Tetrachlorobisphenol A

366.06700

366.07

201-237-4

FO0P9ET4BN

67465|18248

DTXSID3021770

Crystals from acetic acid

40.46000

6.03730

1.479 g/cm3

136-137 °C @ Solvent: Benzene

401.9ºC at 760 mmHg

196.8ºC

1.627

Refrigerator

2X10-8 mm Hg at 25 deg C (est)

Henry's Law constant = 2.8X10-12 atm-cu m/mol at 25 °C (est)

pKa = 6.91 at 25 °C (est)

Hydroxyl radical reaction rate constant = 3.5X10-12 cu cm/molecule-sec at 25 °C (est)

R36/37/38

26-37/39

Xi: Irritant;

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

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|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

LD50 Mouse oral 5050 mg/kg|LD50 Rat oral 7432 mg/kg

2,2',6,6'-Tetrachlorobisphenol A's production and use a monomer for flame-retardant epoxy, polyester, and polycarbonate resins(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6X10+5(SRC), determined from a structure estimation method(2), indicates that 2,2',6,6'-tetrachlorobisphenol A is expected to be immobile in soil(SRC). The estimated pKa of 2,2',6,6'-tetrachlorobisphenol A is 6.91(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 2,2',6,6'-tetrachlorobisphenol A from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 2,2',6,6'-Tetrachlorobisphenol A is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6X10+5(SRC), determined from a structure estimation method(2), indicates that 2,2',6,6'-tetrachlorobisphenol 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 2.8X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 5900(SRC), from an estimated log Kow of 6.22(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). 2,2',6,6'-Tetrachlorobisphenol 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(5); therefore, photo-oxidation may have some importance as a fate process for 2,2',6,6'-tetrachlorobisphenol A in natural water(SRC). 2,2',6,6'-Tetrachlorobisphenol A has been shown to undergo anaerobic biodegradation in estuarine sediment with the formation of a persistent dichlorinated bisphenol A isomer(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2',6,6'-tetrachlorobisphenol A, which has an estimated vapor pressure of 3X10-8 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 2,2',6,6'-tetrachlorobisphenol 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 3.5 days(SRC), calculated from its rate constant of 3.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase 2,2',6,6'-tetrachlorobisphenol A may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of 2,2',6,6'-tetrachlorobisphenol A with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,2',6,6'-Tetrachlorobisphenol A is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 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(3); therefore, photo-oxidation may have some importance as a fate process for 2,2',6,6'-tetrachlorobisphenol A in natural water(SRC).

An estimated BCF of 5900 was calculated in fish for 2,2',6,6'-tetrachlorobisphenol A(SRC), using an estimated log Kow of 6.22(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 2,2',6,6'-tetrachlorobisphenol A can be estimated to be 6X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2',6,6'-tetrachlorobisphenol A is expected to be immobile mobility in soil. The estimated pKa of 2,2',6,6'-tetrachlorobisphenol A is 6.91(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 2,2',6,6'-tetrachlorobisphenol A is estimated as 2.8X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2',6,6'-tetrachlorobisphenol A is expected to be essentially nonvolatile from water surfaces(2). 2,2',6,6'-Tetrachlorobisphenol A's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 2,2',6,6'-Tetrachlorobisphenol A is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3X10-8 mm Hg(SRC), determined from a fragment constant method(1).

SURFACE WATER: 2,2',6,6'-Tetrachlorobisphenol A was qualitatively detected in samples collected from the lower Fox River system in Wisconsin during 1976-1977 monitoring(1).

