4-bromo-N-butyl-N-methylaniline | 156808-76-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-bromo-N-butyl-N-methylaniline
• 英文别名: (4-Bromo-phenyl)-butyl-methyl-amine
• CAS: 156808-76-3
• 化学式: C₁₁H₁₆BrN
• 分子量: 242.159
• InChiKey: GRGCSRZFEGIWOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  丙烯酰碘 、 4-bromo-N-butyl-N-methylaniline 生成 (+/-)-N-allyl-4-bromo-N-butyl-N-methyl-anilinium; iodide
  参考文献：
  名称：

  Everatt, Journal of the Chemical Society, 1908, vol. 93, p. 1236

  摘要：

  DOI：
• 作为产物：
  描述：

  N-butyl-N-methylaniline 在 二溴亚砜 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.75h， 生成 4-bromo-N-butyl-N-methylaniline
  参考文献：
  名称：

  亚硫酰卤处理N，N-二烷基苯胺N-氧化物合成卤代苯胺

  摘要：

  N，N-二烷基苯胺N-氧化物的特殊反应性使得可以方便实用地获得富含电子的芳基卤化物。一对互补的反应协议允许用于选择性对-bromination或邻位的-chlorination N，N- -dialkylanilines在高达69％的分离收率。通过将N，N-二烷基苯胺暂时氧化为相应的N，N-二烷基苯胺N-氧化物并去除生成的弱N – O ，可以生成各种卤化苯胺 通过在低温下用亚硫酰溴或亚硫酰氯处理可实现键合。

  DOI：

  10.1021/acs.joc.8b01590

文献信息

• PROCESS FOR THE REMOVAL AND RETURN OF A CATALYST TO A LIQUID PHASE MEDIUM
  申请人：PHOSPHONICS LTD

  公开号：US20150299229A1

  公开（公告）日：2015-10-22

  A process for the selective removal of a component from a liquid phase and subsequently returning the component to a liquid phase is disclosed. A novel compound of formula (I) [SUP]-[[L]-[G]]a (I) in which L is a linking group, G is an aryl group having a leaving group LG selected from Cl, Br, I, sulfonate such as triflate, a diazo group, a nitrile, an ester and an alkoxy group and substituent Q is selected from H, NR2, OR, C02R, F, Cl, N02 CN and SUP is a support having a plurality of groups -[L]-[G] bound to the support is contacted with the liquid phase to bind the component to the compound I thereby forming a captured component which is separated from and may be returned to the liquid phase. The compound I is especially useful in binding homogeneous catalysts to remove it from a reaction medium and selectively returning the catalyst to the reaction medium at a later stage. The compound is particularly useful for cross-coupling reactions, for example in Suzuki reactions.

  揭示了一种从液相中选择性去除组分并随后将该组分返回到液相的方法。公开了一种具有式(I)的新化合物[SUP]-[[L]-[G]]a (I)，其中L是连接基团，G是一种芳基团，具有从Cl、Br、I、磺酸盐（如三氟甲磺酸盐）、重氮基团、腈基、酯基和烷氧基中选择的离去基团LG，取代基Q从H、NR2、OR、C02R、F、Cl、N02、CN中选择，SUP是具有多个与支持物相结合的基团-[L]-[G]的支持物，与液相接触以将组分结合到化合物I中，从而形成被捕获的组分，该组分与液相分离并可以返回到液相中。化合物I在将均相催化剂结合以将其从反应介质中去除，并在后续阶段选择性地将催化剂返回到反应介质中方面特别有用。该化合物特别适用于交叉偶联反应，例如在铃木反应中。
• Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using n Bu4NBr
  作者：Wenxia Xie、Shulin Ning、Nian Liu、Ya Bai、Shutao Wang、Siyu Wang、Lingling Shi、Xin Che、Jinbao Xiang

  DOI：10.1055/s-0037-1611545

  日期：2019.7

  Electrochemical regioselective bromination of electron-rich aromatic rings using stoichiometric tetrabutylammonium bromide ( n Bu4NBr) has been accomplished under mild conditions. This protocol provides an environmentally friendly and simple way for the construction of C–Br bond in moderate to high yields with wide functional group tolerance.

  使用化学计量的四丁基溴化铵 (n Bu4NBr) 在温和条件下完成了富电子芳环的电化学区域选择性溴化。该协议为构建具有广泛官能团耐受性的中等至高产率的 C-Br 键提供了一种环境友好且简单的方法。
• Copper-Promoted <i>N</i>-Alkylation and Bromination of Arylamines/Indazoles Using Alkyl Bromides as Reagents for Difunctionalization
  作者：Tingting Wen、Baihui Liang、Jiacheng Liang、Dongyi Wang、Jianyi Shi、Shengting Xu、Weidong Zhu、Xiuwen Chen、Zhongzhi Zhu

  DOI：10.1021/acs.joc.2c01356

  日期：2022.9.16

  Practical copper-promoted N-alkylation and bromination of arylamines/indazoles with alkyl bromides are described; the N-alkylation-C-4-bromination and N-dialkylation-C-4-bromination of arylamines, and N-alkylation-C-3-bromination of indazoles, with alkyl bromides have been analyzed. The full use of alkyl bromides as alkylating and brominating building blocks without atom wastage, indicating excellent

  描述了实用的铜促进芳胺/吲唑与烷基溴的N-烷基化和溴化；分析了芳胺的N-烷基化-C-4-溴化和N-二烷基化-C-4-溴化，以及吲唑与烷基溴的N-烷基化-C-3-溴化。充分利用烷基溴作为烷基化和溴化结构单元而不会浪费原子，表明其具有优异的原子和步骤经济性，这一点得到了强调。环保氧气和水分别是反应的氧化剂和副产物。
• Surfactant control of the ortho/para ratio in the bromination of anilines. 2.
  作者：Giorgio Cerichelli、Giovanna Mancini、Luciana Luchetti

  DOI：10.1016/s0040-4020(01)90399-0

  日期：1994.3

  We report the bromination of some N,N-disubstituted anilines (N-ethyl-N-methylaniline, N,N-diethylaniline, N-butyl-N-methylaniline, 1-phenylpyrrolidine, 1-phenylpiperidine) both in aqueous suspension of cetyltrimethylammonium tribromide (CTAB3) and in homogeneous solution (CHCl3). In the presence of surfactant we observed a regioselectivity different from that observed in homogeneous conditions. The regioselectivity seems to depend on the nature of the substituents on the nitrogen of the aniline as well as on the temperature. An explanation based on specific interactions between the aniline and the packed structure of the aggregate is proposed.
• Cerichelli Giorgio, Mancini Giovanna, Tetrahedron, 50 (1994) N 12, S 3797-3802
  作者：Cerichelli Giorgio, Mancini Giovanna

  DOI：——

  日期：——