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Record Information
Version2.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2014-12-24 20:24:38 UTC
Accession NumberT3D1789
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.
Compound Type
  • Amide
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-Bromo-2,5-pyrrolidine-dione
1-Bromo-2,5-pyrrolidinedione
1-Bromopyrrolidine-2,5-dione
Bromosuccinimide
N-bromosuccimide
N-bromsuccinimid
N-bromsuccinimide
NBS
Succinbromide
Succinbromimide
Succinibromimide
Succinimide, N-bromo- (8CI)
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 KeyInChIKey=PCLIMKBDDGJMGD-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)]
LogPNot Available
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-af8c58f131eb63263f0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-fd6ddb376630861a73dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-6900000000-1cd07d24b08a19aa81f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-03054e667064cb5c80b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-ba2d3526800562b9664aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9600000000-827453cae6295a7d2f43JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-004i-9100000000-f52966c78c61213113b8JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
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. (3)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID67184
ChEMBL IDNot Available
ChemSpider ID60528
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID53174
BioCyc IDNot Available
CTD IDNot Available
Stitch IDN-Bromosuccinimide
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1789.pdf
General References
  1. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  2. Wikipedia. N-Bromosuccinimide. Last Updated 22 May 2009. [Link]
  3. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
  2. Wikipedia. N-Bromosuccinimide. Last Updated 22 May 2009. [Link]