We present the synthesis, characterization, biological and sensing applications of a Schiff base, (E)-3-((5-bromo-2-hydroxy-3-methoxycyclohexa-1, 3-dienyl)methyleneamino)-6-(hydroxymethyl)-tetrahydro-2H-pyran-2,4,5-triol. Characterization of the title compound was carried out using theoretical quantum-mechanical calculations and experimental spectroscopic methods. The molecular structure of the title compound was confirmed using NMR and FTIR, which was in good agreement with the structure predicted by the theoretical calculations. The title compound was evaluated for its ability to detect anions in DMSO and on a solid surface and for its antimicrobial activity against several common microorganisms.