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N-Bromosuccinimide or NBS is a chemical reagent used in radical substitution, electrophilic addition, and electrophilic substitution reactions in organic chemistry. NBS can be a convenient source of Br •, the bromine radical.
The Wohl–Ziegler reaction [1] [2] is a chemical reaction that involves the allylic or benzylic bromination of hydrocarbons using an N-bromosuccinimide and a radical initiator. [3] Best yields are achieved with N-bromosuccinimide in carbon tetrachloride solvent. Several reviews have been published. [4] [5]
Bromine itself can be used, but due to its toxicity and volatility, safer brominating reagents are normally used, such as N-bromosuccinimide. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution. [15]
Photocyclization can be used as the final step of a sequence to generate a fused aromatic ring at a benzylic position. After benzylic bromization with N-bromosuccinimide, transformation to the phosphonium salt, and a Wittig reaction with anaromatic aldehyde, photocyclization fuses the aromatic rings. Iteration of this sequence results in helicenes.
This compound is also the starting material for the dibromide through N-bromosuccinimide (NBS) and silver nitrate: Cadiot–Chodkiewicz coupling application. The coupling reaction itself takes place in methanol with piperidine, the hydrochloric acid salt of hydroxylamine and copper(I) bromide. [3]
N-Bromosuccinimide: used in radical substitution and electrophilic addition reactions in organic chemistry. Also acts as a mild oxidizer to oxidize benzylic or allylic alcohols. Butanone (methyl ethyl ketone) organic compound; similar solvent properties to acetone but has a significantly slower evaporation rate
Maleimide, N-Chlorosuccinimide, N-Bromosuccinimide: Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], ...
The fluorescence quenching reaction between N-acetyltryptophanamide (NAT) and N-bromosuccinimide (NBS), as described by Peterman, is a commonly used method for measuring the dead time of a stopped-flow instrument.