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Home > Encyclopedia > 2,4,6-Tribromophenol

2,4,6-Tribromophenol

2,4,6-Tribromophenol structure

2,4,6-Tribromophenol 

structure
  • CAS No:

    118-79-6

  • Formula:

    C6H3Br3O

  • Chemical Name:

    2,4,6-Tribromophenol

  • Synonyms:

    Phenol,2,4,6-tribromo-;2,4,6-Tribromophenol;Bromol;Bromkal Pur 3;Flammex 3BP;1,3,5-Tribromo-2-hydroxybenzene;NSC 2136;PH 73

  • Categories:

    Catalyst and Auxiliary  >  Coupling Agent

Description

WHITE TO SLIGHTLY BROWN POWDER Long, soft white crystals. 2,4,6-Tribromophenol has a penetrating bromine odor.ChEBI: A bromophenol that is phenol substituted by bromo groups at positions 2, 4 and 6. It is commonly used as a fungicide and in the preparation of flame retardants.Soft, long, white crystals with a bromine odor.


2,4,6-Tribromophenol (TBP) is a brominated derivative of phenol. It is used as a fungicide, as a wood preservative, and an intermediate in the preparation of flame retardants.


Soft, long, white crystals with a bromine odor. (NTP, 1992)|DryPowder; Liquid|Solid|WHITE-TO-PINK POWDER.


Soft, long, white crystals with a bromine odor. (NTP, 1992)|2,4,6-tribromophenol is a bromophenol that is phenol in which the hydrogens at positions 2, 4 and 6 have been replaced by bromines. It is commonly used as a fungicide and in the preparation of flame retardants. It has a role as an environmental contaminant, a fungicide and a marine metabolite.

2,4,6-Tribromophenol Basic Attributes

330.801

330.80

204-278-6

YS6K3EU393

1563

2136

2811|3082

DTXSID6021959

Needles from alcohol; prisms from benzene|Long crystals|Soft, white needles

2908199090

Characteristics

20.2

4.4

Soft, long, white crystals with a bromine odor. (NTP, 1992)

2.55 g/cm3 @ Temp: 20 °C

94-96 °C

286 °C

282-290°C subl.

1.5580 (estimate)

Solubility in water, g/100ml at 25°C: 0.007

Keep tightly closed.

Vapour pressure, Pa at 25°C: 0.007

Relative vapour density (air = 1): 2.5

Penetrating bromine odor

Sweet

6.8(at 25 °C)

Henry's Law constant = 4.77X10-8 atm-cu m/mol at 25 °C (est)

6.8 (at 25 °C)|pKa = 6.80

Hydroxyl radical reaction rate constant = 4.75X10-13 cu cm/molec-sec at 25 °C (est)

Slightly soluble in water.

Phenols and Cresols

2,4,6-TRIBROMOPHENOL can react with oxidizing materials (NTP, 1992).

Safety Information

III

9

UN 1230 3/PG 2

2

R20/22;R36/37/38;R51/53

26-36-61-37/39-45-36/37-16-7-24/25-23-53-37

SN1225000

Xi,N,Xn,T,F

P273-P280-P305 + P351 + P338

H317-H319-H400

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.

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.

UN 1230 3/PG 2

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

|Warning|H317 (94.97%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, P391, and P501|Aggregated GHS information provided by 180 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P309+P311, P314, P321, P330, P333+P313, P337+P313, P363, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

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)|Respiratory: Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Hand: Compatible chemical-resistant gloves. Eye: Chemical safety goggles.|ENGINEERING CONTROLS: Use only in a chemical fume hood. Safety shower and eye bath.

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.

Sweep up, place in a bag and hold for waste disposal. Avoid raising dust. Ventilate area and wash spill site after material pickup is complete.

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.

Irritating to eyes, respiratory system and skin.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers.

A harmful concentration of airborne particles can be reached quickly when dispersed.

The substance is irritating to the eyes.

Repeated or prolonged contact may cause skin sensitization.

See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE. STRICT HYGIENE!

Avoid inhalation of dust.

Protective gloves.

Wear safety goggles.

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).

SEDIMENT: Upper river and marine sediment layers in Osaka Prefecture, Japan, collected in 1981 through 1983 at 12 different locations, contained 2,4,6-tribromophenol at concentrations ranging from <0.2 ppb to 35 ug/kg (dry weight basis)(1). Surficial sediments from the Rhone estuary, collected in 1987/1988, contained 2,4,6-tribromophenol at concentrations of 26 to 3690 ng/g, dry weight basis, from 5 sampling sites(2).

