HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2,4-Xylenol
2,4-XYLENOL · 2,4-DMP · Phenol,2,4-dimethyl- · gallex · bacticin · ai3-17612 · m-4-Xylenol · as-m-xylenol
Identifikatoren & physikalische Daten
| CAS No. | 105-67-9 |
|---|---|
| Summenformel | C8H10O |
| Durchschnittliche Molmasse | 122,16 g/mol |
| Monoisotopische Masse | 122,07316494 g/mol |
| SMILES | Cc1ccc(O)c(C)c1 |
| InChIKey | KUFFULVDNCHOFZ-UHFFFAOYSA-N |
| PubChem CID | 7771 |
| ChEMBL | CHEMBL29878 |
| ChEBI | CHEBI:34241 |
| EC No. | 203-321-6 |
| DTXSID | DTXSID2021864 |
| Lokaler Name | 2,4-Xylenol |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 90,6 |
| Stoffklassen | Other Classes -> Phenols |
| Kosmetika | Cosmetics ingredient -> FragranceOther (Specify) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Duftstoffe | Fragrance Ingredient (2,4-Xylenol) -> IFRA transparency List |
| Pestizide | Pesticide -> EPA IRISSemi-Volatile Organic Compound (SVOC) (Pesticide) |
| LogP (Verteilungskoeffizient) | log Kow= 2.302.48 |
| Geschmack | 0.5 mg/l (taste threshold concn) |
| Dichte | 1.0276 at 57 °F (NTP, 1992) - Denser than waterwill sink0.9650 @ 20 °C/4 °C0.97 g/cm³0.9650 @ 20°C1.011 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | CrystalsNEEDLES FROM WATERColorless needles |
| Löslichkeit | less than 1 mg/mL at 64 °F (NTP, 1992)Miscible in ethyl alcohol, ethyl ethersoluble in carbon tetrachlorideVery sol in benzene, chloroformIn water, 7.87X10+3 mg/l @ 25 °C.Soluble in oxygenated and aromatic solvents7.2 x 10 (-2) mol/l, at pH 5.1 and 25 °C.5.0g/l0.5 g/100 mL (25 ºC) |
| Flammpunkt | greater than 235 °F (NTP, 1992)Flash point > 112 °C>112 °C (closed cup)>112 °C c.c.205 °F |
| Schmelzpunkt | 22-23 °C(lit.) |
| Siedepunkt | 211-212 °C(lit.) |
| Dampfdruck | 0.1 mm Hg ( 25 °C) |
| Brechungsindex | n20/D 1.538(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | pK1:10.58 (25°C) |
| Farbe | Clear colorless to yellow |
| Geruch | at 100.00 %. weak smoky roasted dark |
| Geruchsart | smoky |
| Biologische Quelle | synthetic |
| Explosionsgrenze | 1.4%(V) |
| Merck | 14,10082 |
| BRN | 636244 |
| Henry-Konstante | 42.8(x 10-6 atmm3/mol) at 75.9 °C, 74.0 at 88.7 °C, 113.0 at 98.5 °C (VLE circulation still-UV spectrophotometry, Dohnal and Fenclová, 1995) |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C8H10O/c1-6-3-4-8(9)7(2)5-6/h3-5,9H,1-2H3 |
| InChIKey | KUFFULVDNCHOFZ-UHFFFAOYSA-N |
| SMILES | Cc1ccc(O)c(C)c1 |
| LogP (Verteilungskoeffizient) | 2.61 |
| CAS Datenbank | 105-67-9(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 2,4-dimethyl-(105-67-9) |
| EPA chemische Informationen | 2,4-Dimethylphenol (105-67-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)H301 (99.1%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2,4-dimethyl-Hazard Traits - HematotoxicityNeurotoxicityCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Phenol, 2,4-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,4-dimethyl- 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)Status: Active Update: 18-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/331252,4-Xylenol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Xylenols: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include severe irritation of the skin and eyes, dizziness, stomach pain, exhaustion and damage to the liver and kidneys. Other symptoms include headache, nausea and vomiting. It may cause severe burns of the eyes and skin, irritation of the respiratory tract and coma. It may also cause corrosion of tissue of the mucous membranes and upper respiratory tract, eyes and skin. Inhalation may result in burning sensation, coughing, wheezing, laryngitis and short ness of breath. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Symptoms of exposure to this class of compounds include profuse sweating, skin sensitization, painless blanching or erythema of the skin, intense thirst diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, fall in blood pressure, hyperpnea, abdominal pain, hemolysis and convulsions. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. |
