(2-bromo-1,1,2,2-tetrafluoroethyl)(phenyl)sulfane | 83015-33-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-bromo-1,1,2,2-tetrafluoroethyl)(phenyl)sulfane
• 英文别名: (2-bromo-1,1,2,2-tetrafluoroethyl)sulfanylbenzene
• CAS: 83015-33-2
• 化学式: C₈H₅BrF₄S
• 分子量: 289.091
• InChiKey: ACKRNLPIVVTRML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险类别：
  9
• 危险性防范说明：
  P501,P273,P260,P270,P264,P280,P391,P314,P337+P313,P305+P351+P338,P301+P312+P330
• 危险品运输编号：
  3082
• 危险性描述：
  H302,H319,H372,H410
• 包装等级：
  III
• 储存条件：
  2-8°C，干燥

反应信息

• 作为反应物：
  描述：

  (2-bromo-1,1,2,2-tetrafluoroethyl)(phenyl)sulfane 在 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate 、 二氧化硫 、 magnesium 、 N,N-二异丙基乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 二氯氟甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 21.5h， 生成 N-benzyl-N-(trifluoromethanesulfonyl)-2-(phenylsulfanyl)-1,1,2,2-tetrafluoroethanesulfonamide
  参考文献：
  名称：

  Syntheses of a wide family of new aryl based perfluorosulfonimide lithium salts. Electrochemical performances of the related polymer electrolytes

  摘要：

  This paper reports both on a general multistep synthesis of a wide family of aryl substituted perfluorosulfonimides and on a preliminary electrochemical investigation of two lithium salts hosted by a poly(oxyethylene) homopolymer. Both salts have a cationic transference number more than twice that of LiTFSI. Additionally, one of these salts exhibits markedly higher cationic conductivities than POE/LiTFSI electrolytes. These preliminary data are very encouraging as, thanks to the aryl moiety, a wide variety of salts can be considered in order to still improve the performances of polymer electrolytes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.06.041
• 作为产物：
  描述：

  苯硫酚铜(I) 在 N-溴代丁二酰亚胺(NBS) 、 lithium tert-butoxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.0h， 生成 (2-bromo-1,1,2,2-tetrafluoroethyl)(phenyl)sulfane
  参考文献：
  名称：

  Controllable Double Difluoromethylene Insertions into S−Cu Bonds: (Arylthio)tetrafluoroethylation of Aryl Iodides with TMSCF₂Br

  摘要：

  A new method of constructing “ArSCF₂CF₂Cu” from ArSCu and TMSCF₂Br (TMS=trimethylsilyl) has been developed. The cross‐coupling reactions of the obtained “ArSCF₂CF₂Cu” with diverse aryl iodides (Ar′I) provide an efficient access to Ar′CF₂CF₂SAr. Mechanistic studies demonstrate that the “ArSCF₂CF₂Cu” species were generated through controllable double difluoromethylene insertions into ArS−Cu bonds rather than the 1,2‐addition of ArSCu to tetrafluoroethylene.

  DOI：

  10.1002/anie.202400839

文献信息

• Expanding the Scope of Hypervalent Iodine Reagents for Perfluoroalkylation: From Trifluoromethyl to Functionalized Perfluoroethyl
  作者：Václav Matoušek、Jiří Václavík、Peter Hájek、Julie Charpentier、Zsófia E. Blastik、Ewa Pietrasiak、Alena Budinská、Antonio Togni、Petr Beier

  DOI：10.1002/chem.201503531

  日期：2016.1.4

  A series of new hypervalent iodine reagents based on the 1,3‐dihydro‐3,3‐dimethyl‐1,2‐benziodoxole and 1,2‐benziodoxol‐3‐(1H)‐one scaffolds, which contain a functionalized tetrafluoroethyl group, have been prepared, characterized, and used in synthetic applications. Their corresponding electrophilic fluoroalkylation reactions with various sulfur, oxygen, phosphorus, and carbon‐centered nucleophiles

  基于1,3-二氢-3,3-二甲基-2-1,2-苯并恶唑和1,2-苯并恶唑-3-（1 H）-one骨架的一系列新的高价碘试剂，它们含有功能化的四氟乙基已经制备，表征并用于合成应用。它们与各种硫，氧，磷和以碳为中心的亲核试剂进行相应的亲电氟烷基化反应，可得到具有连接两个功能部分的四氟乙烯单元的产物。一个相关的λ 3含有荧光团的碘已显示在温和条件下与半胱氨酸衍生物反应，生成硫醇标记的产物，该产物在存在过量硫醇的情况下是稳定的。因此，这些新试剂作为快速，不可逆和选择性硫醇生物结合的工具，在化学生物学中显示出巨大的潜力。
• AROMATIC SULPHONYLIMIDES, PREPARATION THEREOF AND USE THEREOF AS ELECTROLYTE
  申请人：Sanchez Jean-Yves

  公开号：US20100174113A1

  公开（公告）日：2010-07-08

  The invention relates to a process for preparing aromatic sulphonylimides, to the sulphonylimides obtained, and to the use thereof as salt of an electrolyte. The sulphonylimides correspond to the formula [R—SO 2 —N—SO 2 R′] r M (I). R′ is an ArZL- group. R′ is a perfluoroalkyl group or an ArZL- group. Z is an S, SO or SO 2 group. L is a —(CF 2 ) n —CFR f — group. n is 0 or 1; R f represents F or a C 1 to C 8 perfluoroalkyl group; Ar is an aromatic group. M represents H, an alkali metal cation, an alkaline earth metal cation, a trivalent or tetravalent metal cation, or an organic cation. The process consists in preparing a compound RSO2N(R′)SO2R′ from RSO 2 F, and in replacing the group R′ by nucleophilic substitution reaction so as to obtain the compound (I), R′ being a benzyl or trimethylsilyl group.

