Phenol, 2,2′,6-tribromo-4,4′-isopropylidenedi-

464.97500

464.97

228-988-0

25MI3KZ1HF

DTXSID3064302

2908199090

40.46000

5.71120

1.873g/cm3

107-110 °C

413.1ºC at 760 mmHg

203.6ºC

1.656

Henry's Law constant = 9.0X10-8 atm-cu m/mol at 25 °C (est)

pKa = 7.80

Hydroxyl radical reaction rate constant = 1.3X10-11 cu cm/molecule-sec at 25 °C (est)

II

UN 3152

P273, P391, P501

H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

|Warning|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 14 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Tribromobisphenol A's production as a by-product impurity in the commercially important tetrabromobisphenol A, which is used as a reactive intermediate in the manufacture of flame-retardant epoxy and polycarbonate resins and as an additive flame in the manufacture of acrylonitrile-butadiene-styrene (ABS) resins(1) may result in its release to the environment through various waste streams(SRC). Tribromobisphenol A has been identified as a direct photolysis product of tetrabromobisphenol A(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+5(SRC), determined from a structure estimation method(2), indicates that tribromobisphenol A is expected to be immobile in soil(SRC). The pKa of tribromobisphenol A is 7.80(3), indicating that this compound will exist partially 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 tribromobisphenol A from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.0X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Tribromobisphenol A is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.5X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). By analogy to tetrabromobisphenol A(5-7), tribromobisphenol A is expected to biodegrade anaerobically via dehalogenation (near complete degradation within 64 days or less) with a final formation of bisphenol A(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.7X10+5(SRC), determined from a structure estimation method(2), indicates that tribromobisphenol A 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 9.0X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 2,000(SRC), from an estimated log Kow of 5.51(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Phototransformation studies of tribromobisphenol A in aqueous solution determined a UV absorption maximum at 306 nm, a quantum yield of 0.083 and decomposition rates ranging from 1.6X10-4 (at pH 6.6) to 7.5X10-4 (at pH 9.5) per second, corresponding to a half-life range 15 minutes to 69 minutes(5). Tribromobisphenol A is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy radicals with half-lives on the order of days to weeks at the water surface(4); therefore, photo-oxidation may have some importance as a fate process for tribromobisphenol A in natural water(SRC). By analogy to tetrabromobisphenol A(6-8), tribromobisphenol A is expected to biodegrade anaerobically via dehalogenation (near complete degradation within 64 days or less) with a final formation of bisphenol A(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tribromobisphenol A, which has an estimated vapor pressure of 7.5X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tribromobisphenol A is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase tribromobisphenol A may be removed from the air by wet and dry deposition(SRC). Aqueous photolysis studies have demonstrated that tribromobisphenol A degrades through direct photolysis in the environmental spectrum(3).

The rate constant for the vapor-phase reaction of tribromobisphenol A with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phototransformation studies of tribromobisphenol A in aqueous solution determined a UV absorption maximum at 306 nm, a quantum yield of 0.083 and decomposition rates ranging from 1.6X10-4 (at pH 6.6) to 7.5X10-4 (at pH 9.5) per second which correspond to a half-life range 15 minutes to 69 minutes(2). Tribromobisphenol A is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl and peroxy (RO2) radicals with half-lives on the order of days to weeks at the water surface(4); therefore, photo-oxidation may have some importance as a fate process for tribromobisphenol A in natural water(SRC).

An estimated BCF of 2,000 was calculated in fish for tribromobisphenol A(SRC), using an estimated log Kow of 5.51 derived from an experimental value adjustment method(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tribromobisphenol A can be estimated to be 1.7X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that tribromobisphenol A is expected to be immobile in soil. The pKa of tribromobisphenol A is 7.80(3), indicating that this compound will exist partially 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).

