N-Bromosuccinimide (CHEM001539)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2026-03-26 22:52:58 UTC
Accession NumberCHEM001539
Identification
Common NameN-Bromosuccinimide
ClassSmall Molecule
Descriptionn-Bromosuccinimide (NBS) is a organobromide compound used in a variety of bromination reactions for chemical synthesis. It can be used to donate bromine to alkenes, to allylic or benzyl compounds, to carbonyl-containing compounds as well as aromatic compounds such as phenols, anilines, and various aromatic heterocycles. NBS will decompose over time giving off bromine. Pure NBS is white, but it is often found to be off-white or brown colored by bromine. NBS can be used as a protein modification agent that targets tryptophan and histidine residues.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Bromo-2,5-pyrrolidine-dioneChEBI
1-Bromo-2,5-pyrrolidinedioneChEBI
N-BromosuccimideChEBI
NBSChEBI
SuccinbromideChEBI
SuccinbromimideChEBI
SuccinibromimideChEBI
N BromosuccinimideMeSH
BromosuccinimideMeSH
Chemical FormulaC4H4BrNO2
Average Molecular Mass177.984 g/mol
Monoisotopic Mass176.943 g/mol
CAS Registry Number128-08-5
IUPAC Name1-bromopyrrolidine-2,5-dione
Traditional NameN-bromosuccinimide
SMILESBrN1C(=O)CCC1=O
InChI IdentifierInChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
InChI KeyPCLIMKBDDGJMGD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentPyrrolidine-2-ones
Alternative Parents
Substituents
  • 2-pyrrolidone
  • Dicarboximide
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point174°C
Boiling PointNot Available
Solubility14.7 mg/mL at 25°C [MERCK INDEX (1996)]
Predicted Properties
PropertyValueSource
Water Solubility142 g/LALOGPS
logP-0.65ALOGPS
logP-0.081ChemAxon
logS-0.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area37.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.22 m³·mol⁻¹ChemAxon
Polarizability12.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-af8c58f131eb63263f0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-fd6ddb376630861a73dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6900000000-1cd07d24b08a19aa81f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-03054e667064cb5c80b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-ba2d3526800562b9664aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9600000000-827453cae6295a7d2f43Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9100000000-f52966c78c61213113b8Spectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityOrganobromide compounds such as n-Bromosuccinimide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines), methionines as well as tryptophan and histidine residues on the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs
MetabolismBromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as a laboratory and industrial chemical. Occupational exposure to N-bromosuccinimide may occur through inhalation and dermal contact with this compound at workplaces where N-bromosuccinimide is produced or used.
Minimum Risk LevelNot Available
Health EffectsStrong lachrymator. Strong irritant to eyes, skin and soft tissues. Toxic if inhaled, swallowed or absorbed through skin. It is extremely destructive to the tissue of the mucous membranes and upper respiratory tract.
SymptomsCauses severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to nausea, vomiting and coma.
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDN-BROMOSUCCINIMIDE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkN-Bromosuccinimide
Chemspider IDNot Available
ChEBI ID53174
PubChem Compound ID67184
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15288278
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15589368
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23935625
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24344777
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24437567