Schiff bases exhibit diverse biological properties due to the presence of imine group. In the present work, we have synthesized a novel Schiff base S1 (2-((5-bromothiophen-2-yl)methyleneamino)benzenethiol) via condensation of 5‑bromo-2-thiophene carboxaldehyde and 2-aminothiophenol by a simple and efficient method, and its derivatives which are already known were synthesized by using different thiophene carboxaldehydes for biological activities. The authenticity of the synthesized compound was established using ¹H NMR, ¹³C NMR, HRMS, and IR study. Further, DFT studies were utilized as a tool to predict the feasibility of various reactions. The newly synthesized compound S1 was checked for its antioxidant behaviour and also an antimicrobial activity against E. coli, P. aeruginosa, and S. Aureus was checked. It was observed that compound S1 is an efficient antimicrobial as well as an antioxidant agent. Even though compound C1 (2-(5-bromothiophen-2-yl)benzo[d]thiazole) is a known compound we have given a cheaper and more efficient route for its synthesis as it is quite expensive compound. Further, it has been used as a precursor for the synthesis of the novel C-S coupled product, CS1 (2-(5-(p-tolylthio)thiophen-2-yl)benzo[d]thiazole). The structural features of CS1 have been explored on the basis of X-ray crystallographic data. To the best of our knowledge, this is the first crystallographic evidence in the area of benzothiazole.