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1,2,3,4-Tetrachlorbenzol
Tetrachlorobenzene · NSC 50729 · 1,2,3,4-tcb · 1.2.3.4-Tetrac · 1,2,3,4-tetrachloro-benzen · 1,2,3,4-TETRACHLOROBENZENE · 1,2,3,4-four chlorobenzene · BENZENE,1,2,3,4-TETRACHLORO-
Identifikatoren & physikalische Daten
| CAS No. | 13280-72-3 |
|---|---|
| Summenformel | C6H2Cl4 |
| Durchschnittliche Molmasse | 215,9 g/mol |
| Monoisotopische Masse | 213,891061 g/mol |
| SMILES | Clc1ccc(Cl)c(Cl)c1Cl |
| InChIKey | GBDZXPJXOMHESU-UHFFFAOYSA-N |
| PubChem CID | 12463 |
| ChEMBL | CHEMBL46422 |
| ChEBI | CHEBI:18855 |
| EC No. | 211-214-0 |
| DTXSID | DTXSID6026088 |
| Lokaler Name | 1,2,3,4-Tetrachlorbenzol |
Chemische & physikalische Eigenschaften
| XLogP | 4,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 102 |
| LogP (Verteilungskoeffizient) | log Kow= 4.64 |
| Dichte | 1.70 kg/l1.7 @25 °C1,73 g/cm3 |
| Color/Form | Colorless needles |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)Slightly soluble in ethanolvery soluble in ether and carbon disulfide.In water, 5.92 mg/l at 25 °C.0.0028g/l5.92mg/L(25 ºC) |
| Flammpunkt | greater than 235 °F (NTP, 1992)Flash point > 113 °C>230 °F |
| Siedepunkt | 489 °F at 760 mmHg (NTP, 1992)254 °C @ 760 MM HG254 °C @760 [mm Hg]254 °C761 mm Hg(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen chloride/. |
| Schmelzpunkt | 113 to 115 °F (NTP, 1992)47.5 °C44 °C |
| Dampfdruck | 1 mmHg at 155.3 °F5 mmHg at 211.3 °F760 mmHg at 489 °F (NTP, 1992)0.03 [mmHg]3.9X10-2 mm Hg at 25 °C0.039 [mm Hg] @25 °C1.5 (extrapolated from vapor pressures determined at higher temperatures, Tesconi andYalkowsky, 1998) |
| Heat of Vaporization | 268.9 J/g |
| Henry-Konstante | Henry's Law constant= 6.9X10-4 atm-cu m/mol at 25 °C3.6 at 10 °C (Koelmans et al., 1999) |
| Physical Description | 1,2,3,4-tetrachlorobenzene appears as white to off-white crystals. (NTP, 1992)White solid[Hawley] Colorless crystals[MSDSonline] |
| Brechungsindex | 1.5348 (estimate) |
| Lagerbedingungen | APPROX 4°C |
| Aggregatzustand | chunks |
| Farbe | White crystals or needles |
| BRN | 1910025 |
| Dielektrizitätskonstante | 3.2000000000000002 |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C6H2Cl4/c7-3-1-2-4(8)6(10)5(3)9/h1-2H |
| InChIKey | GBDZXPJXOMHESU-UHFFFAOYSA-N |
| SMILES | Clc1ccc(Cl)c(Cl)c1Cl |
| CAS Datenbank | 634-66-2(CAS DataBase Reference) |
| EPA chemische Informationen | 1,2,3,4-Tetrachlorobenzene (634-66-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.2% (1 of 45) of reports.WarningH302 (97.8%): Harmful if swallowed [Warning Acute toxicity, oral]H400 (88.9%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (88.9%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 45 reports by companies.There are 4 notifications provided by 44 of 45 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, 1,2,3,4-tetrachloro-Hazard Traits - BioaccumulationEnvironmental PersistenceAuthoritative List - Canada PBiTsReport - if used as a fragrance or flavor ingredient |
| Brandgefahren | This chemical is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin. (NTP, 1992) |
| Gefahrenübersicht | A decrease in the number of fetuses was the only significant effect observed at the highest dose level (200 mg/kg) in a study with pregnant rats (no teratogenic effects or histopathological changes in mothers or fetuses)Caused histological changes to liver and kidney in 13 week feeding study with rats[HSDB] May cause irritation to skin, eyes, nose, throat, and respiratory tractLong term exposure may cause kidney and liver injury[CHEMINFO] Effects to the liver in short term gavage studies with rats include porphyria, enlargement, and focal necrosisHistopathological changes observed to kidney and liver in 90 day feeding study with rats[INCHEM] |
| Reaktive Gruppe | Aryl Halides |
| Special Reports | USEPAAmbient Water Quality Criteria Doc: Chlorinated Benzenes (1980) EPA 440/5-80-028Health Assessment Document: Chlorinated Benzenes (1985) EPA-600/8-84-015 |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2,3,4-Tetrachlorobenzene is included on this list. |
