1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene | 528869-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene
• 英文别名: 4-(1,3-dioxolan-2-yl)-2,3,5,6-tetrafluorobenzaldehyde
• CAS: 528869-11-6
• 化学式: C₁₀H₆F₄O₃
• 分子量: 250.149
• InChiKey: UXKXQQOZHSCYJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  238.1±40.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene 在 盐酸 、 dimethyl sulfide borane 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 生成 2,3,5,6-四氟对苯二甲醇
  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
• 作为产物：
  描述：

  1,2,4,5-四氟苯 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene
  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

• Fluorinated styrene-based monomers for cyclopolymerizations
  作者：Arvind K. Sharma、Dario Pasini

  DOI：10.1016/j.jfluchem.2011.07.021

  日期：2011.11

  alkylation on the malonate moiety in mild conditions affords difunctional monomer 3. Through sequential esterifications on the malonate moiety, and subsequent alkylation, compound 4, a difunctional monomer for cyclopolymerization bearing one styrene and one perfluoroaryl styrene moiety, has been obtained. Preliminary experiments show that it is possible to cyclopolymerize 4 under free radical conditions

  介绍了用于进行聚合物研究和环聚合的通用氟化合物和单体的合成。半保护2,3,5,6- tetrafluoroterephthaldehyde 1可以通过Wittig烯化化学，脱保护和还原被阐述以先前未知的4-乙烯基-2,3,5,6- tetrafluorobenzylalcohol 8以良好的收率。化合物8可以反应形成丙二酸酯，然后在温和条件下在丙二酸酯部分上烷基化得到双官能单体3。通过对丙二酸酯部分进行顺序酯化，然后进行烷基化，化合物4获得了具有一个苯乙烯和一个全氟芳基苯乙烯部分的用于环聚合的双官能单体。初步实验表明，有可能在自由基条件下使4发生环聚合。