Bromophenol blue (CHEM017736)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:35:27 UTC
Update Date2026-04-16 22:18:16 UTC
Accession NumberCHEM017736
Identification
Common NameBromophenol blue
ClassSmall Molecule
Description3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3,5-dibromo-4-hydroxyphenyl groups. It is used as a laboratory indicator, changing from yellow below pH 3 to purple at pH 4.6, and as a size marker for monitoring the progress of agarose gel and polyacrylamide gel electrophoresis. It has also been used as an industrial dye.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000019000-3552c09445abf532890eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0100119000-3951a8a6bca3311e3046Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbf-3931231000-53c41a582e7a1e0f6b52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000029000-5eaa1001dd691eb3f96cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0040029000-8f4883d142b15586801cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0190231000-7cc4aa6726ceafb54775Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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 ReferencesNot Available