Chemical Properties
clear colorless to light yellow liquid
Uses
Dimethyl bromomalonate may be used in the enantioselective synthesis of nitrocyclopropanes.
General Description
Dimethyl bromomalonate undergoes manganese(III)-promoted free-radical chain addition reaction with olefins, to yield dimethyl 2-bromoalkylmalonates. Organocatalyzed Michael addition of dimethyl bromomalonate to nitrostyrenes to yield synthetically useful nitrocyclopropanes has been reported. Dimethyl bromomalonate reacts readily with arylnitroso compounds to yield the corresponding
N-aryl-
C,C-dimethoxycarbonylnitrones.
Synthesis
The Preparative Method of Dimethyl Bromomalonate: by treatment of Malonic Acid with Bromine in diethyl ether followed by esterification with HCl in methanol; by electrolytic bromination of dimethyl malonate with Magnesium Bromide or Copper(II) Bromide and Sodium Methoxide in acetonitrile-water at 2-3 °C.