  该发明涉及一种制备芳香磺酰亚胺的方法，所得的磺酰亚胺以及将其用作电解质盐。磺酰亚胺对应于式[R—SO2—N—SO2R′]rM（I）。R′是ArZL-基团。R′是全氟烷基基团或ArZL-基团。Z是S、SO或SO2基团。L是—(CF2)n—CFRf—基团。n为0或1；Rf代表F或C1到C8的全氟烷基基团；Ar是芳香族基团。M代表H、碱金属阳离子、碱土金属阳离子、三价或四价金属阳离子或有机阳离子。该方法包括从RSO2F制备化合物RSO2N(R′)SO2R′，并通过亲核取代反应将基团R′替换为以获得化合物（I），其中R′是苄基或三甲基硅基团。
• An Efficient Preparation of New Sulfonyl Fluorides and Lithium Sulfonates
  作者：Fabien Toulgoat、Bernard. R. Langlois、Maurice Médebielle、Jean-Yves Sanchez

  DOI：10.1021/jo701318n

  日期：2007.11.1

  polyfluoroalkanesulfonyl fluorides is reported. This method, based on the synthesis of polyfluoroalkyl trimethyl silanes (precursors of polyfluoroalkylsulfinates) as intermediates, allows the successive transformations to be carried out in one pot. Moreover, these sulfonyl fluorides can be obtained from the corresponding sulfinates by electrophilic fluorination. This original approach avoids isolation and purification

  报道了几种多氟链烷磺酰氟的有效制备方法。该方法基于多氟烷基三甲基硅烷（多氟烷基亚磺酸盐的前体）作为中间体的合成，可以在一个罐中进行连续的转化。而且，这些磺酰氟可以通过亲电氟化从相应的亚磺酸盐获得。这种原始方法避免了某些热或水解不稳定中间体的分离和纯化。因此，已经从卤代二氟甲基化的前体RCF 2 X（X = F，Br; R = ArC（O），ArS（O）n（CF 2）m ; n = 0，1，2; m制备了一系列新的磺酰氟。 = 1、2），并已转化为相应的磺酸锂，它们有潜力用作锂电池的电解质。
• Development of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Preparation of Tetrafluoroethyl-Substituted Alcohols and Tetrafluorotetrahydropyrans
  作者：Yana Chernykh、Katarina Hlat-Glembová、Blanka Klepetářová、Petr Beier

  DOI：10.1002/ejoc.201100667

  日期：2011.8

  PhSCF2CF2SiMe3 (1) was developed as a tandem anion and radical tetrafluoroethylene equivalent for the introduction of a CF2CF2 moiety. Fluoride-initiated nucleophilic additions of 1 to carbonyl compounds provide the corresponding alcohol adducts 2. Reduction of 2 gives tetafluoroethyl-containing alcohols 3, whereas 6-exo radical cyclizations of allyl ethers 4 yield tetrafluorotetrahydropyrans 5.

  PhSCF2CF2SiMe3 (1) 被开发为串联阴离子和自由基四氟乙烯等价物，用于引入 CF2CF2 部分。1 与羰基化合物的氟化物引发的亲核加成提供相应的醇加合物 2。 2 的还原产生含四氟乙基的醇 3，而烯丙基醚 4 的 6-外自由基环化产生四氟四氢吡喃 5。
• Process for the preparation of azidoperfluoroalkanes and N-polyfluoroalkyl azides
  申请人：Ustav organicke chemie a biochemie AV CR, v.v.i.

  公开号：US20190161452A1

  公开（公告）日：2019-05-30

  Process for the preparation of azidoperfluoroalkanes and azidopolyfluoroalkanes of general formula R F —N 3 , where R F is chosen from a group containing C n F 2n+1 , C n F x H 2n+1−x , C n F x X 2n+1−x or R 1 CF 2 CF 2 , where n is an integer in the range of 1 to 10, x is an integer in the range of 2 to 20, X is Cl, Br, or I, R 1 is C 1-10 alkyl, ArO, ArS, imidazolyl, benzimidazolyl, or pyrazolyl and Ar is phenyl or substituted phenyl, by the reaction of electrophilic azidation reagent of general formula R 2 —N 3 , where R 2 is n-C 4 F 9 SO 2 , ArSO 2 , Br, I, with synthetic equivalent of polyfluoroalkylated carbanion of general formula [R F ] − .

  通用公式RF—N3的叠氮全氟烷和叠氮多氟烷的制备过程，其中RF选择自包含CnF2n+1、CnFxH2n+1−x、CnFxX2n+1−x或R1CF2CF2的一组化合物，其中n为1至10范围内的整数，x为2至20范围内的整数，X为Cl、Br或I，R1为C1-10烷基、ArO、ArS、咪唑基、苯并咪唑基或吡唑基，Ar为苯基或取代苯基，通过亲电性叠氮试剂R2—N3的反应，其中R2为n-C4F9SO2、ArSO2、Br、I的通用公式，与通用公式[RF]−的多氟烷基化碳负离子的合成等效物的反应。