五氟(二氟碘)苯 | 24973-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 五氟(二氟碘)苯
• 英文名称: pentafluoro(difluoroiodo)benzene
• 英文别名: pentafluorophenyliodine difluoride；Pentafluorphenyl-difluoriodid；(Difluoroiodo)pentafluorobenzene；difluoro-(2,3,4,5,6-pentafluorophenyl)-λ3-iodane
• CAS: 24973-39-5
• 化学式: C₆F₇I
• 分子量: 331.959
• InChiKey: RUNIGPOHWQJKPF-UHFFFAOYSA-N

物化性质

• 熔点：
  46-47 °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：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  五氟(二氟碘)苯 在 三氟化硼 作用下， 以 1,1,1,3,3-五氟丙烷 为溶剂， 反应 0.33h， 以46 mg的产率得到
  参考文献：
  名称：

  A widely varying range of products in reactions of C6F5BrF2, C6F5IF2, and C6F5IF4 with Lewis acids of different strength

  摘要：

  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.

  DOI：

  10.1016/j.jfluchem.2008.11.004
• 作为产物：
  描述：

  1,2,3,4,5-pentafluoro-6-iodosylbenzene 在 sulfur tetrafluoride 作用下， 以 二氯甲烷 为溶剂， 生成 五氟(二氟碘)苯
  参考文献：
  名称：

  Lyalin,V.V. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 317 - 319

  摘要：

  DOI：

文献信息

• Electrophilic Oxygenation with XeF₂ - H₂O in Hydrogen Fluoride, Part 2. Electrophilic Oxygenation of Pentafluorobenzene Derivatives C₆F₅X
  作者：H. J. Frohn、V. V. Bardin

  DOI：10.1515/znb-1996-0718

  日期：1996.7.1

  Electrophilic oxygenation of polyfluorobenzenes C₆F₅X (X = F. Cl. Br. H, CF₃, NH₃ ⁺, NMe₃ ⁺, OH and OCH₂CF₃) with XeF₂ and H₂O in HF leads to the formation of polyfluorinated 1,4- cyclohexadienones. Pentafluoroiodobenzene is converted into C₆F₅IF₂ and C₆F₅IF₄, whereas [CeF₅N₂]⁺ [NbF₆]^- is unreactive towards this new type of electrophilic oxygenation.

  多氟苯C6F5X（X = F. Cl. Br. H, CF3, NH3+, NMe3+, OH 和 OCH2 ）在HF中使用XeF2和H2O进行亲电氧化反应，形成多氟化的1,4-环己二酮。五氟碘苯转化为C6F5IF2和C6F5IF4，而[CeF5N2]+[NbF6]-对这种新型亲电氧化反应不活跃。
• Fluorination reactions of organoelement compounds with elemental fluorine
  作者：R. Kasemann、G. Klein、D. Naumann

  DOI：10.1016/s0022-1139(00)83335-7

  日期：1985.8

  The fluorination reactions of some pentafluorphenyl element compounds with elemental fluorine at low temperature in the liquid phase are described.

  描述了一些五氟苯基元素化合物在液相中在低温下与元素氟的氟化反应。
• Explored routes to unknown polyfluoroorganyliodine hexafluorides, RFIF6
  作者：Hermann-Josef Frohn、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2010.07.005

  日期：2010.10

  Two routes to RFIF6 compounds were investigated: (a) the substitution of F by RF in IF7 and (b) the fluorine addition to iodine in RFIF4 precursors. For route (a) the reagents C6F5SiMe3, C6F5SiF3, [NMe4][C6F5SiF4], C6F5BF2, and 1,4-C6F4(BF2)2 were tested. C6F5IF4 and CF3CH2IF4 were used in route (b) and treated with the fluoro-oxidizers IF7, [O2][SbF6]/KF, and K2[NiF6]/KF. The observed sidestep reactions

