Bromobenzene
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Basic Info
| Common Name | Bromobenzene(F04345) |
| 2D Structure | |
| Description | Bromobenzene 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. |
| FRCD ID | F04345 |
| CAS Number | 108-86-1 |
| PubChem CID | 7961 |
| Formula | C6H5Br |
| IUPAC Name | bromobenzene |
| InChI Key | QARVLSVVCXYDNA-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H |
| Canonical SMILES | C1=CC=C(C=C1)Br |
| Isomeric SMILES | C1=CC=C(C=C1)Br |
| Synonyms |
NCI-C55492
BROMOBENZENE
108-86-1
Benzene, bromo-
Monobromobenzene
Phenyl bromide
BROMO-BENZENE
PhBr
bromo benzene
C6H5Br
|
| Classifies |
Predicted: Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Halobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Bromobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Bromobenzene - Aryl halide - Aryl bromide - Hydrocarbon derivative - Organobromide - Organohalogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as bromobenzenes. These are organic compounds containing a bromine atom attached to a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 157.01 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 46.1 |
| Monoisotopic Mass | 155.957 |
| Exact Mass | 155.957 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9824 |
| Human Intestinal Absorption | HIA+ | 0.9910 |
| Caco-2 Permeability | Caco2+ | 0.8639 |
| P-glycoprotein Substrate | Non-substrate | 0.8382 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9738 |
| Non-inhibitor | 0.9881 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8514 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4849 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8642 |
| CYP450 2D6 Substrate | Non-substrate | 0.7980 |
| CYP450 3A4 Substrate | Non-substrate | 0.7792 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6929 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.7239 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9492 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6494 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9350 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7252 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9412 |
| Non-inhibitor | 0.9477 | |
| AMES Toxicity | Non AMES toxic | 0.9496 |
| Carcinogens | Non-carcinogens | 0.5898 |
| Fish Toxicity | High FHMT | 0.9035 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9997 |
| Honey Bee Toxicity | High HBT | 0.7657 |
| Biodegradation | Not ready biodegradable | 0.8596 |
| Acute Oral Toxicity | III | 0.8834 |
| Carcinogenicity (Three-class) | Warning | 0.4875 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.3529 | LogS |
| Caco-2 Permeability | 2.0500 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0566 | LD50, mol/kg |
| Fish Toxicity | 0.8171 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5491 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Protective effect of ginger extract against bromobenzene-induced hepatotoxicity in male rats. | Food Chem Toxicol | 2009 Jul | 19371770 |
| Ecotoxicological assessment of bromobenzene using a test battery with five model systems. | Food Chem Toxicol | 2007 Apr | 17126977 |
| Toxicogenomic analysis of gene expression changes in rat liver after a 28-day oral benzene exposure. | Mutat Res | 2005 Aug 4 | 15878777 |
| Antimutagenic activity of flavonoids from the heartwood of Rhus verniciflua. | J Ethnopharmacol | 2004 Jan | 14698512 |
| Dose-dependent kinetics and metabolism of 1,2-dichlorobenzene in rat: effect of pretreatment with phenobarbital. | Xenobiotica | 1996 Jan | 8851824 |
| Toxicological significance of covalently-bound residues. | Food Addit Contam | 1984 Apr-Jun | 6536527 |
| Protective role of dietary butylated hydroxyanisole against chemical-induced acute liver damage in mice. | Toxicol Appl Pharmacol | 1983 Jun 15 | 6857690 |
Targets
- 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
- Mechanism of Action:
- Bromobenzene binds to fatty acid-binding protein.
References
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to selenium-binding protein.
References
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to thioredoxin.
References
- 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 ]
- 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
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to transthyretin.
References
- 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 ]
- General Function:
- Ubiquitin protein ligase binding
- Gene Name:
- TPI1
- Uniprot ID:
- P60174
- Molecular Weight:
- 30790.785 Da
- Mechanism of Action:
- Bromobenzene binds to triosephosphate isomerase.
References
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to UDP-glucose 6-dehydrogenase.
References
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to certain glutathione S-transferase.
References
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to regucalcin.
References
- 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 ]
- 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
- Mechanism of Action:
- Bromobenzene binds to thioredoxin.
References
- 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 ]