1,2,4,5-四氟-3,6-(三氟甲基)苯 | 651-89-8

• 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: 1,2,4,5-四氟-3,6-(三氟甲基)苯
• 英文名称: 1,2,4,5-tetrafluoro-3,6-bis-trifluoromethyl-benzene
• 英文别名: Perfluor-p-xylol；perfluoro-p-xylene；p-decafluoroxylene；Benzene, 1,2,4,5-tetrafluoro-3,6-bis(trifluoromethyl)-；1,2,4,5-tetrafluoro-3,6-bis(trifluoromethyl)benzene
• CAS: 651-89-8
• 化学式: C₈F₁₀
• 分子量: 286.072
• InChiKey: WWZNHODBHBVRID-UHFFFAOYSA-N

物化性质

• 沸点：
  121-122
• 密度：
  1.650±0.06 g/cm3(Predicted)
• 保留指数：
  636.1;636.1

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  1,2,4,5-四氟-3,6-(三氟甲基)苯 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,5-(CF3)2-C6F3NHNH2
  参考文献：
  名称：

  572.芳香多氟化合物。第十八部分。全氟邻二甲苯和对二甲苯的一些置换反应

  摘要：

  DOI：

  10.1039/jr9640002975
• 作为产物：
  描述：

  1,1,2,2,3,4,4,5,5,6-十氟代-3,6-双(三氟代甲基)环己烷 在 铁粉 作用下， 生成 1,2,4,5-四氟-3,6-(三氟甲基)苯
  参考文献：
  名称：

  Gething et al., Journal of the Chemical Society, 1961, p. 1574

  摘要：

  DOI：
• 作为试剂：
  描述：

  2,3,4,5,6-五氟苯胺 、 四氟-1,3-二(三氟甲基)苯 在 三氯化铝 、 1,2,4,5-四氟-3,6-(三氟甲基)苯 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 N-(pentafluorophenyl)-2,4,5,6-tetrafluoro-3-trichloromethylbenzimidoyl chloride 、 N-(pentafluorophenyl)-(6-chloro-3-trichloromethyl-2,4,5-trifluorobenz)imidoyl chloride 、 2,3,5,6-tetrafluoro-N-(2,3,4,5,6-pentafluorophenyl)-4-(trichloromethyl)benzenecarboximidoyl chloride 、
  参考文献：
  名称：

  Reactions of pentafluoroaniline with aromatic trihalomethyl derivatives in the presence of AlCl3

  摘要：

  The reactions of pentafluoroaniline with aromatic CX(3)-derivatives (X = F, Cl) in the presence of AlCl3 were studied. It was shown that compounds with a CF3 group can be used 3 in reactions with polyfluoroaromatic amines instead of CCl3-derivatives for the synthesis of imidoyl chlorides. In the case of compounds with several CX(3) groups, the formation of the 3 imidoyl chloride moiety predominantly involves one of the CX(3) groups under the conditions studied. The introduction of a second CX(3) group can be carried out only under more drastic conditions.

  DOI：

  10.1007/bf01558072

文献信息

• [EN] COMPLEXES FOR NUCLEOPHILIC, RADICAL, AND ELECTROPHILIC POLYFLUOROALKYLATION<br/>[FR] COMPLEXES POUR POLYFLUOROALKYLATION NUCLÉOPHILE, RADICALAIRE ET ÉLECTROPHILE
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2017223406A1

  公开（公告）日：2017-12-28

  Disclosed herein are borazine complexes and use of the same in perfluoroalkylation reactions.

  本文披露了硼氮烷配合物及其在全氟烷基化反应中的应用。
• Borazine‐CF ₃ ⁻ Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation
  作者：Jacob B. Geri、Michael M. Wade Wolfe、Nathaniel K. Szymczak

  DOI：10.1002/anie.201711316

  日期：2018.1.26

  A fluoroform‐derived borazine CF3− transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C−H and C−X

