2,6-ジブロモ-4-[1-(3-ブロモ-4-ヒドロキシフェニル)-1-メチルエチル]フェノール

This chemical does not meet GHS hazard criteria for 72.5% (37 of 51) of all reports.

Warning

H351 (25.5%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

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).

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).

/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.

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).

ANAEROBIC: The structurally similar tetrabromobisphenol A has been shown to biodegrade anaerobically in soil and sediment studies (near complete degradation within 64 days or less) with an intermediate formation of tri- and dibrominated bisphenol A and a final formation of only bisphenol A(1-3); therefore, tribromobisphenol A is expected to biodegrade via dehalogenation to bisphenol A(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).

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).

/ENDOCRINE MODULATION/ /The authors/ investigated the effects of the brominated phenolic and phenol compounds, some of which are brominated flame retardants, on the binding of (125)I-3,3',5-L-triiodothyronine ((125)I-T(3)) to purified Xenopus laevis transthyretin (xTTR) and to the ligand-binding domain of X. laevis thyroid hormone receptor beta (xTR LBD), on the induction of a T(3)-responsive reporter gene in a recombinant X. laevis cell line (XL58-TRE-Luc) and on T(3)-induced or spontaneous metamorphosis in X. laevis tadpoles. Of the brominated phenolic and phenol compounds tested, 3,3',5-tribromobisphenol A and 3,3'-dibromobisphenol A were the most potent competitors of (125)I-T(3) binding to xTTR and the xTR LBD, respectively. Structures with a bromine in either ortho positions with respect to the hydroxy group competed more efficiently with T(3) binding to xTTR and the xTR LBD. 3,3',5-Tribromobisphenol A and 3,3',5,5'-tetrabromobisphenol A, at 0.1-1.0 uM, exerted both T(3) agonist and antagonist activities in the T(3)-responsive reporter gene assay. Sera obtained from fetal bovine and bullfrog tadpoles weakened the T(3) agonist and antagonist activities of 3,3',5-tribromobisphenol A, but not the T(3) antagonist activity of o-t-butylphenol, for which xTTR has no significant affinity. The T(3) agonist and antagonist activities of 0.5 uM 3,3',5-tribromobisphenol A were confirmed in the in vivo, short-term gene expression assay in premetamorphic X. laevis tadpoles using endogenous, T(3)-responsive genes as molecular markers. ...Results suggest that 3,3',5-tribromobisphenol A affects T(3) binding to xTTR and xTR and that it interferes with the intracellular T(3) signaling pathway.

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).

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)

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, may result in its release to the environment through various waste streams. Tribromobisphenol A has been identified as a direct photolysis product of tetrabromobisphenol A. If released to air, an estimated vapor pressure of 7.5X10-8 mm Hg at 25 °C indicates tribromobisphenol A will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase tribromobisphenol A will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 10 hours. Particulate-phase tribromobisphenol A will be removed from the atmosphere by wet and dry deposition. Tribromobisphenol A is susceptible to direct photolysis in sunlight. If released to soil, tribromobisphenol A is expected to have no mobility based upon an estimated Koc of 1.7X10+5. The pKa of tribromobisphenol A is 7.80, 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. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 9.0X10-8 atm-cu m/mole. Tribromobisphenol A is not expected volatilize from dry soil surfaces based upon its vapor pressure. By analogy to tetrabromobisphenol A, tribromobisphenol A is expected to biodegrade anaerobically via dehalogenation (near complete degradation within 64 days or less) with a final formation of bisphenol A. If released into water, tribromobisphenol A is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 2,000 suggests the potential for bioconcentration in aquatic organisms is very high. In laboratory tests, tribromobisphenol A had direct photolysis half-lives of 15 to 69 minutes in aqueous solutions at various pH. Sensitized photo-oxidation may have some importance as a fate process for tribromobisphenol A in sunlit natural water. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. 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)

/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/

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.

Tribromobisphenol A occurs as a by-product impurity (0.79 to 1.0%) 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.

Phenol, 2,6-dibromo-4-[1-(3-bromo-4-hydroxyphenyl)-1-methylethyl]-: ACTIVE

A by-product impurity in the commercially important tetrabromobisphenol A