An exclusive nucleophillic substitution reaction occurred resulting in the formation of 2- carbethoxy-4-nitrophenylhydrazine from 2-chloro-5-nitroethylbenzoate rather than expected 2- chloro-5-nitrobenzhydrazide. The 2-carbethoxy-4-nitrophenyl when treated with suitably substituted aldehydes gave corresponding 1-(substituted benzylidine)-2-(2-carbethoxy-4- nitrophenyl)hydrazines. Structures of the newly synthesized compounds were established on the basis of spectral and analytical data. The new compounds were also evaluated for their in vitro antioxidant, antibacterial and antifungal activity.