6-methyl-N-phenylbenzene-1,3-diamine | 41131-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methyl-N-phenylbenzene-1,3-diamine
• 英文别名: 5-Amino-2-methyl-diphenylamin；4-methyl-N³-phenyl-m-phenylenediamine；4-Amino-2-anilino-toluol；4-Methyl-N³-phenyl-m-phenylendiamin；4-methyl-3-N-phenylbenzene-1,3-diamine
• CAS: 41131-23-1
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: PTUSJMIOOGSMNE-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C
• 沸点：
  196-199 °C(Press: 4 Torr)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-N-phenylbenzene-1,3-diamine 、 4-[(4-甲基哌嗪-1-基)甲基]苯甲酸甲酯 在 二(三甲基铝)-1,4-二氮杂二环[2.2.2]辛烷加合物 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到N-(4-methyl-3-(phenylamino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide
  参考文献：
  名称：

  Investigating Scale-Up and Further Applications of DABAL-Me₃ Promoted Amide Synthesis

  摘要：

  Methods for the batch scale up of DABAL-Me-3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me-3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h(-1)). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me-3, resulting in the clean formation of free amidines (16 examples) and amidrazones.

  DOI：

  10.1021/acs.oprd.5b00101
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 盐酸 、 异戊醇 、 铜 、 potassium carbonate 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 6-methyl-N-phenylbenzene-1,3-diamine
  参考文献：
  名称：

  Weiss; Katz, Monatshefte fur Chemie, 1928, vol. 50, p. 227

  摘要：

  DOI：

文献信息

• Weiss; Katz, Monatshefte fur Chemie, 1928, vol. 50, p. 227
  作者：Weiss、Katz

  DOI：——

  日期：——
• Investigating Scale-Up and Further Applications of DABAL-Me₃ Promoted Amide Synthesis
  作者：Darren S. Lee、Zacharias Amara、Martyn Poliakoff、Thomas Harman、Gary Reid、Barrie Rhodes、Steve Brough、Thomas McInally、Simon Woodward

  DOI：10.1021/acs.oprd.5b00101

  日期：2015.7.17

  Methods for the batch scale up of DABAL-Me-3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me-3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h(-1)). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me-3, resulting in the clean formation of free amidines (16 examples) and amidrazones.