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2,4,6-Tribromphenol
TRIBROMOPHENOL · 2,4,6-Tribromphenol · Phenol, 2,4,6-tribromo- · BROMOL · TA 10 · FR-613 · Emery 9332 · flammex3bp
Identifikatoren & physikalische Daten
| CAS No. | 118-79-6 |
|---|---|
| Summenformel | C6H3Br3O |
| Durchschnittliche Molmasse | 330,8 g/mol |
| Monoisotopische Masse | 327,77340102 g/mol |
| SMILES | Oc1c(Br)cc(Br)cc1Br |
| InChIKey | BSWWXRFVMJHFBN-UHFFFAOYSA-N |
| PubChem CID | 1483 |
| ChEMBL | CHEMBL220087 |
| ChEBI | CHEBI:47696 |
| EC No. | 204-278-6 |
| DTXSID | DTXSID6021959 |
| Lokaler Name | 2,4,6-Tribromphenol |
Chemische & physikalische Eigenschaften
| XLogP | 4,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 108 |
| Stoffklassen | Other Classes -> PhenolsChlorinated/Brominated phenol |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Fusion temperature |
| LogP (Verteilungskoeffizient) | log Kow = 4.134.24 |
| Geruch | Penetrating bromine odor |
| Geschmack | Sweet |
| Dichte | 2.55 at 68 °F (NTP, 1992) - Denser than waterwill sink2.55 g/cu cm at 20 °C2.55 g/cm³ |
| Color/Form | Needles from alcoholprisms from benzeneLong crystalsSoft, white needles |
| Löslichkeit | Slightly soluble (1-10 mg/ml) (NTP, 1992)Sol in alcohol, chloroform, ether, glycerol oilsVery soluble in ethanolsoluble in ether, benzene, carbon tetrachloride, chloroform, acetic acidSol in caustic alkaline solutionsIn water, 70 mg/L at 15 °Cwater: soluble0.007g/100ml at 25°C71 mg/L (15 ºC) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Siedepunkt | 471 °F at 760 mmHg (Sublimes at 540-554 °F at 764 mmHg) (NTP, 1992)286 °C282-290 °C746 mm Hg(lit.) |
| Decomposition | Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide, Hydrogen bromide gas. |
| Schmelzpunkt | 90-94 °C(lit.) |
| Dampfdichte | 11.4 (vs air) |
| Dampfdruck | 0.042-0.063Pa at 25℃ |
| Brechungsindex | 1.5580 (estimate) |
| Flammpunkt | 282-290°C subl. |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | 6.34±0.23(Predicted) |
| Farbe | White to slightly brown |
| Merck | 14,9613 |
| BRN | 776920 |
| Henry-Konstante | 2.1×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| Hauptanwendungen | environmental |
| InChI | 1S/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H |
| InChIKey | BSWWXRFVMJHFBN-UHFFFAOYSA-N |
| SMILES | Oc1c(Br)cc(Br)cc1Br |
| LogP (Verteilungskoeffizient) | 3.7-3.89 at 23.5-25℃ |
| CAS Datenbank | 118-79-6(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 2,4,6-tribromo-(118-79-6) |
| EPA chemische Informationen | 2,4,6-Tribromophenol (118-79-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.5% (1 of 184) of reports.WarningH317 (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 |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2,4,6-tribromo-Hazard Traits - CarcinogenicityEndocrine ToxicityPhenol, 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 |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Data is not available for this compound. It is probably non-flammable. (NTP, 1992)Not combustible. |
| Gesundheitsgefahren | SYMPTOMS: This chemical may cause severe irritation to the skin, eyes, and mucous membranes. |
| Gefahrenübersicht | Hazardous by inhalation, ingestion, and skin absorptionA strong skin irritant[Hawley] A severe skin, eye, and mucous membrane irritant[CAMEO] An eye irritantMay cause skin sensitization[ICSC] An irritant[MSDSonline] |
| Reaktive Gruppe | Phenols and Cresols |
| Special Reports | U.S. EPAHigh 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, 2008WHOConcise 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 DevelopmentScreening 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. |
| TSCA-Anforderungen | 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 1/11/90Reporting 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 1/11/90Sunset date: 6/30/98. |
| Reactivity Profile | 2,4,6-TRIBROMOPHENOL can react with oxidizing materials (NTP, 1992). |
| Air and Water Reactions | Slightly soluble in water. |
| Other Hazardous Reactions | Highly Flammable |
| Hazard Classes and Categories | Skin Sens. 1 (94.6%)Acute toxicity (Oral) - Category 4Hazardous to the aquatic environment (Acute) - Category 1 |
| Brandbekämpfung | 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. |
| Erste-Hilfe-Maßnahmen | 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 . |
| Erste Hilfe | 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. |
| Brandbekämpfungsverfahren | 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. |
| Lagerbedingungen | Keep tightly closed. |
| Reinigungsverfahren | 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. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand 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. |
| Verschüttetes entsorgen | 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. |
| Preventive Measures | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Eye Prevention | Wear safety goggles. |
| Körperbelastung | 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). |
| Ökotoxizitätswerte | EC50Species: Daphnia magna (Water flea, age 12 hr)Conditions: freshwater, static, 18 °CConcentration: 1310 ug/L for 48 hrEffect: intoxication, immobilization /formulated product/LC50Species: Cyprinus carpio (Common carp)Concentration: 1.1 mg/L for 96 hr /Conditions of bioassay not specified in source examined/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 cycleConcentration: 1.5 mg/L for 96 hrSpecies: Pimephales promelas (Fathead minnow)Conditions: static, 25+/-2 °C, Light Condition: A constant 16-hr photoperiod was usedConcentration: 10 mg/L for 48 hrFor more Ecotoxicity Values (Complete) data for 2,4,6-TRIBROMOPHENOL (8 total), please visit the HSDB record page. |
| Umweltverhalten | 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). |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Expositionspfade | The substance can be absorbed into the body by ingestion. |
| Toxizitätsübersicht | 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.[ |
| Ökotoxizitätsauszüge | /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. |
| Signs and Symptoms | Redness. Pain. |
| Effluent Concentrations | 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 testsbromides 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). |
| ICSC Environmental Data | This substance may be hazardous to the environment. Special attention should be given to aquatic organisms. Bioaccumulation of this chemical may occur in fish. |
| Soil Adsorption/Mobility | 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). |
| Natural Pollution Sources | 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/ |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1230 3/PG 2 |
| Zollcode | 29081990 |
| RTECS-Nr. | SN1225000 |
| R-Sätze (R) | 36/37/38-51/53-20/22-39/23/24/25-23/24/25-11-63-43-45-50-36-67-40-22 |
| Toxizität | guinea pig,LDLo,oral,3gm/kg (3000mg/kg),National Technical Information Service. Vol. OTS0522208, |
| Gefahrensymbole | Xi,N,Xn,T,F |
| Sicherheitshinweise (S) | 26-36-61-37/39-45-36/37-16-7-24/25-23-53-37 |
| Gefahrenklasse | 9Aquatic Acute 1Eye Irrit. 2Skin Sens. 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 118-79-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
2,4,6-Tribromophenol is used as a certified reference standard for the determination of the analyte in multiple solid formulation drug products using gas chromatography coupled to tandem mass spectrometry.