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Chemical Crystal Movie Gallery

Bromo-Succinimide Movie #6

Used by the pharmaceutical and chemical industries as an intermediary, N-bromosuccinimide serves as an oxidizing agent in the synthesis of drugs and hormones. For isolating rare elements in the laboratory or on an industrial scale, N-bromosuccinimide is utilized as an extraction solvent.

N-bromosuccinimide (NBS) is characterized by a molecular weight of 177.99, a chemical composition of 4 carbon, 4 hydrogen, 1 bromine, 1 nitrogen, and two oxygen atoms per molecule, and a faint bromine odor. Appearing as an off-white powder, N-bromosuccinimide melts between 173 and 176 degrees Celsius, and is soluble in acetone and slightly soluble in water. Alternatively, bromosuccinimide is known to biochemists as 1-bromo-2,5-pyrolidinedione or succinibromide. For the laboratory synthesis of NBS, succinimide is dissolved in a solution of sodium hydroxide, ice, and water, then bromine is added, and the N-bromosuccinimide is filtered out as a precipitate. In chemical production processes, bromopyrolidinedione is used to brominate alkenes at the allylic position, and as a mild and efficient catalyst for converting carbonyl compounds by diethyl- and cyclic acetalization.

As a hazardous chemical, N-bromosuccinimide is harmful if swallowed, inhaled, or absorbed through the skin, and can cause severe irritation to skin, eyes, and the respiratory tract. Decomposition products include oxides of nitrogen and carbon, and hydrogen bromide. Because many reactions involving N-bromosuccinimide are extremely exothermic, including violent or explosive reactions with aniline, diallylsulfide, hydrazine, and propiononitrile, special care is necessary for storage and handling. Heating NBS leads to cleavage of the molecule, and the production of a highly reactive free radical, plus bromine gas.

Contributing Authors

Omar Alvarado, Thomas J. Fellers and Michael W. Davidson - National High Magnetic Field Laboratory, 1800 East Paul Dirac Dr., The Florida State University, Tallahassee, Florida, 32310.



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