37853-59-1Brc1cc(Br)c(OCCOc2c(Br)cc(Br)cc2Br)c(Br)c1YATIGPZCMOYEGE-UHFFFAOYSA-N1,2-bis(2,4,6-tribromophenoxy)ethane is a white powder. (NTP, 1992)
Needles from benzene/ethanol
White, crystalline powder
Insoluble at 66 °F) (NTP, 1992)
Insoluble in water (<1 mg/mL at 19 °C)
DMSO: Insoluble (<1 mg/mL at 19 °C); 95% ethanol: Insoluble (<1 mg/mL at 19 °C)
When heated to decomposition it emits toxic vapors of bromide.
1,2-bis-(2,4,6-tribromophenoxy)ethane (BTBPE) is currently one of the most utilised novel brominated flame retardants. In this contribution, ... the mechanisms pertinent to its thermal decomposition in view of analogous experimental findings /were analyzed in detail/. ... A 1,3-hydrogen shift, leading to 2,4,6-tribromophenol (M9) and 1,3,5-tribromo-2-(vinyloxy)benzene (M10) molecules, dominates direct scission of O-CH2 bonds up to a temperature of ~ 680 K /was demonstrated/. H atom abstraction from CH2 sites, followed by a fission of a C-C bond, produces a 2,4,6-tribromophenoxy radical (M2) and a M10 molecule. Bimolecular condensation reactions involving M2, M9 and M10 produce several congeners of brominated diphenyl ethers and their OH/OCHCH2 substituents, which serve as direct precursors for the formation of polybrominated dibenzo-p-dioxins. Reaction of M9 with a model compound of a hydrocarbon chain preferentially yields M2. Strong adsorption energy of the latter on a radical site of a hydrocarbon chain suggests that mechanisms such as Langmuir-Hinshelwood, Eley-Rideal and Diels-Alder might be operating during the formation of PBDD/Fs from brominated flame retardants (BFRs).
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
This chemical does not meet GHS hazard criteria for 90.9% (30 of 33) of all reports.
Not Classified
Aggregated GHS information provided per 33 reports by companies from 4 notifications to the ECHA C&L Inventory.
Chemical: Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis[2,4,6-tribromo-
Hazard Traits - Bioaccumulation; Endocrine Toxicity; Environmental Persistence
T - indicates a substance that is the subject of a final TSCA section 4 test rule.
Substance: 1,1'-[ethane-1,2-diylbisoxy]bis[2,4,6-tribromobenzene]
Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis[2,4,6-tribromo-: Does not have an individual approval but may be used under an appropriate group standard
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 1/11/90; Reporting date: 3/12/90.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Bis(tribromophenoxy)ethane is included on this list. Effective date: 1/11/90; Sunset date: 6/30/98.
A single oral dose of (14)C 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) was administered to conventional and bile-duct cannulated male Sprague-Dawley rats. ... Metabolites were excreted in the urine, bile and feces, but at a very low level. Fecal metabolites were characterized as monohydroxylated, monohydroxylated with debromination, dihydroxylated/debrominated on a single aromatic ring, monohydroxylated on each aromatic ring with accompanying debromination, and cleavage on either side of the ether linkage to yield tribromophenol and tribromophenoxyethanol. Despite a limited quantity of stable metabolites extractable in the feces, non-extractable 14C levels were relatively high (39% of the 0-24 hr fecal (14)C), which suggested that BTBPE could be metabolically activated in the rat and covalently bound to fecal proteins and/or lipids. It was concluded that limited absorption and metabolism of BTBPE would occur by ingestion in mammals.
... Debrominated and hydroxylated metabolites were not detected in liver extracts and suggest that either biotransformation or storage of BTBPE-metabolites in the hepatic system of fish is minor or that our exposure time frame was too short. ...
... Fathead minnows from each treatment exhibited several brominated transformation products. ...
(14)C1,2-Bis(2,4,6-tribromophenoxy)ethane (FF-680) was administered at 0.05, 0.5, or 5% in the diet for 1 day to three groups (four rats per group) of rats, and daily at 0.05% in the diet for 10 days to another group of five rats. In addition, another group of four rats were given a single oral gavage dose of 200 mg/kg of ((14)C)FF-680 in corn oil and were used for bile collection. At all dose levels, (14)CFF-680-derived radioactivity was excreted almost totally via the fecal route (> 99% of the total excreted (14)C), with < 1% recovered in the urine. No radioactivity was detected in the expired air, and very little radioactivity was excreted in the bile (ca. 0.04% of the dose). At 4 days after the start of administration of the dosed diet for 1 day, no radioactivity was detected in any tissue analyzed, except adipose tissue, skin, and thymus, in which trace concentrations of radioactivity were detected in some animals. At 10 days after the start of administration of dosed diet to rats dosed for 10 days, trace but detectable levels of radioactivity were observed in all tissues analyzed except the brain of some animals. Excluding the gastrointestinal tract, adipose tissue contained the highest concentration of (14)C radioactivity, followed by kidney, skin, and thymus, whereas brain, testes, and spleen contained the lowest concentrations of radioactivity. No parent compound was detected in the urine, while fecal radioactivity was identified as the parent compound. Mean recovery of radioactivity ranged from ca. 86-101% of the ((14)C) FF-680 consumed. The data indicate that FF-680 was very poorly absorbed from the gastrointestinal tract. However, following daily administration for 10 days, trace amounts of radioactivity accumulated in tissues to provide detectable levels.
