Bromophenol Blue

HCID 8272CAS 115-39-9

Basic information

Standard SMILES
O=S1(=O)OC(c2cc(Br)c(O)c(Br)c2)(c2cc(Br)c(O)c(Br)c2)c2ccccc21
InChIKey
UDSAIICHUKSCKT-UHFFFAOYSA-N
Molecular formula
C19H10Br4O5S
Average molar mass
670 g/mol
Monoisotopic mass
665.69824

Names & identifiers

Preferred name
Bromophenol Blue
IUPAC
2,6-dibromo-4-[3-(3,5-dibromo-4-hydroxyphenyl)-1,1-dioxo-2,1lambda6-benzoxathiol-3-yl]phenol
English name
Bromophenol Blue
Molecular formula
C19H10Br4O5S
Molecular weight
669.96

Names & synonyms

Bromophenol blue115-39-9BROMPHENOL BLUEAlbutestTetrabromphenol Blue3,3',5,5'-Tetrabromophenolsulfonphthalein3',3'',5',5''-TetrabromophenolsulfonephthaleinDTXSID6041682NSC-78183',3'',5',5''-TetrabromophenolsulfophthaleinCHEBI:594240R2969YC90
Show more names
BPBBromophemol blueBROMOPHENOL BLUE INDICATORNSC 7818AalbutestBromophnol bluebleudebromophenol
DTXCID4021682Blue, BromphenolBlue, BromophenolBlue, TetrabromophenolRefChem:5618Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis(2,6-dibromo)-, S,S-dioxide204-086-2MFCD00005875

Database identifiers

CAS
115-39-9
PubChem CID
8272
DTXSID
DTXSID6041682
ChEMBL
CHEMBL2103765
ChEBI
CHEBI:59424
UNII
0R2969YC90
Nikkaji
J39.162J

Properties

Computed structural properties

XLogP
5.8
Topological polar surface area
92.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
29

Experimental & physicochemical properties

Color/Form · 2 items

Hexagonal prisms from acetic acid and acetone

Elongated hexagonal prisms from acetic acid and acetone

Solubility · 3 items

Soluble in acetic acid

Soluble in water (about 0.4 g/100 mL); more soluble in methyl and ethyl alcohol, and in benzene. Freely soluble in NaOH solutions with the formation of a water-soluble sodium salt.

In water, 3 mg/mL

Melting PointDecomposes at 279 °C (An orange discoloration with formation of a green sublimate sets in at 210 °C)
Physical DescriptionOdorless solid; Color varies (tan, orange, light pink, purple, or red) [CHEMINFO] Slightly soluble in water; [MSDSonline]
Dissociation ConstantspKa = 4.0
Collision Cross Section214.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6041682]

Physicochemical properties

Melting point
273 °C · 273 °C
Density
0.954 g/mL · 0.954 g/mL at 20 °C
bulk density
730 kg/m3 · 730kg/m3
Flash point
58 °C · 58 °C
storage temp.
Store at RT.
solubility
10 mg/mL · methanol: soluble10mg/mL

Safety & regulation

Hazard information

Regulatory Information · 3 items

Chemical: Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis[2,6-dibromo-, S,S-dioxide

Hazard Traits - Bioaccumulation; Environmental Persistence;Authoritative List - Canada PBiTs;Report - if used as a fragrance or flavor ingredient

Bromophenol blue: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis[2,6-dibromo-, S,S-dioxide: Human health tier I assessment
Hazards SummaryA skin, eye, and respiratory tract irritant; [MSDSonline]
Toxic Combustion ProductsHazardous decomposition products formed under fire conditions: Carbon oxides, sulphur oxides, hydrogen bromide gas.
Skin, Eye, and Respiratory IrritationsMay cause respiratory tract irritation. May be harmful if absorbed through skin. May cause skin irritation. May cause eye irritation.
Hazardous Reactivities and IncompatibilitiesMaterials to avoid: Strong oxidizing agents.

Safety & protection

Fire Fighting Procedures · 2 items

Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Keep in dry place..
Cleanup Methods · 4 items

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

Personal precautions: Avoid dust formation.

Environmental precautions: Do not let product enter drains.

Methods for cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.

Disposal Methods · 2 items

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Observe all federal, state, and local environmental regulations.

Preventive Measures · 5 items

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Hygiene measures: General industrial hygiene practice.

In case of skin contact: Wash off with soap and plenty of water.

In case of eye contact: Flush eyes with water as a precaution.

Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.

