Nomenclature
CAS number: 684-16-2
1,1,1,3,3,3-Hexafluoro-2-propanone.
C
3F
6O; mol wt 166.02.
C 21.70%, F 68.66%, O 9.64%.
Description and references
Synthon in organic and inorganic reactions
with an exceptionally electron deficient carbonyl group. Prepn:
N. Fukuhara, L. A. Bigelow, J. Am. Chem. Soc. 63, 788 (1941). Comprehensive review: C. G. Krespan,
W. J. Middleton in Fluorine Chem. Rev. vol. 1, P. Tarrant, Ed. (Marcel Dekker, New York, 1967)
pp 145-196. Review of reactivity: H. W. Roesky, J. Fluorine Chem. 30, 123-139 (1985); of use
in inorganic chemistry: M. Witt et al., Adv. Inorg. Chem. Radiochem. 30, 223-312 (1986); in polymer chemistry: P. E. Cassidy et al., J. Macromol. Sci. Rev. Macromol. Chem. Phys. C29, 365-429 (1989); in peptide chemistry: K. Burger et al., Amino Acids 8, 195-199 (1995); of toxicology: G. L. Kennedy, Jr., Crit. Rev. Toxicol. 21, 149-170
(1990).
Properties
bp760 27.4°. mp 122°. d23.3 1.323; d44.4 1.149. uv max: 302 nm (ε 16.9). Critical pressure: 411 psia.
Critical temp: 84.1°. Heat capacity (Btu/lb/°F) of liquid at 0°:
0.192; of vapor: 0.23. Poisonous, corrosive. Reacts with water to form hydrates. LD50 (mg/kg) in rats: 190 orally (trihydrate), 670 dermally (sesquihydrate); in
mice: 250 i.p., 180 i.v.;
in rabbits: 113 dermally (trihydrate) (Kennedy).Use
Protecting and activating reagent in peptide chemistry;
in synthesis of high performance fluoropolymers, pharmaceutical and
agricultural chemicals; in
19F NMR. Solvent for polyamides,
polyesters, polyacetals, polyols.