N-Fluoropyridinium triflate

N-Fluoropyridinium triflate is an organofluorine compound with the formula [C5H5NF]O3SCF3. It is a white solid with low solubility in polar organic solvents. The compound is used as an electrophilic fluorinating agent. It is a salt, consisting of the N-fluoropyridinium cation ([C5H5NF]+) and the triflate anion.[1] Related reagents include Selectfluor, which is also an N-fluorinated salt.

N-Fluoropyridinium triflate
Names
Preferred IUPAC name
1-Fluoropyridin-1-ium trifluoromethanesulfonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.154.995
  • InChI=1S/C5H5FN.CHF3O3S/c6-7-4-2-1-3-5-7;2-1(3,4)8(5,6)7/h1-5H;(H,5,6,7)/q+1;/p-1
    Key: JFZMMCYRTJBQQI-UHFFFAOYSA-M
  • c1cc[n+](cc1)F.C(F)(F)(F)S(=O)(=O)[O-]
Properties
C6H5F4NO3S
Molar mass 247.16 g·mol−1
Appearance White solid
Melting point 185–187 °C (365–369 °F; 458–460 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

N-Fluoropyridinium cations are not only electrophilic fluorinating agents (i.e., sources of "F+"), they are also one-electron oxidants.[2]

References
  1. Teruo Umemoto, Ahmad El-Awa "N-Fluoropyridinium Triflate" e-EROS Encyclopedia of Reagents for Organic Synthesis. Published Online: 22 APR 2013 doi:10.1002/047084289X.rf012.pub2
  2. Kiselyov, A. S., "Chemistry of N-fluoropyridinium salts", Chemical Society Reviews 2005, vol. 34, page 1031. doi:10.1039/B509217P
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