1,2-Dinitro-hexafluorpropan | 507-58-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1,2-Dinitro-hexafluorpropan
• 英文别名: 1,1,1,2,3,3-hexafluoro-2,3-dinitro-propane；hexafluoro-1,2-dinitro-propane；Hexafluor-1,2-dinitro-propan；2,3-Dinitro-1,1,1,2,3,3,-hexafluor-propan；1,1,1,2,3,3-Hexafluor-2,3-dinitro-propan；1,2-Dinitroperfluorpropan；Hexafluoro-1,2-dinitropropane；1,1,1,2,3,3-hexafluoro-2,3-dinitropropane
• CAS: 507-58-4
• 化学式: C₃F₆N₂O₄
• 分子量: 242.034
• InChiKey: HNGYZRZFNYQFMT-UHFFFAOYSA-N

物化性质

• 沸点：
  76 °C
• 密度：
  1.637 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  六氟丙烯 在 二氧化氮 作用下， 以60%的产率得到1,2-Dinitro-hexafluorpropan
  参考文献：
  名称：

  Bayley, E.; Birchall, J. M.; Haszeldine, R. N., Journal of the Chemical Society C: Organic

  摘要：

  DOI：

文献信息

• Kinetics and Mechanism of the Thermal Gas-Phase Reaction between NO₂ and Perfluoropropene
  作者：R. M. Romano、Joanna Czarnowski

  DOI：10.1524/zpch.218.5.575.30504

  日期：2004.5.1

  The reaction of NO₂ with perfluoropropene (C₃F₆) has been studied at 413.1, 421.0 and 432.8K, using a conventional static system. The initial pressure of NO₂ was varied between 43.6 and 204.0Torr and that of C₃F₆ between 10.2 and 108.5Torr. Several experiments were made adding CF₄, varying its pressure from 338.8 to 433.6Torr. Four products were observed: NO and perfluoropropene oxide (PFPO), formed in equivalent amounts, CF₃CF(NO₂)CF₂NO₂ and CF₃C(O)CF₂NO₂. The relation R=[PFPO]/([CF₃CF(NO₂)CF₂NO₂] + [CF₃C(O)CF₂NO₂]) increases with temperature and decreases as the concentration of NO₂ and the total pressure M increase. The yields of PFPO, based on the amount of C₃F₆ consumed, varied between 63 and 89% and those of CF₃CF(NO₂)CF₂NO₂ between 0.33 and 0.08%. Increasing the temperature, the yields of CF₃C(O)CF₂NO₂ decreased from 0.04 to 0.01%. The reaction is homogenous and the consumption rate of perfluoropropene, −d[C₃F₆]/dt= k ₁[C₃F₆][NO₂], is independent of the total pressure. The following mechanism is postulated to explain the experimental results: 1) C₃F₆ + NO₂ → CF₃C^•FCF₂NO₂, 2) CF₃C^•FCF₂NO₂ → PFPO+NO, 3) CF₃C^•FCF₂NO₂ + NO₂+M → CF₃CF(NO₂)CF₂NO₂+M, 4) CF₃C^•FCF₂NO₂ + NO₂ → CF₃C(O)CF₂NO₂+FNO. k ₁=(4.57±1.4)×10⁶exp(−(15.44±1.2) kcal mol⁻¹/RT) dm³mol⁻¹s⁻¹. The value of k ₂, the rate constant for the unimolecular dissociation of the radical CF₃C^•FCF₂NO₂, was found to be of order of 10¹⁴s⁻¹.

  摘要：研究了NO₂与全氟丙烯（C₃F₆）在413.1、421.0和432.8K下的反应，采用传统的静态系统。NO₂的初始压力在43.6至204.0Torr之间变化，C₃F₆的压力在10.2至108.5Torr之间变化。进行了几次实验，添加了CF₄，将其压力从338.8至433.6Torr之间变化。观察到四种产物：NO和全氟丙烯氧化物（PFPO），它们的数量相等，CF₃CF(NO₂)CF₂NO₂和CF₃C(O)CF₂NO₂。关系R=[PFPO]/([CF₃CF(NO₂)CF₂NO₂]+[CF₃C(O)CF₂NO₂])随着温度的升高而增加，随着NO₂和总压力M的浓度增加而减小。基于消耗的C₃F₆的数量，PFPO的产率在63％至89％之间变化，CF₃CF(NO₂)CF₂NO₂的产率在0.33％至0.08％之间变化。随着温度的升高，CF₃C(O)CF₂NO₂的产率从0.04降至0.01％。反应是均相的，全氟丙烯的消耗速率，−d[C₃F₆]/dt=k₁[C₃F₆][NO₂]，独立于总压力。提出以下机理来解释实验结果：1）C₃F₆+NO₂→CF₃C^•FCF₂NO₂，2）CF₃C^•FCF₂NO₂→PFPO+NO，3）CF₃C^•FCF₂NO₂+NO₂+M→CF₃CF(NO₂)CF₂NO₂+M，4）CF₃C^•FCF₂NO₂+NO₂→CF₃C(O)CF₂NO₂+FNO。k₁=(4.57±1.4)×10⁶exp(−(15.44±1.2) kcal mol⁻¹/RT) dm³mol⁻¹s⁻¹。发现k₂，自由基CF₃C^•FCF₂NO₂的单分子解离速率常数，约为10¹⁴s⁻¹。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.8, 2.4, page 2 - 54
  作者：

  DOI：——

  日期：——
• Knunjanz; Fokin, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 1439,1450;engl.Ausg.S.1462,1471
  作者：Knunjanz、Fokin

  DOI：——

  日期：——
• Fluorinated C-Nitroso Compounds. The Action of Nitric Oxide on Some Fluoroolefins. I
  作者：J. D. PARK、A. P. STEFANI、G. H. CRAWFORD、J. R. LACHER

  DOI：10.1021/jo01067a069

  日期：1961.9
• Knunjanz; Fokin, Doklady Akademii Nauk SSSR, 1956, vol. 111, p. 1035,1037
  作者：Knunjanz、Fokin

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  日期：——