Bromocresol Purple

HCID 8273CAS 115-40-2

Basic information

Standard SMILES
Cc1cc(C2(c3cc(C)c(O)c(Br)c3)OS(=O)(=O)c3ccccc32)cc(Br)c1O
InChIKey
ABIUHPWEYMSGSR-UHFFFAOYSA-N
Molecular formula
C21H16Br2O5S
Average molar mass
540.2 g/mol
Monoisotopic mass
537.90851881

Overview

Bromocresol purple is a member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-methylphenyl groups. A hydrophilic dye that is used as a pH indicator and to measure serum albumin concentrations. It has a role as a dye, an acid-base indicator and a two-colour indicator. It is a polyphenol, an organobromine compound, a 2,1-benzoxathiole, a sultone and an arenesulfonate ester.

Names & identifiers

Preferred name
Bromocresol Purple
IUPAC
2-bromo-4-[3-(3-bromo-4-hydroxy-5-methylphenyl)-1,1-dioxo-2,1λ6-benzoxathiol-3-yl]-6-methylphenol
English name
Bromocresol Purple
Molecular formula
C21H16Br2O5S
Molecular weight
540.22

Names & synonyms

Bromocresol purple115-40-2BROMCRESOL PURPLEDTXSID3059428HSDB 7729201C22C3ECNSC-374134Phenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-methyl-CHEBI:86154Phenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis(2-bromo-6-methyl-Purple, BromcresolPurple, Bromocresol
Show more names
BCPbromocresolBROMOCRESOL PURPLE SOLUTION4,4’-(3h-2,1-benzoxathiol-3-ylidene)bis(2-bromo-6-methylphenol)s,s-dioxideNsc 374134M.W. 540.24BromocresolredBromocresolPurpbeBromocresol purpl
RefChem:121504DTXCID8033354Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis(2-bromo-6-methyl)-, S,S-dioxide204-087-83,3-Bis(3-bromo-4-hydroxy-5-methylphenyl)-3H-benzo[c][1,2]oxathiole 1,1-dioxideMFCD000116815,5'-Dibromo-o-cresolsulfonphthaleinNSC374134

Database identifiers

CAS
115-40-2
PubChem CID
8273
DTXSID
DTXSID3059428
ChEBI
CHEBI:86154
UNII
201C22C3EC
EC Number
204-087-8

Properties

Computed structural properties

XLogP
5.1
Topological polar surface area
92.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
29

Experimental & physicochemical properties

Chemical ClassesDyes -> Indicator Dyes
Color/FormMinute, slightly yellow crystals
SolubilitySoluble in alcohol, dilute alkalies
Melting Point · 2 items

241.5 °C

241.5 °C

Physical DescriptionOdorless, pale-yellow to purple solid; Available as pure compound, monosodium salt, and dilute solutions; [CHEMINFO]
Dissociation ConstantspKa = 6.3

Physicochemical properties

Melting point
240 °C · 240 °C (dec.) (lit.)
bulk density
515 kg/m3 · 515kg/m3
Density
1.6509 · 1.6509 (estimate)
Flash point
36 °C · 36 °C
storage temp.
5 °C · Store at +5°C to +30°C.
solubility
1 mg/mL · ethanol: soluble1mg/mL

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 6.9% (7 of 101) of reports.

Warning

H315 (93.1%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 101 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

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

Hazard Traits - Bioaccumulation; Environmental Persistence

Phenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-methyl-: 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-bromo-6-methyl-, S,S-dioxide: Human health tier I assessment
Hazards SummaryDust may be irritating if inhaled; [CHEMINFO]
Hazard Classes and CategoriesSkin Irrit. 2 (93.1%)
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

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

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

Storage ConditionsKeep container tightly closed in a dry and well-ventilated 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: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.

Environmental precautions: Do not let product enter drains.

Methods for cleaning up: Pick up and arrange disposal without creating dust. 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.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

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

In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.

For more Preventive Measures (Complete) data for Bromocresol Purple (6 total), please visit the HSDB record page.

Protective Action Criteria (PAC) · 3 items

12 [mg/m3]

130 [mg/m3]

790 [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 bromocresol purple is expected to be immobile in soil(SRC). The pKa of bromocresol purple is 6.3(3), indicating that this compound will partially 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 of bromocresol purple from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Bromocresol purple is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-15 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2009); however, structurally similar bromophenol blue has been shown to be biodegraded by certain fungi(7).

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 bromocresol purple is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.0X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4800(SRC), from an estimated log Kow of 6.08(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound it not metabolized by the organism(SRC). Bromocresol purple is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2009); however, structurally similar bromophenol blue has been shown to be biodegraded by certain fungi(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromocresol purple, which has an estimated vapor pressure of 1.1X10-15 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 bromocresol purple may be removed from the air by wet or dry deposition(SRC). Bromocresol purple has a maximum absorbance wavelength of 419 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 bromocresol purple can be estimated to be 1.5X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that bromocresol purple is expected to be immobile in soil. The pKa of bromocresol purple is 6.3(3), indicating that this compound will partially 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 SourcesBromocresol purple's production and use as a pH indicator(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

PURE CULTURE: Biodegradation data for bromocresol purple were not available(SRC, 2009). However, structurally similar bromophenol blue has been shown to be biodegraded by three birds' nest fungi, Cyathus bulleri, C. stercoreus, and C. striatus(1).

Environmental Bioconcentration · 1 item

An estimated BCF of 4800 was calculated in fish for bromocresol purple(SRC), using an estimated log Kow of 6.08(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

The Henry's Law constant for bromocresol purple is estimated as 1.0X10-18 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bromocresol purple is expected to be essentially nonvolatile from water surfaces(2). Bromocresol purple is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-15 mm Hg(SRC), determined from a fragment constant method(3).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
ridadr
UN 1993 3/PG 3
hs_code
29349990
risk_code
36/37/38-10-20/21/22

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

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)

Uses & manufacturing

Uses · 2 items

A sulfonphthalein dye used as a pH indicator; [CHEMINFO] Used as a pH indicator for the pH range of 5.2-6.8 and 10.2-11.8; [Ullmann]

As indicator, pH 5.2 yellow; pH 6.8 purple

Methods of ManufacturingPrepared by treating o-cresol red with bromine in glacial acetic acid.
General Manufacturing InformationPhenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-methyl-: ACTIVE
Applications · 4 items

UsesAs indicator, pH 5.2 yellow; pH 6.8 purple.

UsesIt is used as a pH indicator and to measure serum albumin concentrations. It is used as a pH indicator (5.2-6.8 : yellow to blue-purple) and also used in spectrophotometric determination of serum-albumin.

UsesBromocresol purple has been used as a pH indicator in the yeast culture media. It has been used as a pH indicator in the culture media of Geobacillus stearothermophilus subsp. Calidolactis.

General DescriptionBromocresol purple is a pH indicator, which changes color from yellow (at low pH 5.2) to violet (above pH 6.8). It aids in determining the dead cell count for cells with plasma membrane damage. Bromocresol purple is widely used as a fluorescent stain in yeast cells. Cells with an intact plasma membrane are not stained, while damaged cells are seen as blue-grey ghosts.

Upstream & downstream products

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: A member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-methylphenyl groups. A hydrophilic dye that is used as a pH indicator and to measure serum albumin concentrations.

Related reactions

2 records

Linked notes

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