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Tetrabromophenolphthalein ethyl ester

HCID 92873
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Basic information

CAS
1176-74-5
Standard SMILES
CCOC(=O)c1ccccc1C(=C1C=C(Br)C(=O)C(Br)=C1)c1cc(Br)c(O)c(Br)c1
InChIKey
SQFXATUXPUCFFO-UHFFFAOYSA-N
Molecular formula
C22H14Br4O4
Average molar mass
662 g/mol
Monoisotopic mass
657.76256

Overview

RN given refers to parent cpd

Names & identifiers

Preferred name
Tetrabromophenolphthalein ethyl ester
IUPAC
ethyl 2-[(3,5-dibromo-4-hydroxyphenyl)-(3,5-dibromo-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzoate
English name
Tetrabromophenolphthalein ethyl ester
Molecular formula
C22H14Br4O4
Molecular weight
661.96

Names & synonyms

Tetrabromophenolphthalein ethyl ester1176-74-53',3'',5',5''-Tetrabromophenolphthalein ethyl esterBromophthalein Magenta EEthyl tetrabromophenolphthaleinDTXSID5044520TBPPE6D91NS781ONSC-16214DTXCID3024520Benzoic acid, 2-((3,5-dibromo-4-hydroxyphenyl)(3,5-dibromo-4-oxo-2,5-cyclohexadien-1-ylidene)methyl)-, ethyl esterBenzoic acid, 2-[(3,5-dibromo-4-hydroxyphenyl)(3,5-dibromo-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-, ethyl ester
Show more names
NSC 16214BROMOPHTALEIN MAGENTA EPHENOLTETRABROMOPHTHALEINterabormophenolphthalein ethyl esterTetrabromophenolphthalein ethyl ester, pureTetrabroMophenolphthalein ethyl ester, pure 1GR3',3'',5',5''-Tetrabromophenolphthaleineethylester
RefChem:188395214-645-2ethyl 2-((3,5-dibromo-4-hydroxyphenyl)(3,5-dibromo-4-oxocyclohexa-2,5-dien-1-ylidene)methyl)benzoateBrom Phthalein Magenta EBromophthalein Margenta EMFCD00066387C22H14Br4O4ethyl 2-[(3,5-dibromo-4-hydroxyphenyl)-(3,5-dibromo-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]benzoate

Properties

Computed structural properties

XLogP
7.6
Topological polar surface area
63.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
30
Formal charge
0
Complexity
752

Experimental & physicochemical properties

Color/FormYellow crystals from benzene
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point210 °C

Physicochemical properties

Melting point
208 · 208-211 °C
Boiling point
619.9 · 619.9±55.0 °C(Predicted)
Density
1.9236 · 1.9236 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
pka
6.25 · 6.25±0.40(Predicted)
form
Powder
color
Yellow to red
BRN
2228548 · 2228548
Henry's Law Constant
1 · 1.0×1011 mol/(m3Pa) at 25℃, Zhang et al. (2010)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (5 of 5) of all reports.

Not Classified

Aggregated GHS information provided per 5 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationHazard Traits - Bioaccumulation; Environmental Persistence
Toxic Combustion ProductsHazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen bromide gas.
Hazard Classes and CategoriesNot Classified
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.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Light sensitive. Store under inert gas. Air sensitive. Air and light sensitive.

Chemistry & industry

Uses & manufacturing

UsespH indicator
General Manufacturing InformationBenzoic acid, 2-[(3,5-dibromo-4-hydroxyphenyl)(3,5-dibromo-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-, ethyl ester: ACTIVE
Applications · 2 items

Uses3′,3″,5′,5″-Tetrabromophenolphthalein ethyl ester (TBPE) is an anionic dye used as a counter ion in the spectrophotometric determination of cationic surfactants. TBPE is also used in the spectrometric determination of aliphatic primary, secondary and tertiary amines.

General DescriptionVisit our Sensor Applications portal to learn more.

