Bromobenzene (T3D1779)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (11)XML
Targets (11)
Record Information
Version2.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2014-12-24 20:24:37 UTC
Accession NumberT3D1779
Identification
Common NameBromobenzene
ClassSmall Molecule
DescriptionBromobenzene is used for organic synthesis, especially in the production of the synthetic intermediate phenyl magnesium bromide (a Grignard reagent). Bromobenzene is also used as an additive to motor oils and as a crystallizing solvent. Release of bromobenzene to the environment may occur during its production and the production of phenyl magnesium bromide, as well as in its use as a solvent and as an additive in motor oil (HSDB, 2003). It has been detected at low frequencies and at low concentrations in samples of food, ambient air, and finished water.
Compound Type
  • Bromide Compound
  • Food Toxin
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1-Bromobenzene
4-Bromopolystyrene
Bromo-benzene
bromobenzene, 14C-labeled
C6H5Br
Monobromobenzene
PhBr
Phenyl bromide
Chemical FormulaC6H5Br
Average Molecular Mass157.008 g/mol
Monoisotopic Mass155.957 g/mol
CAS Registry Number108-86-1
IUPAC Namebromobenzene
Traditional Namebromobenzene
SMILESBrC1=CC=CC=C1
InChI IdentifierInChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H
InChI KeyInChIKey=QARVLSVVCXYDNA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bromobenzenes. These are organic compounds containing a bromine atom attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentBromobenzenes
Alternative Parents
Substituents
  • Bromobenzene
  • Aryl halide
  • Aryl bromide
  • Hydrocarbon derivative
  • Organobromide
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless to pale yellow liquid.
Experimental Properties
PropertyValue
Melting Point-30.6°C
Boiling PointNot Available
Solubility0.446 mg/mL at 30°C [CHIOU,CT et al. (1977)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP2.65ALOGPS
logP2.74ChemAxon
logS-2.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.68 m³·mol⁻¹ChemAxon
Polarizability12.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-a65455f1083f38c81a192016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-a65455f1083f38c81a192016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1900000000-ff28b9f2f548369eaf8c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-d6ab0c078e4a0ed08ec72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-d6ab0c078e4a0ed08ec72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-20a1296288313ea622592016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-9500000000-9fb9b32ecd9708ec32a22014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityThe hepatotoxicity of bromobenzene is due to the production of reactive metabolites that modify or alkylated DNA, RNA and proteins. These reactive metabolites arise from the action of the CYP enzymes that are concentrated in the liver that lead to the production of cytotoxic compounds such as the 2,3- and 3,4-oxides of bromobenzene, the oxides of the bromophenols, 1,4-benzoquinone, and the radicals and quinones derived from redox cycling of the 2- and 4-bromocatechols. Similar reactive metabolites lead to renal damage, albeit at higher doses.
MetabolismBromobenzene is converted to either the 3,4-oxide derivative catalyzed primarily by phenobarbital-induced cytochrome isozymes (e.g., CYP 450 1A2, 2A6, 2B6, and 3A4), or the 2,3-oxide derivative catalyzed primarily by 3-methylcholanthrene and β-naphthoflavone-induced CYP isozymes (e.g., CYP 450 1A1, 1A2, and 1B1). This is followed by urinary excretion as premercapturic and mercapturic acids.
Toxicity ValuesLD50: 2699 mg/kg (Oral, Rat) (3) LD50: 1000 mg/kg (Intraperitoneal, Mouse) (3) LD50: 2000 mg/kg (Subcutaneous, Mouse) (3) LC50: 20 400 mg/kg (Inhalation, Rat) (3)
Lethal Dose50-500 mg/kg
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as an industrial chemical for production of Grignard reagents. Also used as an additive in certain motor oils.
Minimum Risk LevelNot Available
Health EffectsThe toxic effects of bromobenzene following acute exposure have been extensively studied in animals. Liver, kidney, and lung have been identified as the target organs for this chemical by a variety of routes. It can cause liver and nervous system damage if inhaled, ingested, or absorbed through the skin (4).
SymptomsIf inhaled, bromobenzene causes irritation to the respiratory tract. Symptoms may include coughing, shortness of breath. Affects central nervous system causing dizziness, incoordination and unconsciousness. May be absorbed into the bloodstream with symptoms similar to ingestion. If the compound is ingested it can cause abdominal pain, nausea, vomiting, diarrhea, headache, dullness, central nervous system effects and liver damage. Estimated lethal human dose is 50 - 500 mg/kg. Contact with skin or eyes causes irritation, redness and pain.
