2,4,6-트리브로모페놀

Other Classes -> Phenols

Chlorinated/Brominated phenol

log Kow = 4.13

4.13

4.13

4.24

2.55 at 68 °F (NTP, 1992) - Denser than water; will sink

2.55 g/cu cm at 20 °C

2.55 g/cm³

Needles from alcohol; prisms from benzene

Long crystals

Soft, white needles

Slightly soluble (1-10 mg/ml) (NTP, 1992)

Sol in alcohol, chloroform, ether, glycerol oils

Very soluble in ethanol; soluble in ether, benzene, carbon tetrachloride, chloroform, acetic acid

Sol in caustic alkaline solutions

In water, 70 mg/L at 15 °C

471 °F at 760 mmHg (Sublimes at 540-554 °F at 764 mmHg) (NTP, 1992)

286 °C

286 °C

This chemical does not meet GHS hazard criteria for 0.5% (1 of 184) of reports.

Warning

H317 (94.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 184 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Chemical: Phenol, 2,4,6-tribromo-

Hazard Traits - Carcinogenicity; Endocrine Toxicity

Phenol, 2,4,6-tribromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,4,6-tribromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

REACH registered substance: 2,4,6-tribromophenol (EC: 204-278-6)

Phenol, 2,4,6-tribromo-: Does not have an individual approval but may be used under an appropriate group standard

Data is not available for this compound. It is probably non-flammable. (NTP, 1992)

Not combustible.

U.S. EPA; High Production Volume Information System (HPVIS) Detailed Chemical Results for Phenol, 2,4,6-tribromo- (118-79-6). Available at http://iaspub.epa.gov/oppthpv/quicksearch.display?pChem=101310 as of nNovember 24, 2008

WHO; Concise International Chemical Assessment Document No. 66, 2,4,6 Tribromophenol and other simple brominated phenols. Available at http://www.inchem.org/documents/cicads/cicads/cicad66.htm as of September 24, 2008.

Organization for Economic Cooperation and Development; Screening Information Data Set for 2,4,6 TRIBROMOPHENOL (118-79-6) p.81-5 (November 2003). Available from the Database Query page at: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html as of October 1, 2008.

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. 2,4,6-Tribromophenol is included on this list. Effective date 1/11/90; Sunset date: 6/30/98.

Skin Sens. 1 (94.6%)

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 1

Acute toxicity (Oral) - Category 4

Extinguish fires involving this chemical with a dry chemical, water spray, foam, or halon extinguisher. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media.

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

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.

Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.

Suitable: Water spray. Carbon dioxide, dry chemical powder, or appropriate foam.

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol 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 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.

Contact a licensed professional waste disposal service to dispose of this material. Observe all federal, state, and local environmental regulations.

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: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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 leak or spill, wear respirator, chemical safety goggles, rubber boots, and heavy rubber gloves.

For more Preventive Measures (Complete) data for 2,4,6-TRIBROMOPHENOL (7 total), please visit the HSDB record page.

2,4,6-Tribromophenol concentrations ranged from 0.077 to 1.3 ng/g lipids in serum samples collected from males ages 40 to 50 during 1977 to 1999 in Norway. In serum samples collected in 1998 in Norway from varying aged males and females, concentrations of 2,4,6-tribromophenol ranged from 0.20 to 26 ng/g lipids(1).

EC50; Species: Daphnia magna (Water flea, age 12 hr); Conditions: freshwater, static, 18 °C; Concentration: 1310 ug/L for 48 hr; Effect: intoxication, immobilization /formulated product/

LC50; Species: Cyprinus carpio (Common carp); Concentration: 1.1 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Oryzias latipes (Japanese medaka); Conditions: semistatic, 24+/-1 °C, pH 7.7, hardness (as CaCO3) 53 mg/L, Light Condition: 16:8 hours, light-darkness cycle; Concentration: 1.5 mg/L for 96 hr

LC50; Species: Pimephales promelas (Fathead minnow); Conditions: static, 25+/-2 °C, Light Condition: A constant 16-hr photoperiod was used; Concentration: 10 mg/L for 48 hr

