4-bromo-2,6-bis(bromomethyl)benzonitrile | 289617-96-5

• 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: 4-bromo-2,6-bis(bromomethyl)benzonitrile
• 英文别名: 4-bromo-2,6-bis-bromomethyl-benzonitrile
• CAS: 289617-96-5
• 化学式: C₉H₆Br₃N
• 分子量: 367.865
• InChiKey: NBZOKKSHQYTZHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-bromo-2,6-bis(bromomethyl)benzonitrile 在 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 sodium hydride 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.25h， 生成 4,4'-dicyano-3,3',5,5'-tetrakis-(2,5,8-trioxanonyl)tolan
  参考文献：
  名称：

  Hydrophilic-to-Hydrophobic Volume Ratios as Structural Determinant in Small-Length Scale Amphiphilic Crystalline Systems:  Silver Salts of Phenylacetylene Nitriles with Pendant Oligo(ethylene Oxide) Chains

  摘要：

  A series of 13 silver salts of phenylacetylene nitriles with pendant oligo(ethylene oxide) side chains have been crystallized, and their structures have been determined by single-crystal X-ray methods. All the organic molecules are amphiphilic in that they contain either a hydrophobic rigid linear or 3-fold planar phenylacetylene backbone to which are attached four to six rather plastic hydrophilic oligo(ethylene oxide) side chains. Six of the crystal structures have one-dimensional coordination networks based on Ag-N and Ag-O bonding, while the remainder are two-dimensional. Considering the hydrophilic and hydrophobic portions of these crystals as separate components of the crystal structure, five of the crystal structures contain parallel columns of hydrophobic moieties within a matrix of hydrophilic groups, four contain layers of hydrophilic and hydrophobic portions stacked one on top of the other, two have perforated lamellar structures and two are bicontinuous. Volume ratios of hydrophilic to hydrophobic portions prove a strong determinant as to which crystal topology is adopted for a given crystal composition. Such volume ratios can be calculated from knowledge of the molecular structure alone. A comparison is made to similar columnar and lamellar structures found in block copolymers and liquid crystalline systems. Finally, a similar breakdown of crystal topology as a function of volume ratios is found for aromatic-oligo(ethylene oxide) molecules in the Cambridge Structural Database.

  DOI：

  10.1021/ja0006651
• 作为产物：
  描述：

  4-溴-2,6-二甲基苯腈 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 苯 为溶剂， 反应 30.0h， 以50%的产率得到4-bromo-2,6-bis(bromomethyl)benzonitrile
  参考文献：
  名称：

  Hydrophilic-to-Hydrophobic Volume Ratios as Structural Determinant in Small-Length Scale Amphiphilic Crystalline Systems:  Silver Salts of Phenylacetylene Nitriles with Pendant Oligo(ethylene Oxide) Chains

  摘要：

  A series of 13 silver salts of phenylacetylene nitriles with pendant oligo(ethylene oxide) side chains have been crystallized, and their structures have been determined by single-crystal X-ray methods. All the organic molecules are amphiphilic in that they contain either a hydrophobic rigid linear or 3-fold planar phenylacetylene backbone to which are attached four to six rather plastic hydrophilic oligo(ethylene oxide) side chains. Six of the crystal structures have one-dimensional coordination networks based on Ag-N and Ag-O bonding, while the remainder are two-dimensional. Considering the hydrophilic and hydrophobic portions of these crystals as separate components of the crystal structure, five of the crystal structures contain parallel columns of hydrophobic moieties within a matrix of hydrophilic groups, four contain layers of hydrophilic and hydrophobic portions stacked one on top of the other, two have perforated lamellar structures and two are bicontinuous. Volume ratios of hydrophilic to hydrophobic portions prove a strong determinant as to which crystal topology is adopted for a given crystal composition. Such volume ratios can be calculated from knowledge of the molecular structure alone. A comparison is made to similar columnar and lamellar structures found in block copolymers and liquid crystalline systems. Finally, a similar breakdown of crystal topology as a function of volume ratios is found for aromatic-oligo(ethylene oxide) molecules in the Cambridge Structural Database.

  DOI：

  10.1021/ja0006651

文献信息

• Porous Siloxane Linked Phenylacetylene Nitrile Silver Salts from Solid State Dimerization and Low Polymerization
  作者：Y.-H. Kiang、Geoffrey B. Gardner、Stephen Lee、Zhengtao Xu

  DOI：10.1021/ja0009119

  日期：2000.7.26

  Three 3-fold symmetric rigid backbone phenylacetylene nitrile molecules have been prepared to which one to six hydroxy side chains have been attached. These molecules were cocrystallized with silver(I) trifluoromethanesulfonate (triflate) to form microcrystalline porous solids. X-ray powder data show that all three crystal structures are isotypic to the crystal structures found in previous single crystal studies on related systems. Structural models based on these earlier single crystal structures have theoretical powder patterns in reasonable agreement with the experimentally observed patterns. These crystalline materials were allowed to react with silyl triflates. H-1 NMR and X-ray powder studies show that the silyl triflate groups react with the alcohol terminated side chains to form siloxane linkages with retention of the initial crystal structure. In the case of 1,3,5-tris(4-((4-cyanophenyl)ethynyl)-2-((4-hydroxybutoxy)methyl)phenylethynyl)benzene, a phenylacetylene nitrile molecule with three alcohol side chains, the introduction of di-tert-butylsilyl bis(trifluoromethanesulfonate) resulted in the formation of low polymers with average weight molecular weight of 7 x 10(4). This polymerized material shows increased chemical robustness in contrast to the unpolymerized material. It is stable in a variety of solvents, including overnight exposure to boiling water. Exchange experiments with toluene show that this final material is still porous.