1,1,1,2,2,3,3,4-八氟丁烷 | 662-35-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 中文名称: 1,1,1,2,2,3,3,4-八氟丁烷
• 英文名称: 1,1,1,2,2,3,3,4-octafluorobutane
• 英文别名: 1H,1H-perfluorobutane；1,1,1,2,2,3,3,4-octafluoro-butane
• CAS: 662-35-1
• 化学式: C₄H₂F₈
• mdl: MFCD00236695
• 分子量: 202.047
• InChiKey: XALFNZSGFNPWSM-UHFFFAOYSA-N

物化性质

• 熔点：
  -132°C
• 沸点：
  25°C
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 危险等级：
  IRRITANT, GAS
• 危险品标志：
  Xi
• 安全说明：
  S23,S38
• 危险品运输编号：
  UN 3163

反应信息

• 作为反应物：
  描述：

  1,1,1,2,2,3,3,4-八氟丁烷 、 2-碘异丙基苯 在 四(三苯基膦)钯 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.5h， 生成 (Z)-1-(2-isopropylphenyl)perfluorobut-1-ene 、 (E)-1-(2-isopropylphenyl)perfluorobut-1-ene
  参考文献：
  名称：

  An efficient stereoselective preparation of cis-perfluoroalkenylzinc reagents [(E)-RFCFCFZnCl] by the metallation of 1H,1H-perfluoroalkanes and their derivatization to cis-1-arylperfluoroalkenes [(Z)-RFCFCFAr]

  摘要：

  Various 1H1H-perfluoroalkanes (RFCF2CH2F, R-F = CF3, C2F5, C4F9, C5F11, C6F13, C10F21) were metallated using LDA in a THF solution of ZnCl2 at RT or -78 degrees C to produce the corresponding perfluoroalkenylzinc reagents (RFCF=CFZnCl) in a cis-selective fashion. An increased yield (75-83%) and cis-selectivity (>89%) of the perfluoroalkenylzinc reagents were observed for metallation reactions performed at -78 degrees C. The cis selectivity was excellent for 1H,1H-perfluoroalkanes with larger RF groups (C4F9, C5F11, C6F13, >96%). The cis-perfluoroalkenylzinc [(E)-RFCF=CFZnCl] reagents were coupled with aryl iodides to obtain cis-1-arylperfluoroalkenes [(Z)-RFCF=CFAr] in 71-95% isolated yields. The cis-perfluoroalkenylzinc reagents upon iodinolysis produced cis-1-iodoperfluoroalkenes [(E)-RFCF=CFI] in 68-70% isolated yield. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.12.022
• 作为产物：
  描述：

  丁烷 在 cobalt (III) fluoride 作用下， 以2.7%的产率得到1H,3H-octafluorobutane
  参考文献：
  名称：

  丁烷在三氟化钴上的氟化

  摘要：

  丁烷在三氟化钴上的氟化产生了部分氟化化合物的复杂混合物：已鉴定出其中的51种化合物，占产品总量的99％以上。大部分是聚氟丁烷，但1-2％是聚氟-2-甲基丙烷。该反应没有合成效用。氟化具有一定的选择性：仲CH比初CH更容易转化为CF，双价和邻位氟减少了特定H的取代难度。氟化计算机仅部分成功，也许是因为氟化过程部分是通过简单的F取代H进行的，部分是通过烯烃进行的：该模型仅允许前者进行。

  DOI：

  10.1016/s0022-1139(00)83070-5

文献信息

• An efficient stereoselective preparation of cis-perfluoroalkenylzinc reagents [(E)-RFCFCFZnCl] by the metallation of 1H,1H-perfluoroalkanes and their derivatization to cis-1-arylperfluoroalkenes [(Z)-RFCFCFAr]
  作者：Anilkumar Raghavanpillai、Donald J. Burton

  DOI：10.1016/j.jfluchem.2005.12.022

  日期：2006.5

  Various 1H1H-perfluoroalkanes (RFCF2CH2F, R-F = CF3, C2F5, C4F9, C5F11, C6F13, C10F21) were metallated using LDA in a THF solution of ZnCl2 at RT or -78 degrees C to produce the corresponding perfluoroalkenylzinc reagents (RFCF=CFZnCl) in a cis-selective fashion. An increased yield (75-83%) and cis-selectivity (>89%) of the perfluoroalkenylzinc reagents were observed for metallation reactions performed at -78 degrees C. The cis selectivity was excellent for 1H,1H-perfluoroalkanes with larger RF groups (C4F9, C5F11, C6F13, >96%). The cis-perfluoroalkenylzinc [(E)-RFCF=CFZnCl] reagents were coupled with aryl iodides to obtain cis-1-arylperfluoroalkenes [(Z)-RFCF=CFAr] in 71-95% isolated yields. The cis-perfluoroalkenylzinc reagents upon iodinolysis produced cis-1-iodoperfluoroalkenes [(E)-RFCF=CFI] in 68-70% isolated yield. (C) 2006 Elsevier B.V. All rights reserved.
• The fluorination of Butane over cobalt trifluoride
  作者：James Burdon、Saleh T. Ezmirly、Thomas N. Huckerby

  DOI：10.1016/s0022-1139(00)83070-5

  日期：1988.8

  The fluorination of butane over cobalt trifluoride has given a complex mixture of partially fluorinated compounds: 51 of these have been identified, comprising over 99% of the products. Most were polyfluorobutanes but 1-2% were polyfluoro-2-methylpropanes. The reaction has no synthetic utility. There was some selectivity in the fluorination: secondary C-H was converted into C-F more easily then primary

  丁烷在三氟化钴上的氟化产生了部分氟化化合物的复杂混合物：已鉴定出其中的51种化合物，占产品总量的99％以上。大部分是聚氟丁烷，但1-2％是聚氟-2-甲基丙烷。该反应没有合成效用。氟化具有一定的选择性：仲CH比初CH更容易转化为CF，双价和邻位氟减少了特定H的取代难度。氟化计算机仅部分成功，也许是因为氟化过程部分是通过简单的F取代H进行的，部分是通过烯烃进行的：该模型仅允许前者进行。