Pentafluorphenyl-trifluormethylsulfid | 38086-98-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Pentafluorphenyl-trifluormethylsulfid
• 英文别名: 1,2,3,4,5-Pentafluoro-6-[(trifluoromethyl)thio]benzene；1,2,3,4,5-pentafluoro-6-(trifluoromethylsulfanyl)benzene
• CAS: 38086-98-5
• 化学式: C₇F₈S
• 分子量: 268.13
• InChiKey: NTYHNSIHOLSATG-UHFFFAOYSA-N

物化性质

• 沸点：
  72.4±40.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  五氟苯硫酚 在 三氯化铝 、 五氟化锑 作用下， 反应 10.0h， 生成 Pentafluorphenyl-trifluormethylsulfid
  参考文献：
  名称：

  Fluoro-organic sulphur-containing compounds. IV. Haloalkylation reactions of polyfluorinated thiophenols with CHal3R compounds in the presence of AlCl3

  摘要：

  The haloalkylation of polyfluorothiophenols with CHal(3)R compounds (Hal=Cl, F; R=Cl, H, C6H5, C6F5) in the presence of AlCl3 has been investigated. The reactions of polyfluorothiophenols 4-XC6F4SH (X=F, H, CH3) with CCl4 and AlCl3 lead to dichloromethane derivatives (4-XC6F4S)(2)CCl2. The reaction of pentafluorothiophenol with CHCl3 in the presence of AlCl3 gave (C6F5S)(2)CHCl and (C6F5S)(3)CH (ratio by GLC 8:1). In the reaction of pentafluorothiophenol with ArCX3 (Ar=C6H5, C6F5; X=Cl, Fl compounds (C6F5S)(2)CClAr (Ar=C6H5, C6F5) together with C6F5SCCl2Ar (Ar=C6H5. C6F5) are formed. Peculiarities of these processes are considered. The hydrolysis of (C6F5S)(2)CCl2 and C6F5SCCl2C6H5 leads to bis(pentafluorophenyl)dithiocarbonate and the S-(pentafluorophenyl) ester of thiobenzoic acid, respectively. Compounds (C6F5S)(2)CF2 and (C6F5S)(2)CClF were obtained from (C6F5S)(2)CCl2 by the action of caesium fluoride. An attempt to produce these compounds through the action of antimony fluorides was unsuccessful. The compounds (C6F5S)(2)CCl2, (C6F5S)(2)CClF and (C6F5S)(2)CF2 are stable to oxidation. The reactions of (C6F5S)(2)CF2 and (C6F5S)(2)CClF with CrO3 in acetic acid proceeded only with the formation of mono-sulphoxide. The conversion is low in the former case. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00080-9

文献信息

• Preparation and Properties of some Non-Metallic Derivatives of Pentafluorothiophenol
  作者：M. E. Peach、H. G. Spinney

  DOI：10.1139/v71-103

  日期：1971.2.15

  Various non-metallic derivatives of pentafluorothiophenol, containing sulfur bonded to boron, carbon, silicon, germanium, phosphorus, arsenic, antimony, sulfur, and chlorine, have been prepared, mainly from the reaction of Pb(SC₆F₅)₂ with a non-metallic halide, and characterized. The ¹⁹F n.m.r. spectra have been examined. The coordinating power of sulfur attached to a C₆F₅ group is minimal.

  五氟硫酚的各种非金属衍生物，含有硫与硼、碳、硅、锗、磷、砷、锑、硫和氯键合，主要是通过Pb(S )2与非金属卤化物反应制备的，并进行了表征。已经检查了19F核磁共振谱。硫与C6F5基团结合的配位能力是最小的。
• Perfluoroalkyl derivatives of sulphur. Part VIII. Synthesis and reactions of perfluoroethylenesulphonyl fluoride
  作者：R. E. Banks、G. M. Haslam、R. N. Haszeldine、A. Peppin

