1-(4-dimethylaminopyridinium)-2-bromo-1,1,2,2-tetrafluoroethane bromide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-dimethylaminopyridinium)-2-bromo-1,1,2,2-tetrafluoroethane bromide
• 英文别名: 1-(2-bromo-1,1,2,2-tetrafluoroethyl)-N,N-dimethylpyridin-1-ium-4-amine;bromide
• 化学式: Br*C₉H₁₀BrF₄N₂
• 分子量: 381.993
• InChiKey: XUSBAYPRASOMIQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  7.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-dimethylaminopyridinium)-2-bromo-1,1,2,2-tetrafluoroethane bromide 在 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 生成 1-(4-dimethylaminopyridinium)-1,1,2,2-tetrafluoroethane bromide
  参考文献：
  名称：

  4-Dimethylaminopyridinium derivatives of 1,2-dibromo-1,1,2,2-tetrafluoroethane: molecular structure of 1-(4-dimethylaminopyridinium)-2-bromo-1,1,2,2-tetrafluoroethane bromide and 1-(4-dimethylamino-pyridinium)-1,1,2,2-tetrafluoroethane bromide

  摘要：

  The molecular structures of 1-(4-dimethylaminopyridinium)-2-bromo-1, 1, 2, 2-tetrafluoroethane bromide (1-Br) (triclinic, P (1) over bar, a = 538.80(10), b = 916.6(3), c = 1372.8(3) pm, alpha = 81.56(2)degrees, beta = 81.76(2)degrees, gamma = 82.53(2)degrees) and 1-(4-dimethylaminopyridinium)-1, 1, 2, 2-tetrafluoroethane bromide (2-Br) (monoclinic, Cm, a = 1159.6(2), b = 2780.2(6), c = 577.90(10) pm, beta = 95.78(3)degrees) were determined. The two bromides crystallize with one water molecule per formula unit. In cation 1 a hypervalent ion-pairing Br-...BrCF2CF2N (320.7 pm) was observed. A radical mechanism for the interaction of 4-dimethylaminopyridine with 1, 2-dibromo-tetrafluoroethane is proposed. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-1139(97)00037-7
• 作为产物：
  描述：

  4-二甲氨基吡啶 、 1,1,2,2-四氟-1,2-二溴乙烷 在 铜 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以80%的产率得到1-(4-dimethylaminopyridinium)-2-bromo-1,1,2,2-tetrafluoroethane bromide
  参考文献：
  名称：

  Facile new method for synthezising N-polyfluoroalkylated heterocycles – molecular structure of N-(bromodifluoromethyl)-4-dimethylaminopyridinium bromide

  摘要：

  Carbon-bromine bond cleavage is observed when 4-dimethylaminopyridine is treated with CF2Br2 and BrCF2CF2Br to yield N-(bromodifluoromethyl) and N-(2-bromo-1,1,2,2-tetrafluoromethyl)pyridinium bromides, 1-Br and 2-Br, which are reductively debrominated using Bu(3)SnH and fluorinated by anhydrous Me(4)N(+)F(-); the molecular structure of 1-Br is determined by single crystal X-ray crystallography to reveal a partial quinoidal character in the pyridine system and a hypervalent Br-... BrCF2 pairing.

  DOI：

  10.1039/cc9960000335

文献信息

• Facile new method for synthezising N-polyfluoroalkylated heterocycles – molecular structure of N-(bromodifluoromethyl)-4-dimethylaminopyridinium bromide
  作者：Alexander Kolomeitsev、Ralph-Matthias Schoth、Enno Lork、Gerd-Volker Röschenthaler

  DOI：10.1039/cc9960000335

  日期：——

  Carbon-bromine bond cleavage is observed when 4-dimethylaminopyridine is treated with CF2Br2 and BrCF2CF2Br to yield N-(bromodifluoromethyl) and N-(2-bromo-1,1,2,2-tetrafluoromethyl)pyridinium bromides, 1-Br and 2-Br, which are reductively debrominated using Bu(3)SnH and fluorinated by anhydrous Me(4)N(+)F(-); the molecular structure of 1-Br is determined by single crystal X-ray crystallography to reveal a partial quinoidal character in the pyridine system and a hypervalent Br-... BrCF2 pairing.
• 4-Dimethylaminopyridinium derivatives of 1,2-dibromo-1,1,2,2-tetrafluoroethane: molecular structure of 1-(4-dimethylaminopyridinium)-2-bromo-1,1,2,2-tetrafluoroethane bromide and 1-(4-dimethylamino-pyridinium)-1,1,2,2-tetrafluoroethane bromide
  作者：R.M. Schoth、E. Lork、A.A. Kolomeitsev、G.-V. Röschenthaler*

  DOI：10.1016/s0022-1139(97)00037-7

  日期：1997.8

  The molecular structures of 1-(4-dimethylaminopyridinium)-2-bromo-1, 1, 2, 2-tetrafluoroethane bromide (1-Br) (triclinic, P (1) over bar, a = 538.80(10), b = 916.6(3), c = 1372.8(3) pm, alpha = 81.56(2)degrees, beta = 81.76(2)degrees, gamma = 82.53(2)degrees) and 1-(4-dimethylaminopyridinium)-1, 1, 2, 2-tetrafluoroethane bromide (2-Br) (monoclinic, Cm, a = 1159.6(2), b = 2780.2(6), c = 577.90(10) pm, beta = 95.78(3)degrees) were determined. The two bromides crystallize with one water molecule per formula unit. In cation 1 a hypervalent ion-pairing Br-...BrCF2CF2N (320.7 pm) was observed. A radical mechanism for the interaction of 4-dimethylaminopyridine with 1, 2-dibromo-tetrafluoroethane is proposed. (C) 1997 Elsevier Science S.A.