Concentrations of 2,4,6-tribromophenol were measured in brown algae (14 to 38 ug/kg wet weight), red algae (4.5 to 68 ug/kg), bryozoa (24 and 27 ug/kg), a hydroid (29 ug/kg), and sponges (0.22 to 240 ug/kg) collected from Exmouth Gulf, Australia, in October 1990(1).

Toxicity

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.[

LD50 Rat dermal >2,000 mg/kg bw.|LD50 Rat oral 1,486 mg/kg bw.|LC50 Rat Inhalation >50000 mg/cu m 4 hr|LC50 Rat Inhalation >200000 mg/cu m 1 hr.|LD50 Rat Oral >5000 mg/kg

/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.

Study demonstrates the wide occurrence of bromophenols in marine algae and provides a possible source of such compounds in fish that feed predominantly on ocean plants. /Bromophenols/

2,4,6-Tribromophenol's production and use as an reactive flame retardant(1), flame retardant intermediate(2,3), or as a wood preservative(3) 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 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).

The rate constant for the vapor-phase reaction of 2,4,6-tribromophenol with photochemically-produced hydroxyl radicals has been estimated as 4.8X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 34 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4,6-Tribromophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,4,6-Tribromophenol does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

512.86|BCF values of 513(1,3) and 83(2) were measured in Brachydanio rerio and fathead minnow, respectively, for 2,4,6-tribromophenol. According to a classification scheme(4), these BCF values suggest the potential for bioconcentration in aquatic organisms is moderate to high.

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).

The Henry's Law constant for 2,4,6-tribromophenol is estimated as 4.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4,6-tribromophenol is expected to be essentially nonvolatile from water surfaces(2). 2,4,6-tribromophenol's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). 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(3).

DRINKING WATER: 2,4,6-Tribromophenol was detected at unreported concentrations in 1 of 3 drinking water samples collected in Cincinnati, OH in October, 1978(1). 2,4,6-Tribromophenol was monitored in 40 potable water treatment plants in Canada; mean concentrations for October/December 1984, February/March 1985, and May/June 1985 were 0.6 and 1.3 (raw water and treated water, respectively), 0.2 and 0, and 0 and 0.5 ng/L, respectively(2). Raw water from water treatment plants in 6 Canadian cities and treated water from water treatment plants in 5 of 6 Canadian cities, collected in February 1985, contained 2,4,6-tribromophenol at concentrations below the quantitation limit; one sample of treated water contained 2,4,6-tribromophenol at 5 ng/L(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,427 workers (734 of these were female) were potentially exposed to 2,4,6-tribromophenol in the US(1). Occupational exposure to 2,4,6-tribromophenol may occur through inhalation and dermal contact with this compound at workplaces where 2,4,6-tribromophenol is produced or used. Limited monitoring data indicate that the general population may be exposed to 2,4,6-tribromophenol via ingestion of food and drinking water, or dermal contact with products containing 2,4,6-tribromophenol(SRC).

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).

Drug Information

... 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.

Two male and 10 female Holzman's albino rats (2 or 3 rats per group) /were administered/ a single oral administration at doses from 4 to 5.3 mg/kg body weight. The half-life in blood was 2.03 hr.

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.

SYMPTOMS: This chemical may cause severe irritation to the skin, eyes, and mucous membranes. ACUTE/CHRONIC HAZARDS: This chemical and its decomposition products are considered to be very toxic by: ingestion, inhalation and skin absorption. It emits toxic fumes. It may react violently with oxidizing materials. It is also known to be a strong skin irritant. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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.

