bis(2-chloro-2,2-difluoroethyl) difluoroformal | 771480-04-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: bis(2-chloro-2,2-difluoroethyl) difluoroformal
• 英文别名: Ethane, 1,1'-[(difluoromethylene)bis(oxy)]bis[2-chloro-2,2-difluoro-；1-chloro-2-[(2-chloro-2,2-difluoroethoxy)-difluoromethoxy]-1,1-difluoroethane
• CAS: 771480-04-7
• 化学式: C₅H₄Cl₂F₆O₂
• 分子量: 280.982
• InChiKey: JTMUGYAOYNIPNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis(2-chloro-2,2-difluoroethyl) difluoroformal 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以77.3%的产率得到2-[(2,2-Difluoro-vinyloxy)-difluoro-methoxy]-1,1-difluoro-ethene
  参考文献：
  名称：

  Synthesis and Properties of Partially Fluorinated Amorphous Ring Containing Polymers:  Poly[bis(2,2-difluorovinyl)formal], Poly[bis(2,2-difluorovinyl)difluoroformal], and Poly[bis(1-deuterio-2,2-difluorovinyl)difluoroformal]

  摘要：

  Three novel partially fluorinated monomers, bis(2,2-difluorovinyl)formal (I), bis(2,2-difluorovinyl)difluoroformal (II), and bis(1-deuterio-2,2-difluorovinyl)difluoroformal (III), were prepared. These monomers were polymerized in bulk via free radical mechanism. Monomer I produced a crosslinked polymer, but monomers II and III yielded amorphous polymers (II-P and III-P) having five- and six-membered rings along the backbone. Polymers II-P and III-P were soluble not only in fluorinated solvents but also in nonfluorinated solvents such as THF, 1, 4-dioxane, DMF, and DMSO. They have good thermal stability (onset of decomposition > 400 degreesC), high glass transition temperatures (105 degreesC), and low dielectric constant (1.98-1.82 at frequency ranging from 0.1 to 3 x 10(6) Hz). Furthermore, these polymers are completely amorphous and possess outstanding optical clarity extending from visible to near-IR regions. The refractive indices of both polymers were measured at various wavelengths to evaluate material dispersion. The material dispersions of II-P and III-P were similar and had low values, which are comparable to perfluorinated polymers and much lower than perdeuterioPMMA. The unique optical properties of these polymers make them attractive for use as optical materials.

  DOI：

  10.1021/ma049462d
• 作为产物：
  描述：

  bis(2-chloro-2,2-difluoroethyl) thionocarbonate 在 溴 、 三氟化锑 、 氯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 bis(2-chloro-2,2-difluoroethyl) difluoroformal
  参考文献：
  名称：

  氟代甲醛和氟醚的脱氟化为氟碳酸盐和氟代酸酯

  摘要：

  在室温下，用SbF 3和催化量的Br 2在SO 2 Cl 2中进行氟代甲醛和氟代醚的脱氟。将双（2-氯-2,2-二氟乙基）二氟甲醛和2-氯-1,1,2-三氟乙基甲基醚分别转化为碳酸双（2-氯-2,2-二氟乙基）酯和氯氟乙酸甲酯。

  DOI：

  10.1016/j.jfluchem.2003.12.006

文献信息

• Defluorinations of fluoroformal and fluoroether to fluorocarbonate and fluoroester
  作者：Yu Yang、František Mikeš、Yoshi Okamoto

  DOI：10.1016/j.jfluchem.2003.12.006

  日期：2004.5

  fluoroether were carried out with SbF3 and a catalytic amount of Br2 in SO2Cl2 at room temperature. Bis(2-chloro-2,2-difluoroethyl) difluoroformal and 2-chloro-1,1,2-trifluoroethyl methyl ether were converted to bis(2-chloro-2,2-difluoroethyl) carbonate and methyl chlorofluoroacetate, respectively.

