2-甲基-N-间甲苯基苯胺 | 34801-11-1

• 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-甲基-N-间甲苯基苯胺
• 英文名称: 2-methyl-N-(m-tolyl)aniline
• 英文别名: 2-Methyl-N-(3-methylphenyl)aniline
• CAS: 34801-11-1
• 化学式: C₁₄H₁₅N
• 分子量: 197.28
• InChiKey: BAWMCGDLFJGWSX-UHFFFAOYSA-N

物化性质

• 沸点：
  187 °C/22 mmHg

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  适宜在室温且干燥的环境中存放。

反应信息

• 作为反应物：
  描述：

  2-甲基-N-间甲苯基苯胺 以80%的产率得到
  参考文献：
  名称：

  GANSSER C.; VILAR A.; RUMPF P., EUR. J. MED. CHEM., 1977,

  摘要：

  DOI：
• 作为产物：
  描述：

  N-m-tolyl-N-o-tolyl-benzamide 在 氢氧化钾 作用下， 生成 2-甲基-N-间甲苯基苯胺
  参考文献：
  名称：

  Gibson; Johnson, Journal of the Chemical Society, 1929, p. 2748

  摘要：

  DOI：

文献信息

• Application of a 2-aryl indenylphosphine ligand in the Buchwald–Hartwig cross-coupling reactions of aryl and heteroaryl chlorides under the solvent-free and aqueous conditions
  作者：Yan Liu、Jia Yuan、Zi-Fei Wang、Si-Hao Zeng、Meng-Yue Gao、Mei-Lin Ruan、Jian Chen、Guang-Ao Yu

  DOI：10.1039/c7ob01199g

  日期：——

  An efficient solvent-free protocol for the Buchwald–Hartwig cross-coupling reaction of aryl and heteroaryl chlorides with primary and secondary amines using the Pd(dba)2/ligand 1 catalytic system has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

  使用Pd（dba）2 /配体1催化系统开发了一种有效的无溶剂方案，用于芳基和杂芳基氯化物与伯胺和仲胺的布赫瓦尔德-哈特维格交叉偶联反应。值得注意的是，催化体系还可以在水性条件下有效地催化反应。
• Smiles rearrangement for the synthesis of diarylamines
  作者：Xiao Tian、Ren-Min Wu、Gang Liu、Zhu-Bo Li、He-Lin Wei、Hao Yang、Dong-Soo Shin、Li-Ying Wang、Hua Zuo

  DOI：10.3998/ark.5550190.0012.a10

  日期：——

  A protocol for the one-pot synthesis of diarylamines via Smiles rearrangement under microwave irradiation has been developed. Various diarylamines were effectively synthesized starting from readily available substituted phenols, arylamines and chloroacetyl chloride in moderate to good yields (58–92%).

  已经开发了一种在微波辐射下通过 Smiles 重排一锅合成二芳胺的协议。从容易获得的取代酚、芳胺和氯乙酰氯开始，以中等至良好的产率（58-92%）有效合成了各种二芳胺。
• Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine
  作者：Edson Barrera、R. Israel Hernández‐Benitez、Carlos A. González‐González、Carlos H. Escalante、Aydeé Fuentes‐Benítes、Carlos González‐Romero、Elvia Becerra‐Martínez、Francisco Delgado、Joaquín Tamariz

  DOI：10.1002/ejoc.202200364

  日期：2022.6.27

  A versatile and efficient methodology for the synthesis of 1-methyl and 1,4-dimethyl 3-formylcarbazoles is described. Microwave-promoted one-pot cascade reactions of 4-oxazolin-2-ones afforded methylated diarylamines, which were cyclized into a series of carbazoles, including the formal total synthesis of the naturally occurring pyrido[4,3-b]carbazole alkaloids ellipticine and olivacine.

  描述了一种用于合成 1-甲基和 1,4-二甲基 3-甲酰基咔唑的通用且有效的方法。微波促进 4-恶唑啉-2-酮的一锅级联反应得到甲基化二芳基胺，将其环化成一系列咔唑，包括天然存在的吡啶并[4,3- b ]咔唑生物碱玫瑰树碱的正式全合成和橄榄素。
• Pyrrole-2-carboxylic Acid as a Ligand for the Cu-Catalyzed Reactions of Primary Anilines with Aryl Halides
  作者：Ryan A. Altman、Kevin W. Anderson、Stephen L. Buchwald

  DOI：10.1021/jo8008676

  日期：2008.7.1

  Pyrrole 2-carboxylic acid (L5) was found to be an effective ligand for the Cu-catalyzed monoarylation of anilines with aryl iodides and bromides. Under the reported conditions (10% CuI/20% L5/DMSO/K(3)PO(4)/80-100 degrees C/20-24 h), a variety of useful functional groups were tolerated, and moderate to good yields of the diaryl amine products were obtained.
• Aliphatic CH, N-insertion versus aromatic N-substitution in the reaction of arylnitrenium-boron trifluoride complexes with methylated benzenes
  作者：Piero Spagnolo、Paolo Zanirato

  DOI：10.1016/s0040-4039(00)95887-8

  日期：1987.1