Selectfluor® Fluorinating Reagent  

An Electrophilic Fluorinating Compound for Pharmaceutical and Agricultural Applications

Chemical Name and Structure

1-Chloromethyl-4-Fluoro-1, 4-Diazoniabicyclo[2.2.2]Octane Bis-(Tetrafluoroborate)

Properties and Special Features

• MOL Formula: C₇ H₁₄ B₂ CIF₉ N₂
• MOL Weight: 354.26 g/MOLE
• Active Fluorine: 53.63 g/kg F-TEDA-BF₄ or 2.82 MMOL/g F-TEDA-BF₄
• Easy to Handle, Thermally Stable, Free-Flowing White Crystals
• Solubility*
  Water: 0.16 g/cc
  Acetonitrile: 0.05 g/cc
• High Regioselectivity
• High Purity (>98% F-Active)
• Commercially Packaged in Drums
• Available in Ton Quantities

* Also, very soluble in dilute hydrochloric acid, moderately soluble in dimethyl formamide (DMF), slightly soluble in acetone.

Safety and Handling Information

F-TEDA-BF₄ is a fairly strong oxidizing compound (capable of oxidizing Br to 1/2 Br₂, but not Cl to 1/2 Cl₂) and should be used and handled accordingly. Vigorous reactivity with some reducing agents and certain strong bases may be expected.

The reagent may be harmful if swallowed, inhaled, or absorbed through the skin. In particular the dust may be irritating or destructive to tissue of the mucous membranes, upper respiratory tract, eyes and skin and should be avoided.

The reagent material should be stored below 30 °C. Solid F-TEDA-B₄ decomposes exothermally at >100 ° C.

Use approved respirator, gloves and safety glasses when handling the product. Use in accordance with Air Products' Material Safety Data Sheet (supplied with material). Read all product labeling carefully.

F-TEDA-BF₄ The Fluorinating Reagent of Choice

The pharmaceutical and agricultural industries have, over time, experimented with and, in limited cases, used various fluorinating reagents, including N-F class electrophilic reagents. Many of the reagents, however, have serious limitations. Some have proven very costly and difficult to manufacture and are not commercially viable. Other reagents tried have lacked sufficient fluorinating power to make an impact on chemical synthesis, or leave behind impurities difficult to separate. Still others are dangerously reactive and difficult to handle.

F-TEDA-BF₄ solves these problems. The reagent, available in bulk, offers relatively high fluorination performance in a safe and easy to use manner. Covered by a 1992 composition of matter patent, F-TEDA-BF₄ is built upon a relatively common amine starting compound called triethylenediamine (TEDA, for short). Used in large quantities in the production of polyurethane foams, TEDA is also manufactured and marketed by Air Products.

Reagent Applications

F-TEDA-BF₄ is sufficiently reactive to selectively fluorinate a wide variety of organic molecules in both the pharmaceutical and agricultural industries. A sampling of the reagent's use in model fluorination reactions is shown below:

Note: The information is in PDF format. You will need the free Adobe Acrobat Reader to view this information.

6-Position Fluorination of Steroids (PDF, 45K)	16-Position Fluorination of Steroids (PDF, 30K)
Fluorination of Pyrimidine Bases (PDF, 28K)	Fluorination of Stabilized Carbanions (PDF, 30K)
Fluorination of Nucleoside Sugar Components(PDF, 47K)	Fluorination of Activated Aromatics (PDF, 32K)
Sulfides - Synthesis of 2 - Fluorosulfide,(PDF, 33K)	Olefins - Fluorination of styrene and substituted      (PDF, 36K)
Fluorination of ß-dicarbonyl compounds*     (PDF, 56K)

References

1. Lal, G. S., J. Org. Chem. 1993, 58, 2791.
2. Banks, R. E.; Mohialdin-Khaffa, S. N.; Lal, G. S.; Sharif, I.; Syvret, R. G., J. Chem. Soc., Chem. Commun. 1992, 595.
3. Lal, G. S., Synth. Commun. 1995, 25 (5), 725
4. Banks, R. E.; Lawrence, N. J.; Popplewell, A. L., J. Chem. Soc., Chem. Commun. 1994, 343.
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.