A series of 1,4-benzoquinone derivatives from 2,5-dichloro-3,6-diethoxy-1,4-benzoquinone and 2,6-dichloro-3,5-diethoxy-1,4-benzoquinone were prepared by nucleophilic substitution reactions of sulfur and nitrogen nucleophiles. Spectral techniques (H-1 NMR, C-13 NMR, FT-IR, and LC-MS) were employed to structurally characterize the reaction products of alkoxy, chloro substituted-1,4-benzoquinones with thiols and amines in the presence of sodium carbonate in ethanol at room temperature. The orientations and the regioselectivity of the reactions of alkoxy, chloro substituted-1,4-benzoquinones with various thiol and amine nucleophiles are discussed. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.