2,3,5,6-四氟对二溴苄 | 776-40-9

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯甲酸系列
• 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: 2,3,5,6-四氟对二溴苄
• 中文别名: 2-氯-4,5-二氟苯甲酸；2,3,5,6-四氟二苄溴
• 英文名称: 1,4-bis(bromomethyl)-2,3,5,6-tetrafluorobenzene
• 英文别名: 1,2,4,5-tetrafluoro-3,6-bis(bromomethyl)benzene
• CAS: 776-40-9
• 化学式: C₈H₄Br₂F₄
• 分子量: 335.921
• InChiKey: WTBYGXCRADGSLY-UHFFFAOYSA-N

物化性质

• 熔点：
  103-106℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 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：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39,S39
• 危险类别码：
  R34,R36/37/38,R41
• 海关编码：
  2903999090
• 危险品运输编号：
  UN 1759
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P501,P260,P234,P264,P280,P390,P303+P361+P353,P301+P330+P331,P363,P304+P340+P310,P305+P351+P338+P310,P406,P405
• 危险性描述：
  H314,H290
• 储存条件：
  室温

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2,3,5,6-四氟对二甲苯	2,3,5,6-tetrafluoro-p-xylene	703-87-7	C8H6F4	178.129
  四氟对苯二甲醛	2,3,5,6-tetrafluoroterephthalaldehyde	3217-47-8	C8H2F4O2	206.096
  2,3,5,6-四氟对苯二甲醇	2,3,5,6-tetrafluoro-1,4-benzenedimethanol	92339-07-6	C8H6F4O2	210.128
  2,3,5,6-四氟-1,4-双(氯甲基)苯	1,4-bis(chloromethyl)tetrafluorobenzene	131803-37-7	C8H4Cl2F4	247.019
  2,3,5,6-四氟苯甲醛	2,3,5,6-tetrafluorobenzaldehyde	19842-76-3	C7H2F4O	178.086

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2,3,5,6-四氟对苯二甲胺	4-aminomethyl-2,3,5,6-tetrafluoro-phenylmethanamine	89992-50-7	C8H8F4N2	208.159
  ——	1,4-bis (mercaptomethyl)-2,3,5,6-tetrafluorobenzene	106112-30-5	C8H6F4S2	242.261
  ——	tetrafluoro<2.2> paracyclophane	22557-12-6	C16H12F4	280.265
  ——	tetrafluoro-2,11-dithia<3.3>paracyclophane	106112-31-6	C16H12F4S2	344.397
  派瑞林 F 二聚体	4,5,7,8,12,13,15,16-octafluoro(2.2)paracyclophane	1785-64-4	C16H8F8	352.227

反应信息

• 作为反应物：
  描述：

  2,3,5,6-四氟对二溴苄 在 lithium sulfide 、 亚磷酸三乙酯 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 派瑞林 F 二聚体
  参考文献：
  名称：

  聚氟芳基[2.2]环烷的合成

  摘要：

  描述了4,5,7,8-四氟和4,5,7,8,12,13,15,16-八氟[2.2]对环烷的新型合成方法。概述了新化合物4,5,7,8-四氟[2.2]间对环环烷的制备。

  DOI：

  10.1016/s0022-1139(00)85095-2
• 作为产物：
  描述：

  1,2,4,5-四氟苯 在 盐酸 、 正丁基锂 、 dimethyl sulfide borane 、 三溴化磷 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.58h， 生成 2,3,5,6-四氟对二溴苄
  参考文献：
  名称：

  Fluorinated molecules relevant to conducting polymer research

  摘要：

  The synthesis of versatile fluorine compounds for conducting polymer research on fluorinated materials is presented. 1,2,4,5-Tetrafluorobenzene was converted to 1,2,4,5-tetrafluorobenzaldehyde (1) and protected as an acetal. This gave the acetals 1,2,4,5-tetrafluoro-3(1,3-dioxol-2-yl)benzene (2a) and 1,2,4,5-tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)benzene (2b). Compounds 2a and 2b were converted into the semiprotected 2,3,5,6-tetrafluoroterephthaldehydes: 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene (3a) and 1,2,4,5-tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)-6-formylbenzene (3b). While 3a was easily deprotected to give 2,3,5,6-tetrafluoroterephthaidehyde (4) compound 3b proved very resilient to hydrolysis and gave a 1: 1 mixture of 4 and 1,2,4,5-tetrafluoro-3,6-bis(5,5-dimethyl- 1,3-dioxan-2yl)benzene (5). Compound 4 was reduced to 1,2,4,5-tetrafluoro-3,6-dihydroxymethylbenzene (6) and converted into 1,2,4,5-tetrafluoro-3,6-dibromomethylbenzene (7). Compound 7 was finally converted into 1,2,4,5-tetrafluoro-3,6-bis(diethylphosponylmethyl)benzene (8). Compounds 4 and 8 are versatile fluorinated molecules that can be used to replace their hydrogen counterparts in many molecules and materials. To illustrate this compounds 4 and 8 were oligomerised to give partially fluorinated polyphenylenevinylene (9). (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00289-0