  研究了制备R F IF 6化合物的两种途径：（a）在IF 7中用R F取代F，以及（b）在R F IF 4前体中向碘中添加氟。对于路线（a），试剂C 6 F 5 SiMe 3，C 6 F 5 SiF 3，[NMe 4 ] [C 6 F 5 SiF 4 ]，C 6 F 5 BF 2和1,4-C 6 F 4（BF 2）2经过测试。在路线（b）中使用了C 6 F 5 IF 4和CF 3 CH 2 IF 4，并用了氟氧化剂IF 7，[O 2 ] [SbF 6 ] / KF和K 2 [NiF 6 ] / KF进行了处理。 。讨论了在路线（a）和（b）情况下观察到的回避反应。的C相互作用6 ˚F 5的SiX 3（X = Me中，F），C 6 ˚F 5 BF 2，1,4-C 6 ˚F 4（BF 2）2与IF 7仅给出相应的环氟化产物，全氟化环己二烯和环己烯衍生物，而[NMe 4 ] [C 6 F 5 SiF
• Substituent-controlled, mild oxidative fluorination of iodoarenes: synthesis and structural study of aryl I(<scp>iii</scp>)- and I(<scp>v</scp>)-fluorides
  作者：Joel Häfliger、Cody Ross Pitts、Dustin Bornemann、Roland Käser、Nico Santschi、Julie Charpentier、Elisabeth Otth、Nils Trapp、René Verel、Hans Peter Lüthi、Antonio Togni

  DOI：10.1039/c9sc02162k

  日期：——

  of difluoro(aryl)-λ3-iodanes (aryl-IF2 compounds) and tetrafluoro(aryl)-λ5-iodanes (aryl-IF4 compounds) using trichloroisocyanuric acid (TCICA) and potassium fluoride (KF). Under these reaction conditions, selective access to either the I(III)- or I(V)-derivatives is predictable based solely on the substitution pattern of the iodoarene starting material. Moreover, the discovery of this TCICA/KF approach

  我们报告了一种使用三氯异氰尿酸 (TCICA) 和钾合成二氟(芳基)-λ 3 -碘(芳基-IF 2化合物)和四氟(芳基)-λ 5 -碘(芳基-IF 4化合物)的温和方法氟化物（KF）。在这些反应条件下，仅根据碘芳烃起始材料的取代模式即可预测选择性获得 I( III )-或 I( V )-衍生物。此外，这种TCICA/KF方法的发现促使人们对精心设计的探针分子上的IF 2基团和邻位取代基之间的关系进行了详细的动态NMR、动力学、计算和晶体学研究。正是在这些实验中，揭示了邻位取代基在与TCICA和KF反应期间抑制I( III )-化合物进一步氧化氟化为I( V )-化合物的作用。此外，本文还讨论了这一经验趋势的一个值得注意的例外。
• Preparation of polyfluorinated cycloalk-1-enyl-, alk-1-enyl-, and alkyliodine tetrafluorides using XeF2 in the presence of appropriate Lewis acids as fluorooxidant
  作者：Hermann Josef Frohn、Vadim V. Bardin

  DOI：10.1016/j.jfluchem.2005.03.008

  日期：2005.7

  obtained from pentafluoroiodobenzene using XeF2–NbF5 in aHF. The reaction of C6F5I with the weaker fluorooxidant XeF2–BF3 in 1,1,1,3,3-pentafluorobutane (PFB) yielded C6F5IF2, perfluorocyclohexa-1,4-dienyliodine difluoride, C6F5IF4, perfluorocyclohexa-1,4, and 1,3-dienyliodine tetrafluoride as intermediate products on parallel reaction routes. Both perfluoroalkenyl iodides, cis- and trans-(CF3)2CFCFCFI

  以高收率制备了以前未知的多氟环己烯基和无环全氟烯基碘四氟化物。使用XeF 2 -NbF 5在aHF中从五氟碘苯制得全氟环己-1-烯基碘四氟化物。C 6 F 5 I与较弱的氟氧化剂XeF 2 -BF 3在1,1,1,3,3-五氟丁烷（PFB）中的反应生成C 6 F 5 IF 2，全氟环己-1,4-二烯基碘二氟化物，C 6 F 5中频4，全氟环己-1,4和1,3-二烯基碘四氟化物作为平行反应路线上的中间产物。全氟链烯基碘化物的顺式和反式（CF 3）2 CFCFCFIFI与XeF 2 -BF 3在PFB中反应，得到相应的全氟链烯基碘化物四氟化物，顺式和反式（CF 3）2 CFCFCFIF 4。如从C 6 F 13制备C 6 F 13 IF 4所证明的那样，甚至该试剂也可以氟化全氟烷基碘。I.通常， 环状或无环全氟链烯基碘化合物R F IF n中的CFCIF n片段（n = 0、2或4）没有转化为