氟试剂

化合物

氟试剂(英语:Selectfluor),又名1-氯甲基-4-氟-1,4-氮鎓双环[2.2.2]辛烷双(四氟硼酸盐),是Air Products and Chemicals公司的商品名,在化学中用作供体试剂。它是杂环化合物DABCO的衍生物。它最初于1992年被报道,为无色固体。[2]它在有机氟化学中用作亲电氟化试剂。

氟试剂
IUPAC名
1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate
别名 F-TEDA
1-氯甲基-4-氟-1,4-氮𬭩双环[2.2.2]辛烷双(四氟硼酸盐)
氟化剂
识别
CAS号 140681-55-6  checkY
PubChem 2724933
ChemSpider 2007047
SMILES
 
  • [B-](F)(F)(F)F.[B-](F)(F)(F)F.C1C[N+]2(CC[N+]1(CC2)CCl)F
InChI
 
  • 1/C7H14ClFN2.2BF4/c8-7-10-1-4-11(9,5-2-10)6-3-10;2*2-1(3,4)5/h1-7H2;;/q+2;2*-1
InChIKey TXRPHPUGYLSHCX-UHFFFAOYAI
EINECS 414-380-4
性质
化学式 C7H14B2ClF9N2
摩尔质量 354.26 g·mol⁻¹
外观 无色固体
熔点 190 °C(463 K)(>80 °C时开始分解,实际熔点不明[1]
相关物质
相关化学品 1-氯甲基-1,4-二氮杂二环[2.2.2]辛烷氯化物
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

制备

氟试剂可由下列方法制备:[2]

 

参考文献

  1. ^ Banks, R. Eric; Murtagh, Vincent; An, Ilhwan; Maleczka, Robert E. 1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane Bis(tetrafluoroborate). Encyclopedia of Reagents for Organic Synthesis. 2007. ISBN 978-0471936237. doi:10.1002/047084289X.rc116.pub2. 
  2. ^ 2.0 2.1 Banks, R. Eric; Mohialdin-Khaffaf, Suad N.; Lal, G. Sankar; Sharif, Iqbal; Syvret, Robert G. 1-Alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts: a novel family of electrophilic fluorinating agents. Journal of the Chemical Society, Chemical Communications. 1992, (8): 595. doi:10.1039/C39920000595. 

拓展阅读

  1. Lal, G. S., J. Org. Chem. 1993, 58, 2791.
  2. Lal, G. S., Synth. Commun. 1995, 25 (5), 725.
  3. Banks, R. E.; Lawrence, N. J.; Popplewell, A. L., J. Chem. Soc., Chem. Commun. 1994, 343.
  4. Banks, R. E., J. Fluorine Chem. 1998, 87, 1.
  5. Zupan, M.; Iskra, J.; Stavber, S., J. Fluorine Chem., 1995, 70, 7.
  6. Matthews, D.P.; Miller, S. C.; Jarvi E. T.; Sabol, J. S.; McCarthy, J. R., Tettrahedron Lett. 1993, 34 (19), 3057.
  7. Brunaus, M.; Dell, C. P.; Owton, W. M., J. Fluorine Chem. 1994, 201.
  8. McClinton, M. A. ; Sik, V., J. Chem. Soc., Perkin Trans. I, 1992, 1891.
  9. Hodson, H. F.; Madge, D. J.; Slawin, A. N. Z.; Widdawson, D. A.; Williams, D. J., Tetrahedron, 1994, 50 (6), 1899.
  10. Stavber, S.; Zupan, M., J. Chem. Soc., Chem. Commun. 1994, 149.
  11. Stavber, S.; Sotler, J.; Zupan, M., Tettrahedron Lett. 1994, 35 (7), 1105.

专利文献

  • US 5459267  "1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts and their application as fluorinating agents"
  • US 55227493  "Fluorinated Sulfonamide Derivatives"
  • US 5086178  "Fluorinated Diazabicycloalkane Derivatives"
  • US 5473065  "Fluorinated Diazabicycloalkane Derivatives"
  • US 5442084  "Method of Selective Fluorination"