氟试剂

氟试剂（英语：Selectfluor），又名1-氯甲基-4-氟-1,4-氮𬭩双环[2.2.2]辛烷双(四氟硼酸盐)，是Air Products and Chemicals公司的商品名，在化学中用作氟供体试剂。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  Y
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. 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"