Related reactions

1 records
New reaction record
HRID 1356939 reaction equation
HRID 1356939As reactantuspto-grants-2003_07

Compound notes

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Database identifiers

CAS
1176-74-5
PubChem CID
92873
DTXSID
DTXSID5044520
ChEMBL
CHEMBL3187347
UNII
6D91NS781O
EC Number
214-645-2
Nikkaji
J203.434D
InChI
InChI=1S/C22H14Br4O4/c1-2-30-22(29)14-6-4-3-5-13(14)19(11-7-15(23)20(27)16(24)8-11)12-9-17(25)21(28)18(26)10-12/h3-10,27H,2H2,1H3
InChIKey
SQFXATUXPUCFFO-UHFFFAOYSA-N
SMILES
C(OCC)(=O)C1=CC=CC=C1/C(/C1=CC(Br)=C(O)C(Br)=C1)=C1\C=C(Br)C(=O)C(Br)=C\1
FDA UNII
6 D91NS781O · 6D91NS781O
EPA Substance Registry System
2 · Benzoic acid, 2-[(3,5-dibromo-4-hydroxyphenyl)(3,5-dibromo-4-oxo-2,5-cyclohexadien-1-ylidene)methyl]-, ethyl ester (1176-74-5)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
22 · 22-24/25
WGK Germany
3 · 3
F
8 · 8-10-23
TSCA
TSCA listed
HS Code
29189900 · 29189900
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
1176 · 1176-74-5(Hazardous Substances Data)
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 precauitions: 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 · 4 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.

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

Personal Protective Equipment (PPE) · 4 items

Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Hand protection: For prolonged or repeated contact use protective gloves.

Eye protection: Safety glasses.

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

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.2X10+5(SRC), determined from a structure estimation method(2), indicates that Bromophthalein Magenta E is expected to be immobile in soil(SRC). The estimated pKa of Bromophthalein Magenta E is 4.5(3), indicating that this compound will primarily 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 Bromophthalein Magenta E from moist soil surfaces is not expected to be an important fate process(SRC) given the pKa(3). Bromophthalein Magenta E is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2X10-15 mm Hg(SRC), determined from a fragment constant method(5).Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.2X10+5(SRC), determined from a structure estimation method(2), indicates that Bromophthalein Magenta E is expected to adsorb to suspended solids and sediment(SRC). A estimated pKa of 4.5(3) indicates Bromophthalein Magenta E 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 7,700(SRC), from an estimated log Kow of 6.4(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). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 5.8 years and 210 days at pHs 7 and 8, respectively(8). Biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Bromophthalein Magenta E, which has an estimated vapor pressure of 1.2X10-14 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 Bromophthalein Magenta E may be removed from the air by wet or dry deposition(SRC). Bromophthalein Magenta E contains chromophores that absorb at wavelengths >290 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 Bromophthalein Magenta E can be estimated to be 3.2X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that Bromophthalein Magenta E is expected to be immobile in soil. The estimated pKa of Bromophthalein Magenta E is 4.5(3), indicating that this compound will primarily 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 SourcesBromophthalein Magenta E's production and use as a pH indicator(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 7700 was calculated in fish for Bromophthalein Magenta E(SRC), using an estimated log Kow of 6.4(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

An estimated pKa of 4.5(1) indicates Bromophthalein Magenta E will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces or moist soil is not expected to be an important fate process(2). Bromophthalein Magenta E is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.2X10-15 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1 item

A base-catalyzed second-order hydrolysis rate constant of 3.8X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 5.8 years and 210 days at pH values of 7 and 8, respectively(1). Bromophthalein Magenta E contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human ExposureOccupational exposure to Bromophthalein Magenta E may occur through dermal contact with this compound at workplaces where Bromophthalein Magenta E is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 item

Bromophthalein Magenta E's production and use as a pH indicator may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.2X10-14 mm Hg at 25 °C indicates Bromophthalein Magenta E will exist solely in the particulate phase in the atmosphere. Particulate-phase Bromophthalein Magenta E will be removed from the atmosphere by wet or dry deposition. Bromophthalein Magenta E contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, Bromophthalein Magenta E is expected to have no mobility based upon an estimated Koc of 3.2X10+5. The estimated pKa of Bromophthalein Magenta E is 4.5, indicating that this compound will exist almost entirely 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. Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize. Biodegradation data were not available. If released into water, Bromophthalein Magenta E is expected to adsorb to suspended solids and sediment based upon the estimated Koc. The estimated pKa indicates Bromophthalein Magenta E 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. An estimated BCF of 7700 suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important process based on estimated hydrolysis half-lives of 5.8 years and 210 days at pHs 7 and 8, respectively. Occupational exposure to Bromophthalein Magenta E may occur through dermal contact with this compound at workplaces where Bromophthalein Magenta E is produced or used. (SRC)

Antidote and Emergency Treatment · 3 items

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Safety data

F
8-10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29189900
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazardous Substances Data
1176-74-5(Hazardous Substances Data)