perfluorohexyldifluoroborane | 329009-01-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: perfluorohexyldifluoroborane
• 英文别名: Difluoro(tridecafluorohexyl)borane；difluoro(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)borane
• CAS: 329009-01-0
• 化学式: C₆BF₁₅
• 分子量: 367.853
• InChiKey: HWYKNSRMIKVTDH-UHFFFAOYSA-N

物化性质

• 沸点：
  72.0±50.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  perfluorohexyldifluoroborane 在 三氟化溴 作用下， 以 1,1,1,3,3-五氟丙烷 为溶剂， 反应 3.0h， 生成 1-溴全氟乙烷 、 全氟己烷
  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
• 作为产物：
  描述：

  potassium (perfluorohexyl)trifluoroborate 在 五氟化砷 作用下， 以 1,1,1,3,3-五氟丙烷 为溶剂， 以90%的产率得到perfluorohexyldifluoroborane
  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

• The Reaction of 2-X-1, 2-Difluoroalk-1-enyldifluoroboranes with Xenon Difluoride. A Methodical Approach to 1, 2-Difluoroalk-1-enylxenon(II) Salts
  作者：Hermann-Josef Frohn、Nicolay Yu. Adonin、Vadim V. Bardin

  DOI：10.1002/zaac.200300234

  日期：2003.12

  2-X-1, 2-Difluoroalk-1-enylxenon(II) salts were prepared by the reaction of XeF2 with XCF=CFBF2 (X = F, trans-H, cis-Cl, trans-Cl, cis-CF3, cis-C2F5) but no organoxenon(II) compounds were obtained when the trans-isomers of boranes, trans-XCF=CFBF2 (X = CF3, C4F9, C4H9, Et3Si), were used under similar conditions. Reaktionen von 2-X-1, 2-Difluoralk-1-enyldifluorboranen mit Xenondifluorid. Untersuchung

  2-X-1, 2-Difluoroalk-1-enylxenon(II) 盐是通过 XeF2 与 XCF=CFBF2 (X = F, trans-H, cis-Cl, trans-Cl, cis-CF3, cis -C2F5) 但在类似条件下使用硼烷的反式异构体反式-XCF=CFBF2 (X = CF3、C4F9、C4H9、Et3Si) 时，没有得到有机氧 (II) 化合物。Reaktionen von 2-X-1, 2-Difluoralk-1-enyldifluorboranen mit Xenondifluorid。Untersuchung des methodischen Zugangs zu 1, 2-Difluoralk-1-enylxenon(II)salzen 2-X-1, 2-Difluoralk-1-enylxenon(II)salze wurden bei der Reaktion
• Thermal decomposition of 4-fluorobenzenediazonium perfluoroorganyl(fluoro)borates, [4-FC6H4N2]Y (Y=RFBF3 (RF=C6F5, C6F13, trans-C4F9CFCF, cis-C6F13CFCF, CF3CC) and (C6F13)2BF2)
  作者：Vadim V. Bardin、Hermann-Josef Frohn

  DOI：10.1016/j.jfluchem.2013.08.001

  日期：2013.12

  Heating of the neat salts [4-FC6H4N2][RFRF3] (R-F = C6F5, C6F13 trans-C4F9CF=CF, cis-C6F13CF=CF, CF3C C or in solid mixtures with NaF gives the principal product 1,4-C6F2H4 besides RFBF2 or Na[RFBF3], respectively. Thermolysis of [4-FC6H4N2][(C6F13)(2)BF2] in NaF results in 1,4-C6F2H4, Na[BF4], Na[(C6F13)(2)BF2], and a new type of product, the isomer Na[C6F13CF(BF3)C5F11]. (C) 2013 Elsevier B.V. All rights reserved.
• A Preparative Method for Perfluoroalkyltrifluoroborates and Perfluoroalkyldifluoroboranes
  作者：H.-J. Frohn、V. V. Bardin

  DOI：10.1002/1521-3749(200101)627:1<15::aid-zaac15>3.0.co;2-a

  日期：2001.1

  A convenient new preparative method for the unknown class of perfluoroalkyltrifluoroborates K[CnF2n + 1BF3] and perfluoroalkyldifluoroboranes CnF2n + 1BF2 (n > 1) is elaborated. The perfluoroalkyl group is introduced into the boric acid ester by using CnF2n + 1MgBr. Treatment with K[HF2] and HF,, results in K[CnF2n + 1BF3] which can be defluoridated by AsF5 to the corresponding boranes CnF2n + 1BF2.
• 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.
• The first perfluoro alkyl(aryl)iodonium salt synthesised on two complementary routes
  作者：Hermann-Josef Frohn、Frank Bailly、Vadim V. Bardin

  DOI：10.1016/j.mencom.2009.03.004

  日期：2009.3

  The first representatives of the previously unknown perfluoroalkyl(perfluoroaryl)iodonium salts [CnF2n+1(Ar-F)I]y were prepared by reaction of perfluorinated alkyliodine difluorides CnF2n+1IF2 with aryldifluoroborane C6F5BF2 and on the complementary route from perfluorinated aryliodine difluoride C(6)F(5)IF2 and alkyldifluoroborane C6F13BF2.