8425. Selectfluor(R) (Air Prods. Chem.)

Nomenclature

CAS number: 140681-55-6
1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis[tetrafluoroborate(1-)]; F-TEDA-BF4.
C7H14B2ClF9N2; mol wt 354.26.
C 23.73%, H 3.98%, B 6.10%, Cl 10.01%, F 48.27%, N 7.91%.

Description and references

Electrophilic N‐F fluorinating agent. Prepn: R. E. Banks, US 5086178 (1992 to Air Prods. Chem.); idem et al., J. Chem. Soc. Chem. Commun. 1992, 595; and applications as an electrophilic fluorinating agent: idem et al., J. Chem. Soc. Perkin Trans. 1 1996, 2069. X-ray crystal structure: idem et al., Acta Crystallogr. C49, 492 (1993). Review of properties and applications in organic synthesis: R. E. Banks, J. Fluorine Chem. 87, 1-17 (1998); of commercial development: J. J. Hart, R. G. Syvret, ibid. 100, 157-161 (1999); of applications and mechanism of fluorination: P. T. Nyffeler et al., Angew. Chem. Int. Ed. 44, 192-212 (2005).

Chemical structure

Properties

White, free-flowing, non-hygroscopic crystalline solid, mp 225° (dec). Soly (g/l): water 176 (20°); acetonitrile 50. Slightly sol in lower alcohols, acetone. LD50 in male rats: 640 mg/kg orally; >2 g/kg dermally (Banks, 1998).

Caution

Exothermic decompn can occur at temp >80° (Banks, 1996).

Use

Mild, versatile fluorinating reagent used in pharmaceutical and agricultural applications.