明，两种低聚物都显示出相同的中间相。虽然 X 射线研究表明中间相的结构类似于矩形柱状 (Col r ) 中
• Sweet switches: azobenzene glycoconjugates synthesized by click chemistry
  作者：Vijayanand Chandrasekaran、Thisbe K. Lindhorst

  DOI：10.1039/c2cc33542e

  日期：——

  Azobenzene glycoconjugates can be switched between two isomeric states, E and Z, to change the spatial orientation of the conjugated carbohydrate ligands. Mono-, di- and trivalent azobenzene glycoconjugates were synthesized using click chemistry and their photochromic properties determined. Multivalency effects were observed in photoisomerisation.

  偶氮苯糖缀合物可以在E和Z两种异构态之间转换，从而改变所连接的碳水化合物配体的空间取向。单、二和三价偶氮苯糖缀合物通过点击化学合成，并测定了它们的光致变色性质。观察到了多价效应在光异构化过程中的作用。
• A smart approach to achieve an exceptionally high loading of metal nanoparticles supported by functionalized extended frameworks for efficient catalysis
  作者：Bappaditya Gole、Udishnu Sanyal、Partha Sarathi Mukherjee

  DOI：10.1039/c4cc09228g

  日期：——

  Pores of MOFs were decorated with terminal alkyne to achieve very high loading of gold nanoparticles for efficient catalytic reduction of aromatic nitro-compounds.

  金属有机框架(MOFs)的孔隙被端炔修饰，以实现金纳米粒子的非常高的负载量，用于有效催化还原芳香硝基化合物。