Bromophenol blue (CED0001091)

Record Information
Version1.0
Creation Date2016-05-22 04:35:27 UTC
Update Date2026-08-20 01:45:14 UTC
Accession NumberCHEM017736
Identification
Common NameBromophenol blue
ClassSmall Molecule
Description
Bromophenol blue belongs to the benzofuranones, a subclass of benzofurans within the organic compounds. With an average molecular weight of 669.96 g/mol, Bromophenol blue is a heavy molecule. It has the chemical formula C19H10Br4O5S and is classified as an organoheterocyclic compound. In industrial contexts, it is utilized as a biocide and an antioxidant. The compound is found in or released from 27 recorded sources. Within electrical and electronic equipment, it is associated with antennas, electrodes, discharge lamps, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials, among six others. It is also linked to food, food processing and cookware, including food preservation, food contact materials, fermentation processes for beer, and the preparation of malt, wine, or sparkling wine, among three other sources. In the category of household cleaning and consumer products, it appears in soap detergents, bleaching agents, tobacco product moisture control, cigar cigarettes, and perfumes within detergents and soaps, along with one additional source. Further sources include key rings under household items and stairs and ramps within building and construction. Exposure to bromophenol blue may occur through oral, inhalation, and touch routes. Regarding its presence in plastics, it has not been detected in polycarbonate, while results for polystyrene remain inconclusive.
Contaminant Type
  • Phenolic Antioxidant
Chemical Structure
Synonyms
ValueSource
3',3'',5',5''-TetrabromophenolsulfonephthaleinChEBI
3',3'',5',5''-TetrabromophenolsulfophthaleinChEBI
Bromophenol blue, sultone formChEBI
3',3'',5',5''-TetrabromophenolsulphonephthaleinGenerator
3',3'',5',5''-TetrabromophenolsulphophthaleinGenerator
Blue, bromphenolMeSH
Blue, tetrabromophenolMeSH
Tetrabromophenol blueMeSH
Bromophenol blueMeSH
Bromphenol blueMeSH
Blue, bromophenolMeSH
Chemical FormulaC19H10Br4O5S
Average Molecular Mass669.960 g/mol
Monoisotopic Mass665.698 g/mol
CAS Registry Number115-39-9
IUPAC Name3,3-bis(3,5-dibromo-4-hydroxyphenyl)-3H-2,1λ⁶-benzoxathiole-1,1-dione
Traditional Namebromophenol blue
SMILESOC1=C(Br)C=C(C=C1Br)C1(OS(=O)(=O)C2=CC=CC=C12)C1=CC(Br)=C(O)C(Br)=C1
InChI IdentifierInChI=1S/C19H10Br4O5S/c20-12-5-9(6-13(21)17(12)24)19(10-7-14(22)18(25)15(23)8-10)11-3-1-2-4-16(11)29(26,27)28-19/h1-8,24-25H
InChI KeyUDSAIICHUKSCKT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassBenzofuranones
Direct ParentBenzofuranones
Alternative Parents
Substituents
  • Benzofuranone
  • Phthalide
  • Benzoxathiole
  • 2-halophenol
  • 2-bromophenol
  • Bromobenzene
  • Phenol
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Organosulfonic acid ester
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organobromide
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00073 g/LALOGPS
logP4.96ALOGPS
logP7.18ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)6.41ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity124.61 m³·mol⁻¹ChemAxon
Polarizability48.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0000019000-3552c09445abf532890eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0100119000-3951a8a6bca3311e3046Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kbf-3931231000-53c41a582e7a1e0f6b52Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0000029000-5eaa1001dd691eb3f96cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0040029000-8f4883d142b15586801cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0190231000-7cc4aa6726ceafb54775Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3803.0Log mg/kg[2100:6800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
491Industrial manufacturing & chemical processingNot Available
494Food contact materialsFood, food processing & cookwareNot Available
500Stairs And RampsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
568Tobacco Product Moisture ControlHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
573Key RingsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
597ChemosterilantsAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP00469Lactobacillus caseiPredicted (SEA)10.9767
Click to view 3D structureThymidylate synthaseP0CS13Cryptococcus neoformans var. neoformans B-3501APredicted (SEA)0.389246
Click to view 3D structureThymidylate synthaseC3SWJ7Escherichia coliPredicted (SEA)13.7015
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP04818HumansPredicted (SEA)32.3074
Click to view 3D structureIsocitrate lyaseQ9P8Q7Candida albicansPredicted (SEA)3.50322
Dihydrofolate reductase structureClick to view 3D structureDihydrofolate reductaseP00374HumansPredicted (SEA)373.053
Solute carrier family 22 member 12 structureClick to view 3D structureSolute carrier family 22 member 12Q96S37HumansPredicted (SEA)48.033
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)5676.14
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP0A884Escherichia coli (strain K12)Predicted (SEA)4.28171
RAF proto-oncogene serine/threonine-protein kinase structureClick to view 3D structureRAF proto-oncogene serine/threonine-protein kinaseP04049HumansPredicted (SEA)2543.88
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)5862.51
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)2534.85
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)5977.73
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)3279.01
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)2875.75
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)2979.29
Polyunsaturated fatty acid lipoxygenase ALOX12 structureClick to view 3D structurePolyunsaturated fatty acid lipoxygenase ALOX12P18054HumansPredicted (SEA)244.602
Alpha-ketoglutarate-dependent dioxygenase FTO structureClick to view 3D structureAlpha-ketoglutarate-dependent dioxygenase FTOQ9C0B1HumansPredicted (SEA)282.203
Click to view 3D structureProtein phosphatase EYA3Q99504HumansPredicted (SEA)39.236
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)2521.46
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)5909.77
Transthyretin structureClick to view 3D structureTransthyretinP02766HumansPredicted (SEA)578.342
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)2550.42
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)961.049
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)4317.83
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBromophenol blue
Chemspider IDNot Available
ChEBI ID59424
PubChem Compound ID8272
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References