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37853-59-1DTXSID1024627222 °C
Melting point = 224 °C (commercial products are mixtures; the melting point given is for the low end of the range)
1,2-bis(2,4,6-tribromophenoxy)ethane is a white powder. (NTP, 1992)
White solid; [HSDB] White to off-white crystalline powder; [MSDSonline]
white powder
Simple aromatic halogenated organic compounds, such as 1,2-BIS(2,4,6-TRIBROMOPHENOXY)ETHANE, are very unreactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
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.
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Adults and toddlers were exposed to 1,2-bis(2,4,6-tribromophenoxy)ethane with high dust ingestion at 0.01 ng/kg bw/day and 0.05 ng/kg bw/day, respectively(1). 1,2-Bis(2,4,6-tribromophenoxy) ethane, in paired human maternal serum and breast milk samples was reported at not detected (detection limit 3.2 ng/g lipid) to 16 ng/g lipid and not detected (detection limit 0.86 ng/g lipid), respectively, samples collected from women in Sherbrooke, Canada in 2008 and 2009(2).
LC50; Species: Lepomis macrochirus (Bluegill) weight 1.4 g, mean length 50 mm: freshwater, static, 18 °C, pH 6.5-7.5, dissolved oxygen: >5.0 mg/L; Concentration: >3160000 ug/L for 24 hr /100% purity/
LC50; Species: Lepomis macrochirus (Bluegill) weight 1.4 g, mean length 50 mm: freshwater, static, 18 °C, pH 6.5-7.5, dissolved oxygen: >5.0 mg/L; Concentration: 1977000 ug/L (95% confidence interval: 1734000-2256000 ug/L) for 48 hr /100% purity/
LC50; Species: Lepomis macrochirus (Bluegill) weight 1.4 g, mean length 50 mm: freshwater, static, 18 °C, pH 6.5-7.5, dissolved oxygen: >5.0 mg/L; Concentration: 1531000 ug/L (95% confidence interval: 1317000-1780000 ug/L) for 96 hr /100% purity/
LC50; Species: Oryzias latipes (Japanese Medaka) mature organism, weight 0.2 g; Conditions: freshwater, flow through, 25 °C; Concentration: 230000 ug/L (95% confidence interval: 1317000-1780000 ug/L) for 48 hr /100% purity/
For more Ecotoxicity Values (Complete) data for 1,2-Bis(2,4,6-tribromophenoxy)ethane (7 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 910,000(SRC), determined from a log Kow of 8.9(2) and a regression-derived equation(3), indicates that 1,2-bis(2,4,6-tribromophenoxy)ethane is expected to be immobile in soil(SRC). Volatilization of 1,2-bis(2,4,6-tribromophenoxy)ethane from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.3X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 1,2-Bis(2,4,6-tribromophenoxy)ethane is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Utilizing a screening test using an acclimated soil/sewage inoculum, 1.1 to 1.41% of the total 14C-activity evolved as CO2 after 26 to 30 weeks(5) which indicates that biodegradation is not an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 910,000(SRC), determined from a log Kow of 8.9(2) and a regression-derived equation(3), indicates that 1,2-bis(2,4,6-tribromophenoxy)ethane is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 4.3X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), BCF values ranging from 8.6 to 43.6 in carp(7) suggest the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Biodegradation data in water were not available(SRC, 2014).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-bis(2,4,6-tribromophenoxy)ethane, which has an estimated vapor pressure of 1.9X10-10 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 1,2-bis(2,4,6-tribromophenoxy)ethane may be removed from the air by wet and dry deposition(SRC). 1,2-Bis(2,4,6-tribromophenoxy)ethane contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
IDENTIFICATION AND USE: 1,2-Bis(2,4,6-tribromophenoxy)ethane (BTBPE) is a white, crystalline powder. It is used as a flame retardant for many thermoplastic and thermoset systems. HUMAN EXPOSURE AND TOXICITY: In occupational setting BTBPE was detected in less than 10% of the human serum samples. ANIMAL STUDIES: There was concordance between the BTBPE-induced transcriptional responses in vitro and in ovo for CYP1A4/5 (up-regulated) and type III iodothyronine 5'-deiodinase (DIO3; down-regulated) in chicken embryonic hepatocytes and chicken embryo. BTBPE was negative in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: Juvenile rainbow trout (Oncorhynchus mykiss) treated with BTBPE did not show any effects on concentrations of circulating thyroid hormones, liver deiodinase enzyme activity, or thyroid glandular histology suggesting that BTBPE is not a potent thyroid axis disruptor.
