Ming-Rong Zhang, M. Ogawa, Kenji Furutsuka
Dec 1, 2004
Citations
0
Influential Citations
25
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract In this study, we report the synthesis and reactivity of [ 18 F]fluoromethyl iodide ([ 18 F]FCH 2 I) with various nucleophilic substrates and the stabilities of [ 18 F]fluoromethylated compounds. [ 18 F]FCH 2 I was prepared by reacting diiodomethane (CH 2 I 2 ) with [ 18 F]KF, and purified by distillation in radiochemical yields of 14–31% ( n = 25). [ 18 F]FCH 2 I was stable in organic solvents commonly used for labeling and aqueous solution with pH 1–7, but was unstable in basic solutions. [ 18 F]FCH 2 I displayed a high reactivity with various nucleophilic substrates such as phenol, thiophenol, amide and amine. The [ 18 F]fluoromethylated compounds synthesized by the reactions of phenol, thiophenol and tertiary amine with [ 18 F]FCH 2 I were stable for purification, formulation and storage. In contrast, the [ 18 F]fluoromethylated compounds synthesized by the reactions of primary or secondary amines, and amide with [ 18 F]FCH 2 I were too unstable to be detected or purified from the reaction mixtures. Defluorination of these [ 18 F]fluoromethyl compounds was a main decomposition route.