128-08-5

white to light yellow crystalline powder

In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.

N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.

ChEBI: N-bromosuccinimide is a five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom. It has a role as a reagent. It is a dicarboximide, a pyrrolidinone and an organobromine compound. It is functionally related to a succinimide.

N-Bromosuccinimide (128-08-5) is a widely used mild brominating agent and used as chemical intermediate and building block for several chemical production processes, especially in pharma related applications.

1.62mol (160g) succinimide is dissolved in a mixture of 1.60mol (64g) NaOH, 300g crushed ice and 400ml water. Cool the mixture in an ice bath, and add 85ml (1.65 mol, 264g) Br2 at once while stirring violently. Stir for two more minutes, then filter the precipitated product and wash with ice water. Dry in a desiccator. Yield 75-81%.
Don't clean up NBS too much, the stinky yellow stuff still containing a bit of Br2 works best.

Nonflammable

N-Bromosuccinimide (30g) is purified by dissolving rapidly in 300mL of boiling water and filtering through a fluted filter paper into a flask immersed in an ice bath, and left for 2hours. The crystals are filtered off, washed thoroughly with ca 100mL of ice-cold water and drained on a Büchner funnel before drying under vacuun over P2O5 or CaCl2 [Dauben & McCoy J Am Chem Soc 81 4863 1959]. This brominating agent has also been crystallised from acetic acid or water (10 parts), washed in water and dried in vacuo [Wilcox et al. J Am Chem Soc 108 7693 1986, Shell et al. J Am Chem Soc 108 121 1986, Phillips & Cohen J Am Chem Soc 108 2013 1986, Beilstein 21/9 V 543.]