2,3-Naphthalimidoacetyl Chloride as a Labeling Reagent for Aliphatic Amines and Alcohols in Liquid Chromatography

Abstract

A new, highly reactive and sensitive labeling reagent, 2,3-naphthalimidoacetyl chloride, has been synthesized and used to determine aliphatic amines and alcohols using high-performance liquid chromatogaphy. Primary and secondary amines can be completely labeled with the reagent within 1 min in acetonitrile at room temperature in the absence of and in the presence of triethylamine, respectively. Reactions of the reagent with aliphatic primary and secondary alcohols proceed to completion within 10 min in benzene at room temperature in the presence of 4-dimethylaminopyridine. The derivatives could be readily eluted with acetonitrile:water (90:10). The detection limits (signal-to-noise ratio = 3) with fluorescence detection were 4 fmol (λ ex = 258 nm, λ em = 391 nm).