For more Ecotoxicity Values (Complete) data for 2,4,6-TRIBROMOPHENOL (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,200(SRC), determined from a log Kow of 4.13(2) and a regression-derived equation(3), indicates that 2,4,6-tribromophenol is expected to have very slight mobility in soil(SRC). The pKa of 2,4,6-tribromophenol is 6.80(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 2,4,6-tribromophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 2,4,6-Tribromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-4 mm Hg(SRC), determined from a fragment constant method(7). A theoretical BOD of 49% using activated sludge in the Japanese MITI test(8) suggests that biodegradation may not be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,200(SRC), determined from a log Kow of 4.13(2) and a regression-derived equation(3), indicates that 2,4,6-tribromophenol 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 4.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a BCF of 83(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). A theoretical BOD of 49% using activated sludge in the Japanese MITI test(7) suggests that biodegradation may not be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,6-tribromophenol, which has an estimated vapor pressure of 3.0X10-4 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 2,4,6-tribromophenol 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 34 days(SRC), calculated from its rate constant of 4.8X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,4,6-tribromophenol may be removed from the air by wet or dry deposition(SRC). 2,4,6-Tribromophenol does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION: 2,4,6-Tribromophenol is a white to almost white crystalline powder with an acrid odor like phenol. 2,4,6-Tribromophenol is an intermediate in the synthesis of fire retardants. 2,4,6-tribromophenol is produced in closed reactors by a non-aqueous processed and discharged as a melt and pelleted for easy handling. It is the most widely produced brominated phenol. HUMAN EXPOSURE: Occupational exposures to this compound may occur by both inhalation and dermal routes. Exposure to 2,4,6-tribromophenol would be trough drinking water and consumption of seafood. ANIMAL/INVERTEBRATE/PLANT STUDIES: 2,4,6-Tribromophenol is rapidly absorbed by the gastrointestinal tract in mammals and also rapidly excreted via the urine and feces. This compound was not an irritant to rabbit skin, but was moderately irritating to the rabbit eye. It is a skin sensitizer in guinea pigs. A combined repeated dose oral toxicity study with reproduction/developmental toxicity screening test on 2,4,6-tribromophenol in rats showed reduced body weight gain, increases in absolute and liver weights in both sexes, increases in total protein, albumin, albumin/globulin ratio and ALP in blood of male rats. Salivation was noted in both sexes and increase in blood creatinine was observed in male rats. No adverse effects were noted on esterous cyclicity, copulation index, fertility index, duration of gestation period, number of corpora lutea, number of imnplants, toat number of pups and live pups, implantation index, or delivery index in any treated group. Neonatal viability on day four of lactation was and neonatal body weights were lower than controls. In vitro reverse mutation studies with this compound in two types of bacteria were negative. One in vitro chromosomal aberration test was positive with and without metabolic activation. One in vivo micronucleus assay up to the maximum tolerated dose was negative. In the marine environment, 2,4,6-tribromophenol is found in pristine soft bottom habitats. Brominated phenols including 2,4,6-tribromophenol are biosynthesized by algae, polychetes, hemichordates along with marine sponges.[

/AQUATIC SPECIES/Bromophenols are present in polychaetes as well as in algae in marine environments including the North Sea. They are thought to cause the typical sea-like taste and flavor. The ecological function of brominated phenols is not clear yet, but they may play a role in chemical defense and deterrence ... In this study 2-bromophenol (2-BP), 4-bromophenol (4-BP), 2,4-dibromophenol (2,4-DBP), 2,6-dibromophenol (2,6-DBP) and 2,4,6-tribromophenol (2,4,6-TBP), all of which are present in marine organisms, were tested. Especially 2,4-DBP and 2,4,6-TBP showed a significant effect on the Ca2+ homeostasis in endocrine cells (PC 12). The reduction of depolarization induced Ca2+ elevations by 2,4-DBP and 2,4,6-TBP and the increase of intracellular Ca2+ by both substances, partly released from intracellular stores, may suggest a link to the disrupting effect of endocrine systems by brominated phenols. 2,4-DBP was the most potent substance ... tested in respect to inhibition of voltage dependent Ca2+ currents as revealed in whole cell patch clamp experiments. Brominated phenols disturb cellular Ca2+ signaling with differential efficacy, depending on the number and position of bromine.

An effluent sample collected from an advanced waste treatment plant in Blue Plains, Washington, DC, contained an unreported concentration of 2,4,6-tribromophenol(1). The raw flue gas from a Swedish hazardous waste incinerator, located at Norrtorp, and fed chlorinated (mainly solvents) and brominated waste (tetrabutylammonium bromide) contained 2,4,6-tribromophenol at <14, 380, and 260 ng/cu m over three tests; bromides were present initially at 32, 110, and 530 mg/cu m (2). Flue gas from this incinerator, fed municipal waste, contained 2,4,6-tribromophenol at 4-5 ng/cu m(2). Peat combustion released 2,4,6-tribromophenol at concentrations of <5 to 60 ng/cu m(2).

The Koc of 2,4,6-tribromophenol is estimated as 4,200(SRC), using a log Kow of 4.13(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4,6-tribromophenol is expected to have slight mobility in soil. The pKa of 2,4,6-tribromophenol is 6.80(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

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. 2,4,6-Tribromophenol is included on this list. Effective date 1/11/90; Sunset date: 6/30/98.

