N-(3-tolyl)-N-(4-tolyl)aniline | 1403782-98-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(3-tolyl)-N-(4-tolyl)aniline
• 英文别名: 3,4'-Dimethyltriphenylamine；3-methyl-N-(4-methylphenyl)-N-phenylaniline
• CAS: 1403782-98-8
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: XZEGQPSNQVPGPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  phenyl-meta-tolyltrimethylsilylamine 、 对溴甲苯 在 cesium fluoride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 0.5h， 以90%的产率得到N-(3-tolyl)-N-(4-tolyl)aniline
  参考文献：
  名称：

  Silicon-based C–N Cross-coupling Reaction

  摘要：

  研究发现，在 1,3-二甲基-2-咪唑烷酮（DMI）中存在氟活化剂的情况下，N-三甲基硅胺与芳基溴化物和氯化物的钯催化 C-N 键形成交叉偶联反应可以进行，并以极高的产率得到三芳基胺。在该反应中使用芳基溴和双(硅烷基)胺时，可获得高产率的双 C-N 键形成产物。本反应被成功应用于 C-N 键形成聚合反应。

  DOI：

  10.1246/cl.131075

文献信息

• Catalytic Carbon–Nitrogen Bond-Forming Cross-Coupling Using <i>N</i>-Trimethylsilylamines
  作者：Yasunori Minami、Takeshi Komiyama、Kenta Shimizu、Tamejiro Hiyama、Osamu Goto、Hideyuki Ikehira

  DOI：10.1246/bcsj.20150179

  日期：2015.10.15

  Carbon–nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C–N coupling to give multiply C–N coupled products in high yields. The novel C–N cross-coupling reaction was successfully applied to C–N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.

  在钯催化剂和氟化物活化剂的帮助下，卤代烯烃与 N-三甲基硅烷基（TMS）取代的仲芳基和伯芳基胺发生了碳-氮键形成交叉偶联反应。各种 TMS-N（芳基）2、TMS-NH（芳基）和 TMS-N（烷基）2 在高产率下反应生成相应的偶联产物。N,N-(TMS)2-苯胺和 N,N′-Ph2-N,N′-(TMS)2-对苯二胺等多重 TMS-amine 亲核物也参与了这种 C-N 偶联反应，从而以高产率得到多重 C-N 偶联产物。新型 C-N 交叉偶联反应被成功应用于 C-N 键形成的聚合反应。对溴甲苯与 N-TMS 取代的伯胺和仲胺发生交叉偶联的相对速率表明，N-TMS-二苯胺的反应速度快于 N-TMS-N-methylaniline 或 N-TMS-aniline，而 N-TMS-morpholine 的反应速度最低，这表明氮亲核体的低碱性是顺利偶联的关键。
• Perylene Charge-Transport Materials, Methods of Fabrication Thereof, and Methods of Use Thereof
  申请人：Marder Seth

  公开号：US20080223444A1

  公开（公告）日：2008-09-18

  Briefly described, embodiments of this disclosure include perylenetetracarboxylic diimide charge-transport materials, methods of forming perylenetetracarboxylic diimide charge-transport materials, and methods of using the perylenetetracarboxylic diimide charge-transport materials.

  简单描述，本公开的实施例包括苝四羧二酰亚胺电荷传输材料、形成苝四羧二酰亚胺电荷传输材料的方法，以及使用苝四羧二酰亚胺电荷传输材料的方法。
• Organic electroluminescence device
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：EP2270117A2

  公开（公告）日：2011-01-05

  The invention is an organic electroluminescent device that comprises organic compound layer(s) including at least one organic emitting layer sandwiched between a pair of electrodes, wherein at least one organic compound layer is formed from an organic compound material having an impurity concentration of lower than 1000 ppm. The device has the advantages of applicability to lightweight, thin and low-voltage driving displays, good luminescent capacity attenuating little even in long-term driving operation, and good durability.

  本发明是一种有机电致发光器件，包括夹在一对电极之间的至少一个有机发光层的有机化合物层，其中至少一个有机化合物层由杂质浓度低于 1000 ppm 的有机化合物材料形成。该器件具有适用于轻型、薄型和低电压驱动显示器、即使在长期驱动操作中发光能力衰减小、耐用性好等优点。
• ORGANIC LIGHT-EMITTING ELEMENT
  申请人：Kyushu University, National University Corporation

  公开号：EP3171421A1

  公开（公告）日：2017-05-24

  An organic light-emitting device containing a host material, a delayed fluorescent material and a light-emitting material satisfying ES1(H)>ES1(F)>ES1(D) has a high light emission efficiency. ES1(H) represents a lowest excited singlet energy level of the host material, ES1(F) represents a lowest excited singlet energy level of the delayed fluorescent material, and ES1(D) represents a lowest excited singlet energy level of the light-emitting material.

  一种含有宿主材料、延迟荧光材料和发光材料的有机发光器件具有很高的光发射效率，该器件满足ES1(H)>ES1(F)>ES1(D)的要求。ES1(H)代表主材料的最低激发单线能级，ES1(F)代表延迟荧光材料的最低激发单线能级，ES1(D)代表发光材料的最低激发单线能级。
• PHOTOELECTRIC CONVERSION ELEMENT, DYE-SENSITIZED SOLAR CELL, METAL COMPLEX DYE, DYE SOLUTION AND OXIDE SEMICONDUCTOR ELECTRODE
  申请人：Fujifilm Corporation

  公开号：EP3309804A1

  公开（公告）日：2018-04-18

  Provided are a photoelectric conversion element and a dye-sensitized solar cell, each including a photoconductor layer having semiconductor fine particles carrying a metal complex dye represented by Formula (1); and a metal complex dye, a dye solution, and an oxide semiconductor electrode. In the formula, M represents a metal ion. Ar11 to Ar14 each represent a phenyl group, or a phenyl group having an alkyl group or the like, and Ar11 and Ar12 each represent different phenyl groups. R11 to R14 each represent an alkyl group or the like. n11 and n12 each represent an integer of 0 to 3. n13 and n14 each represent an integer of 0 to 4. M1 and M2 each represent a proton or a cation, and L3 and L4 each represent a monodentate ligand.

  本发明提供了一种光电转换元件和染料敏化太阳能电池，每种元件和电池都包括一个光电导体层，该光电导体层具有携带由式（1）表示的金属络合染料的半导体微粒；以及金属络合染料、染料溶液和氧化物半导体电极。 式中，M 代表金属离子。Ar11 至 Ar14 分别代表苯基，或具有烷基或类似基团的苯基，Ar11 和 Ar12 分别代表不同的苯基。n11 和 n12 分别代表 0 至 3 的整数，n13 和 n14 分别代表 0 至 4 的整数，M1 和 M2 分别代表质子或阳离子，L3 和 L4 分别代表单齿配体。