4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione | 485403-06-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione
• 英文别名: 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-1,2-dithiole-3-thione；4-Fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiol-3-thione；4-fluoro-5-(1,1,2,2-tetrafluoroethyl)dithiole-3-thione
• CAS: 485403-06-3
• 化学式: C₅HF₅S₃
• 分子量: 252.253
• InChiKey: MRAGIUXOXPHMBH-UHFFFAOYSA-N

物化性质

• 沸点：
  206.4±50.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-1,2-dithiole-3-thione S-oxide
  参考文献：
  名称：

  Chlorination and oxidation of 4-fluoro-5-tetrafluoroethyl-1,2-dithiole-3-thione

  摘要：

  Chlorination of 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-1,2-dithiole-3-thione with an equimolar amount of chlorine or sulfuryl chloride gives 3-chlorosulfanyl-4-fluoro-5-(1.1,2,2-tetrafluoroethyl)-1,2-dithiolium chloride. The reaction of the title compound with excess chlorinating agent leads to 3,3,4,5-tetrachloro-4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-1,2-dithiolane. By oxidation and oxidative imination of 4-fluoro-5-(l,1,2,2-tetrafluoroethyl)-1,2-dithiole-3-thione, the corresponding S-oxide and sulfmide were obtained, respectively.

  DOI：

  10.1134/s1070428006010192
• 作为产物：
  描述：

  1,1-bis(ethylthio)-2,3,3,4,4,5,5-heptafluoropentene 在 sulfur 、 magnesium bromide 作用下， 反应 0.08h， 以80%的产率得到4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  氟化乙烯酮二硫缩醛。第九部分 新型氟化3 H -1,2-二硫代-3-硫酮的合成及一些化学性质

  摘要：

  通过将相应的乙烯酮二硫缩醛与溴化镁和元素硫一起加热，制得4-氟-5-全氟烷基-3 H -1,2-二硫基-3-硫酮。它们在环加成反应中以亲双烯体和1,3-偶极子的形式反应，生成新的氟化有机硫化合物。

  DOI：

  10.1016/s0040-4039(02)01179-6

文献信息

• Synthesis of 3-imino and 3-ylideno derivatives of 4-fluoro-5-polyfluoroalkyl-1,2-dithiolenes
  作者：I. N. Fesun、V. M. Timoshenko、Yu. G. Shermolovich

  DOI：10.1134/s1070428002120187

  日期：2006.2

  Reactions of 4-fluoro-5-polyfluoroalkyl-1,2-dithiol-3-thiones with hydroxylamine and hydrazines occur with replacement of the thiocarbonyl by imino group affording oximes and hydrazones respectively. N-Alkyl- and N-aryl-3-imino-1,2-dithiolenes formed in reactions of 3-chlorothio-1,2-dithiolium salts with primary alkyl- or arylamines. 3-Chlorothio-1,2-dithiolium salts react with compounds possessing an active methylene group yielding 3-ylideno derivatives of 1,2-dithiolenes.
• Reduction of 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione with sodium sulfide: Synthesis of fluoro-containing sulfur-rich heterocycles
  作者：Igor M. Fesun、Alexander B. Rozhenko、Vadim M. Timoshenko

  DOI：10.1016/j.jfluchem.2006.02.013

  日期：2006.6

  Treatment of 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-3H-1,2-dithiole-3-thione with 2 equivalents of sodium sulfide gives after acidification 3,4-difluoro-2-mercapto-1,6,6a gimel(4)-trithiapentalene, which can be further reduced by sodium sulfide to 3,5-difluoro-4-mercapto-thiopyran-2-thione. (c) 2006 Elsevier B.V. All rights reserved.
• Fluorinated ketene dithioacetals. Part IX. Synthesis and some chemical properties of new fluorinated 3H-1,2-dithiole-3-thiones
  作者：Vadim M Timoshenko、Jean-Philippe Bouillon、Yuriy G Shermolovich、Charles Portella

  DOI：10.1016/s0040-4039(02)01179-6

  日期：2002.8

  4-Fluoro-5-perfluoroalkyl-3H-1,2-dithiole-3-thiones were prepared by heating the corresponding ketene dithioacetals with magnesium bromide and elemental sulfur. They reacted as dienophiles and 1,3-dipoles in cycloaddition reactions to give new fluorinated organosulfur compounds.

  通过将相应的乙烯酮二硫缩醛与溴化镁和元素硫一起加热，制得4-氟-5-全氟烷基-3 H -1,2-二硫基-3-硫酮。它们在环加成反应中以亲双烯体和1,3-偶极子的形式反应，生成新的氟化有机硫化合物。
• Chlorination and oxidation of 4-fluoro-5-tetrafluoroethyl-1,2-dithiole-3-thione
  作者：I. N. Fesun、V. M. Timoshenko、A. N. Chernega、Yu. G. Shermolovich

  DOI：10.1134/s1070428006010192

  日期：2006.1

  Chlorination of 4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-1,2-dithiole-3-thione with an equimolar amount of chlorine or sulfuryl chloride gives 3-chlorosulfanyl-4-fluoro-5-(1.1,2,2-tetrafluoroethyl)-1,2-dithiolium chloride. The reaction of the title compound with excess chlorinating agent leads to 3,3,4,5-tetrachloro-4-fluoro-5-(1,1,2,2-tetrafluoroethyl)-1,2-dithiolane. By oxidation and oxidative imination of 4-fluoro-5-(l,1,2,2-tetrafluoroethyl)-1,2-dithiole-3-thione, the corresponding S-oxide and sulfmide were obtained, respectively.