1,2-Dibromoethane (CED0000024)

Record Information
Version1.0
Creation Date2009-03-06 18:57:57 UTC
Update Date2026-08-22 09:39:13 UTC
Accession NumberCHEM000031
Identification
Common Name1,2-Dibromoethane
ClassSmall Molecule
Description
1,2-Dibromoethane belongs to the organobromides, a class of organohalogen compounds within the organic compounds. This exogenous compound has the chemical formula C2H4Br2 and an average molecular weight of 187.86 g/mol. At room temperature, it exists as a liquid. It serves as a fumigant and an industrial insecticide, and it is identified as a mutagen, a carcinogenic agent, and a marine metabolite (PMC2958679). The compound is released from 43 recorded sources, including aquatic systems and sediments such as seawater, groundwater, freshwater, and surface water; drinking water and water supply including bottled, tap, desalinated, and drinking water; and wastewater, sanitation and biosolids including mine wastewater, industrial wastewater, and wastewater treatment effluent. Other sources include food, food processing and cookware such as food preservation, fermentation processes for beer, and the preparation of wine or sparkling wine or processing meats; building and construction materials including tents or canopies, waterproofing sprays, and sunshades awnings or outside screens; and electrical and electronic equipment such as communication cables or conductors, antennas, discharge lamps, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. Exposure routes include oral, touch, and inhalation. 1,2-Dibromoethane interacts with four recorded protein targets. It binds to serum albumin (ALB) and inhibits the estrogen receptor (ESR1 and ESR2), causing endocrine disruption in humans. It also targets methylated-DNA-protein-cysteine methyltransferase (MGMT). Additionally, its metabolite, S-(2-bromoethyl)glutathione, binds to DNA to exert carcinogenic and genotoxic effects. Results regarding its presence in superabsorbent polymer plastics are inconclusive.
Contaminant Type
  • Bromide Compound
  • Gasoline Additive/Component
  • Human Neurotoxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organobromide
  • Organochloride
  • PMT
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
alpha,beta-DibromoethaneChEBI
alpha,Omega-dibromoethaneChEBI
DBEChEBI
EDBChEBI
Ethylene bromideChEBI
Ethylene dibromideChEBI
Sym-dibromoethaneChEBI
a,b-DibromoethaneGenerator
Α,β-dibromoethaneGenerator
a,Omega-dibromoethaneGenerator
Α,omega-dibromoethaneGenerator
Bromide, ethyleneHMDB
Dibromide, ethyleneHMDB
Dibromides, ethyleneHMDB
Dowfume W 85HMDB
Dowfume w85HMDB
Ethylene dibromidesHMDB
1,2 DibromoethaneHMDB
Sym dibromoethaneHMDB
Carboxylic acidGenerator
Carboxylic acidGenerator
Chemical FormulaC2H4Br2
Average Molecular Mass187.861 g/mol
Monoisotopic Mass185.868 g/mol
CAS Registry Number106-93-4
IUPAC Name1,2-dibromoethane
Traditional Namedibromoethane
SMILESBrCCBr
InChI IdentifierInChI=1S/C2H4Br2/c3-1-2-4/h1-2H2
InChI KeyPAAZPARNPHGIKF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organobromides. Organobromides are compounds containing a chemical bond between a carbon atom and a bromine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganobromides
Sub ClassNot Available
Direct ParentOrganobromides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organobromide
  • Alkyl halide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point9.9°C
Boiling PointNot Available
Solubility3.91 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
Predicted Properties
PropertyValueSource
Water Solubility3.06 g/LALOGPS
logP2.08ALOGPS
logP1.87ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.62 m³·mol⁻¹ChemAxon
Polarizability10.74 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a6r-5900000000-0f8e5929b65c18ffe174Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a6r-5900000000-0f8e5929b65c18ffe174Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4r-3900000000-703ca88896dc7f353fc6Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-9059cc10a7a8eb687facNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0900000000-ee5e7d28ff43cd849c39Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-2578b34097bd653c4d1bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-51a6eb4c9e7aa0216f9bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-541ce06a61a5a4e27f0aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-c16dec5f28cf43cf1857Not AvailableView Spectrum
MSMS Spectrumsplash10-0a6r-7900000000-505389611033d5f531b3Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityThe metabolite 2-bromoacetaldehyde produces liver damage by binding to cellular proteins. S-(2-bromoethyl)glutathione, another metabolite, exerts genotoxic and carcinogenic effects by binding to DNA. Antispermatogenic effects of 1,2-dibromoethanes metabolites may be caused by their covalent binding to thiol groups of nucleoproteins in nuclei of spermatozoa. Such adduct formation interferes with DNA, causing improper packing of the chromatin. (2)
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (3)
Minimum Risk LevelNot Available
SymptomsRedness and inflammation, including skin blisters and mouth and stomach ulcers, can occur if large amounts of 1,2-dibromoethane are swallowed. Breathing high levels may cause depression and collapse. (2)
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
108.0mg/kgNot AvailableRatLD50OralexperimentalT14
300.0mg/kgNot AvailableRatLD50DermalexperimentalT14
220.0mg/kgNot AvailableMouseLD50IntraperitonealexperimentalT14
14300.0mg/m3Not AvailableRatLC50Inhalation (30 minutes)experimentalT14
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
233BrushesPersonal care & cosmeticsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
577Watch ChainsHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structurePhospho-2-dehydro-3-deoxyheptonate aldolaseC3TIE2Escherichia coliPredicted (SEA)37.679
Click to view 3D structureBeta-lactamase VIM-1Q9XAY4Pseudomonas aeruginosaPredicted (SEA)136.859
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)7784.61
Click to view 3D structureCytochrome P450 2C23P24470Rattus norvegicusPredicted (SEA)4101.17
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)7784.61
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)7784.61
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)7784.22
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)7784.53
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)7784.53
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)7784.61
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)7784.61
Metallo-beta-lactamase type 2 structureClick to view 3D structureMetallo-beta-lactamase type 2C7C422Klebsiella pneumoniaePredicted (SEA)7782.98
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)7784.46
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)7784.61
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)7784.61
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)7784.61
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)7784.69
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)7784.61
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)7784.61
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)7784.53
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)7784.53
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)7784.69
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)7784.61
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)7784.53
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)7784.69
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansKnownCauses endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Methylated-DNA--protein-cysteine methyltransferase structureClick to view 3D structureMethylated-DNA--protein-cysteine methyltransferaseP16455HumansKnownNot Available
Albumin structureClick to view 3D structureAlbuminP02768HumansKnown1,2-Dibromoethane binds to serum albumin. (A83)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0060334
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID12-DIBROMOETHANE
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link1,2-Dibromoethane
Chemspider IDNot Available
ChEBI ID28534
PubChem Compound ID7839
Kegg Compound IDC11088
YMDB IDNot Available
ECMDB IDECMDB23742
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10088182
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11312844
3. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.