<p>A novel Schiff base derivative, (E)-1-(2,4-dichlorophenyl)-N-(6-methylbenzo [d]thiazol-2-yl)ethan-1-imine (2A6M24D), was successfully synthesized via the condensation reaction of 2-amino-6-methylbenzenethiazole and 2,4-dichloroacetophenone under reflux condition. The synthesised compound structural and electronic properties were examined using multiple spectroscopic techniques, including FT-IR, FT-Raman, UV-vis, fluorescence, and NMR spectroscopy (¹H and ¹³C). The molecular geometry, vibrational frequencies, and electronic properties were further analyzed through Density Functional Theory (DFT) calculations at the B3LYP/cc-pVDZ level. A strong correlation between theoretical and experimental results was observed, confirming the molecular structure and stability. MESP and FMO analyses provided insights into charge distribution and chemical reactivity, while Natural Bond Orbital (NBO) studies elucidated electron delocalization and intramolecular interactions. The NLO properties were evaluated, indicating potential applications in optoelectronic devices. NMR studies were performed experimentally, and the spectra were theoretically analyzed using the GIAO method, showing good agreement between computed and observed chemical shifts. Molecular docking studies were performed to assess the pharmacological potential of the 2A6M24D Schiff base, revealing significant binding interactions with biological targets, primarily via hydrophobic and π-π stacking interactions. The moderate binding affinity suggests that the 2A6M24D compound could serve as a starting material for further drug development. The comprehensive spectroscopic and computational analysis confirms the structural, electronic, and pharmacological relevance of the synthesized 2A6M24D compound, highlighting its potential applications in medicinal chemistry and materials science.</p>