/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/

/SIGNS AND SYMPTOMS/ Irritating to eyes, respiratory system and skin.|/ALTERNATIVE and IN VITRO TESTS/ /A/ previous study demonstrated that compounds in indoor dusts strongly inhibit thyroxine (T4) binding to the human thyroid hormone transport protein transthyretin (TTR) in vitro. ... Here, ... chemical fractionation /was used/ with in vitro competitive human TTR-binding assay and GC-MS to analyze the TTR-binding compounds in a sulfuric-acid-treated dust extract. 2,4,6-Tribromophenol (TriBPh) and 2,3,4,5,6-pentachlorophenol (PeCPh) were potent TTR-binding compounds in all dust samples. 2,4,6-TriBPh- and 2,3,4,5,6-PeCPh-derived theoretical T4 equivalents (T4EQs), calculated arithmetically from the concentrations and relative potencies, accounted for about 40-70% of experimental T4EQs detected in indoor dusts, indicating that these compounds contributed strongly to the TTR-binding potency of indoor dust...|/ALTERNATIVE and IN VITRO TESTS/ /The/ study assessed the potential effects of nineteen polybrominated diphenyl ethers (BDEs), five hydroxylated BDEs (OH-BDEs), one methoxylated BDE (CH(3)O-BDE), tetrabromobisphenol-A (TBBPA), its dibromopropane ether derivative (TBBPA-DBPE), and the brominated phenols/anisols 2,4,6-tribromophenol (TBP), 4-bromophenol (4BP) and 2,4,6-tribromoanisole (TBA) on the catalytic activity of the steroidogenic enzyme aromatase (CYP19) in H295R human adrenocortical carcinoma cells. Effects were studied in the concentration range from 0.5 to 7.5 uM; exposures were for 24 hr. Both 6-OH-BDE47 and 6-OH-BDE99 showed an inhibitory effect on aromatase activity at concentrations >2.5 uM and >5 uM, respectively. However, 6-OH-BDE47 also caused a statistically significant increase in cytotoxicity (based on mitochondrial MTT reduction and lactate dehydrogenase-leakage [LDH]) at concentrations >2.5 uM that could explain in part the apparent inhibitory effect on aromatase activity. Compared to 6-OH-BDE47, the methoxy analog (6-CH(3)O-BDE47) did not elicit a cytotoxic effect, whereas significant inhibition of aromatase remained. TBP caused a concentration-dependent induction of aromatase activity between 0.5 and 7.5 uM (with a maximum of 3.8-fold induction at 7.5 uM). This induction was not observed when a OH- group replaced the CH(3)O- group or when bromine atoms adjacent to this OH- group were absent...

2,4,6-tribromophenol

The substance can be absorbed into the body by ingestion.

Redness. Pain.

2,4,6-Tribromophenol Use and Manufacturing

Methods of Manufacturing

... 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.

Uses

Intermediates

Production

(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#5449]|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

All other basic inorganic chemical manufacturing|Phenol, 2,4,6-tribromo-: ACTIVE|T - indicates a substance that is the subject of a final TSCA section 4 test rule.|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.

A solid-phase microextraction (SPME) method for the ultra-trace determination of brominated phenols in aqueous samples ... is reported ... . 3,5,3',5'-tetrabromobisphenol A (TBBPA), the most widely used brominated flame retardant, and other phenolic flame retardants in commercial use, such as 2,4-dibromophenol (2,4-DBP), 2,4,6-tribromophenol (TBP) and pentabromophenol (PBP) have been included as target analytes. The analytical procedure involves the in situ acetylation-SPME and gas chromatography-mass spectrometry (GC-MS) determination of the target analytes. ...|The use of 2,4,6-tribromophenol (2,4,6-TBP)-contaminated wood materials in the food industry poses a risk of significant economical losses due to food contamination. In this work an efficient and reliable immunochemical method for analysis of TBP in wood samples has been established consisting of alkaline wood extraction followed by analysis on a microplate ELISA (enzyme-linked immunosorbent assay). TBP is efficiently extracted from wood samples in 10 min and directly measured after 10-fold buffer dilution to avoid matrix interferences. The analytical procedure has a limit of detection of 45 ng/g of TBP in wood (1.5 ug/L in extracts)...|A METHOD FOR DETERMINING TRACE CONCN OF CARBOXYLIC ACIDS & PHENOLS, INCLUDING 2,4,6-TRIBROMOPHENOL, FROM AQUEOUS SOLUTION IS DESCRIBED. THIS IS ACCOMPLISHED BY A CONCN STEP USING MACRORETICULAR RESINS WITH PYRIDINE ELUTION, SUBSEQUENT DERIVATIZATION WITH BIS-TRIMETHYLSILYL ACETAMIDE, & ANALYSIS BY GAS CHROMATOGRAPHY.|STEAM DISTILLATION SEPARATES HYDROCARBONS & VOLATILE PHENOLS, INCLUDING 2,4,6-TRIBROMOPHENOL, FROM ACIDIFIED SEDIMENT SAMPLE. SEPARATION OF PHENOLS FROM CARBOXYLIC ACIDS IS ACHIEVED BY EXTRACTIVE ACETYLATION OF PHENOLS FROM AN ALKALINE BUFFER.|Method: DOE OM100R; Procedure: gas chromatography with mass spectrometer ion trap detector; Analyte: 2,4,6-tribromophenol; Matrix: solid waste matrices, soils, and groundwater; Detection Limit: 26 ug/L.

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 sulfuric 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 plasma, respectively. ... The estimated detection limits of TriBP, PeBP, TCBP-A and TBBP-A were 0.3, 0.4, 3.0 and 0.8 pg/g plasma, respectively. The method has been used for analysis of plasma samples from potentially occupationally exposed human individuals.

Computed Properties

Molecular Weight:330.80
XLogP3:4.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:329.77135
Monoisotopic Mass:327.77340
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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