HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
4-Bromphenylphenylether
1-Bromo-4-phenoxybenzene · 4-BROMODIPHENYL ETHER · pbde 3 · PBDE No. 3 · β-Naphthylether · P-BROMDIPHENYL ETHER · BDE No 3 solution · 4-bromo-diphenylethe
Identifikatoren & physikalische Daten
| CAS No. | 101-55-3 |
|---|---|
| Summenformel | C12H9BrO |
| Durchschnittliche Molmasse | 249,1 g/mol |
| Monoisotopische Masse | 247,98368 g/mol |
| SMILES | Brc1ccc(Oc2ccccc2)cc1 |
| InChIKey | JDUYPUMQALQRCN-UHFFFAOYSA-N |
| PubChem CID | 7565 |
| ChEMBL | CHEMBL1873236 |
| ChEBI | CHEBI:77421 |
| EC No. | 202-952-4 |
| DTXSID | DTXSID8023927 |
| Lokaler Name | 4-Bromphenylphenylether |
Chemische & physikalische Eigenschaften
| XLogP | 4,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 9,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 158 |
| Dichte | 1.4208 at 68 °F (NTP, 1992) - Denser than waterwill sink1.6088 @ 20 °C/4 °C1.6088 @ 20°C1.423 g/mL at 25 °C (lit.) |
| Löslichkeit | Insol in water> 10% in ethyl etherSoluble in ether (Weast, 1986) and many other solvents including 1,4-dioxane, benzene, and toluene. |
| Flammpunkt | greater than 234 °F (NTP, 1992)>230 °F |
| Siedepunkt | 581 °F at 760 mmHg (NTP, 1992)310.1 °C @ 760 MM HGBP: 124-8 °C @ 3-4 mm Hg310.1 °C @760 [mm Hg]305 °C (lit.) |
| Schmelzpunkt | 63 °F (NTP, 1992)18.72 °C18 °C (lit.) |
| Dampfdruck | 0.0015 [mmHg]0.0015 torr @ 20 °C (calc)0.0015 [mm Hg] @20 °C1.94 x 10-3 mmHg at 25 °C (subcooled liquid, Tittlemier et al., 2002) |
| Brechungsindex | Index of refraction: 1.6084 @ 20 °Cn20/D 1.607(lit.) |
| Physical Description | 4-bromophenyl phenyl ether appears as liquid. Freezing point 18 °C. Density 1.423 g / cm3. Insoluble or slightly soluble in water.mp = 18.72 deg C[HSDB] Liquidmp = 18 deg C[CAMEO] Colorless liquidmp = 17-18 deg C[MSDSonline] |
| Kovats Retention Index | 16391661.716411669.716521659.31685285.82394 |
| Collision Cross Section | 142.5 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs] |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Colorless to Almost colorless |
| BRN | 1308972 |
| Henry-Konstante | 2.27 at 25 °C (integrated gas-stripping method, GC, Lau et al., 2006) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C12H9BrO/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9H |
| InChIKey | JDUYPUMQALQRCN-UHFFFAOYSA-N |
| SMILES | Brc1ccc(Oc2ccccc2)cc1 |
| CAS Datenbank | 101-55-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, 1-bromo-4-phenoxy-(101-55-3) |
| EPA chemische Informationen | p-Bromophenyl phenyl ether (101-55-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 14.3% (3 of 21) of reports.DangerH302 (28.6%): Harmful if swallowed [Warning Acute toxicity, oral]H317 (28.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (28.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H400 (66.7%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (33.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]H411 (19%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 21 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 3 of 21 reports by companies.There are 7 notifications provided by 18 of 21 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, 1-bromo-4-phenoxy-Hazard Traits - BioaccumulationEnvironmental PersistenceEnvironmental toxAuthoritative List - CWA 303(c)CWA 303(d)US EPA NWMP PBTsReport - if used as a fragrance or flavor ingredientS - indicates a substance that is identified in a final Significant New Use Rule.Status: Active Update: 15-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32702The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Class 9 |
| Brandgefahren | Combustible. (NTP, 1992) |
| Gesundheitsgefahren | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or asphyxiation. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024) |
| Gefahrenübersicht | May form unstable pyrophoric peroxides on exposure to air[CAMEO]See Decabromodiphenyl ether. |
| Reaktive Gruppe | EthersAryl Halides |
| Special Reports | Borzelleca JFA review of volatile organic contaminant dataProc AWWA Water Qual Technol Conf 225-44 (1983) A review of toxicity data of volatile org contaminants of water to mice after subchronic & chronic administration.USEPAHealth and Environmental Effects Profile for p-Bromophenyl Phenyl Ether (1980) ECAO-CIN-P174 |
| RCRA-Anforderungen | U030As stipulated in 40 CFR 261.33, when 4-bromophenyl phenyl ether, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| Reactivity Alerts | Peroxidizable Compound |
| Reactivity Profile | 4-BROMOPHENYL PHENYL ETHER oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164]. |
| Air and Water Reactions | Insoluble in water. |
| EPA Hazardous Waste Number | U030A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate. |
| Brandbekämpfung | A fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992) |