/AQUATIC SPECIES/ Juvenile rainbow trout (Oncorhynchus mykiss) were exposed in the laboratory to an environmentally relevant dose of 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) via their diet for 49 days, followed by 154 days of untreated food to examine bioaccumulation parameters, potential biochemical effects, and metabolic products. There was a linear increase in the amount of BTBPE in fish during the uptake phase of the experiment, and an uptake rate constant of 0.0069 +/- 0.0012 (arithmetic mean +/- 1 x standard error) nmoles per day was calculated. The elimination of BTBPE from the fish obeyed first-order depuration kinetics (r2 = 0.6427, p < 0.001) with a calculated half-life of 54.1 +/- 8.5 days. The derived biomagnification factor of 2.3 +/- 0.9 suggests that this chemical has a high potential for biomagnification in aquatic food webs. Debrominated and hydroxylated metabolites were not detected in liver extracts and suggest that either biotransformation or storage of BTBPE-metabolites in the hepatic system of fish is minor or that our exposure time frame was too short. Similar concentrations of circulating thyroid hormones, liver deiodinase enzyme activity, and thyroid glandular histology suggest that BTBPE is not a potent thyroid axis disruptor.
/AQUATIC SPECIES/ The phaseout of polybrominated diphenyl ethers (PBDEs) has prompted the search for appropriate substitutes. These substitutes, referred to as novel brominated flame retardants (NBFRs), are poorly characterized in terms of their persistence, bioaccumulation, and toxicity. The authors assessed the bioaccumulation potential of 3 non-PBDE brominated flame retardants: 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE), tetrabromobisphenol A bis(2,3-dibromopropylether) (TBBPA-BDBPE), and BZ-54, a mixture of bis(2-ethylhexyl)tetrabromophthalate) (BEH-TEBP) and 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (EH-TBB). Replicate outdoor aquatic mesocosms were treated individually at concentrations designed to give a maximum load of 500 ng/g of flame retardant in the upper 5 cm of the sediment. Caged fathead minnows (Pimephales promelas, 24 fish per replicate) were introduced to each mesocosm and acclimated for 10 d prior to exposure. The exposure period was 42 d, followed by 28 d of depuration after transfer to a control mesocosm, during which physical, reproductive, and biochemical end points were examined. Tissue samples were taken to measure the accumulation, depuration, and biotransformation of NBFRs. Fathead minnows were observed to accumulate, after growth adjustment, BTBPE (16-4203 ng/g lipid) and TBBPA-BDBPE (>1000 ng/g lipid) but with a lack of consistent accumulation observed for EH-TBB and BEH-TEBP. However, limited biologically meaningful or consistent responses were observed in the monitored physical, reproductive, and biochemical parameters. Fathead minnows from each treatment exhibited several brominated transformation products. ... These NBFRs have the potential to be bioaccumulative and persistent in vivo and, therefore, warrant further study of physiological effects linked to chronic, sublethal responses.
1,2-Bis(2,4,6-tribromophenoxy)ethane was detected in Herring Gull (Larus argentatus) eggs collected from six colonies from Agawa Rock, Gull Island, Channel-Shelter Island, Fighting Island, Niagra River, and Toronto Harbour in the Laurentian Great Lakes at concentrations of 0.06, 0.16, 0.04, 0.26, 0.70, 0.04 ng/g ww, respectively(1). 1,2-Bis(2,4,6-tribromophenoxy)ethane was also detected in Herring Gull eggs in 2006 from seven colonies of the Laurentian Great Lakes (Agawa Rocks, Gull Island, Channel-Shelter Island, Chantry Island, Fighting Island, Niagara River, and Toronto Harbour) at 0.11, <0.06, 0.08, 0.10, 0.20, 0.11, and 0.09 ng/g ww, respectively(2).
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of September 4, 2014: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=37853-59-1]
The Koc of 1,2-bis(2,4,6-tribromophenoxy)ethane is estimated as 910,000(SRC), using a log Kow of 8.9(1) and a regression-derived equation(2). According to a classification scheme(2), this estimated Koc value suggests that 1,2-bis(2,4,6-tribromophenoxy)ethane is expected to be immobile in soil.