| Reactivity Profile | Simple aromatic halogenated organic compounds, such as 1,2,3,4-TETRACHLOROBENZENE, are very unreactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (97.8%)Aquatic Acute 1 (88.9%)Aquatic Chronic 1 (88.9%)Acute toxicity (Oral) - Category 4Reproductive toxicity - Category 1BSpecific target organ toxicity - Single exposure - Category 2 (systemic toxicity), Category 3 (narcotic effects)Specific target organ toxicity - Repeated exposure - Category 2 (liver)Hazardous to the aquatic environment (Acute) - Category 1Hazardous to the aquatic environment (Long-term) - Category 1 |
| Critical Temperature and Pressure | Critical Temperature: 450 °CCritical Pressure: 3380 kPa |
| Hazardous Reactivities and Incompatibilities | IN MFR OF SODIUM SALT OF TRICHLOROPHENOL, SODIUM HYDROXIDE, METHYL ALCOHOL & TETRACHLOROBENZENE WERE HEATED. DURING HEATING PROCESS, PRESSURE SUDDENLY INCR RAPIDLY & EXPLOSION OCCURRED. /TETRACHLOROBENZENE/ |
| Brandbekämpfung | Fires involving this material should be controlled using 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) |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a 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 store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.... Halogenated compounds may be disposed of by incineration provided they are blended with other compatible wastes or fuels so that the composite contains less than 30% halogens and the heating value is from 7000 to 9000 BTU/lb. Liquid injection, rotary kiln, and fluidized bed incinerators are typically used to destroy liquid halogenated wastes. ... Temperatures of at lease 2000-2200 °F and residence times /of more than 2 sec/ ... are required for the destruction of halogenated aromatic hydrocarbons. /Halogenated Aromatic Hydrocarbons/ |
| Protective Action Criteria (PAC) | 3.5 [mg/m3]39 [mg/m3]230 [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. (NTP, 1992) |
| Körperbelastung | 1,2,3,4-Tetrachlorobenzene has been detected in 19 of 108 samples of human adipose tissue at a mean concn of 67 ng/g(1). Combined trichlorobenzene and tetrachlorobenzene isomers were detected in human adipose tissue in Slovenia at a concn of 60 ng/g and in human hair samples at 40 ng/g(2). 1,2,3,4-Tetrachlorobenzene was identified, not quantified, in the adipose tissue of non-occupationally exposed individuals in Germany(3). |
| Wechselwirkungen | Since TeCB's can increase cytochrome p450 levels, ... they appear to induce metabolic enzymes. /This/ induction of microsomal enzyme activity has been shown to enhance the metabolism of a wide variety of drugs, pesticides and other xenobiotics. Exposure to TeCB could therefore result in decreased pharmacologic and/or toxicologic activity of numerous compounds. /In the event/ that chemical agents are metabolized to more active or toxic reactive intermediates ... exposure to TeCB would result in enhanced activity and/or toxicity of these agents. /Tetrachlorobenzenes/ |
| Ökotoxizitätswerte | LC50 Pimephales promelas (fathead minnow) 1.1 mg/l 96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/l CaCO3, temp: 25 +/- 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturation |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.5-4.8(2) measured in soil, 1,2,3,4-tetrachlorobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2,3,4-tetrachlorobenzene is expected from moist soil surfaces given its Henry's Law constant of 6.9X10-4 atm-cu m/mole at 25 °C(3), but adsorption may attenuate this process(SRC). Volatilization of 1,2,3,4-tetrachlorobenzene from dry soil surfaces is not expected based on a vapor pressure of 0.04 mm Hg at 25 °C(3). Biodegradation is expected to occur slowly based on a half-life of 1,2,3,4-tetrachlorobenzene in sewage sludge amended soil of 34.5 days(4).AQUATIC FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.5-4.7(2,3) measured in sediment, 1,2,3,4-tetrachlorobenzene is expected to adsorb to suspended solids and sediment in water(SRC). 1,2,3,4-Tetrachlorobenzene is expected to volatilize from water surfaces(4,SRC) given its Henry's Law constant of 6.9X10-4 atm-cu m/mole at 25 °C(5), but adsorption may attenuate this process(SRC). Estimated volatilization half-lives for a model river and model lake are 6 and 150 hours, respectively when neglecting adsorption(4,SRC). The volatilization half-life from a model pond is about 128 days when adsorption is considered(6). According to a classification scheme(7), BCF values in the range of 490 to 1,700, measured in carp(8) and log BCF values of 3.7-4.1 measured in trout(9), suggest that bioconcentration in aquatic organisms is high. Biodegradation is expected to occur slowly based on a half-life of 18 days measured in anaerobic river sediment(10). When irradiated with light greater than 285 nm, this compound was degraded 46 percent in 40 hrs in a water solution(11), suggesting that photolysis in surface waters may be important(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,3,4-tetrachlorobenzene, which has a vapor pressure of 0.04 mm Hg at 25 °C(2), is expected to exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,2,3,4-tetrachlorobenzene 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 200 days(SRC) from its estimated rate constant of 8.2X10-14 cu cm/mole-sec(3). |