| Gefahrenübersicht | A corrosive substance that can cause injury to the skin, eyes, and respiratory tractMay cause pulmonary edemaMay cause skin sensitization[ICSC] Corrosive to tissuesInhalation may cause laryngeal spasm, edema of the bronchi, and chemical pneumonitisMay induce methemoglobinemia and injury to the liver and kidneys[CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitisMay be absorbed through skin[MSDSonline] As the six dimethylphenol isomers and the mixed isomer substance are generally similar in toxicity, a common TLV for these substances is appropriate. . . . In mice, oral exposure to 250 mg/kg/day produced changes in blood parameters including statistically significant decreases in mean corpuscular volume and mean corpuscular hemoglobin concentration (4 and 3% reduction in mean values, respectively. . . . Available data on skin sensitization from exposure to dimethylphenol are mixed but warrant the addition of a DSEN notation. . . . All six dimethylphenol isomers were tested in a mouse local lymph node assay and the results found 2.4, 2,5, and 3,4-dimethylphenol to be positive for skin sensitization. There are no epidemiology studies. In a case report, ingestion of about 250 ml of a mixture of dimethylphenol isomers resulted in CNS depression, hypotension, and death. [ACGIH] See Phenol. |
| Reaktive Gruppe | Phenols and Cresols |
| EG-Einstufung | Symbol: T, NR: 24/25-34-51/53S: (1/2)-26-36/37/39-45-61Note: C |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | USEPAAmbient Water Quality Criteria Doc: 2,4 Dimethylphenol (1980) EPA 440/5-80-044.Toxikologische Bewertung. 137 (1995). Summary and assessment of 2,4-xylenol.EPA. EPA/600/8-88/031 p.30 (1987). Health effects assessment for dimethylphenols.Tucker JD et alMutat Res 297 (2): 101-80 (1993). Sister-chromatid exchange: second report of the Gene-Tox Program. |
| RCRA-Anforderungen | U101As stipulated in 40 CFR 261.33, when 2,4-dimethylphenol, 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 Profile | 2,4-DIMETHYLPHENOL is a very weak acid (pKa = 10.6) (NTP, 1992). Incompatible with acid chlorides, acid anhydrides, bases and oxidizing agents. Corrodes steel, brass, copper and copper alloys (NTP, 1992). |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. 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. |
| Sichere Lagerung | Separated from food and feedstuffs, acid anhydrides, acid chlorides, bases and oxidants. |
| Lagerbedingungen | Rooms used for storage only should be soundly constructed and fitted with secure locks. Floors should be kept clear, and the pesticides clearly identified. /Pesticides/ |
| Reinigungsverfahren | FOUNDRY PLANT WASTE GASES WERE DEODORIZED WITH POTASSIUM PERMANGANATE, AND DEODORIZATION EFFICIENCY WAS MEASURED BY PRESENCE OF 2,4-XYLENOL IN SCRUBBED WASTE GASES. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, 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 60-70% ethanol 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. |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U101, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A good 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 good 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 pilot plant study was conducted to evaluate the fate and behavior of 22 toxic organic compounds in conventional activated sludge wastewater treatment plants. The organic cmpd, 2,4-dimethylphenol, spiked at a nominal concn of 50 ug/l was about 99% removable. Results showed that biodegradability was variable and was a function of molecular structure.The effectiveness of anaerobic filters containing granular activated carbon in treating synthetically prepared wastewaters that contained phenols, polycyclic hydroxy compounds, monocyclic N-aromatics, polycyclic N-aromatics, & aliphatic acids was evaluated. The ability of the activated carbon to retain these compounds along with its external surface, which provides vast sheltered microbial attachment areas, renders activated carbon a very unique medium for anaerobic filter treatment of coal gasification wastewater.For more Disposal Methods (Complete) data for 2,4-DIMETHYLPHENOL (6 total), please visit the HSDB record page. |
| Verschüttetes entsorgen | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. If liquid: collect leaking liquid in covered plastic containers. |
| Preventive Measures | Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/ |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles, face shield or eye protection in combination with breathing protection. |
| Körperbelastung | Urine from 35 varnishing workers in six different workplaces contained an average 2,4-dimethylphenol concn of 3.8 mg/lphenols are metabolites of benzene and alkyl benzenes in the varnish(1). |
| Wechselwirkungen | A SPONTANEOUSLY DEVELOPING VASOCONSTRICTION IN ISOLATED PERFUSED LUNG AND THE VASOCONSTRICTION CAUSED BY ARTERIALLY INJECTED ATP 50 UG WERE BOTH INHIBITED BY THE ADDITION TO THE PERFUSATE OF VARIOUS PHENOLS INCLUDING 2,4-XYLENOL. |
