2,4-dimethylphenylimidazole | 25364-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-dimethylphenylimidazole
• 英文别名: 1-(2,4-dimethylphenyl)-1H-imidazol；1-(2,4-dimethylphenyl)-1H-imidazole；1-(2,4-dimethylphenyl)imidazole
• CAS: 25364-50-5
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: QHZMTARJNZPNHE-UHFFFAOYSA-N

物化性质

• 沸点：
  305.8±31.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-dimethylphenylimidazole 以 二甲基亚砜 、 甲苯 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  访问螯合扩展接头双（NHC）钯（II）配合物：立体触发的发散反应途径

  摘要：

  我们已经证明了乙烯连接的双（N-杂环卡宾）（bis（NHC））物种的N-取代空间位阻对其通过Pd（OAc）2辅助脱金属形成的机理具有深远的影响。乙烯连接的双（NHC）配体具有N -2,4-Me 2 C 6 H 3取代基但形成带有N -2,6-咪唑侧基的单（NHC）时，其结合方式为螯合。i Pr 2 C 6 H 3。安N如在DFT计算中所预测的，在两个上述取代基之间具有空间本体中间体的-间甲氧基-取代的双（NHC）产生两种螯合的纯正/正常和杂配的正常/异常双（NHC）复合物的混合物。有趣的是，后者被认为易于还原消除，提供了新型的三环单齿NHC配体。

  DOI：

  10.1021/acs.organomet.9b00356
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硝酸 作用下， 生成 2,4-dimethylphenylimidazole
  参考文献：
  名称：

  Marckwald, Chemische Berichte, 1892, vol. 25, p. 2362

  摘要：

  DOI：

文献信息

• Salts Comprising Aryl-Alkyl-Substituted Imidazolium and Triazolium Cations and the Use Thereof
  申请人：Strassner Thomas

  公开号：US20110105761A1

  公开（公告）日：2011-05-05

  The present invention relates to salts comprising novel aryl-alkyl-substituted imidazolium and triazolium cations and arbitrary anions. The invention further relates to methods for the chemical conversion and separation of substances, comprising the salts according to the invention as solvents, solvent additives, or extraction means, and to the use of the salts according to the invention, for example as solvents or solvent additives in chemical reactions, as extracting agents for the separation of substances, or for storing hydrogen. According to the invention, the object is achieved by salts of the general formula (I), where X— is an anion, Y1 and Y2 are CH, or Y1 is CH and Y2 is N, or Y1 is N and Y2 is CH, n is a number from 1 up to an including 18, Q is selected from —CH3, —OH, —ORx, —S03H, —S03Rx, —COOH, —COORx, —CORx, NH2, —NHRx, —N(Rx)2, and —CH(Rx)2, Z is H or Rx, R1, R2, R3, R4 and R5 independently from each other are —H, -halogen, —N02, —NH2, —NHRx, —N(Rx)2, —Rx, —COORx or —ORx, where Rx is an optionally substituted and/or branched C1 to C18-alkyl group, excluding compounds of the general formula (I), where Y1 and Y2 are CH and R1, R2, R3, R4 and R5 are H, excluding compounds of the general formula (I), where Y1 and Y2 are CH, R1=R3=R5=CH3 is true, n=1, 2, 6 and Q=CH3 is true, excluding compounds of the general formula (I), where Y1 is CH and Y2 is N, R1, R2, R3, R4 and R5 are H, n=1 is true, and Q=CH3 is true, and excluding compounds of the general formula (I), where Y1 and Y2 are CH, R1, R2, R4, R5=H is true, R3=ORx is true, and Rx is a hydrocarbon having 3 or 12 carbon atoms.

  本发明涉及包含新颖芳基-烷基取代咪唑和三唑阳离子以及任意阴离子的盐。该发明还涉及一种化学转化和物质分离的方法，包括作为溶剂、溶剂添加剂或萃取剂的本发明盐，并且涉及使用本发明的盐，例如作为化学反应中的溶剂或溶剂添加剂，作为物质分离的萃取剂，或用于储存氢。根据本发明，通过一般式(I)的盐实现了该目的，其中X—是一个阴离子，Y1和Y2为CH，或者Y1为CH且Y2为N，或者Y1为N且Y2为CH，n是从1到18的数字，Q从—CH3、—OH、—ORx、—S03H、—S03Rx、—COOH、—COORx、—CORx、NH2、—NHRx、—N(Rx)2和—CH(Rx)2中选择，Z为H或Rx，R1、R2、R3、R4和R5彼此独立地为—H、-卤素、—N02、—NH2、—NHRx、—N(Rx)2、—Rx、—COORx或—ORx，其中Rx是一个可选择地取代和/或支链的C1到C18烷基基团，不包括一般式(I)的化合物，其中Y1和Y2为CH且R1、R2、R3、R4和R5为H，不包括一般式(I)的化合物，其中Y1和Y2为CH，R1=R3=R5=CH3为真，n=1、2、6且Q=CH3为真，不包括一般式(I)的化合物，其中Y1为CH且Y2为N，R1、R2、R3、R4和R5为H，n=1为真，且Q=CH3为真，不包括一般式(I)的化合物，其中Y1和Y2为CH，R1、R2、R4、R5=H为真，R3=ORx为真，且Rx是一个具有3或12个碳原子的碳氢化合物。
• Synthesis and Physical Properties of Tunable Aryl Alkyl Ionic Liquids (TAAILs)
  作者：Swantje Lerch、Thomas Strassner

