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3,4-Dichlor-α,α,α-trifluortoluol
1,2-DICHLORO-4-(TRIFLUOROMETHYL)BENZENE · 3,4-DichL · 3,4-DCBTE · 3,4-dichlo · orobenzotrifL · 3,4-Dichlorobenzotri · 3,4Dichlorobenzotrifl · 3,4-DICHLOROBENZOTRIFLUORIDE
Identifikatoren & physikalische Daten
| CAS No. | 328-84-7 |
|---|---|
| Summenformel | C7H3Cl2F3 |
| Durchschnittliche Molmasse | 215 g/mol |
| Monoisotopische Masse | 213,95639012 g/mol |
| SMILES | FC(F)(F)c1ccc(Cl)c(Cl)c1 |
| InChIKey | XILPLWOGHPSJBK-UHFFFAOYSA-N |
| PubChem CID | 9481 |
| ChEMBL | CHEMBL3184329 |
| EC No. | 206-337-1 |
| DTXSID | DTXSID5027142 |
| Lokaler Name | 3,4-Dichlor-α,α,α-trifluortoluol |
Chemische & physikalische Eigenschaften
| XLogP | 4,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 157 |
| Stoffklassen | Other Classes -> Halogenated Monoaromatics |
| PFAS | PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008 |
| SpringerMaterials Properties | Boiling point |
| Geruch | Aromatic |
| Dichte | 1.4781.478 g/mL at 25 °C (lit.) |
| Color/Form | Clear, colorless liquid |
| Löslichkeit | Soluble in petroleum ether and acetonitrile.Chloroform (Sparingly), Ethyl Acetate (Slightly) |
| Flammpunkt | [ChemIDplus] 65 °C65 °C (150 °F) |
| Siedepunkt | 173-174 °C173-174 °C (lit.) |
| Schmelzpunkt | -13 to -12 °C-13--12 °C (lit.) |
| Dampfdruck | 2.36 [mmHg]2.36 mm Hg at 25 °C1.6 mm Hg ( 20 °C) |
| Brechungsindex | Index of refraction (for sodium D line @ 20 °C) = 1.4750n20/D 1.475(lit.) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Oil |
| Farbe | Colourless |
| Wichte | 1.478 |
| BRN | 1950151 |
| Henry-Konstante | 3.8×10-4 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C7H3Cl2F3/c8-5-2-1-4(3-6(5)9)7(10,11)12/h1-3H |
| InChIKey | XILPLWOGHPSJBK-UHFFFAOYSA-N |
| SMILES | FC(F)(F)c1ccc(Cl)c(Cl)c1 |
| CAS Datenbank | 328-84-7(CAS DataBase Reference) |
| NIST chemische Informationen | 3,4-Dichlorobenzotrifluoride(328-84-7) |
| EPA chemische Informationen | 3,4-Dichlorobenzotrifluoride (328-84-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.8% (5 of 180) of reports.WarningH302 (12.2%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 180 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, 1,2-dichloro-4-(trifluoromethyl)-Status: Active Update: 26-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27050Benzene, 1,2-dichloro-4-(trifluoromethyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Gesundheitsgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Gefahrenübersicht | May cause skin, eye, nose, and throat irritationA moderate skin and mild eye irritant in rabbitsHistopathological observations in oral study with rats include hemorrhagic lungs and darkened liver[HSDB] Has irritating and narcotic effects in high concentrations[CAMEO] Causes lacrimation, somnolence, and dyspnea in lethal concentration studies of rats[RTECS] |
| Reaktive Gruppe | Fluorinated Organic Compounds |
| Special Reports | ITC/USEPAInformation Review #346 (Draft) 3,4-Dichlorobenzotrifluoride (1983) |
| 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. 3,4-Dichlorobenzotrifluoride is included on this list. |
| Reactivity Profile | Simple aromatic halogenated organic compounds are very unreactivehalogenated aliphatic compounds are moderately or very reactive. Both subgroups generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. |
| Air and Water Reactions | Flammable. Slightly soluble in water. |
| Toxic Combustion Products | Upon exposure to fire, will decompose giving off hydrogen chloride and hydrogen fluoride. |
| Hazard Classes and Categories | Acute Tox. 4 (12.2%)Flammable liquids - Category 4 |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Erste Hilfe | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 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. |
| Preventive Measures | Potential exposures are minimized by the use of closed process equipment.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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Required use of rubber gloves and splash goggles and the use of hoods for sampling. |
| Umweltverhalten | Aquatic: Very little of the cmpd should reside in aqueous solution due to its low est water solubility.TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,800(SRC), determined from an estimated log Kow of 4.2(2,SRC) and a regression-derived equation(3), indicates that 3,4-dichlorobenzotrifluoride is expected to have slight mobility in soil(SRC). Volatilization of 3,4-dichlorobenzotrifluoride from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of 3,4-dichlorobenzotrifluoride from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.36 mm Hg at 25 °C(5). However, adsorption to soil is expected to attenuate volatilization(SRC). No biodegradation data for 3,4-dichlorobenzotrifluoride were found(SRC)biodegradation is expected to be slow(SRC) as reported for other compounds containing a large number of halogens(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,800(SRC), determined from an estimated log Kow of 4.2(2) and a regression-derived equation(3), indicates that 3,4-dichlorobenzotrifluoride is expected to adsorb to suspended solids and sediment in water(SRC). 