1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is used as a reagent for electrophilic fluorination and also acts as a selective oxidizing agent. It is a highly effective and versatile source of electrophilic fluorine and also used in the synthesis of organofluorine.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) is used as a reagent for electrophilic fluorination and also acts as a selective oxidizing agent. It is a highly effective and versatile source of electrophilic fluorine and also used in the synthesis of organofluorine.
Solubility
Soluble in water, acetonitrile, alcohol, acetone, dimethylformamide, pyridine and dimethylsulfoxide.
Notes
Moisture sensitive. Incompatible with strong oxidizing agents, reducing agents, strong acids and bases.
RUO – Research Use Only
General References:
- SELECTFLUOR is a registered trademark of Air Products & Chemicals Inc.
- Water- and organic-soluble reagent developed by R. E. Banks and co-workers for electrophilic fluorination of a variety of substrates under mild conditions: USP 5,086,178 (1992 to Air Products & Chemicals, Inc.); review: J. Fluorine Chem., 87, 1 (1998). In acetonitrile, activated aromatics can be fluorinated in good yield: J. Chem. Soc., Perkin 1., 2069 (1996). Less active substrates can be fluorinated in the presence of triflic acid: Israel J. Chem., 39, 207 (1999). In acetonitrile, vinylsilanes undergo fluorodesilylation to give vinyl fluorides with retention of configuration: Chem. Commun., 233 (2001).
- Stabilized carbanions can be selectively mono- or difluorinated: J. Chem. Soc., Chem. Commun., 343 (1994); Tetrahedron, 51, 3587 (1995). Fluorinated steroids have been prepared from enol acetates or silyl enol ethers: J. Org. Chem., 58, 2791 (1993). 5-Fluoropyrimidine nucleosides can be obtained by treatment of protected nucleosides with the reagent in the presence of water or methanol, followed by elimination of the resulting fluorohydrin derivative: J. Org. Chem., 60, 7340 (1995).
- For use in the synthesis of fluorinated carbohydrates by reaction with glycals, see: J. Am. Chem. Soc., 119, 11743 (1997); J. Org. Chem., 64, 5264 (1999).
- For application to N-fluorination of amines, see: Chem. Commun., 1196 (2001). Review of mechanistic insight and applications of the reagent: Angew. Chem. Int Ed., 44, 192 (2005). Brief feature on uses in synthesis: Synlett, 807 (2006). Review of electrophilic N-F fluorinating agents: Chem. Rev., 96, 1737 (1996).