三溴乙酰胺 | 594-47-8

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 三溴乙酰胺
• 中文别名: 三溴乙醯胺
• 英文名称: tribromo-acetic acid amide
• 英文别名: tribromoacetamide；Tribromacetamid；2,2,2-Tribromoacetamide
• CAS: 594-47-8
• 化学式: C₂H₂Br₃NO
• 分子量: 295.756
• InChiKey: ORCCSQMJUGMAQU-UHFFFAOYSA-N

物化性质

• 熔点：
  121.5°C
• 沸点：
  263.0±40.0 °C(Predicted)
• 密度：
  2.901±0.06 g/cm3(Predicted)
• 溶解度：
  乙腈（微溶）、氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924199090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  三溴乙酰胺 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 N-Brom-tribromacetamid
  参考文献：
  名称：

  An Investigation of the Hofmann Reaction of Perhaloacetamides

  摘要：

  DOI：

  10.1021/jo01056a040
• 作为产物：
  描述：

  四溴乙烯 在 氧气 、 氨 作用下， 以 甲苯 为溶剂， 反应 90.0h， 以5.2 g的产率得到三溴乙酰胺
  参考文献：
  名称：

  Liquid-phase oxidation of bromovinyl compounds with molecular oxygen

  摘要：

  Liquid-phase oxidation of bromovinyl compounds with the aim to obtain the corresponding (x-bromo acids was studied.

  DOI：

  10.1134/s1070427206110218

文献信息

• Experimental and Computational Probes of the Nature of Halogen Bonding: Complexes of Bromine-Containing Molecules with Bromide Anions
  作者：Sergiy V. Rosokha、Charlotte L. Stern、Jeremy T. Ritzert

  DOI：10.1002/chem.201300577

  日期：2013.7.1

  [RBr, Br−] complexes show intense absorption bands in the 200–350 nm range which follow the same Mulliken correlation as those observed for the charge‐transfer associates of bromide anions with common organic π‐acceptors. For a wide range of the associates, intermolecular RBr⋅⋅⋅Br− separations decrease and intramolecular CBr bond lengths increase proportionally to the Br−→RBr charge transfer; and the

  卤键的性质通过一系列电bromocarbons R的联营的实验和计算表征检查溴R（ BR = CBR 3楼CBR 3 NO 2，CBR 3 COCBr 3，CBR 3 CONH 2，CBR 3 CN等）和溴化物阴离子。的[R 溴，溴- ]配合物表现出在200-350纳米范围内强烈吸收带，其遵循相同的马利肯相关的那些用于与普通有机π共受体溴化物阴离子的电荷转移联营观察。对于广泛的同伴，分子间RBr⋅⋅⋅Br -分离减少和分子内Ç  Br键长度成比例地增加于BR - →R 溴电荷转移; 和R的能量 Br⋅⋅⋅Br -键与轨道（电荷转移）和静电相互作用的线性组合相关。上的整体，光谱，结构和热力学特性[R 溴，溴- ]络合物表明除了静电，轨道（电荷转移）的相互作用在R发挥至关重要的作用 Br⋅⋅⋅Br -卤素键。这表明，除了控制超分子组装体的几何形状以外，卤素键还导致相互作用的物
• Halogen bonding of electrophilic bromocarbons with pseudohalide anions
  作者：Sergiy V. Rosokha、Charlotte L. Stern、Alan Swartz、Rory Stewart

  DOI：10.1039/c4cp00976b

  日期：——

  associates between bromocarbons and polydentate pseudohalide anions. Specifically, in the (Pr4N)NCO·CBr4, (Pr4N)N3·CBr4 and (Pr4N)NCO·CBr3NO2 co-crystals, bromine substituents of the electrophiles are halogen-bonded with the (CN or NN) π-bonds of the cyanate or azide anions. Co-crystals of CBr4 with (Pr4N)NCS show two modes (C–Br⋯S–C and C–Br⋯NC) of halogen bonding, while tribromoacetamide molecules form C–Br⋯S–C

  紫外可见测量表明，拟卤化物阴离子的相互作用，A -（A - = N 3 -，NCO -，NCS - ）中，用亲电bromocarbons，R-溴（R-BR = CBR 4，CBR 3 NO 2，CBR 3 CONH 2，CBR 3 H，CBR 3楼CBR 3 CN或C 3溴2 ˚F 6），在溶液中导致形成[R-BR，A的-]复合体。这些缔合体的特征是在200-350 nm范围内有很强的吸收带，显示出与相互作用的阴离子和R-Br亲电试剂的前沿（HOMO-LUMO）轨道的分离具有明显的Mulliken相关性。X射线晶体学研究确定了溴碳与多齿假卤化物阴离子之间的卤素键联缔合物​​的主要结构特征。具体地，在（Pr 4 N）NCO·CBr 4，（Pr 4 N）N 3 ·CBr 4和（Pr 4 N）NCO·CBr 3 NO 2共晶体中，亲电子体的溴取代基与卤素键合。 （C N或NN）氰酸根或叠氮化物阴离子的π键。CBr
• Continuum of covalent to intermolecular bonding in the halogen-bonded complexes of 1,4-diazabicyclo[2.2.2]octane with bromine-containing electrophiles
  作者：Craig Weinberger、Rachel Hines、Matthias Zeller、Sergiy V. Rosokha

  DOI：10.1039/c8cc04629h

  日期：——

  A gradual change of Br⋯N bond lengths and strengths from the values typical for intermolecular associates to that characteristic of a covalent bond was observed in a series of halogen-bonded complexes. This continuum reveals a fundamental relationship between the limiting types of bonding and implies the onset of covalency in the intermolecular interactions.

  在一系列卤素键合的配合物中，观察到Br⋯N键长和强度从分子间缔合体的典型值到共价键特征的逐渐变化。该连续体揭示了键合的限制类型之间的基本关系，并暗示了分子间相互作用中共价的开始。
• Perhaloketones—XVII
  作者：E.E. Gilbert

  DOI：10.1016/s0040-4020(01)82752-6

  日期：1969.1
• Hydrolysis of haloacetonitriles: LINEAR FREE ENERGY RELATIONSHIP, kinetics and products
  作者：Victor Glezer、Batsheva Harris、Nelly Tal、Berta Iosefzon、Ovadia Lev

  DOI：10.1016/s0043-1354(98)00361-3

  日期：1999.6

  The hydrolysis rates of mono-, di- and trihaioacetonitriles were studied in aqueous buffer solutions at different pH. The stability of haloacetonitriles decreases and the hydrolysis rate increases with increasing pH and number of halogen atoms in the molecule: The monochloroacetonitriles are the most stable and are also less affected by pH-changes, while the trihaloacetonitriles are the least stable and most sensitive to pH changes. The stability of haloacetonitriles also increases by substitution of chlorine atoms with bromine atoms. The hydrolysis rates in different buffer solutions follow first order kinetics with a minimum hydrolysis rate at intermediate pH. Thus, haloacetonitriles have to be preserved in weakly acid solutions between sampling and analysis. The corresponding haloacetamides are formed during hydrolysis and in basic solutions they can hydrolyze further to give haloacetic acids. Linear free energy relationship can be used for prediction of degradation of haloacetonitriles during hydrolysis in water solutions. (C) 1999 Elsevier Science Ltd. All rights reserved.