2,4,6-tribromo-N,N-dimethylaniline | 63812-39-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,4,6-tribromo-N,N-dimethylaniline
• 英文别名: N,N-dimethyl-2,4,6-tribromoaniline；2,4,6-tribromodimethylaniline；2,4,6-tribromo-N,N-dimethyl-aniline；2,4,6-Tribrom-N,N-dimethyl-anilin；2,4,6-Tribrom-N,N-dimethyl-anilin；N,N-Dimethyl-2,4,6-tribrom-anilin
• CAS: 63812-39-5
• 化学式: C₈H₈Br₃N
• 分子量: 357.87
• InChiKey: PQQDTJFBGJYZIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: ethanol (64-17-5))
• 沸点：
  332.2±42.0 °C(Predicted)
• 密度：
  2.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-tribromo-N,N-dimethylaniline 在 sodium amalgam 、 deuteriomethanol 作用下， 反应 6.0h， 以2.06 g的产率得到N,N-dimethylaniline-2,4,6-d₃
  参考文献：
  名称：

  Diastereoselective Tandem Addition−Cyclization Reactions of Unsaturated Tertiary Amines Initiated by Photochemical Electron Transfer (PET)

  摘要：

  Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of or-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is greater than or equal to 90%. The alpha -aminoalkyl radicals were produced from tertiary amines by photachemical-induced electron transfer. When N,N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of 1 during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tettahydroquinolines 21a-i, 22a-f, and 26g-i were doubled.

  DOI：

  10.1021/jo001166l
• 作为产物：
  描述：

  N,N-二甲基苯胺 在 potassium permanganate 、 氢溴酸 作用下， 以 乙腈 为溶剂， 以95%的产率得到2,4,6-tribromo-N,N-dimethylaniline
  参考文献：
  名称：

  Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCl (HBr) Acetonitrile Reagent

  摘要：

  AbstractAddition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25‐60 °C) with excellent to moderate yields.

  DOI：

  10.1002/jccs.199600010

文献信息

• Novel bromination reagents. Electrophilic aromatic bromination by hexabromocyclopentadiene
  作者：Benzion Fuchs、Yigal Belsky、Evgeny Tartakovsky、Jakob Zizuashvili、Sarah Weinman

  DOI：10.1039/c39820000778

  日期：——

  Hexabromocyclopentadiene efficiently and regioselectively brominates activated aromatic compounds, in a process which is interpretde as involving ready formation of the pentabromocyclopentadienide anion by bromonium ion release.

  六溴环戊二烯有效和区域选择性地溴化活化的芳族化合物，该过程被解释为涉及通过溴离子的释放容易形成五溴环戊二烯阴离子。
• “Buttressing Effect” in the Halogen‐Lithium Exchange in <i>ortho</i>‐Bromo‐<i>N,N</i>‐dimethylanilines and Related Naphthalenes
  作者：Stepan A. Meshalkin、Semyon V. Tsybulin、Victor G. Bardakov、Ilya A. Tatarinov、Daniil A. Shitov、Elena Y. Tupikina、Mariia M. Efremova、Alexander S. Antonov

  DOI：10.1002/chem.202303956

  日期：2024.3.7

  The manifestation of the “buttressing effect” – an indirect interaction between two substituents issued by the presence of a third group – and its influence on the ease and selectivity of the bromine-lithium exchange and the reactivity of formed aryllithiums is presented. In naphthalene substrates bearing two bromines, the impact on regioselectivity of the reaction is demonstrated.

  介绍了“支撑效应”的表现——第三基团的存在导致两个取代基之间的间接相互作用——及其对溴-锂交换的容易性和选择性以及所形成的芳基锂的反应性的影响。在带有两个溴的萘底物中，证明了对反应区域选择性的影响。
• Clarke; Gillespie; Weisshaus, Journal of the American Chemical Society, 1933, vol. 55, p. 4576
  作者：Clarke、Gillespie、Weisshaus

  DOI：——

  日期：——
• Methylanilines by Demethylation of Dimethylanilines
  作者：William S. Emerson

  DOI：10.1021/ja01852a502

  日期：1941.7
• Xin-teng, Ding; Guo-bin, Liu, Synthetic Communications, 1989, vol. 19, # 7,8, p. 1261 - 1266
  作者：Xin-teng, Ding、Guo-bin, Liu

  DOI：——

  日期：——