2,4,6-tribromophenol decreased the respiration rate of isolated rat liver mitochondria by inhibiting the NAD-dependent dehydrogenases. The higher pK value & stronger the hydrophobic properties, the greater the inhibitory effect on respiration.

... The absorption, distribution, and elimination of /tribromophenol/ were examined in male or female Holzman albino rats after a single oral administration at doses from 4.04 to 5.34 mg/kg. /Tribromophenol/ was rapidly absorbed in rats. The bulk of the radioactivity (77 %) was readily excreted via urine and 2 to 14 % were eliminated in the feces, within 48 hours. The pharmacokinetics of this substance in rats appeared to follow a one compartment open model system.

Absorption, distribution, and elimination of 2,4,6-TBP were examined in 2 male and 10 female Holzman's albino rats (2 or 3 rats per group) after a single oral administration at doses from 4 to 5.3 mg/kg body weight. 2,4,6-TBP was rapidly absorbed, with the concentration in blood peaking after 1 hr at 4.6 mg/kg body weight. The bulk of radioactivity (50-91%) was rapidly excreted via urine, with 4-14% eliminated in the feces within 48 hr. The 2,4,6-TBP concentration in blood fell to 0.002 mg/kg within 24 hr. About 0.01% of the administered dose was retained in all tissues after 48 hr, with detectable residues (>2 ug/kg) in the kidneys (27 ug/kg), liver (6 ug/kg), and lungs (14 ug/kg). The pharmacokinetics in the rats appeared to follow a one-compartment model system. 2,4,6-TBP was rapidly distributed in the body, and the rate of elimination in urine was proportional to the concentration in the blood. The rate constant for elimination was 0.3, and the half-life in blood was 2.03 hr.

The binding of two organohalogen substances, pentabromophenol (PBP) and 2,4,6-tribromophenol (TBP), to human transthyretin (TTR), a thyroid hormone transport protein, has been studied by in vitro competitive binding assays and by X-ray crystallography. Both compounds bind to TTR with high affinity, in competition with the natural ligand thyroxine (T4). The crystal structures of the TTR-PBP and TTR-TBP complexes show some unusual binding patterns for the ligands. They bind exclusively in the `reversed' mode, with their hydroxyl group pointing towards the mouth of the binding channel and in planes approximately perpendicular to that adopted by the T4 phenolic ring in a TTR-T4 complex, a feature not observed before. The hydroxyl group in the ligands, which was previously thought to be a key ingredient for a strong binding to TTR, does not seem to play an important role in the binding of these compounds to TTR. In the TTR-PBP complex, it is primarily the halogens which interact with the TTR molecule and therefore must account for the strong affinity of binding. The interactions with the halogens are smaller in number in TTR-TBP and there is a decrease in affinity, even though the interaction with the hydroxyl group is stronger than that in the TTR-PBP complex.

Used as an antiseptic and germicide; as a chemical intermediate for its bismuth salt (antiseptic), pentachlorophenol, 2,4,6-tribromophenoxy compounds, and 2,4,6-tribromophenyl allyl ether; as a wood preservative; as a flame retardant intermediate; and as a reactive flame retardant; [HSDB]

Applying Wood Preservatives [Category: Other]

ANTISEPTIC & GERMICIDE (EG, IN PHARMACEUTICAL PREPNS)

CHEM INT FOR ITS BISMUTH SALT (ANTISEPTIC)

CHEM INT FOR PENTACHLOROPHENOL

CHEM INT FOR 2,4,6-TRIBROMOPHENOXY COMPOUNDS

2023: 10,000,000 - <50,000,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS

2,4,6-Tribromophenol 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 volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5444]

2,4,6-TBP is by far the most widely produced brominated phenol. The production volume of 2,4,6-TBP was estimated at approximately 2500 tonnes/year in Japan and 9500 tonnes/year worldwide in 2001

... By controlled bromination of phenol.

Phenol + bromine (ring bromination)

... When a solution of phenol in methanol is reacted with bromine, aromatic substitution produces a 96% yield of the flame retardant intermediate, 2,4,6-tribromophenol.

All Other Basic Organic Chemical Manufacturing

Phenol, 2,4,6-tribromo-: ACTIVE

THE FORMATION OF 2,4,6-TRIBROMOPHENOL RESULTS FROM THE CHLORINATION OF WATER CONTAINING PHENOL & BROMINE AT PH 7.4. DIRECT BROMINATION WITH HYPOBROMOUS ACID IS COMPARED WITH BROMINATION BY HYPOCHLOROUS ACID & BROMINE ION. UNDER CONDITIONS WHEN HOCL IS NOT LIMITING, A HIGHER YIELD OF BROMINE SUBSTITUTION PRODUCTS CAN BE EXPECTED FROM BROMINATION BY HOCL + BROMINE ION THAN BY DIRECT BROMINATION BY HOBR.