| 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.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 areatake 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 usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure 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) |
| Reinigungsverfahren | Adsorption capacities of activated carbon for /wastewater pollutants/: 4-bromophenyl phenyl ether 144 mg/g. /From table/ |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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 contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992) |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U030, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. |
| Isolation and Evacuation | Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: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 the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Minimum Risk Level | Intermediate Inhalation: 0.006 mg/m3 (L134) Acute Oral: 0.03 mg/kg/day (L134) Intermediate Oral: 0.007 mg/kg/day (L134) |
| Protective Action Criteria (PAC) | 0.41 [mg/m3]4.5 [mg/m3]27 [mg/m3] |
| Personal Protective Equipment (PPE) | 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.RECOMMENDED GLOVE MATERIALS: Permeation data indicate that nitrile gloves may provide protection to contact with this compound. Nitrile over latex gloves is recommended. However, if this chemical makes contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992) |
| Treatment | EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
| Gesundheitliche Auswirkungen | Polybrominated diphenyl ethers may affect the thyroid gland and liver. Animals studies have also shown that PDBEs can cause neurobehavioral alterations and affect the immune system. (L628) |
| Ökotoxizitätswerte | LC50 Lepomis macrochirus (bluegill) 51 mg/l/24 hr, age young, wt 0.32-1.2 g, static bioassay, total hardness of water 32-48 mg/l CaCO3, total alkalinity 28-34 mg/l CaCO3, pH 6.7-7.8, dissolved oxygen concn 7.0-8.8 mg/l, temp 22 + or - °C /Sample purity > 80%/LC50 Lepomis macrochirus (bluegill) 5.9 mg/l/98 hr, age young, wt 0.32-1.2 g, static bioassay, total hardness of water 32-48 mg/l CaCO3, total alkalinity 28-34 mg/l CaCO3, pH 6.7-7.8, dissolved oxygen concn 7.0-8.8 mg/l, temp 22 + or - °C /Sample purity > 80%/LC50 Daphnia magna (Water flea) 0.46/mg/l/24 hr. /Conditions of bioassay not specified/LC50 Daphnia magna (Water flea) 0.36 mg/l/48 hr. /Conditions of bioassay not specified/For more Ecotoxicity Values (Complete) data for P-BROMOPHENYL PHENYL ETHER (8 total), please visit the HSDB record page. |
| Umweltverhalten | AQUATIC FATE: No information was found in the reviewed literature that would indicate hydrolysis as an aquatic fate for this cmpd. It is ... considered to be unlikely that any of the covalent bonds of 4-bromophenyl phenyl ether will hydrolyze at ambient environmental conditions, since the negative charge-density of the aromatic ring will impede the nucleophilic attack of water or hydroxide ion.AQUATIC FATE: No information was found in the reviewed literature that would support any role for oxidn of this cmpd as an aquatic fate. Indirect photolysis involving interaction of hydroxyl radical with the aromatic ring, is considered to be too slow in water to be environmentally significant for this cmpd. It is at present uncertain how much of this pollutant will volatilize into the atmosphere from surface waters. Any 4-bromophenyl phenyl ether that enters into the troposphere will be subject to photodegradation and reprecipitation with rain. The /proposed/ atmospheric half-life of unsubstituted benzene ... is 2.4 to 24 hr. ... A halogen substituent on an aromatic ring should decrease its susceptibility to photodegradation in the troposphere. Although the electron donating resonance effect of an oxygen substituent should facilitate destruction, it is uncertain how the presence of both groups will affect the atmospheric destruction of 4-bromophenyl phenyl ether.TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4200(SRC), determined from a structure estimation method(2), indicates that 4-bromophenyl phenyl ether is expected to have slight mobility in soil(SRC). Volatilization of 4-bromophenyl phenyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 4-Bromophenyl phenyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.0012 mm Hg(SRC), determined from a fragment constant method(4). No data are available pertaining to chemical degradation processes for 4-bromophenyl phenyl ether in soil. A single biodegradation study suggests that 4-bromophenyl phenyl ether is resistant to biodegradation(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4200(SRC), determined from a structure estimation method(2), indicates that 4-bromophenyl phenyl ether is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 hours and 10 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1300(SRC), from an estimated log Kow of 4.9(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high. A single biodegradation study suggests that 4-bromophenyl phenyl ether is resistant to biodegradation(8). Aquatic hydrolysis and oxidation (via singlet oxygen and peroxy radicals) are not important(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-bromophenyl phenyl ether, which has an estimated vapor pressure of 1.5X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-bromophenyl phenyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 3 days(SRC), calculated from its rate constant of 5.1X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Expositionspfade | Oral (L628)inhalation (L628)dermal (L628) |