| Lebensmitteluntersuchungswerte | 1,2,3,4-Tetrachlorobenzene was detected in carrots (0.0218 ug/kg (peel)), potatoes (0.0736 ug/kg (peel)), tomatoes (0.01 ug/kg (peel)), and lettuce (0.0041 ug/kg (outer)) sampled in the UK(1). 1,2,3,4-Tetrachlorobenzene was detected in corn oil and sunflower oil samples from Yugoslavia at concns of 0.005 and 0.002 ug/kg, respectively(2). |
| 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. |
| Milk Concentrations | 1,2,3,4-Tetrachlorobenzene was detected in human milk in Canada at 0.01 ng/g (whole milk) and 0.49 ng/g(milk fat)(1). |
| Average Daily Intake | The World Health Organization (WHO) estimates the AVDI of all tetrachlorobenzene isomers for humans is less than 0.1 ng/kg body weight(1). |
| Plant Concentrations | Combined isomers of tri- and tetrachlorobenzene were detected in pine needles at concns of 3-30 ng/g and in grass at 15 ng/g(1). |
| Animal Concentrations | 1,2,3,4-Tetrachlorobenzene residues were found in herring gull eggs from the Detroit River at mean concns of 0.01-1.75 ppm(1). 1,2,3,4-Tetrachlorobenzene was detected in herring gull eggs near Lake Huron at median concns of 0.5-573 ng/g(2), near Lake Superior at concns of 0.004-0.02 ug/g(3) and in several areas of the Great Lakes at 0-0.30 mg/kg(4). 1,2,3,4-Tetrachlorobenzene was detected in eggs of terns(0.001 and 0.003 mg/kg), Canadian geese(0.001 mg/kg), double-crested cormorant(0.003 mg/kg) and black-crowned night herons(0.003 and 0.001 mg/kg)(5). |
| Effluent Concentrations | 1,2,3,4-Tetrachlorobenzene was detected at mean concns of less than 0.01 mg/cu m in the air of municipal landfills in Finland(1). Combined tetrachlorobenzene isomers were detected at concns of 38-1,800,000 ng/cu m in the effluent of a waste gasification and combustion pilot plant(2) and detected at concns of 74.7 and 48 ng/cu m in the effluent of a hazardous waste incinerator in Biebesheim, Germany(3). 1,2,3,4-Tetrachlorobenzene was identified, not quantified, in the effluent from a coal-fired power plant(4). Combined tetrachlorobenzene isomers were detected at concns of 0.01-0.11 ug/l in the effluent of 2 Dow Chemical plants near the St. Claire River, Canada(5). Trace levels of 1,2,3,4-tetrachlorobenzene were detected in the air after a fire at a municipal waste landfill(6). 1,2,3,4-Tetrachlorobenzene was identified, not quantified, in pulp mill effluents in Canada(7). Combined tetrachlorobenzene isomers were detected at concns of 29 and 57 ug/cu m in the effluent of municipal refuse incinerators located in Virginia and Ohio, respectively(8). |
| Soil Adsorption/Mobility | A log Koc value of 3.8(1) was reported for 1,2,3,4-tetrachlorobenzene in soils and log Koc values of 3.5 to 3.8 were reported in sandy and clay loams(2). A log Koc value of 4.4 was reported for 1,2,3,4-tetrachlorobenzene in sediment obtained from Ise Bay, Japan(3) and a log Koc value of 4.7 was reported from sediment of Lake Oostvaardersplassen, Netherlands(4). According to a recommended classification scheme(5), these Koc values suggest that 1,2,3,4-tetrachlorobenzene has low mobility in soil. |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3077 |
| Zollcode | 29039990 |
| RTECS-Nr. | DB9440000 |
| R-Sätze (R) | 22-39/23/24/25-23/24/25-11 |
| Toxizität | Acute oral LD50 for rats 1,167 mg/kg (quoted, RTECS, 1985). |
| Gefahrensymbole | Xn,T,F |
| Sicherheitshinweise (S) | 22-24/25-45-16-7-36/37 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 634-66-2(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1 |
Anwendungen & Verwendung
Verwenden
1,2,3,4-tetrachlorobenzene was used as a model compound to determine the chlorobenzenes (CBs) in soil samples. It was also used for rapid dechlorination of 1,2,3,4-tetrachlorodibenzo-p-dioxin (1,2,3,4-TeCDD).