bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate | 213380-73-5

• 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: bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate
• 英文别名: Terephthalic acid bis(pentafluoroisopropenyl) ester；bis(1,1,3,3,3-pentafluoroprop-1-en-2-yl) benzene-1,4-dicarboxylate
• CAS: 213380-73-5
• 化学式: C₁₄H₄F₁₀O₄
• 分子量: 426.167
• InChiKey: HYUXAUVLAGOQCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  312.6±42.0 °C(Predicted)
• 密度：
  1.565±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  四氢吡喃 、 bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate 以47%的产率得到
  参考文献：
  名称：

  Radiation-Induced Radical Polyaddition of Bis(α-trifluoromethyl-β,β-difluorovinyl) Terephthalate with Excess of Various Ethers

  摘要：

  Radiation-induced radical polyaddition of bis(a-trifluoromethyl-P,P-difluorovinyl) terephthalate [CF2=C(CF3)OCOC6H4COOC(CF3)=CF2] (BFP) in the presence of an excess of cyclic and acyclic ethers in feed was examined at 0 degrees C using gamma-ray irradiation. Irradiation of BFP with an 8-fold excess of 1,4-dioxane (DOX) and diethyl ether (EE) gave monomodal polymers consisting of the alternating unit of BFP and DOX moieties (poly(BFP-alt-DOX) (M) over bar (n,as-prepared) 5.1 x 10(3)) and of BFP and EE (poly(BFPalt-EE) (M) over bar (n,as-prepared) = 3.9 x 10(3)), respectively. The irradiation of BFP with an 8-fold excess of tetrahydrofuran or tetrahydropyran provided only 1:2 addition products in high yields. Monofunctional 2-benzoxypentafluoropropene [CF2=C(CF3)OCOC6H5] (BPFP) as a model compound showed preferential formation of the 2:1 adduct to the 1:1 adduct with DOX and EE. The kinetic analysis of the model reactions revealed that the rate constants for the formation of the 2:1 adducts (k(d)) of BPFP with DOX and EE were 2 orders of magnitude higher than those of the 1:1 adducts (k(m)). Poly(BFP-alt-DOX) showed higher radiation resistance than poly(BFP-alt-EE) in solid state as well as in solution. It was concluded that radiation-induced step-growth polymerization under the stoichiometric imbalance of the two compounds requires a high k(d)/k(m) value as well as high radiation resistance for the formation of high molecular weight polymers.

  DOI：

  10.1021/ma051147j
• 作为产物：
  描述：

  六氟异丙醇 、 对苯二甲酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate
  参考文献：
  名称：

  Novel fluorinated hybrid polymer preparation from silsesquioxanes by radical polyaddition

  摘要：

  Radical polyaddition of bis(alpha-trifluoromethyl-beta,beta-difluorovinyl) terephthalate [CF2=C(CF3)OCOC6H4COOC(CF3)=CF2] (BFP) with silsesquioxanes was investigated in order to produce a polymer possessing silsesquioxane moiety in polymer main chain. 1,3,5,7,9,11,13,15-octakis(dimethylsilyloxy)pentacyclo[9.5.1.1(3,9).1(5,15).17,13]octasiloxane (T8S) with BFP successfully afforded a polymer bearing a molecular weight of about 2.5 x 10(5). The polymer obtained were soluble in usual organic solvent such as methanol, tetrahydrofuran and chloroform. In order to get some information on the polyaddition reaction mechanism, model reactions of 2-benzoxypentafluoropropene [CF2=C(CF3)O-)OCOC6H5] (BPFP) with dimethylphenylsilane, [(CH3)(2)SiHC6H5], BPFP with 1,1,3,3-tetramethyldisiloxane {[(CH3)(2)SiH](20)}, and BFP with dimethylphenylsilane were carried out. The mechanism that the radical abstracts a hydrogen from silane compounds followed by the addition of perfluorcrisopropenyl groups was proposed. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.03.005

文献信息

• JPH10251353A
  申请人：——

  公开号：JPH10251353A

  公开（公告）日：1998-09-22
• Radiation-Induced Radical Polyaddition of Bis(α-trifluoromethyl-β,β-difluorovinyl) Terephthalate with Excess of Various Ethers
  作者：Kazuyuki Enomoto、Yasunari Maekawa、Yosuke Katsumura、Toyoaki Miyazaki、Masaru Yoshida、Hiroshi Hamana、Tadashi Narita

  DOI：10.1021/ma051147j

  日期：2005.11.1

  Radiation-induced radical polyaddition of bis(a-trifluoromethyl-P,P-difluorovinyl) terephthalate [CF2=C(CF3)OCOC6H4COOC(CF3)=CF2] (BFP) in the presence of an excess of cyclic and acyclic ethers in feed was examined at 0 degrees C using gamma-ray irradiation. Irradiation of BFP with an 8-fold excess of 1,4-dioxane (DOX) and diethyl ether (EE) gave monomodal polymers consisting of the alternating unit of BFP and DOX moieties (poly(BFP-alt-DOX) (M) over bar (n,as-prepared) 5.1 x 10(3)) and of BFP and EE (poly(BFPalt-EE) (M) over bar (n,as-prepared) = 3.9 x 10(3)), respectively. The irradiation of BFP with an 8-fold excess of tetrahydrofuran or tetrahydropyran provided only 1:2 addition products in high yields. Monofunctional 2-benzoxypentafluoropropene [CF2=C(CF3)OCOC6H5] (BPFP) as a model compound showed preferential formation of the 2:1 adduct to the 1:1 adduct with DOX and EE. The kinetic analysis of the model reactions revealed that the rate constants for the formation of the 2:1 adducts (k(d)) of BPFP with DOX and EE were 2 orders of magnitude higher than those of the 1:1 adducts (k(m)). Poly(BFP-alt-DOX) showed higher radiation resistance than poly(BFP-alt-EE) in solid state as well as in solution. It was concluded that radiation-induced step-growth polymerization under the stoichiometric imbalance of the two compounds requires a high k(d)/k(m) value as well as high radiation resistance for the formation of high molecular weight polymers.
• Novel fluorinated hybrid polymer preparation from silsesquioxanes by radical polyaddition
  作者：Hirotada Fujiwara、Tadashi Narita、Hiroshi Hamana

  DOI：10.1016/j.jfluchem.2004.03.005

  日期：2004.9

  Radical polyaddition of bis(alpha-trifluoromethyl-beta,beta-difluorovinyl) terephthalate [CF2=C(CF3)OCOC6H4COOC(CF3)=CF2] (BFP) with silsesquioxanes was investigated in order to produce a polymer possessing silsesquioxane moiety in polymer main chain. 1,3,5,7,9,11,13,15-octakis(dimethylsilyloxy)pentacyclo[9.5.1.1(3,9).1(5,15).17,13]octasiloxane (T8S) with BFP successfully afforded a polymer bearing a molecular weight of about 2.5 x 10(5). The polymer obtained were soluble in usual organic solvent such as methanol, tetrahydrofuran and chloroform. In order to get some information on the polyaddition reaction mechanism, model reactions of 2-benzoxypentafluoropropene [CF2=C(CF3)O-)OCOC6H5] (BPFP) with dimethylphenylsilane, [(CH3)(2)SiHC6H5], BPFP with 1,1,3,3-tetramethyldisiloxane [(CH3)(2)SiH](20)}, and BFP with dimethylphenylsilane were carried out. The mechanism that the radical abstracts a hydrogen from silane compounds followed by the addition of perfluorcrisopropenyl groups was proposed. (C) 2004 Elsevier B.V. All rights reserved.