  DOI：10.1002/chem.202102545

  日期：2021.11.5

  Tunable aryl alkyl ionic liquids (TAAILs) based on the imidazolium cation were first reported in 2009. Since then, a series of TAAILs with different properties due to the electron-donating or -withdrawing effect of the substituents at the aryl ring has been developed. Herein, a wide variety of those ionic liquids (ILs) is presented in terms of their cation structure. The authors synthesized ILs containing

  2009 年首次报道了基于咪唑鎓阳离子的可调谐芳烷基离子液体 (TAAIL)。此后，由于芳环上取代基的给电子或吸电子作用，开发了一系列具有不同性质的 TAAIL。在本文中，根据它们的阳离子结构呈现了多种这些离子液体 (IL)。作者合成了含有溴化物或双（三氟甲烷）磺酰亚胺阴离子和 1-芳基-3-烷基咪唑鎓阳离子的离子液体，在苯环的邻位和/或对位具有各种取代基以及不同长度的烷基链，从丁基到十二烷基不等. 根据它们的结构报告了这些 IL 的物理性质（熔点、热分解、粘度、电化学窗口）的差异。
• Cobalt-Catalyzed Hydroarylations and Hydroaminations of Alkenes in Tunable Aryl Alkyl Ionic Liquids
  作者：Felix Schroeter、Swantje Lerch、Maria Kaliner、Thomas Strassner

  DOI：10.1021/acs.orglett.8b02688

  日期：2018.10.5

  Tunable aryl alkyl ionic liquids (TAAILs) are a promising class of imidazolium- or triazolium-based ionic liquids. Contrary to “standard” all-alkyl ionic liquids, these carry an aryl ring together with a linear or branched alkyl chain. Their application in the cobalt-catalyzed hydroarylation/hydroamination of alkenes and anilines is presented. The catalytic system is tolerant toward air and is scalable

  可调节的芳基烷基离子液体（TAAIL）是一类有前途的基于咪唑或三唑鎓的离子液体。与“标准”全烷基离子液体相反，这些液体带有一个芳基环以及一个直链或支链烷基链。介绍了它们在钴催化的烯烃和苯胺的加氢芳基化/加氢胺化中的应用。催化系统对空气具有耐受性，并且具有可扩展性和可重复使用性。它已成功地用于合成与药理学相关的伯至叔芳基胺。
• Efficient Copper-Catalyzed N-Arylation of Amides and Imidazoles with Aryl Iodides
  作者：Tharmalingam Punniyamurthy、Md. Ali、Prasenjit Saha

  DOI：10.1055/s-0029-1218643

  日期：2010.3

  The C-N cross-coupling of amides and imidazoles with aryl iodides is described using CuI in tetrabutylammonium bromide (TBAB) under ligand-free conditions. The reaction is simple, general, and efficient affording the C-N cross-coupled products in shorter time and in high yield. N-arylation - amides - imidazoles - copper iodide - TBAB

  描述了在无配体条件下在四丁基溴化铵（TBAB）中使用CuI将酰胺和咪唑与芳基碘化物进行CN交叉偶联。该反应是简单，通用和有效的，以较短的时间和高的产率提供了CN交叉偶联的产物。 N-芳基化-酰胺-咪唑-碘化铜-TBAB
• Process for preparing aromatic amines in the presence of palladaphosphacyclobutane catalysts
  申请人：Clariant GmbH

  公开号：US06353136B1

  公开（公告）日：2002-03-05

  Aromatic amines of the formula (I) Ar—[NR6R7]n  (I) are prepared by reacting a haloaromatic of the formula (II) Ar—Hal  (II) with an amine of the formula (III) R6R7NH  (III) in the presence of a palladaphosphacyclobutane and a base and in the presence or absence of an ionic halide in a solvent at temperatures of from 20 to 200° C.

  公式（I）Ar—[NR6R7]n的芳香胺通过在20至200°C温度下，在溶剂中，在存在或不存在离子卤化物的情况下，通过将公式（II）Ar—Hal的卤代芳烃与公式（III）R6R7NH的胺在存在钯磷环丁烷和碱的情况下反应制备。