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N-bromosuccinimide
Sign in to saveAlso known as succinibromimide, NBS, succinbromimide, succinbromide, N-bromosuccimide, 1-bromo-2,5-pyrrolidine-dione, 1-bromo-2,5-pyrrolidinedione
'''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.
Chemical data
- Formula
- C4H4BrNO2
- Molecular weight
- 177.98 g/mol
- IUPAC name
- 1-bromopyrrolidine-2,5-dione
- SMILES
- C1CC(=O)N(C1=O)Br
- InChIKey
- PCLIMKBDDGJMGD-UHFFFAOYSA-N
- XLogP
- -0.1
- Polar surface area
- 37.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
1,336 papers- Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide.The Journal of organic chemistry · 2022
- N-bromosuccinimide initiated one-pot synthesis of imidazoline.Organic letters · 2011
- Utility of N-Bromosuccinimide-Water Combination as a Green Reagents for a Validated Indirect Spectrophotometric Determination of Some Antihypertensive Drugs: An Application to Their Monitoring in Marketed Tablets and Capsules.Journal of AOAC International · 2024
- Utilization of N-bromosuccinimide for the sensitive spectrophotometric determination of pipazethate HCl as antitussive drug in pure and dosage forms.Annales pharmaceutiques francaises · 2021
- The effect of N-bromosuccinimide on ferredoxin:NADP+ oxidoreductase.Archives of biochemistry and biophysics · 1995
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- bromine
- Mass
- 176.942540468
Show 3 more facts
- chemical formula
- C₄H₄BrNO₂
- canonical SMILES
- C1CC(=O)N(C1=O)Br
- Commons category
- N-Bromosuccinimide
via Wikidata · CC0
~5 min read
Encyclopedic overview
13 sectionsContents
- Preparation
- Reactions
- Addition to alkenes
- Allylic and benzylic bromination
- Bromination of carbonyl derivatives
- Bromination of aromatic derivatives
- Hofmann rearrangement
- Selective oxidation of alcohols
- Oxidative decarboxylation of α-amino acids
- Precautions
- See also
- References
- External links
'''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.
==Preparation== NBS is commercially available. It can also be synthesized in the laboratory. To do so, sodium hydroxide and bromine are added to an ice-water solution of succinimide. The NBS product precipitates and can be collected by filtration.
Excerpted from Wikipedia’s “N-bromosuccinimide” article, available under the CC BY-SA 4.0 licence.