5108. Ishikawa Reagent

Nomenclature

CAS number: 309-88-6
N,N-Diethyl-1,1,2,3,3,3-hexafluoro-1-propanamine; PPDA.
C7H11F6N; mol wt 223.16.
C 37.67%, H 4.97%, F 51.08%, N 6.28%.

Description and references

Reagent for the fluorination of alcohols and esters; prepd from perfluoropropene and diethylamine. Prepn: I. L. Knunyants et al., Bull. Acad. Sci. USSR Div. Chem. Sci. 1953, 255; D. C. England et al., J. Am. Chem. Soc. 82, 5116 (1960); A. Y. Yakubovich et al., Dokl. Akad. Nauk SSSR (Engl. Transl.) 161, 399 (1965); and use as a fluorinating agent: A. Takaoka et al., Bull. Chem. Soc. Jpn. 52, 3377 (1979). Synthetic applications: S. Watanabe et al., J. Fluorine Chem. 31, 135, 247 (1986); 36, 361 (1987); 38, 243 (1988); 39, 17 (1988); 47, 187 (1990); K. Ogu et al., Tetrahedron Lett. 39, 305 (1998); G. Koch et al., Synlett 2004, 693.

Chemical structure

Properties

bp50 54° (England). Also reported as bp20 38-39° (Yakubovich). nD24 1.2160. d424 1.2127.

Use

Fluorinating agent.