2,2,3,3,4,4,5,5-octafluoropentyl chloroformate | 2157-80-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2,2,3,3,4,4,5,5-octafluoropentyl chloroformate
• 英文别名: 1,1,5-trihydroperfluoropentyl chloroformate；<1,1,5-Trihydro-perfluor-pentyl>-chlorocarbonat；2,2,3,3,4,4,5,5-octafluoropentyl carbonochloridate
• CAS: 2157-80-4
• 化学式: C₆H₃ClF₈O₂
• 分子量: 294.529
• InChiKey: JOTNSWIDQIYHIK-UHFFFAOYSA-N

物化性质

• 沸点：
  50 °C(Press: 11 Torr)
• 密度：
  1.6475 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4,5,5-octafluoropentyl chloroformate 在 sodium peroxide 作用下， 反应 2.0h， 以80%的产率得到di(1,1,5-trihydro-perfluoropentyl)peroxydicarbonate
  参考文献：
  名称：

  Synthesis and properties of di(polyfluoroalkyl) peroxydicarbonates

  摘要：

  Synthesis of di(polyfluoroalkyl)peroxydicarbonates [X(CF(2)) (n) CH(2)OC(O)O](2), where X = H, F; n = 1, 2, 4, 6 (yield 80%) involves the step of the chloroformate formation (yield up to 93%) via the phosgenation of polyfluorinated alcohols followed by the reaction with sodium peroxide. The rate constant of monomolecular decomposition k (term) was found to decrease as the polyfluoroalkyl groups were incorporated into the peroxide: it equaled 3.30 and 3.10 s(-1) for X = H, n = 2 and 4, respectively, and 7.36 s(-1) for di-n-butylperoxydicarbonate. The new peroxides are a source of the polyfluoroalkoxy radicals and nano-modifiers of the polymers to improve their heat resistance and light stability.

  DOI：

  10.1134/s1070363211050100
• 作为产物：
  描述：

  光气 、 2,2,3,3,4,4,5,5-八氟-1-戊醇 在 N,N-二甲基甲酰胺 作用下， 反应 2.5h， 以90%的产率得到2,2,3,3,4,4,5,5-octafluoropentyl chloroformate
  参考文献：
  名称：

  Catalytic synthesis of polyfluoroalkyl chloroformates

  摘要：

  DOI：

  10.1134/s1070363208050289

文献信息

• Synthesis of Highly Fluorinated Chloroformates and Their Use as Derivatizing Agents for Hydrophilic Compounds and Drinking-Water-Disinfection By-Products
  作者：Marco Vincenti、Nicoletta Ghiglione、Maria Carmen Valsania、Patrizia Davit、Susan D. Richardson

  DOI：10.1002/hlca.200490034

  日期：2004.2

  A rapid, safe, and efficient procedure was developed to synthesize, on a small scale, fluorinated chloroformates often required to perform analytical derivatizations. This new family of agents allows straightforward derivatization of highly polar compounds (with multiple hydroxy, carboxy, and amino substituents) in the aqueous phase, compatible with GC and GC/MS analysis. A goal of this work was to

  开发了一种快速，安全和有效的方法，以小规模合成通常需要进行分析衍生化的氟化氯甲酸酯。这种新的试剂家族允许在水相中直接衍生出高极性化合物（具有多个羟基，羧基和氨基取代基），与GC和GC / MS分析兼容。这项工作的目标是开发一种衍生化程序，使之能够检测和鉴定饮用水中的高极性消毒副产物。
• Metal Halide Catalyzed Ortho Ester Formation^1a,b
  作者：Marion E. Hill、Daniel T. Carty、Derek Tegg、Janis C. Butler、Albert F. Stang

  DOI：10.1021/jo01013a025

  日期：1965.2
• Catalytic synthesis of polyfluoroalkyl chloroformates
  作者：A. I. Rakhimov、L. A. Butkovskaya、A. V. Baklanov

  DOI：10.1134/s1070363208050289

  日期：2008.5
• Synthesis and properties of di(polyfluoroalkyl) peroxydicarbonates
  作者：A. I. Rakhimov、L. A. Butkovskaya

  DOI：10.1134/s1070363211050100

  日期：2011.5

  Synthesis of di(polyfluoroalkyl)peroxydicarbonates [X(CF(2)) (n) CH(2)OC(O)O](2), where X = H, F; n = 1, 2, 4, 6 (yield 80%) involves the step of the chloroformate formation (yield up to 93%) via the phosgenation of polyfluorinated alcohols followed by the reaction with sodium peroxide. The rate constant of monomolecular decomposition k (term) was found to decrease as the polyfluoroalkyl groups were incorporated into the peroxide: it equaled 3.30 and 3.10 s(-1) for X = H, n = 2 and 4, respectively, and 7.36 s(-1) for di-n-butylperoxydicarbonate. The new peroxides are a source of the polyfluoroalkoxy radicals and nano-modifiers of the polymers to improve their heat resistance and light stability.