  甲三氟甲烷衍生的环硼氮烷CF 3 -转移试剂在25用来快速作用的亲核反应在不存在添加剂时，在几分钟内℃。可以高产率地将跨越周期表的七个基团的无机亲电试剂三氟甲基化，包括用于催化三氟甲基化的过渡金属。有机亲电试剂包括（杂）芳烃，可实现CH和CX三氟甲基化反应。机理分析支持CF解离机构3 -转移，和阳离子改性，得到具有增强的稳定性的试剂。
• A Key Intermediate in Copper‐Mediated Arene Trifluoromethylation, [ <i>n</i> Bu ₄ N][Cu(Ar)(CF ₃ ) ₃ ]: Synthesis, Characterization, and C(sp ² )−CF ₃ Reductive Elimination
  作者：Zehai Lu、He Liu、Shihan Liu、Xuebing Leng、Yu Lan、Qilong Shen

  DOI：10.1002/anie.201904041

  日期：2019.6.17

  characterization, and C(sp2)−CF3 reductive elimination of stable aryl[tris(trifluoromethyl)]cuprate(III) complexes [nBu4N][Cu(Ar)(CF3)3] are described. Mechanistic investigations, including kinetic studies, studies of the effect of temperature, solvent, and the para substituent of the aryl group, as well as DFT calculations, suggest that the C(sp2)−CF3 reductive elimination proceeds through a concerted

  描述了稳定的芳基[三（三氟甲基）]铜（III）配合物[ n Bu 4 N] [Cu（Ar）（CF 3）3 ]的合成，表征和C（sp 2）-CF 3还原消除。机械研究，包括动力学研究，温度，溶剂和芳基对位取代基的影响研究以及DFT计算，均表明C（sp 2）-CF 3的还原消除是通过协调一致的碳进行的。碳键形成途径。
• FLUORINATED AROMATIC COMPOUND, METHOD FOR ITS PRODUCTION, CURABLE MATERIAL, ITS CURED PRODUCT, AND OPTICAL MEMBER
  申请人：ASAHI GLASS COMPANY, LIMITED

  公开号：US20160137572A1

  公开（公告）日：2016-05-19

  To provide a novel fluorinated aromatic compound having at least two carbon-carbon unsaturated bonds, a method for its production, a curable material comprising the fluorinated aromatic compound, a cured product thereof, and an optical member. The fluorinated aromatic compound is represented by formula (A), wherein n is an integer of 0 to 6, a is an integer of 0 to 5, b is an integer of 0 to 4, c is an integer of 0 to 4, a+c+n is 2 to 6, a+b is 2 to 9, Z is a single bond, —O—, —S—, —CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —SO—, or —SO 2 —, Rf 1 is a C 1-8 fluoroalkyl group, Y 1 and Y 2 are each independently a group represented by formula (1) (s is 0 or 1, and R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom or a fluorine atom), and F in the aromatic ring indicates that hydrogen atoms in the aromatic ring are all substituted by fluorine atoms.

  提供一种至少具有两个碳-碳不饱和键的新型氟芳香化合物，一种其生产方法，包括所述氟芳香化合物的可固化材料，其固化产物以及光学部件。所述氟芳香化合物由式（A）表示，其中n为0至6的整数，a为0至5的整数，b为0至4的整数，c为0至4的整数，a+c+n为2至6，a+b为2至9，Z为单键，—O—，—S—，—CO—，—C(CH3)2—，—C(CF3)2—，—SO—，或—SO2—，Rf1为C1-8氟烷基，Y1和Y2分别独立地表示由式（1）表示的基团（s为0或1，R1、R2、R3和R4分别独立地表示氢原子或氟原子），芳香环中的F表示芳香环中的氢原子均被氟原子取代。
• Mechanisms of reactions of halogenated compounds
  作者：Richard D. Chambers、Peter A. Martin、Graham Sandford、D. Lyn H. Williams

  DOI：10.1016/j.jfluchem.2008.04.009

  日期：2008.10

  The effect of fluorine as a substituent group on nucleophilic aromatic substitution is discussed, where a fluorine atom located ortho to the point of substitution may be of variable activating influence, whereas fluorine located para is slightly deactivating and meta is activating. A rationale of these effects is presented and evidence to support polar influences by ortho fluorine is advanced. The

  讨论了氟作为取代基对亲核芳族取代的影响，其中位于邻位的氟原子可能具有可变的激活影响，而位于对位的氟则略微失活，而间位则被激活。提出了这些效应的原理，并提出了支持邻氟对极性影响的证据。CN，CF 3，CF 2 H和CFH 2的影响也可以通过比较合适的测得的速率常数并与环氮的活化作用来确定。

表征谱图