2,3-dichloro-2,3-difluoropropan-1-ol | 1647-61-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 2,3-dichloro-2,3-difluoropropan-1-ol
• 英文别名: 2,3-Dichloro-2,3-difluoropropanol；2,3-dichloro-2,3-difluoro-propan-1-ol；2,3-dichloro-2,3-difluoro-1-propanol；2,3-Dichlor-2,3-difluor-propan-1-ol；1-Propanol, 2,3-dichloro-2,3-difluoro-
• CAS: 1647-61-6
• 化学式: C₃H₄Cl₂F₂O
• 分子量: 164.967
• InChiKey: LQNWCZOSOUKVMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-2,3-difluoropropan-1-ol 在 硝酸 作用下， 反应 24.0h， 以65%的产率得到2,3-dichloro-2,3-difluoropropanoic acid
  参考文献：
  名称：

  Radical Copolymerization of α,β-Difluoroacrylic Acid with Vinylidene Fluoride.

  摘要：

  The synthesis of alpha,beta-difluoroacrylic acid (FHC=CF-CO2H, DiFAA) and its radical copolymerization with vinylidene fluoride (CH2=CF2, VDF) are presented. First, DiFAA was synthesized in three steps from the radical addition of methanol onto 1,2-dichloro-1,2-difluoroethylene leading to HCFCICFCICH2OH in 78% yield. Then, oxidation of the hydroxymethyl end-group followed by zinc-mediated dehalogenation of 2,3-dichloro-2,3-difluoropropanoic acid led to (Z) isomer of DiFAA in 29% overall yield. The homopolymerization of DiFAA was successfully achieved by radical polymerization initiated by tert-butylperoxypivalate (TBPPi) at 74 degrees C in 32% yield. Its radical copolymerization with VDF was carried out for the first time and at various compositions leading to functional poly(VDF). The resulting poly(VDF-co-DiFAA) copolymers, characterized by H-1 and F-19 NMR spectroscopies, exhibited a statistic microstructure. The kinetics of this radical copolymerization led to the assessment of the reactivity ratios (r(DiFAA) = 0.86 and r(VDF) = 0.34 at 74 degrees C), and showed that DiFAA was more reactive than VDF in copolymerization. Thermal properties of these poly(DiFAA-co-VDF) copolymers were also investigated. Differential scanning calorimetry analyses showed a decrease of the glass transition temperature (T-g) with increasing VDF content. Calculations using the Fox's equation led to the determination of the T-g for poly(DiFAA) homopolymer (T-g = 145 degrees C) in good agreement with the literature. Thermogravimetric analyses displayed increased thermostability of the resulting copolymers with increasing VDF content.

  DOI：

  10.1021/ma100506e
• 作为产物：
  描述：

  1,2-dichlorodifluoroethylene 、 二叔丁基过氧化物 以 甲醇 为溶剂， 生成 2,3-dichloro-2,3-difluoropropan-1-ol
  参考文献：
  名称：

  Process for preparing adducts of alcohols, ethers and esters with

  摘要：

  通用公式的制备化合物如下：##STR1##其中：R.sub.1 =H，或含有1至10个碳原子的烷基或酰基，R.sub.2、R.sub.3，相同或不同，可以是H，或含有1至10个碳原子的烷基，其中R.sub.1和R.sub.2可以共同形成含有2至10个碳原子的烷基基团，链中还可以包括最多2个氧原子，通过由1,2-二氯二氟乙烯引发的自由基引发的加成反应，将其与以下通用公式的醇、醚或酯反应：##STR2##其中：R.sub.1、R.sub.2、R.sub.3如上定义。

  公开号：

  US04827002A1

文献信息

• Synthesis of fluorinated telomers
  作者：J??r??me Guiot、Bruno Ameduri、Bernard Boutevin、Alain Fruchier

  DOI：10.1039/b205500g

  日期：2002.11.20

  this study has shown the influence of the fluorine and chlorine atoms of the olefin in directing the radical reaction. Hence, by its polar and steric effects, the chlorine atom in these alkenes does not favor the radical addition of HOCH2˙. In contrast, the inductive effects of the fluorine atom increase the reactivity of the hydroxymethyl radical. A decreasing reactivity series of different chlorofluoroolefins