  DOI：10.1039/j39660001171

  日期：——

  hydrogen fluoride at 60° to yield 1,2,2,2-tetrafluoroethanesulphonyl fluoride. The last product is also obtained by treatment of perfluoroethylenesulphonyl fluoride with anhydrous potassium fluoride in formamide at 35°. Thus the olefin is polarised in the sense [graphics omitted]·SO2F. The compounds CF2Br·CHF·SO2F, CF2Br·CFBr·SO2F, and CF2Cl·CFCl·SOF are obtained in high yield by free-radical hydrobromination

  由三氟氯乙烯或全氟丙烯分六步和三步制得的全氟乙烯磺酰氟，与氢氧化钠水溶液反应，得到全氟乙烯磺酸钠，与甲醇在0°下反应，得到1,2,2-三氟-2-甲氧基乙烷磺酰氟，与二乙胺在- 30°提供2-二乙基氨基-1,2,2-三氟乙烷磺酰氟，并在60°提供无水氟化氢，得到1,2,2,2-四氟乙烷磺酰氟。最后的产品也可以通过在35°F下用无水氟化钾在甲酰胺中处理全氟乙烯磺酰氟来获得。因此，烯烃在[省略图示]·SO 2 F的意义上被极化。化合物CF 2 Br·CHF·SO 2 F，CF 2 Br·CFBr·SO通过全氟亚乙基磺酰氟的自由基氢溴化，溴化和氯化分别以高收率获得2 F和CF 2 Cl·CFCl·SOF。全氟乙烯磺酰氟与三氟亚硝基甲烷的反应产生1：1的交替共聚物。
• The First Organosilver(III) Fluoride, [PPh ₄ ][(CF ₃ ) ₃ AgF]
  作者：Daniel Joven‐Sancho、Miguel Baya、Antonio Martín、Jesús Orduna、Babil Menjón

  DOI：10.1002/chem.201905771

  日期：2020.4.6

  Organosilver(III) fluoride complexes have been assigned a key role in different fluorination processes. To the best of our knowledge, however, none of them seem to have been isolated or even detected thus far. Here we report on the successful synthesis of the trifluoromethyl derivative [PPh4 ][(CF3 )3 AgF], which has been isolated in high yield. The thermodynamic stability of the Ag-F bond is shown

  有机银（III）氟化物络合物已被指定在不同氟化过程中的关键作用。据我们所知，到目前为止，似乎没有一个是孤立的，甚至没有被发现的。在这里，我们报告成功地合成了三氟甲基衍生物[PPh4] [（CF3）3 AgF]，该衍生物已经以高收率分离出来。通过计算显示了Ag-F键的热力学稳定性，并在碰撞诱导解离（CID）条件下通过多级质谱（MSn）对其进行了证明。然而，在Ag-F键（X射线）中发现的大量伸长与末端F配体的显着亲核特性相关。实际上，该Ag-F键具有很强的反应性：它易水解，也被硫醇溶剂化。
• Perfluoroalkyl derivatives of sulphur. Part XIII. The reaction of polyfluoromonoiodoalkanes with diethyl disulphide and of pentafluoroiodobenzene with bis(trifluoromethyl) disulphide
  作者：R. N. Haszeldine、R. B. Rigby、A. E. Tipping

  DOI：10.1039/p19720002180

  日期：——

  Photochemical reactions of trifluoroiodomethane and of heptafluoro-1-iodopropane with diethyl disulphide gives comparable yields (ca. 40%) of the corresponding ethyl polyfluoroalkyl sulphides and 1H-polyfluoroalkanes and lower yields of 1,1,1-trifluoropropane or 1,1,1,2,2,3,3-heptafluoropentane. Pentafluorophenyl trifluoromethyl sulphide, pentafluorophenyl trifluoromethyl disulphide, and trifluoroiodomethane

  三氟碘甲烷和七氟-1-碘丙烷与二乙基二硫化物的光化学反应可得到相应的乙基多氟烷基硫化物和1 H-多氟烷烃可比的产率（约40％），而1,1,1-三氟丙烷或1,1的产率较低。 1,2,2,3,3-七氟戊烷。五氟苯基三氟甲基硫化物，五氟苯基三氟甲基二硫化物和三氟碘甲烷是在五氟碘苯与双（三氟甲基）二硫化物的光化学反应中形成的。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.2, 6.2.1.6.5, page 172 - 209
  作者：

  DOI：——

  日期：——