A crucial role and scientific attention have been shown by chalcone scaffold in development of science and technology. Owing to their importance, the design and development of innovative chalcone structures has been continued topic of research. This article reports the novel chalcone molecules resulting from benzofuran-2-carbaldehyde and various aromatic carbonyl compounds. The use of two different catalysts, KOH and pyrrolidine which accelerates the Claisen–Schmidt condensation reaction dramatically under mild reaction conditions are disclosed. This study reveals pyrrolidine as more efficient catalyst over KOH. Structures of all prepared molecules are well established by various spectral and Single Crystal XRD studies. Selectively-one of the prepared chalcone is investigated for hydrazine sensing study with dual spectroscopic approaches. Detailed processes with working pH range, sensing selectivity among other analytes, soil sample tests are developed and demonstrated with excellent selectivity for hydrazine. The possible mechanism for the detection of hydrazine is also confirmed by spectral analysis and discussed here. These approaches offer straightforward strategy to achieve the high selectivity towards hydrazine and enlightening further development of hydrazine probes for real time applications.