The title compound, (E)-methyl-4-[(2-phenylhydrazono)methyl]benzoate, (I), (C15H14N2O2), has been synthesized by condensation reaction of methyl-4-formylbenzoate and phenylhydrazine. The compound has been characterized by elemental analysis, IR, H-1 NMR, C-13 NMR, UV-Vis spectroscopies and single crystal X-ray diffraction techniques. Optimized molecular structure, harmonic vibrational frequencies, H-1 and C-13 NMR chemical shifts have been investigated by B3LYP/6-31G(d,p) method using density functional theory (DFT). Global chemical reactivity descriptors, natural population analysis (NPA), thermodynamic and non-linear optical (NLO) properties have also been studied. The energetic behavior of the compound has been examined in solvent media using the integral equation formalism polarizable continuum model (IEF-PCM). (C) 2015 Elsevier B.V. All rights reserved.