Schiffbases exhibit diverse biological properties due to the presence of imine group. In the present work, we have synthesized a novel Schiffbase 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 es- tablished 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.