N-Bromosuccinimide Chemical Properties,Uses,Production
white to light yellow crystalline powder
N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.
NBS, is a chemical reagent used in organic chemistry in electrophilic addition reactions and radical substitution
In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.
ChEBI: A five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom.
intraperitoneal route. An irritating poison to
skin, eyes, and mucous membranes. Reacts
explosively with adme, dtallyl sulfide, and
hydrazine hydrate. Explosive reaction with
propiononitrile after heating to 105℃ for 24
hours. Violent reaction with dtbenzoyl
peroxide + 4-tok acid. When heated to
decomposition it emits toxic fumes of Brand NOx. See also BROMIDES and
This common protein-modifying reagent (FW = 178 g/mol; CAS 128-08-5; Abbreviatin: NBS; water solublility = 0.015 g/mL, M.P. = 173-175°C) reacts somewhat selectively under acidic conditions (pH ≤ 4, typically using acetate or formate buffers) with tryptophanyl residues in peptides/proteins. Indole-ring oxidation (detected as an absorbance loss at 280 nm or a gain at 261 nm; e = 10,300 M–1cm–1 in the latter case) induces peptide-bond cleavage on its carboxyl side. (Note: No cleavage occurs at or above neutral pH.) NBS treatment often oxidizes the sulfur atom(s) in cysteinyl, cystinyl, and methionyl residues; histidyl and tyrosyl residues are also oxidized by NBS, albeit more slowly. Accordingly, the proximal cause of lost biological activity of an NBS-treated peptide/protein is often initially uncertain. Note: N-Bromosuccinimide is an eye and skin irritant, necessitating appropriate handling. Avoid inhalation of the easily dispersed dry powder.
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.]
N-Bromosuccinimide Preparation Products And Raw materials