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 ID7961
ChEMBL IDCHEMBL16068
ChemSpider ID7673
KEGG IDC11036
UniProt IDNot Available
OMIM ID
ChEBI ID3179
BioCyc IDCPD-1125
CTD IDC032036
Stitch IDBromobenzene
PDB IDNot Available
ACToR ID7133
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1779.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. Bromobenzene. Last Updated 19 March 2009. [Link]
  3. The Physical and Theoretical Chemistry Laboratory of Oxford University (2008). Material Safety Data Sheet (MSDS) for bromobenzene. [Link]
  4. Toxicological Review of Bromobenzene [Link]
  5. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Wikipedia. Bromobenzene. Last Updated 19 March 2009. [Link]
  2. The Physical and Theoretical Chemistry Laboratory of Oxford University (2008). Material Safety Data Sheet (MSDS) for bromobenzene. [Link]
  3. Toxicological Review of Bromobenzene [Link]
Target Details
2. Fatty acid-binding protein, brain
General Function:
Transporter activity
Specific Function:
B-FABP could be involved in the transport of a so far unknown hydrophobic ligand with potential morphogenic activity during CNS development. It is required for the establishment of the radial glial fiber system in developing brain, a system that is necessary for the migration of immature neurons to establish cortical layers (By similarity).
Gene Name:
FABP7
Uniprot ID:
O15540
Molecular Weight:
14888.855 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
3. Glutathione S-transferase Mu 2
General Function:
Receptor binding
Specific Function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM2
Uniprot ID:
P28161
Molecular Weight:
25744.395 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
4. Regucalcin
General Function:
Zinc ion binding
Specific Function:
Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:
RGN
Uniprot ID:
Q15493
Molecular Weight:
33252.53 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
5. Selenium-binding protein 1
General Function:
Selenium binding
Specific Function:
Selenium-binding protein which may be involved in the sensing of reactive xenobiotics in the cytoplasm. May be involved in intra-Golgi protein transport (By similarity).
Gene Name:
SELENBP1
Uniprot ID:
Q13228
Molecular Weight:
52390.575 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
6. Thioredoxin
General Function:
Protein disulfide oxidoreductase activity
Specific Function:
Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions. Plays a role in the reversible S-nitrosylation of cysteine residues in target proteins, and thereby contributes to the response to intracellular nitric oxide. Nitrosylates the active site Cys of CASP3 in response to nitric oxide (NO), and thereby inhibits caspase-3 activity. Induces the FOS/JUN AP-1 DNA-binding activity in ionizing radiation (IR) cells through its oxidation/reduction status and stimulates AP-1 transcriptional activity.ADF augments the expression of the interleukin-2 receptor TAC (IL2R/P55).
Gene Name:
TXN
Uniprot ID:
P10599
Molecular Weight:
11737.42 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
7. Thioredoxin, mitochondrial
General Function:
Protein disulfide oxidoreductase activity
Specific Function:
Has an anti-apoptotic function and plays an important role in the regulation of mitochondrial membrane potential. Could be involved in the resistance to anti-tumor agents. Possesses a dithiol-reducing activity.
Gene Name:
TXN2
Uniprot ID:
Q99757
Molecular Weight:
18383.165 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
8. Transient receptor potential cation channel subfamily A member 1
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 ]
Target Details
9. Transthyretin
General Function:
Identical protein binding
Specific Function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name:
TTR
Uniprot ID:
P02766
Molecular Weight:
15886.88 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
10. Triosephosphate isomerase
General Function:
Ubiquitin protein ligase binding
Specific Function:
Not Available
Gene Name:
TPI1
Uniprot ID:
P60174
Molecular Weight:
30790.785 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]
Target Details
11. UDP-glucose 6-dehydrogenase
General Function:
Udp-glucose 6-dehydrogenase activity
Specific Function:
Involved in the biosynthesis of glycosaminoglycans; hyaluronan, chondroitin sulfate, and heparan sulfate.
Gene Name:
UGDH
Uniprot ID:
O60701
Molecular Weight:
55023.545 Da
References
  1. Koen YM, Gogichaeva NV, Alterman MA, Hanzlik RP: A proteomic analysis of bromobenzene reactive metabolite targets in rat liver cytosol in vivo. Chem Res Toxicol. 2007 Mar;20(3):511-9. Epub 2007 Feb 17. [17305373 ]