2-bromo-2-phenylethylamine hydrochloride | 24813-65-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-bromo-2-phenylethylamine hydrochloride
• 英文别名: (2-bromo-2-phenylethyl)azanium;chloride
• CAS: 24813-65-8
• 化学式: C₈H₁₀BrN*ClH
• 分子量: 236.539
• InChiKey: ACGSMOYXARUTOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯乙烯 在 盐酸 、 sodium hydrogensulfite 作用下， 以 苯 为溶剂， 反应 5.5h， 生成 2-bromo-2-phenylethylamine hydrochloride
  参考文献：
  名称：

  N，N-二Dihalophosphoramides-XIV：phenylethylenes和α烯烃用二n的两个步骤aminobromination，正dibromophosphoroamidate（DBPA）1

  摘要：

  已经研究了向几种苯基乙烯和末端烯烃中添加DBPA的方法。发现反应在沸腾的二氯甲烷中进行并且取决于反应物的结构和反应性是自发或光解引发的。加成后形成的N-溴加合物可用亚硫酸氢钠溶液原位还原，得到相应的二乙基N-（β-溴烷基）磷酰胺。在室温下用氯化氢在苯中的氯化氢降解，得到纯净的β-溴胺盐酸盐，并且总产率合理。由NMR和MS证实，观察到的抗马氏复合的区域特异性与该反应提出的自由基链机理完全一致。这两个步骤的序列可轻松获得β-溴胺，这是氮丙啶合成的便捷前体。

  DOI：

  10.1016/s0040-4020(01)98974-4

文献信息

• Regioselective aminobromination of terminal alkenes
  作者：Anna Śliwińska、Andrzej Zwierzak

  DOI：10.1016/s0040-4020(03)00907-4

  日期：2003.7

  The addition of t-butyl N,N-dibromocarbamate (BBC) to a variety of terminal alkenes has been studied. The reaction was spontaneously initiated and proceeded smoothly in refluxing dichloromethane. The N-bromo adducts, formed upon addition, could be reduced in situ with aqueous sodium sulfite to give the corresponding 2-bromo-N-Boc-amines. Immediate deprotection of these compounds with gaseous HCl or p-toluenesulfonic acid afforded 2-bromoamine hydrochlorides or tosylates in pure state and good overall yields. The observed regioselectivity for anti-Markovnikov addition, as proven by NMR and MS, is fully consistent with the radical-chain mechanism proposed for the reaction. (C) 2003 Elsevier Ltd. All rights reserved.
• t-Butyl N,N-dibromocarbamate (BBC)—new reagent for aminobromination of terminal alkenes
  作者：Anna Klepacz、Andrzej Zwierzak

  DOI：10.1016/s0040-4039(01)00662-1

  日期：2001.7

  t-Butyl N,N-dibromocarbamate, easily obtained by bromination of t-butyl carbamate in aqueous potassium carbonate, reacts smoothly with a variety of terminal alkenes to afford the corresponding beta -bromo-N-Boc-amines upon reduction with aqueous sodium sulphite. Immediate deprotection of N-Boc-amines with gaseous HCl yields beta -bromoamine hydrochlorides in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• N,N-Dihalophosphoramides—XIV
  作者：S. Zawadzki、A. Zwierzak

  DOI：10.1016/s0040-4020(01)98974-4

  日期：1981.1

  The addition of DBPA to several phenylethylenes and terminal olefins has been studied. The reaction was found to proceed in boiling dichloromethane and was spontaneously or photolytically initiated depending on the structure and reactivity of the reactants. N-Bromo adducts, formed upon addition, could be reduced in situ with sodium bisulphite solution to give the corresponding diethyl N-(β-bromoal

  已经研究了向几种苯基乙烯和末端烯烃中添加DBPA的方法。发现反应在沸腾的二氯甲烷中进行并且取决于反应物的结构和反应性是自发或光解引发的。加成后形成的N-溴加合物可用亚硫酸氢钠溶液原位还原，得到相应的二乙基N-（β-溴烷基）磷酰胺。在室温下用氯化氢在苯中的氯化氢降解，得到纯净的β-溴胺盐酸盐，并且总产率合理。由NMR和MS证实，观察到的抗马氏复合的区域特异性与该反应提出的自由基链机理完全一致。这两个步骤的序列可轻松获得β-溴胺，这是氮丙啶合成的便捷前体。