Dapagliflozin impurity 6

Dapagliflozin impurity 6 is a halogenated aromatic derivative featuring a bromine and chlorine substituent on adjacent positions of a substituted benzene ring, conjugated to an ester-functionalized cyclopropane moiety. This impurity arises from regioselective halogenation during synthetic pathways of dapagliflozin, where bromine and chlorine atoms replace hydrogen atoms on the aromatic core, disrupting the parent drug’s 1,5-benzodioxole pharmacophore. The compound retains the core scaffold’s ester linkage but exhibits altered electronic properties due to the electron-withdrawing halogens, leading to distinct chromatographic behavior. It serves as a critical HPLC reference standard for quantifying process-related impurities in dapagliflozin formulations.