  在室温下，用SbF 3和催化量的Br 2在SO 2 Cl 2中进行氟代甲醛和氟代醚的脱氟。将双（2-氯-2,2-二氟乙基）二氟甲醛和2-氯-1,1,2-三氟乙基甲基醚分别转化为碳酸双（2-氯-2,2-二氟乙基）酯和氯氟乙酸甲酯。
• First examples of stable polyfluorinated bis- and tris-(alkoxy)methyl cations
  作者：Viacheslav Petrov、Alexander A. Marchione、Will Marshall

  DOI：10.1016/j.jfluchem.2005.10.001

  日期：2006.1

  Stable polyfluorinated bis- and tris-(alkoxy)methyl cations were prepared by the reaction of the corresponding difluoroformals (RfO)(2)CF2 (R-f = -CH2CF3, -CH(CF3)(2), -CH2CF2Cl) with an excess of SbF5. Although the cation (CF3CH2O)(2)CF+ (1a) is stable at ambient temperature, the chlorinated analog (ClCF2CH2O)(2)CF+ (3a) can be generated only at low temperature in SO2ClF solvent and rapidly decomposes at ambient temperature. Although the salt [(CF3)(2)CHO](2)CF+SbnF5n+1- (2a) is slightly more stable than the salt of cation 3a, at ambient temperature it undergoes rapid disproportionation with formation of equal amounts of [(CF3)(2)CHO](3)C+SbnF5n+1- (2b) and CF3OCH(CF3)(2) (2c). Stable solid salt 2b (n = 2) 2b (n = 2) was isolated and fully characterized by H-1, F-19 and C-13 NMR spectroscopy and its structure was confirmed by single crystal X-ray diffraction. (C) 2005 Elsevier B.V. All rights reserved.
• Stable bis(2-chloro-2,2-difluoroethoxy)-fluoromethyl cation at room temperature
  作者：Yu Yang、Yoshiyuki Okamoto

  DOI：10.1016/j.jfluchem.2004.06.012

  日期：2004.12

  A stable carbocation was prepared by reacting bis(2-chloro-2,2-difluoroethyl) difluoroformal with SbF5. The carbocation's structure was confirmed by F-19, H-1 and C-13 NMR measurements. The carbocation is stable at room temperature for more than 2 weeks and was converted into the corresponding carbonate when reacted with water. (C) 2004 Elsevier B.V. All rights reserved.
• Synthesis and Properties of Partially Fluorinated Amorphous Ring Containing Polymers:  Poly[bis(2,2-difluorovinyl)formal], Poly[bis(2,2-difluorovinyl)difluoroformal], and Poly[bis(1-deuterio-2,2-difluorovinyl)difluoroformal]
  作者：Yu Yang、František Mikeš、Yasuhiro Koike、Yoshiyuki Okamoto

  DOI：10.1021/ma049462d

  日期：2004.10.1

  Three novel partially fluorinated monomers, bis(2,2-difluorovinyl)formal (I), bis(2,2-difluorovinyl)difluoroformal (II), and bis(1-deuterio-2,2-difluorovinyl)difluoroformal (III), were prepared. These monomers were polymerized in bulk via free radical mechanism. Monomer I produced a crosslinked polymer, but monomers II and III yielded amorphous polymers (II-P and III-P) having five- and six-membered rings along the backbone. Polymers II-P and III-P were soluble not only in fluorinated solvents but also in nonfluorinated solvents such as THF, 1, 4-dioxane, DMF, and DMSO. They have good thermal stability (onset of decomposition > 400 degreesC), high glass transition temperatures (105 degreesC), and low dielectric constant (1.98-1.82 at frequency ranging from 0.1 to 3 x 10(6) Hz). Furthermore, these polymers are completely amorphous and possess outstanding optical clarity extending from visible to near-IR regions. The refractive indices of both polymers were measured at various wavelengths to evaluate material dispersion. The material dispersions of II-P and III-P were similar and had low values, which are comparable to perfluorinated polymers and much lower than perdeuterioPMMA. The unique optical properties of these polymers make them attractive for use as optical materials.