The mutagenicity of 1,2-bis (2,4,6-tribromophenoxy)ethane (TBE) was evaluated in the bacteria Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test), and in the yeast Saccharomyces cerevisiae tester strain D4, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, TBE, diluted in DMSO, was tested for mutagenicity in the bacterial and yeast cultures at concentrations up to 50 ug/plate using the plate overlay method. TBE did not cause a positive response in any of the bacterial or yeast tester strains, either with or without metabolic activation.
RURAL/REMOTE: 1,2-Bis(2,4,6-tribromophenoxy)ethane was detected in the atmosphere at an e-waste site and a rural site in Southern China at concentrations ranging from 4.49 to 398 pg/cu m, average 78.7 pg cu m for the e-waste site and from not detected to 28.4 pg/cu m, average 2.97 for the rural site(1).
SOURCE DOMINATED: 1,2-Bis(2,4,6-tribromophenoxy)ethane was detected in air particulate samples collected at the Michigan Chemical Corporation Plant Site (Velsicol) at concentrations of 39 to 183 ng/cu m(1). 1,2-Bis(2,4,6-tribromophenoxy)ethane was detected, not quantified in Arkansas air particulate; sampling was conducted in areas surrounding the bromine industry in El Dorado and Magnolia. It was not detected in air from similar industrial sites in Bayonne and Sayerville, New Jersey(2). 1,2-Bis(2,4,6-tribromophenoxy)ethane was detected in the vapor phase, particle phase and precipitation at five US Integrated Atmospheric Deposition Network (IADN) sites from the Great Lakes Basin at concentrations of 0.2 to 0.8 pg/cu m, 0.2 to 1 pg/cu m, and 0.01 to 0.1 ng/L; sampling was conducted during 2005-2009(3). 1,2-Bis(2,4,6-tribromophenoxy)ethane was detected in the ambient air in the vicinity of organo-bromine synthesis facilities on July 22, July 24 and July 25, 1977 at 39, 172, and 183 ng/cu m(4).
Two brominated flame retardants, 1,2-bis(2,4,6-tribromophenoxy)ethane (TBE) and 2,3,4,5,6-pentabromoethylbenzene (PEB), were detected and identified in ambient air samples from various sites in the United States. The identifications were confirmed by comparing the gas chromatographic retention times and mass spectra of the compounds found in the environment with those of authentic materials. Generally, the TBE concentrations in air were comparable to those of tetra- through hexabrominated diphenyl ethers (PBDEs) and often higher than those of decabromodiphenyl ether (BDE-209). The atmospheric TBE concentrations at locations in the southern United States were higher than those in the northern United States. ... These occurrences of relatively high concentrations of TBE and PEB in environmental samples may reflect the increasing usage of these compounds as flame retardants.
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 1/11/90; Reporting date: 3/12/90.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Bis(tribromophenoxy)ethane is included on this list. Effective date: 1/11/90; Sunset date: 6/30/98.
A single oral dose of (14)C 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) was administered to conventional and bile-duct cannulated male Sprague-Dawley rats. Tissue disposition, excretion and metabolism was determined. BTBPE is a low-volume brominated flame retardant used in resins or plastics. ... BTBPE was fairly insoluble in lipophilic solutions, which made dose preparation difficult. The great majority of (14)C (>94%) was excreted in the feces of both groups of rats at 72 hr, and tissue retention was minimal. Lipophilic tissues contained the highest concentrations of BTBPE, e.g. thymus, adipose tissue, adrenals, lung, and skin. Metabolites were excreted in the urine, bile and feces, but at a very low level. ... Despite a limited quantity of stable metabolites extractable in the feces, non-extractable (14)C levels were relatively high (39% of the 0-24 hr fecal (14)C), which suggested that BTBPE could be metabolically activated in the rat and covalently bound to fecal proteins and/or lipids. It was concluded that limited absorption and metabolism of BTBPE would occur by ingestion in mammals.
Used as a flame retardant additive for thermoplastic and thermoset systems; [HSDB]
Flame retardant for many thermoplastic and thermoset systems.
Brominated additive flame retardant. /From table/
The principal market ... is in ABS resins.
1,2-Bis(2,4,6-tribromophenoxy)ethane is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Bis(2,4,6-tribromophenoxy)ethane. Aggregated National Production Volume: 1 to < 10 million pounds.
Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis[2,4,6-tribromo-: ACTIVE
The phaseout of polybrominated diphenyl ethers (PBDEs) has prompted the search for appropriate substitutes. These substitutes, referred to as novel brominated flame retardants (NBFRs), are poorly characterized in terms of their persistence, bioaccumulation, and toxicity.
용도One of the major "novel" brominated flame retardants (NBFRs) from varous polymer materials. An environmental pollutant.
일반 설명White powder.