2,3,4,5,6-pentafluorophenyldifluorobromane | 81607-30-9

• 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: 2,3,4,5,6-pentafluorophenyldifluorobromane
• 英文别名: pentafluorphenylbrom(III)difluorid；Difluoro-(2,3,4,5,6-pentafluorophenyl)-lambda3-bromane；difluoro-(2,3,4,5,6-pentafluorophenyl)-λ3-bromane
• CAS: 81607-30-9
• 化学式: C₆BrF₇
• 分子量: 284.959
• InChiKey: DNHCDASRDAPDNG-UHFFFAOYSA-N

物化性质

• 熔点：
  35-36 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯基三氟硅烷 、 2,3,4,5,6-pentafluorophenyldifluorobromane 在 tetrafluoroboric acid 作用下， 以 乙腈 、 水 为溶剂， 以31%的产率得到phenyl(pentafluorophenyl)bromonium tetrafluoroborate
  参考文献：
  名称：

  New types of asymmetrical bromonium salts [RF(RF′)Br]Y where RF and/or RF′ represent perfluorinated aryl, alkenyl, and alkynyl groups

  摘要：

  A series of previously unknown asymmetrical fluorinated bis(aryl)bromonium, alkenyl(aryl)bromonium, and alkynyl(aryl)bromonium salts was prepared by reactions of C6F5BrF2 or 4-CF3C6H4BrF2 with aryl group transfer reagents Ar'SiF3 (Ar' = C6F5, 4-FC6H4, C6H5) or perfluoroorganyl group transfer reagents R-F'BF2 (R-F = C6F5, trans-CF3CF=CF, C3F7C C) preferentially in weakly coordinating solvents (CCl3F, CCl2FCClF2, CH2Cl2, CF3CH2CHF2(PFP), CF3CH2CF2CH3 (PFB)). The presence of the base MeCN and the influence of the adducts R-F'BF2 center dot NCMe (R-F = C6F5, CF3C C) on reactions aside to bromonium salt formation are discussed. Reactions of C6F5BrF2 with Alk(F)'BF2 in PFP gave mainly C6F5Br and Alk(F)'F (Alk(F)' = C6F13, C6F13CH2CH2), presumably, deriving from the unstable salts [C6F5(Alk(F)')Br]Y (Y = [Alk(F)'BF3](-)). Prototypical reactivities of selected bromonium salts were investigated with the nucleophile I- and the electrophile H+. [4-CF3C6H4(C6F5)Br][BF4] showed the conversion into 4-CF3C6H4Br and C6F5I when reacted with [Bu4N]I in MeCN. Perfluoroalkynylbromonium salts [CnF2n+1C C(R-F)Br][BF4] slowly added HF when dissolved in aHF and formed [Z-CnF2n+1CF=CH(R-F)Br][BF4]. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2010.06.022
• 作为产物：
  描述：

  trifluoro(pentafluorophenyl)silane 在 三氟化溴 、 sodium fluoride 、 乙腈 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 生成 2,3,4,5,6-pentafluorophenyldifluorobromane
  参考文献：
  名称：

  双（全氟有机基）溴鎓盐[（R F）2 Br] Y（R F  =芳基，烯基和炔基）

  摘要：

  溴鎓盐[（R ˚F）2溴- ] Y与全氟化基团- [R ˚F Ç 6 ˚F 5，CF 3 CF CF，C 2 ˚F 5 CF CF，和CF 3 C≡C，从BRF的反应分离出3，其中R ˚F BF 2在弱配位溶剂（wcs）中，例如CF 3 CH 2 CHF 2（PFP）或CF 3 CH 2 CF 2 CH 3（PFB），收率30-90％。C 6 F 5高炉2仅仅与化学计量无关地形成[[C 6 F 5）2 Br] [BF 4 ]。BrF 3与硅烷C 6 F 5 SiY 3（Y = F，Me）的1：2反应以不同的产物– C 6 F 5 BrF 2或[（C 6 F 5）2 Br] [SiF 5 ] –终止纯的个体，取决于Y和反应温度（Y = F）。在≥−30°C时使用C 6 F 5 SiF 3 [[C 6 F 5）2 Br] [SiF5 ]导致产率为92％，而具有较少路易斯酸性C 6 F 5 SiMe

  DOI：

  10.1016/j.jfluchem.2010.06.006

文献信息

• A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength
  作者：Hermann-Josef Frohn、Frank Bailly、Dirk Welting、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2008.11.004