  的自由基端粒化 1,1-二氟-2-氯乙烯 和 1,2-二氟-1,2-二氯乙烯 和 甲醇介绍了导致氯氟醇的化合物。合成条件的优化导致3-氯-2,2-二氟丙醇 和 2,3-二氯-2,3-二氟丙醇转化率分别为80％和89％，远高于文献报道的转化率。当达到最佳条件时2,5-双（叔丁基过氧）-2,5-二甲基己烷（DHBP）在407 K下用作引发剂，初始（[MeOH] 0 / [烯烃] 0）摩尔比R 0为40。烯烃 只能导致一种异构体，与之形成的两种异构体相反 三氟氯乙烯。此外，这项研究表明，氟和氯原子的影响烯烃指导自由基反应。因此，由于其极性和空间效应，这些化合物中的氯原子烯烃不利于HOCH 2 the的自由基加成。相反，氟原子的感应作用增加了羟甲基自由基的反应性。相对于自由基加成，不同氯氟烯烃的反应性系列下降甲醇提出了每种端粒化的最佳条件：F 2 C CCl 2 > F 2 C CFCl > ClCF
• Radical additions to 1,2-dichlorodifluoroethene
  作者：S. Modena、A. Fontana、G. Moggi

  DOI：10.1016/s0022-1139(00)80526-6

  日期：1985.10

  Fluorine containing alcohols, esters and ethers have been obtained by peroxide induced radical addition of alcohols, esters and ethers to 1,2-dichlorodifluoroethene.

  通过过氧化物诱导将醇，酯和醚自由基加成到1，2-二氯二氟乙烯中，已经获得了含氟的醇，酯和醚。
• The Radiation-Induced Addition Reaction of Alcohols to Perhalogeno Olefins
  作者：Hiroshige Muramatsu

  DOI：10.1021/jo01054a009

  日期：1962.7
• Process for preparing adducts of alcohols, ethers and esters with
  申请人：Montefluos S.P.A.

  公开号：US04827002A1

  公开（公告）日：1989-05-02

  There are prepared compounds of general formula: ##STR1## wherein: R.sub.1 =H, or alkyl or acyl containing from 1 to 10 carbon atoms, R.sub.2, R.sub.3, like or unlike each other, may be H, or an alkyl containing from 1 to 10 carbon atoms and where R.sub.1 and R.sub.2 may form, together, an alkylene group containing from 2 to 10 carbon atoms, and optionally including up to 2 oxygen atoms in the chain, by means of addition reaction induced by radicalic starters of 1,2-dichlorodifluoroethylene to alcohols, ethers or esters of general formula: ##STR2## wherein: R.sub.1, R.sub.2, R.sub.3 are defined as above.

  通用公式的制备化合物如下：##STR1##其中：R.sub.1 =H，或含有1至10个碳原子的烷基或酰基，R.sub.2、R.sub.3，相同或不同，可以是H，或含有1至10个碳原子的烷基，其中R.sub.1和R.sub.2可以共同形成含有2至10个碳原子的烷基基团，链中还可以包括最多2个氧原子，通过由1,2-二氯二氟乙烯引发的自由基引发的加成反应，将其与以下通用公式的醇、醚或酯反应：##STR2##其中：R.sub.1、R.sub.2、R.sub.3如上定义。
• Radical Copolymerization of α,β-Difluoroacrylic Acid with Vinylidene Fluoride.
  作者：Frédéric Boschet、Jean-Marc Cracowski、Véronique Montembault、Bruno Ameduri

  DOI：10.1021/ma100506e

  日期：2010.6.8

  The synthesis of alpha,beta-difluoroacrylic acid (FHC=CF-CO2H, DiFAA) and its radical copolymerization with vinylidene fluoride (CH2=CF2, VDF) are presented. First, DiFAA was synthesized in three steps from the radical addition of methanol onto 1,2-dichloro-1,2-difluoroethylene leading to HCFCICFCICH2OH in 78% yield. Then, oxidation of the hydroxymethyl end-group followed by zinc-mediated dehalogenation of 2,3-dichloro-2,3-difluoropropanoic acid led to (Z) isomer of DiFAA in 29% overall yield. The homopolymerization of DiFAA was successfully achieved by radical polymerization initiated by tert-butylperoxypivalate (TBPPi) at 74 degrees C in 32% yield. Its radical copolymerization with VDF was carried out for the first time and at various compositions leading to functional poly(VDF). The resulting poly(VDF-co-DiFAA) copolymers, characterized by H-1 and F-19 NMR spectroscopies, exhibited a statistic microstructure. The kinetics of this radical copolymerization led to the assessment of the reactivity ratios (r(DiFAA) = 0.86 and r(VDF) = 0.34 at 74 degrees C), and showed that DiFAA was more reactive than VDF in copolymerization. Thermal properties of these poly(DiFAA-co-VDF) copolymers were also investigated. Differential scanning calorimetry analyses showed a decrease of the glass transition temperature (T-g) with increasing VDF content. Calculations using the Fox's equation led to the determination of the T-g for poly(DiFAA) homopolymer (T-g = 145 degrees C) in good agreement with the literature. Thermogravimetric analyses displayed increased thermostability of the resulting copolymers with increasing VDF content.