Abstract <p>We herein report the synthesis of silatrane-appended 2-(propylsulfanyl)aniline as a versatile organo­functionalized silatrane scaffold. The target silatrane was produced by transesterification of 2-{[3-(triethoxy­silyl)propyl]sulfanyl}aniline with tris(2-hydroxypropyl)amine. The structural determination of the synthesized scaffold was accomplished by ¹H and ¹³C NMR, IR, and mass spectral analysis. Further, the silatrane structure was supported by elemental analysis, and its thermal stability was studied by thermogravimetric analysis. Moreover, the synthesized compound exhibited promising antibacterial activity (MIC = 50 μg/mL) against <i>Escherichia coli</i>, <i>Staphylococcus aureus</i>, and <i>Vibrio cholera</i>e. Further structural insights into the synthesized compound were gained through DFT-optimized geometries, FMOs, MEP plots, as well as global reactivity descriptors (µ, ɳ, <i>S</i>, and ω), to understand its structural features, potential reactivity, and toxicity. Overall, these findings underscore the potential of the synthesized organofunctionalized silatrane as a promising candidate for further development.</p>