3150. Difluoroiodotoluene

Nomenclature

CAS number: 371-11-9
Difluoro(4-methylphenyl)iodine; 4-iodotoluene difluoride; p-tolyliododifluoride.
C7H7F2I; mol wt 256.03.
C 32.84%, H 2.76%, F 14.84%, I 49.57%.

Description and references

Hypervalent iodine(III) difluoride reagent used to transfer of fluorine to organic substrates. Prepn: R. F. Weinland, W. Stille, Ann. 328, 132 (1903); W. Bockemüller, Ber. 64, 522 (1931); and spectral studies: D. Naumann, G. Rüther, J. Fluorine Chem. 15, 213 (1980). Improved prepn: M. Sawaguchi et al., Synthesis 2002, 1802. Synthetic applications in fluorination reactions: W. B. Motherwell et al., J. Chem. Soc. Perkin Trans. 1 2002, 2809; M. A. Arrica, T. Wirth, Eur. J. Org. Chem. 2005, 395.

Chemical structure

Properties

White needles from hexane, mp 98° (Sawaguchi). Also reported as white solid, mp 110° (dec) (Motherwell). Easily sol in chloroform; sparingly sol in petroleum ether, 40% hydrofluoric acid.

Use

Fluorinating agent.