3,4-Dichlorobenzotrifluoride may volatilize from water surfaces(3) based on an estimated Henry's Law constant of 2.6X10-2 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake(3) are 4.3 hours and 5.8 days(SRC), respectively. The volatilization half-life from a model pond 2 m deep is estimated to be about 2.1 days ignoring adsorption(5)when considering maximum adsorption the volatilization half-life increases to 53 days(5). According to a classification scheme(6), a mean BCF of 1,500 in rainbow trout(7) suggests bioconcentration in aquatic organisms is very high(SRC). No biodegradation data for 3,4-dichlorobenzotrifluoride were found(SRC)biodegradation is expected to be slow(SRC) as reported for other compounds containing a large number of halogens(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,4-dichlorobenzotrifluoride, which has a vapor pressure of 2.36 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,4-dichlorobenzotrifluoride is degraded slowly 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(3). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Soil Adsorption/Mobility | The Koc of 3,4-dichlorobenzotrifluoride is estimated as approximately 4,800(SRC), using an estimated log Kow of 4.2(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3,4-dichlorobenzotrifluoride is expected to have slight mobility in soil(SRC). |
| Human Toxicity Excerpts | Prolonged, repeated skin contact may cause dermatitis. Overexposure to vapors may cause irritation of nose and throat. |
| Fish/Seafood Concentrations | 3,4-Dichlorobenzotrifluoride concn in the edible portion of Niagara River fish was 0.02-0.28 mg/kg |
| Artificial Pollution Sources | Environmental releases from two plant sites were reported: Plant site A released 5 lbs/yr into the air and 450 lbs/yr into the waterwhile Plant site B released 100 lbs/yr into the air and 0 lbs/yr into the water. Water releases resulted from drum washings and air releases from storage tank vents.3,4-Dichlorobenzotrifluoride's production and use in the manufacture of herbicides(1) may result in its release to the environment through various waste streams(SRC). |
| Sediment/Soil Concentrations | 0.5-2.0 ppm of dichlorobenzotrifluoride (isomers) was detected near a dump site in Niagara Falls, NY /dichlorobenzotrifluoride isomers/ |
| Environmental Bioconcentration | A mean BCF of 1,500 was measured in rainbow trout using a 3,4-dichlorobenzotrifluoride concentration of 1.0 ng/l(1). According to a classification scheme(2), this BCF suggests bioconcentration in aquatic organisms is very high. |
| Volatilization from Water/Soil | The Henry's Law constant for 3,4-dichlorobenzotrifluoride is estimated as 2.6X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 3,4-dichlorobenzotrifluoride is expected to volatilize rapidly from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is approximately 4.3 hours(SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is approximately 5.8 days(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.1 days ignoring adsorption(3)when considering maximum adsorption the volatilization half-life increases to 53 days(3). 3,4-Dichlorobenzotrifluoride's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 3,4-dichlorobenzotrifluoride from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.36 mm Hg at 25 °C(4). |
| Non-Human Toxicity Excerpts | THE EFFECTS OF RING-SUBSTITUTED, ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENES ON RESPIRATION OF MITOCHONDRIA ISOLATED FROM RAT LIVER (CHARLES RIVER, CD STRAIN) WERE EXAMINED POLAROGRAPHICALLY. A REMARKABLE DECR IN RESPIRATORY CONTROL WAS OBSERVED IN PRESENCE OF 3,4-DICHLOROBENZOTRIFLUORIDE AT A FINAL CONCN OF 0.25 MMOLE. THE DECR IN RESPIRATORY CONTROL CAUSED BY THESE SUBSTITUTED TOLUENES RESULTED FROM INHIBITION OF STATE 3 RESPIRATION &/OR AN ACCELERATION OF STATE 4 RESPIRATION.Negative mutagenicity results were observed in Salmonella typhimurium TA-1535TA-1537TA-1538TA-98& TA-100. Negative mutagenicity results were observed in E. coli W3110/POL A+& P3478/POL A-. Negative mutagenicity results were observed in Saccharomyces cerevisiae D4. Negative results were observed for in vitro transformation of BALB/3T3 cells. Negative results were also produced in a mouse lymphoma forward mutation assay at TK locus in L5178Y cells. /4-chlorobenzotrifluoride/3,4-Dichlorobenzotrifluoride induced unscheduled DNA synthesis in EuE cells. Positive results were observed for sister chromatid exchange in L5178Y mouse lymphoma cells. /Concn not specified/3,4-Dichlorobenzotrifluoride is moderately irritating to rabbit skin (primary irritation score 4.3) and slightly irritating to rabbit eye (conjunctival effects only, all irritation reversible within 72 hrs).Oral doses of 3,4-Dichlorobenzotrifluoride in rats resulted in an LD50 of 1.15 g/kg and produced: salivation, chromorhinitis, tremors, lethargy, body rigidity, diarrhea ... autopsy findings included: hemorrhagic lungs and darkened liver. |
| Populations at Special Risk | /Individuals who suffer from/ skin, liver, kidney, or chronic respiratory disease, will be at an increased risk if they are exposed to chlorobenzenes. /Chlorobenzenes/ |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 3,4-dichlorobenzotrifluoride with photochemically-produced hydroxyl radicals has been estimated as 8.1X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 200 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). 3,4-Dichlorobenzotrifluoride is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 1760 |
| Zollcode | 29036990 |
| RTECS-Nr. | CZ5527510 |
| R-Sätze (R) | 36/37/38-34-22 |
| Gefahrensymbole | Xi,C |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36/37/39-45-60-20 |
| Gefahrenklasse | 8Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 328-84-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
3,4-Dichlorobenzotrifluoride has been used in the preparation of:3,4-difluorobenzotrifluoride by a KF exchange reaction2-chloro-4-trifluoromethylphenyl 4-nitrophenylether (RH-2512), potential diphenyl ether herbicide