| Toxizitätsübersicht | Like other halogenated aromatic hydrocarbons, polybrominated diphenyl ethers bind to the cellular aryl hydrocarbon receptor (AhR), which regulates the synthesis of a variety of proteins. Activation of the AhR induces a number of enzymes, including cytochrome P-450-dependent monooxygenases of the CYP1A and CYP2B families, UDP-glucuronosyltransferase, and ethoxyresorufin-o-deethylase. PBDEs are also believed to disrupt the production, transport, and disposition of thyroid hormones. One mechanism of this involves metabolites ot PDBEs competing with thyroxine to bind to transthyretin, decreasing serum thyroid hormone levels. This change in thyroid hormone levels has been linked to both thyroid toxicity and neurobehavioral alterations. Certain PDBEs and their metabolites are also endocrine disruptors and may act as agonists at the estrogen receptors or antagonists at the androgen and progesterone receptors. (L628, A262) |
| Effluent Concentrations | 4-Bromophenyl phenyl ether was positively detected in 1.2% of 1243 sample water observation points in the US EPA STORET database at a median concn below 10 ppb(1). During a study of 40 POTW plants in the U.S., 1 of 287 influent samples contained 4-bromophenyl phenyl ether, at unreported concentrations(2). 4-Bromophenyl phenyl ether was detected once during a study of Illinois wastewater effluents at a concentration of 1 ug/l(2). |
| EPA IRIS Information | p-Bromodiphenyl ether |
| Soil Adsorption/Mobility | The octanol/water partition coefficient for 4-bromophenyl phenyl ether, corresponding to /calculated/ log p= 4.28 is indicative of a marked preference for lipophilic organic materials over water. In addition, the polar nature of ether bond and the carbon-halogen bond, coupled with the cmpd's miscibility with most lipophilic material ensures sorption of 4-bromophenyl phenyl ether by organic detritus. Adsorption by clay particles is also thought to be highly probable, inasmuch as the polarity and planar geometry of this molecule should facilitate its intercalation within the layered clay structure. Evidence for sorption by suspended organic material is given by a sediment to water distributional ratio of 4:1 for 4-chlorophenyl phenyl ether during biodegradation studies with sludge.Using a structure estimation method based on molecular connectivity indices(1), the Koc for 4-bromophenyl phenyl ether can be estimated to be 4200(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-bromophenyl phenyl ether is expected to have slight mobility in soil. |
| Fish/Seafood Concentrations | Fish samples were collected from Memphis, TN along the Mississippi River from August to September 1982: composite blue catfish 6.20-50 mg/kg 4-bromophenyl phenyl ethercomposite small mouth buffalo 5.2-50 mg/kgchannel catfish 5.3-50 mg/kgcarp 5.4 mg/kg-50 mg/kg(1). |
| Artificial Pollution Sources | 4-Bromophenyl phenyl ether's former production and use as an additive flame retardant(1) may have resulted in its release to the environment through various waste streams(SRC). Bromination of organic precursors has been shown to occur during chlorination treatment operations of water, sewage and leachates(2). Bromide, which is widely distributed in nature, is oxidized by hypochlorous acid to hypobromous acid which is capable of forming bromo-organic compounds(1). |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Clean Water Act Anforderungen | Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Haloethers/ |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 10 ug/l |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3082 9/PG 3 |
| Zollcode | 29093090 |
| R-Sätze (R) | 50/53-67-65-38-11-43-41-22 |
| Toxizität | LC50 (24-h) for Daphnia magna 0.46 mg/L (LeBlanc, 1980). |
| Gefahrensymbole | N,Xn,F |
| Sicherheitshinweise (S) | 60-61-62-36/37/39-26-33-29-16-9 |
| Gefahrenklasse | 9Aquatic Acute 1Aquatic Chronic 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 101-55-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Der 4-Bromdiphenylether bildet farblose, wasserunlösliche Kristalle. Die Verbindung besitzt nur wissenschaftliches Interesse.