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AIR PRODUCTS FLUORINATING REAGENTS

SELECTFLUOR® FLUORINATING REAGENTS

The Selectfluor® reagent family is a series of N-F type electrophilic fluorinating compounds for use in pharmaceutical and agricultural applications. The family includes Selectfluor I and Selectfluor II reagents. Both are versatile, safe and easy-to-use reagents that fluorinate specific positions in complex molecules. Selectfluor reagent rapidly fluorinates a wide range of organic molecules under mild conditions with high efficiency and selectivity. In many cases, Selectfluor reagent can replace toxic or explosive fluorinating reagents such as FClO₃ or CF₃OF. Selectfluor reagents offer a convenient, less complicated alternative to your fluorination process.

Chemical Names and Structures

Selectfluor I	1-Chloromethyl-4-Fluoro-1, 4-Diazoniabicyclo[2.2.2]Octane Bis-(Tetrafluoroborate)
Selectfluor II	1-Methyl-4-Fluoro-1, 4-Diazoniabicyclo[2.2.2]Octane Bis-(Tetrafluoroborate)

Properties and Special Features

* Very soluble in dilute hydrochloric acid, moderately soluble in dimethyl formamide (DMF), and slightly soluble in acetone.
Selectfluor® is a registered trademark of Air Products and Chemicals, Inc.

Selectfluor® – the Fluorinating Reagents of Choice

The pharmaceutical and agricultural industries have experimented with and in limited cases, used various fluorinating reagents, including N-F type electrophilic reagents. Many of them, however, have serious limitations. Some have proven to be very costly and difficult to manufacture and are not commercially viable. Other fluorinating reagents tried have lacked sufficient fluorinating efficiency to make a cost-effective impact on chemical synthesis, or have created impurities that required additional manufacturing steps to remove the impurities from the process.

Selectfluor reagent helps to solve all of these problems. Selectfluor reagent is packaged in convenient quantities for R&D evaluation and commercial manufacturing. Technical assistance is available to provide a solution to your fluorination challenge. Call 800-233-4334 to review your process with our fluorination experts.

Safety and Handling Information

Selectfluor® reagents are moderately strong oxidizing compounds (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 reagents 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 Selectfluor reagent decomposes exothermally at >100°C.

An approved respirator, gloves and safety glasses should be used when handling this product. Use in accordance with Material Safety Data Sheet (supplied with material). Read all product labeling carefully.

Reagent Applications

Selectfluor 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:

More Examples of Fluorination

• 6-Position Fluorination of Steroids    (PDF, 45K) • Fluorination of Pyrimidine Bases    (PDF, 28K) • Fluorination of Nucleoside Sugar Components   (PDF, 47K) • Sulfides - Synthesis of 2 - Fluorosulfide,   (PDF, 33K) • Fluorination of ß-dicarbonyl compounds*    (PDF, 56K)

• 16-Position Fluorination of Steroids    (PDF, 30K) • Fluorination of Stabilized Carbanions    (PDF, 30K) • Fluorination of Activated Aromatics    (PDF, 32K) • Olefins - Fluorination of styrene and substituted    (PDF, 36K)

Selectfluor Flourinating Reagents Datasheet (PDF)

Material Safety Data Sheets

• Selectfluor I (us)	• Selectfluor II (us)
• Selectfluor I (eu)	• Selectfluor II (eu)

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

Reference:

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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.
12. Singh, R.P. and Shreeve, J.M., ACC. Chem. Res. 2004, 37, 31.

Scott Medical Products also offers Air Product's Deoxo-Fluor fluorinating reagent.