  日期：2009.3

  The relative fluoride donor ability: C6F5BrF2 > C6F5IF2 > C6F5IF4 was outlined from reactions with Lewis acids of graduated strength in different solvents. Fluoride abstraction from C(6)F(5)HaIF(2) with BF3.NCCH3 in acetonitrile (donor solvent) led to [C(6)F(5)HaIF-(NCCH3)(n)][BF4]. The attempted generation of [C6F5BrF](+) from C6F5BrF2 and anhydrous HF or BF3 in weakly coordinating SO2CIF gave C6F5Br besides bromoperfluorocycloalkenes C6BrF7 and 1-BrC6F9. In reactions of C6F5IF2 with SbF5 in SO2CIF the primary observed intermediate (F-19 NMR, below 0 degrees C) was the 4-iodo-1,1,2,3,5,6-hexafluorobenzenium cation, which converted into C6F5I and 1-lC(6)F(9) at 20 degrees C. The reaction of C6F5IF4 with SbF5 in SO2CIF below -20 degrees C gave the cation [C6F5IF3](+) which decomposed at 20 degrees C to C6F5I, 1-iodoperfluorocyclohexene, and iodoperfluorocyclohexane. Principally, the related perfluoroalkyl compound C6F13IF4 showed a different type of products in the fast reaction with AsF5 in CCl3F (-60 degrees C) which resulted in C6F14. Intermediate and final products of C(6)F(5)Hal(n-1) (n = 3, 5) with Lewis acids were characterized by NMR in solution. Stable solid products were isolated and analytically characterized. (C) 2008 Elsevier B.V. All rights reserved.
• Frohn; Giesen; Welting, European Journal of Solid State and Inorganic Chemistry, 1996, vol. 33, # 9, p. 841 - 853
  作者：Frohn、Giesen、Welting、Henkel

  DOI：——

  日期：——
• Organobromine(III)-compounds [1]
  作者：H.J. Frohn、M. Giesen

  DOI：10.1016/s0022-1139(00)85557-8

  日期：1983.11
• Beitrage zur chemie des bromtrifluorids 1. Teil pentafluorphenylbrom(III)difluorid und -bis (trifluoracetat)
  作者：Hermann Josef Frohn、Matthias Giesen

  DOI：10.1016/s0022-1139(00)81292-0

  日期：1984.1
• New types of asymmetrical bromonium salts [RF(RF′)Br]Y where RF and/or RF′ represent perfluorinated aryl, alkenyl, and alkynyl groups
  作者：Hermann-Josef Frohn、Matthias Giesen、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2010.06.022

  日期：2010.10

  A series of previously unknown asymmetrical fluorinated bis(aryl)bromonium, alkenyl(aryl)bromonium, and alkynyl(aryl)bromonium salts was prepared by reactions of C6F5BrF2 or 4-CF3C6H4BrF2 with aryl group transfer reagents Ar'SiF3 (Ar' = C6F5, 4-FC6H4, C6H5) or perfluoroorganyl group transfer reagents R-F'BF2 (R-F = C6F5, trans-CF3CF=CF, C3F7C C) preferentially in weakly coordinating solvents (CCl3F, CCl2FCClF2, CH2Cl2, CF3CH2CHF2(PFP), CF3CH2CF2CH3 (PFB)). The presence of the base MeCN and the influence of the adducts R-F'BF2 center dot NCMe (R-F = C6F5, CF3C C) on reactions aside to bromonium salt formation are discussed. Reactions of C6F5BrF2 with Alk(F)'BF2 in PFP gave mainly C6F5Br and Alk(F)'F (Alk(F)' = C6F13, C6F13CH2CH2), presumably, deriving from the unstable salts [C6F5(Alk(F)')Br]Y (Y = [Alk(F)'BF3](-)). Prototypical reactivities of selected bromonium salts were investigated with the nucleophile I- and the electrophile H+. [4-CF3C6H4(C6F5)Br][BF4] showed the conversion into 4-CF3C6H4Br and C6F5I when reacted with [Bu4N]I in MeCN. Perfluoroalkynylbromonium salts [CnF2n+1C C(R-F)Br][BF4] slowly added HF when dissolved in aHF and formed [Z-CnF2n+1CF=CH(R-F)Br][BF4]. (C) 2010 Elsevier B.V. All rights reserved.