The Henry's Law constant for tribromobisphenol A is estimated as 9.0X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tribromobisphenol A is expected to be essentially nonvolatile from water surfaces(2). Tribromobisphenol A's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Tribromobisphenol A is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.5X10-8 mm Hg(SRC), determined from a fragment constant method(1).

Occupational exposure to tribromobisphenol A may occur through dermal contact with this compound at workplaces where tribromobisphenol A is produced or used. The general population may be exposed to tribromobisphenol A via dermal contact with consumer products containing brominated flame retardants (tetrabromobisphenol A) that contain this compound as an impurity. (SRC)

TBBPA /tetrabromobisphenol A/ administered /to rats/ IP in high, single doses was readily absorbed into the blood, distributed in body organs and eliminated. During 72 hr following administration, 51-65% of the given (14)C-dose was excreted in feces, only a slight amount (0.3%) in the urine. The (14)C activity in feces was identified as TBBPA (approximately 90%) and tribromobisphenol A (approximately 10%). The identity of (14)C-activity in blood or organs was not determined.

/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/

/ENDOCRINE MODULATION/ Tetrabromobisphenol A (TeBBPA) is a four-meta-brominated variant of bisphenol A (BPA) and is one of the most commonly used brominated flame retardants worldwide. /The authors/ compared the estrogenic potency of TeBBPA, BPA and the brominated analogs mono- (MBBPA), di- (DBBPA), and tribromobisphenol A (TrBBPA) in the estrogen-dependent human breast cancer cell line MCF-7. All of the compounds competed with 17beta-estradiol for binding to the estrogen receptor, although the affinity of the test chemicals to the estrogen receptor was much lower than that of 17beta-estradiol. TrBBPA and TeBBPA showed a considerably lower access to the estrogen receptors within intact MCF-7 cells incubated in 100% serum compared to incubation in serum-free medium, indicating a strong binding to serum proteins. BPA, MBBPA, and DBBPA showed only a slightly reduced access to the receptors. All of the test compounds induced proliferation in MCF-7 cells, the potential decreasing with increasing number of bromo-substitutions. TeBBPA did not induce maximal cell growth, indicating cytotoxic effects at high concentrations. BPA and the brominated analogs, except TeBBPA, induced progesterone receptor and pS2 to the same extent as 17beta-estradiol, although at much higher concentrations. /These/ studies demonstrate that compared to 17beta-estradiol, BPA and the brominated analogs have much lower estrogenic potencies for all of the endpoints tested, TeBBPA being the least estrogenic compound.

Phenol, 2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]-: ACTIVE|A by-product impurity in the commercially important tetrabromobisphenol A

This paper describes the development of a methodology for the simultaneous determination and quantification of hexabromocyclododecane (HBCD), tetrabromobisphenol A (TBBPA), and related compounds (bisphenol A, monobromobisphenol A, dibromobisphenol A, and tribromobisphenol A) in sludge and sediment samples. The selected method is based on an extraction with dichloromethane: methanol followed by purification via SPE C(18) cartridges. Instrumental determination was carried out by liquid chromatography-quadrupole linear ion trap mass spectrometry (LC-QqLIT-MS), with quantification based on isotopic dilution method. Analyte recoveries were in the range of 39-120% and 88-126% for spiked sewage and sediment, respectively. Repeatability of replicate extractions was better than 13% relative standard deviation. Linearity was checked in the range of 0.05 and 25 injected nanograms. Limits of detection (LODs) and limits of quantification (LOQs) were in the range of 0.6 and 2.7 ng/g and 1.4 and 66 ng/g for sediment and sludge samples, respectively. The developed method was applied to sewage sludge and sediment samples collected along the Ebro River and Cinca River, one of its tributaries (northeast of Spain). TBBPA levels in sewage sludge ranged from not quantified to 1,329 ng/g dw, whereas levels in sediment samples were lower, between not detected and 15 ng/g dw. As regards HBCD, concentrations were between not detected and 375 ng/g for sludge samples and 0.8 and 1850 ng/g for sediments.