Protective Action Criteria (PAC) · 3 items

30 [mg/m3]

330 [mg/m3]

2000 [mg/m3]

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.5X10+6(SRC), determined from a structure estimation method(2), indicates that bromophenol blue is expected to be immobile in soil(SRC). The pKa of bromophenol blue is 4.0(3), indicating that this compound will almost entirely exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil surfaces is not expected because the acid exists as an anion and anions do not volatilize. Bromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-17 mm Hg(SRC), determined from a fragment constant method(5). Bromophenol blue has been found to be biodegraded by select fungi(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.5X10+6(SRC), determined from a structure estimation method(2), indicates that bromophenol blue is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.0(3) indicates bromophenol blue will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 1.4X10+4(SRC), from an estimated log Kow of 6.77(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Bromophenol blue is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(8). Bromophenol blue has been found to be biodegraded by select fungi(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromophenol blue, which has an estimated vapor pressure of 2.7X10-17 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bromophenol blue may be removed from the air by wet or dry deposition(SRC). Bromophenol blue has a maximum absorbance wavelength of 598 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of bromophenol blue can be estimated to be 1.5X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that bromophenol blue is expected to be immobile in soil. The pKa of bromophenol blue is 4.0(3), indicating that this compound will almost entirely exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Artificial Pollution SourcesBromophenol blue's production and use as a pH indicator(1) and in vitreoretinal surgery(2) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationPURE CULTURE: Bromophenol blue has been shown to be biodegraded by the fungi Cyathus bulleri, Cyathus sterocaus, Cyathus striatus(1) and a ligninolytic culture of the white rot fungus Phanerochaete chrysosporium(1,2).
Environmental Bioconcentration · 1 item

An estimated BCF of 1.4X10+4 was calculated in fish for bromophenol blue(SRC), using an estimated log Kow of 6.77(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC).

Volatilization from Water/Soil · 1 item

A pKa of 4.0(1) indicates bromophenol blue will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(2). Bromophenol blue is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.7X10-17 mm Hg(SRC), determined from a fragment constant method(3).

Regulatory information

Regulatory Information · 3 items

Chemical: Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis[2,6-dibromo-, S,S-dioxide

Hazard Traits - Bioaccumulation; Environmental Persistence;Authoritative List - Canada PBiTs;Report - if used as a fragrance or flavor ingredient

Bromophenol blue: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk
3
tsca
TSCA listed
rtecs
SJ7453000
ridadr
UN 2265 3/PG 3
hs_code
29349990
risk_code
61-20/21-36-36/37/38-20/21/22

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.

Absorption, Distribution and Excretion · 1 item

Concentrations of bromophenol blue (I) in plasma, urine, and bile were determined spectrophotometrically after intravenous bolus injections and infusions in rats. The plasma concentrations were found to decrease monoexponentially after all doses except the highest, where the decrease was biexponential. Although the disposition kinetics of I were apparently first-order at all doses, the half-life increased with increasing dose. The area under the plasma concentration-time curve (AUC0-infinity) increased disproportionately with increasing dose. The binding of I to rat plasma proteins, as determined by equilibrium dialysis, showed that the fraction bound (96%) remained constant in the concentration range of 10-300 micrograms/ml. Plasma concentrations were determined at time zero after intravenous administration and after a second dose administered 20 min later when plasma concentrations from the first dose were minimal. The apparent first-order elimination rate constant for the plasma concentration decline following the second dose was significantly less than after the first dose, indicating that the residual dye in the liver altered the elimination of I after the second dose. The fraction of the dose in the liver decreased with increasing dose, indicating a saturable uptake process. The biliary excretion profile reflected the uptake saturation that occurred in the liver and demonstrated that the biliary excretion of I depended on the amount present in the liver. When liver damage was induced by exposure to carbon tetrachloride, dye concentrations in the plasma, liver, and kidney increased markedly.

Uses & manufacturing

Uses · 6 items

Used as a dye, laboratory indicator, and biological stain; [ChemIDplus]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

As indicator, pH 3.0 yellow; pH 4.6 purple.

Vital dye for vitreoretinal surgery

Adsorption Indicators. Indicator: bromophenol blue; Titratable ions: Cl, I; Titrant (Reagent): Ag; Color change: yellow - green - greenish blue. /from table/

Vital dye for vitreoretinal surgery.

Methods of ManufacturingPrepared by slow addition of excess bromine to a hot solution of phenolsulfonphthalein in glacial acetic acid.
General Manufacturing InformationPhenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis[2,6-dibromo-: ACTIVE
Applications · 1 item

UsesBromophenol blue is used as a tracking dye in electrophoresis, as a color marker in gel electrophoresis and polyacrylamide gel electrophoresis. As a biological stain, it plays an important role to stain proteins and nucleic acids. It acts an intermediate and an acid-base indicator in the pH range 3.0 to 4.6.

Preparation methods · 1 item

PreparationBromophenol Blue is prepared by slow addition of excess bromine to a hot solution of phenolsulfonphthalein in glacial acetic acid.Synthesis steps: Dissolve phenol red in glacial acetic acid, add a solution of bromine in glacial acetic acid with stirring, pour into 60°C hot water after stirring for a few minutes, cool to room temperature, and place overnight. Filter, wash the filter cake with glacial acetic acid and benzene in turn, and air dry to obtain bromophenol blue.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Bromophenol blue is 3H-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. It has a role as a two-colour indicator, an acid-base indicator and a dye. It is a sultone, an arenesulfonate ester, a 2,1-benzoxathiole, a member of phenols and an organobromine compound.

Related reactions

24 records

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