1,3-Dibromo-5,5-dimethylhydantoin

Technical Specifications

Product Description & Scientific Applications

1,3-Dibromo-5,5-dimethylhydantoin, also sold as DBDMH or dibromantin (C5H6Br2N2O2, 285.92 g/mol), is the N,N′-dibrominated hydantoin: a bromine on each ring nitrogen, so one molecule carries two.

It is a stronger brominating reagent than N-bromosuccinimide. Head to head as an activator on the same substrate at the same loading, it gave 87% against 65% for NBS and 43% for NCS, and systematic screening of brominating agents has identified it as the optimal reagent.

Applications and Reactions

• Aromatic bromination: delivers the aryl bromide directly at 93% yield, giving a cross-coupling handle in one step.
• Selective heterocycle bromination: on electron-rich heterocycles it gives the monobrominated pyrrole in 81% yield rather than an over-brominated mixture.
• Benzylic bromination: as an alternative bromine source it gave more consistent yields, 57%, than the reagent it replaced.
• Enolate trapping: converts a difluoroenolate quantitatively to a chromatographically stable α-bromide, 79% isolated.
• Polybromination: converts a dibromide to the tribromide in 80% yield.
• Amide N-β-bromination: with a Togni reagent it achieves dehydrogenative N-β-bromination of amides.
• Thioglycoside hydrolysis: in aqueous acetone it hydrolyses thioglycosides, unmasking the anomeric position for donor synthesis.
• Storage: room temperature in a tightly sealed container, protected from moisture.

Shipping Destinations

• EU & UK only: DDP shipping, 3–7 business days. Classified as dangerous goods — shipping restrictions apply.