Occupational exposure to 2,2',6,6'-tetrachlorobisphenol A may occur through dermal contact with this compound at workplaces where 2,2',6,6'-tetrachlorobisphenol A is produced or used. Use data indicate that the general population may be exposed to 2,2',6,6'-tetrachlorobisphenol A via dermal contact with consumer products containing 2,2',6,6'-tetrachlorobisphenol A. (SRC)

/BIOMONITORING/ Bisphenol-A (BPA) and chlorinated derivatives (Cl(x)BPA) were investigated in adipose tissue of women in Southeast Spain. BPA was above limit of detection (LOD) in 11 out of 20 samples (55%). Among Cl(x)BPA, Cl(2)BPA was the most frequent (80%) and abundant, constituting 94.6% of total chlorinated BPA in adipose tissue. Mean +/- S.D. of BPA, monochloro-BPA (ClBPA), dichloro-BPA (Cl(2)BPA), and trichloro-BPA (Cl(3)BPA) were 5.83 +/- 3.48, 3.05 +/- 0.28, 9.21 +/- 9.26, and 0.74 +/- 0.15 ng/g of adipose tissue, respectively. No tetrachloro-BPA (Cl(4)BPA) was found above LOD. There are no published data on BPA in human adipose tissue or on Cl(x)BPA in adipose tissue or blood, limiting comparisons. BPA levels were similar (w/w) to findings in blood (w/v) in other populations and below levels reported in placenta tissue (w/w). Because of the estrogen mimicking effects of BPA and its Cl(x)BPA, further research is needed to explore their combined effects on human health and trends in human exposure.

/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/

/ALTERNATIVE and IN VITRO TESTS/ The capability of the flame retardants tetrabromobisphenol A (TBBPA) and tetrachlorobisphenol A (TCBPA) to activate peroxysome proliferator-activated receptors (PPARs) alpha, beta, and gamma and estrogen receptors (ERs) alpha and beta has been recently investigated, but the activity of their biotransformation products and of their lower molecular weight analogues formed in the environment remains unexplored. The aim of this study was to investigate the relationship between the degree of halogenation of BPA analogues and their affinity and activity towards human PPARgamma and ERs and to characterize active metabolites of major marketed halogenated bisphenols. The biological activity of all compounds was studied using reporter cell lines expressing these nuclear receptors (NRs). /The researchers/ used NR-based affinity columns to rapidly evaluate the binding affinity of halogenated bisphenols for PPARgamma and ERs and to trap active metabolites of TBBPA and TCBPA formed in HepG2 cells. The agonistic potential of BPA analogs highly depends on their halogenation degree: the bulkier halogenated BPA analogs, the greater their capability to activate PPARgamma. In addition, PPARgamma-based affinity column, HGELN-PPARgamma reporter cell line and crystallographic analysis clearly demonstrate that the sulfation pathway, usually considered as a detoxification process, leads for TBBPA and TCBPA, to the formation of sulfate conjugates which possess a residual PPARgamma-binding activity. /The researchers/ results highlight the effectiveness NR-based affinity columns to trap and characterize biologically active compounds from complex matrices. Polyhalogenated bisphenols, but also some of their metabolites, are potential disrupters of PPARgamma activity.

4,4'-(1-methylethylidene)bis(2,6-dichlorophenol)

ESSENTIALLY 100% AS FLAME RETARDANT MONOMER

Phenol, 4,4'-(1-methylethylidene)bis[2,6-dichloro-: INACTIVE|T - indicates a substance that is the subject of a final TSCA section 4 test rule.

A method for determination of phenolic flame-retardants in human plasma utilizing solid-phase extraction (SPE) and gas chromatography with electron-capture mass spectrometric detection (GC-ECMS), has been developed. The plasma lipids were decomposed by application of concentrated sulphuric acid directly on the polystyrene-divinylbenzene SPE column. The method has been validated for 2,4,6-tribromophenol (TriBP), pentabromophenol (PeBP), tetrachlorobisphenol-A (TCBP-A) and tetrabromobisphenol-A (TBBP-A) in the concentration range 1.2-25, 0.4-40, 4-200 and 4-200 pg g(-1) plasma, respectively. The average absolute recovery of the analytes ranged from 51 to 85%. Tetrabromo-o-cresol and chlorotribromobisphenol-A were found suitable as internal standards, and the average recovery of the analytes relative to the internal standards was in the range 93-107%. The repeatability of the method was in the range 4-30% relative standard deviation. The estimated detection limits of TriBP, PeBP, TCBP-A and TBBP-A were 0.3, 0.4, 3.0 and 0.8 pg g(-1) plasma, respectively. The method has been used for analysis of plasma samples from potentially occupationally exposed human individuals.