文献信息

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  DOI：10.1039/c3cc45128c

  日期：——

  The use of aromatic organic macrocycles as supramolecular hosts for non-covalent energy transfer is reported herein. These macrocycles lead to stronger binding and more efficient energy transfer compared to commercially available gamma-cyclodextrin. This energy transfer was particularly efficient for the highly toxic benzo[a]pyrene with a fluorescent BODIPY acceptor, with up to a 5-fold increase in

  本文报道了芳香族有机大环化合物作为非共价能量转移的超分子主体的用途。与可商购的γ-环糊精相比，这些大环化合物具有更强的结合力和更有效的能量转移。这种能量传递对于带有荧光BODIPY受体的剧毒苯并[a] particularly特别有效，观察到的荧光团发射增加了5倍。
• [2]Catenanes Displaying Switchable Gin-Trap-Like Motion
  作者：Chi-You Tsai、Chien-Chen Lai、Yi-Hung Liu、Shie-Ming Peng、Richard P. Cheng、Sheng-Hsien Chiu

  DOI：10.1021/acs.joc.8b00601

  日期：2018.5.18

  Sodium ion-controlled switching from “folded” to “linear” states results in significant changes in the molecular shape of a [2]catenane, such that it mimics the operation of a gin trap, with a fluorescent alarm signal appearing when pyrene side arms were present on its two macrocyclic components.

  钠离子控制的从“折叠”状态到“线性”状态的转换导致[2]烷烃的分子形状发生重大变化，从而模仿了杜松子酒捕集阱的操作，并在pyr侧臂出现时发出荧光警报信号存在于其两个大环组分上。
• Hydrophilic Conjugated Polymers Prepared by Aqueous Horner–Wadsworth–Emmons Coupling
  作者：Zachariah A. Page、Yao Liu、Egle Puodziukynaite、Thomas P. Russell、Todd Emrick

  DOI：10.1021/acs.macromol.5b02501

  日期：2016.4.12

  The synthesis of hydrophilic conjugated polymers typically relies on organometallic coupling methodologies. Here we present an approach to prepare polar poly(arylene–vinylene)s (PAVs) in water using the Horner–Wadsworth–Emmons (HWE) reaction. The additional preparation of discrete arylene vinylene (AVs) afforded insight into HWE kinetics and regioselectivity. Nine novel PAVs and AVs were synthesized

  亲水性共轭聚合物的合成通常依赖于有机金属偶联方法。在这里，我们介绍一种利用霍纳-沃兹沃思-埃蒙斯（HWE）反应在水中制备极性聚（亚芳基-亚乙烯基）（PAV）的方法。离散亚芳基亚乙烯基（AVs）的额外制备提供了对HWE动力学和区域选择性的了解。合成了九种新颖的PAV和AV，以紫外可见吸收和紫外光电子能谱为特征，并研究了它们在传感和光伏应用中的效用。
• Fluoro-functionalized polymeric ionic liquids: highly efficient catalysts for CO₂cycloaddition to cyclic carbonates under mild conditions
  作者：Zhen-Zhen Yang、Yanfei Zhao、Guipeng Ji、Hongye Zhang、Bo Yu、Xiang Gao、Zhimin Liu

  DOI：10.1039/c4gc00730a

  日期：——

  Fluoro-functionalized polymeric ionic liquids (F-PILs) with imidazolium cations and bromide or chloride anions were designed for cycloaddition reactions of CO2 with epoxides. It was found that the fluorine content in F-PILs significantly influenced the catalytic activity of the catalysts, and F-PIL-Br showed three times higher activity for CO2 reacting with styrene oxide than non-fluorous PIL-Br. Moreover, F-PIL-Br could be extended to catalyse a broad range of reactants under 1 MPa CO2 pressure, producing a series of cyclic carbonates in excellent yields (93–99%). In addition, it showed high stability and easy recyclability.

  含氟功能化聚合离子液体（F-PILs）与咪唑鎓阳离子和溴离子或氯离子被设计用于二氧化碳与环氧化物的环加成反应。研究发现，F-PILs中氟的含量显著影响催化剂的催化活性，其中F-PIL-Br在二氧化碳与苯乙烯氧化物反应中的活性是非含氟PIL-Br的三倍。此外，F-PIL-Br能够在1 MPa的二氧化碳压力下催化多种反应物，生产出一系列产率优秀的环碳酸酯（93-99%）。此外，它还表现出高稳定性和易回收性。
• Substituted diethynyldithia[3.3]paracyclophanes—synthetically more accessible new building blocks for molecular scaffolding
  作者：Jian-Long Xia、Chan Zhang、Xingxun Zhu、Yaping Ou、Guo-Jun Jin、Guang-ao Yu、Sheng Hua Liu

  DOI：10.1039/c0nj00553c

  日期：——

  A series of dialkyne building blocks based on the dithia[3.3]paracyclophane unit have been synthesized in good yields. The electronic properties of these novel dialkynes can be tuned through a transannular substitution effect. These synthetically more accessible diethynyldithia[3.3]paracyclophanes are promising candidates for the building of relatively carbon rich molecular scaffolds.

  一系列基于二硫[3.3]邻环烯烃单元的双炔建筑块已高产合成。这些新型双炔的电子性质可以通过穿环取代效应进行调节。这些合成上更易获得的二乙炔基二硫[3.3]邻环烯烃是构建相对富碳分子骨架的有前景的候选材料。