Incompatibilities between N‑Bromosuccinimide and Solvents

Incompatibilities between N-bromosuccinimide (NBS) and solvents were examined by measuring the heat of reaction by an advanced reactive system screening tool (ARSST) and a reaction calorimeter (RC1e). The ARSST experiments showed that amides, THF, and toluene solutions require consideration of incompatibilities with NBS. Isothermal analyses by RC1e revealed accurate heats of incompatibilities and the autocatalytic behaviors of the incompatibilities. Experiments in the presence of a radical initiator or inhibitor demonstrated that the incompatibility is caused by the radical mechanism and the incompatibility is increased by the presence of radical initiators. Further experiments made clear that DBDMH, an alternative brominating reagent, showed behavior similar to that of NBS.