2,6-二溴-1,4-二甲基苯 | 66788-13-4

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 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: 2,6-二溴-1,4-二甲基苯
• 中文别名: 1,3-二溴-2,5-二甲苯
• 英文名称: 2,6-dibromo-1,4-dimethylbenzene
• 英文别名: 2,6-dibromo-p-xylene；1,3-dibromo-2,5-dimethyl-benzene；1,3-Dibrom-2,5-dimethyl-benzol；2,6-Dibrom-p-xylol；1,3-dibromo-2,5-dimethylbenzene
• CAS: 66788-13-4
• 化学式: C₈H₈Br₂
• 分子量: 263.96
• InChiKey: IWZNGNLJRXZVSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  10
• 可旋转键数：
  0
• 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

• 海关编码：
  2903999090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  2,6-二溴-1,4-二甲基苯 在 二异丁基氢化铝 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.0h， 生成 3-bromo-2,5-dimethylbenzaldehyde
  参考文献：
  名称：

  Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes

  摘要：

  8,16-Dimethyl-, 5,8,13,16-tetramethyl, and 4,6,8,12,14,16-hexamethyl[2,2]metacyclophanene have been synthesized from the corresponding methyl-substituted 3-thia[3.2]metacyclophane precursors via a Wittig rearrangement-Hofmann elimination procedure. Simple addition of bromine or similar electrophiles to the bridge double bond of the cyclophane monoenes did not occur; rather, the methyl-substituted dihydropyrenes were formed. However, mono- and bis-tricarbonylchromium and monocyclopentadienyliron complexes were obtained using ligand-exchange reactions. Addition of bromine to the cyclophane bridge double bond of the iron complex did occur, but unusually slowly. Surprisingly, debromination rather than dehydrobromination occurred when the dibromo addition product was treated with a variety of bases. Photoisomerization of the monoenes and nucleophilic substitution of the metal complexes was also investigated. The geometries of the monoenes and their complexes were compared to the cyclophanes and the cyclophanedienes and to the monothia- and dithiacyclophanes, by comparison of X-ray and calculated structural data and NMR spectroscopic data. Introduction of double bonds into the cyclophane bridges causes the cyclophane step to be less steep but increases distortion of the internal atoms out of the plane of the benzene rings. Making the bridges nonidentical also causes a sideways twist of the step.

  DOI：

  10.1021/jo990721k
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 2,6-二溴-1,4-二甲基苯
  参考文献：
  名称：

  Blanksma, Chemisches Zentralblatt, 1913, vol. 84, # I, p. 1108

  摘要：

  DOI：

文献信息

• Improved process for side-chain bromination of alkyl-benzenes
  申请人：Helm AG

  公开号：EP1705168A1

  公开（公告）日：2006-09-27

  A process for the side-chain bromination of alkylbenzenes according to Formula (I) wherein R1 is C1-C6-alkyl; R2 is H or C1-C6-alkyl which can be unsubstituted or substituted by one or more cyano groups; R3 is H or C1-C6-alkyl which can be unsubstituted or substituted by one or more cyano groups; comprising the steps of (1) dissolving the compound of Formula (I) in a solvent which is a nonaromatic non-halogenated hydrocarbon which can be substituted by one or more cyano groups; (2) adding a bromination agent selected from the group consisting of Br2 and N-bromoimides to the solution; and optionally (3) agitating the mixture at a temperature within the range of from room temperature to reflux temperature.

  一种用于侧链溴化烷基苯的工艺，根据式（I）其中R1为C1-C6烷基；R2为H或C1-C6烷基，可以未取代或取代一个或多个氰基；R3为H或C1-C6烷基，可以未取代或取代一个或多个氰基；包括以下步骤：（1）将式（I）化合物溶解在一种溶剂中，该溶剂为一种非芳香族非卤代烃，可以取代一个或多个氰基；（2）向溶液中加入从Br2和N-溴代亚胺中选择的溴化试剂；以及可选的（3）在从室温到沸点温度范围内的温度下搅拌混合物。
• Process for side-chain bromination of alkylbenzenes
  申请人：Schulze Michael

  公开号：US20060217569A1

  公开（公告）日：2006-09-28

  A process for the side-chain bromination of alkylbenzenes according to Formula (I) wherein R 1 is C 1 -C 6 -alkyl; R 2 is H or C 1 -C 6 -alkyl which can be unsubstituted or substituted by one or more cyano groups; R 3 is H or C 1 -C 6 -alkyl which can be unsubstituted or substituted by one or more cyano groups; comprising the steps of (1) dissolving the compound of Formula (I) in a solvent which is a non-aromatic non-halogenated hydrocarbon which can be substituted by one or more cyano groups; (2) adding a bromination agent selected from the group consisting of Br 2 and N-bromoimides to the solution; and optionally (3) agitating the mixture at a temperature within the range of from room temperature to reflux temperature.

  一种用于侧链溴化烷基苯的制备的方法，根据式（I）中R1为C1-C6-烷基；R2为H或C1-C6-烷基，可以是未取代或取代一个或多个氰基；R3为H或C1-C6-烷基，可以是未取代或取代一个或多个氰基；包括以下步骤：（1）将式（I）化合物溶解在一种溶剂中，所述溶剂为一种非芳香族非卤代烃，可以被一个或多个氰基取代；（2）向溶液中加入从Br2和N-溴代亚胺中选择的溴化剂；可选地（3）在室温至沸点温度范围内搅拌混合物。
• 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。
• Hole Transfer Processes in <i>meta-</i> and <i>para-</i>Conjugated Mixed Valence Compounds: Unforeseen Effects of Bridge Substituents and Solvent Dynamics
  作者：Julian Schäfer、Marco Holzapfel、Boryana Mladenova、Daniel Kattnig、Ivo Krummenacher、Holger Braunschweig、Günter Grampp、Christoph Lambert

  DOI：10.1021/jacs.7b01650

  日期：2017.5.3

  accelerate the hole transfer (HT) between redox sites attached in para- or in meta-positions to a central benzene bridge, we investigated three series of mixed valence compounds based on triarylamine redox centers that are connected to a benzene bridge via alkyne spacers at para- and meta-positions. The electron density at the bridge was tuned by substituents with different electron donating or accepting

  为了解决供体取代基是否可用于加速以对位或间位连接到中心苯桥的氧化还原位点之间的空穴转移 (HT) 的问题，我们研究了基于三芳胺氧化还原中心的三个系列混合价化合物通过对位和间位的炔烃间隔基连接到苯桥上。桥上的电子密度由具有不同电子供体或接受特性的取代基调节。通过分析光谱和 DFT 计算，我们表明 HT 性质与其中一个元系列的桥取代基无关，而供体取代基可以强烈降低对系列情况下的内在势垒。形成鲜明的对比，温度依赖性 ESR 测量表明，在对位情况下，强供体取代基的表观势垒和 HT 速率均显着增加。这是由于 HT 机制从过渡态理论描述的机制到溶剂动力学控制的机制发生了前所未有的取代基依赖性变化。对于具有缓慢纵向弛豫的溶剂（PhNO2、oDCB），这通过介电弛豫过程增加了对本征势垒的额外贡献。在分子轨道系数大的位置将供体取代基连接到桥上可加速间位共轭化合物的 HT 速率，就像对系列一样。这种效果表明，
• 含硼和氮的稠合芳香族衍生物及其的制备方法和有机电致发光器件
  申请人：吉林奥来德光电材料股份有限公司

  公开号：CN113024587A

  公开（公告）日：2021-06-25

  本发明涉及有机光电功能材料技术领域，具体而言，涉及含硼和氮的稠合芳香族衍生物及其的制备方法和有机电致发光器件。该含硼和氮的稠合芳香族衍生物选自下述式1‑1或式1‑2所示的化合物中的任意一种，其中，环A和环C各自独立地选自经取代或未经取代的芳基环、经取代或未经取代的杂芳基环和经取代或未经取代的脂肪族环形成的官能团组中的任意一种；X各自独立地选自NR9、CR10R11、O、S、Se和SiR12R13形成的官能团组中的任意一种。该含硼和氮的稠合芳香族衍生物具有更低地驱动电压，发光效率更高，寿命更高，且滚降更低的特点。