| Zielorgane | Hematologic |
| Ökotoxizitätswerte | LC50 Pimephales promelas (fathead minnow) 17 mg/l/96 hr /Flow through bioassay/TLm Carassius carassius (crucian carp) 30 mg/l/24 hr /Conditions of bioassay not specified/LC50 Pimephales promelas (fathead minnow) 16.6 mg/l/96 hr (confidence limit 16.1-17.1 mg/l) at 25.6 °C (hardness 45.7 mg/l CaCO3, pH 8.25) /Conditions of bioassay not specified/LC50 Pimephales promelas (fathead minnow) 13,650 ug/l/192 hr /Static, unmeasured bioassay/For more Ecotoxicity Values (Complete) data for 2,4-DIMETHYLPHENOL (9 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that 2,4-dimethylphenol is expected to have moderate mobility in soil(SRC). Volatilization of 2,4-dimethylphenol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.7X10-5 atm-cu m/mole (4). 2,4-Dimethylphenol is not expected to volatilize from dry soil surfaces(3) based upon a vapor pressure of 0.102 mm Hg at 25 °C(5). 2,4-Dimethylphenol has been reported to completely biodegrade from soil in 4 days at a temperature of 19 °C(6) and the biodegradation half-life of 2,4-dimethylphenol from Texas soil and Mississippi soil was determined to be 1.5 and 3.5 days, respectively(7).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 430(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that 2,4-dimethylphenol is expected to adsorb very little to suspended solids and sediment in water(SRC). 2,4-Dimethylphenol is expected to volatilize from water surfaces(3,SRC) based upon a Henry's Law constant of 1.7X10-5 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 3 days and 22 days, respectively(3,SRC). According to a classification scheme(5), a BCF of 150 in bluegill sunfish(6) suggests bioconcentration in aquatic organisms is moderate(SRC). In humic waters, degradation by the reaction with peroxy radicals should ensue with a half-life on the order of hours(7). 2,4-Dimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Screening studies indicate that 95% removal of 2,4-dimethylphenol was obtained after 5 days using an activated sludge inoculum(8). In addition, it has been reported that 2,4-dimethylphenol was readily degraded in St. Lawrence River water(9). Methanogenic consortia failed to anaerobically biodegrade 2,4-dimethylphenol after 24 days in one study(10)in two standardized anaerobic bioassays using a digester sludge, 2,4-dimethylphenol yielded no more than 10% of theoretical methane(11).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4-dimethylphenol, which has a vapor pressure of 0.102 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4-dimethylphenol 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 5.3 hours(SRC) from its rate constant of 7.20X10-11 cu cm/molecule-sec at 25 °C(3). 2,4-Dimethylphenol has an absorption band at 296 nm (maximum) and extends over 320 nm, thus making it a candidate for direct photochemical degradation(5,6). Night-time degradation in urban areas should occur rapidly through reaction with atmospheric nitrate radicals, as rate constants for this reaction with phenolic compounds are approximately 250 times faster than with hydroxyl radicals(7,SRC). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| Expositionspfade | The substance can be absorbed into the body by inhalation, by ingestion and through the skin. |
| Plant Concentrations | A field study of industrial organic uptake by growing crops was conducted during 1990 at the St. David Coal Refuse Pile Reclamation Site, Fulton County, IL2,4-dimethylphenol was detected in coal refuse and plant materials, concns unknown(1). |
| Signs and Symptoms | Burning sensation. Cough. Sore throat. Shortness of breath.Redness. Pain. Skin burns.Redness. Pain. Severe burns.Burning sensation. Abdominal pain. Nausea. Vomiting. Shock or collapse. |
| Effluent Concentrations | 2,4-Dimethylphenol was detected in raw sludge and treated sludge, concns unknown, in samples taken from 37 water pollution control plants in Ontario, Canada between January and July 1986(1). Waste water from the gasification of Indian Head lignite coal in North Dakota was determined to have an estimated 2,4/2,5-dimethylphenol concn of 368 mg/l(1). A summary of analysis for 2,4-dimethylphenol in effluent reports that it was found 3 times in residential, 8 times in industrial, and 2 times in commercial effluent, with an overall source average discharge concn of 0.7, 0.0, and 74.0 ug/l, respectively(3). 2,4-Dimethylphenol was identified but not quantified in leachate collected from a Swedish municipal landfill in May 1990(4). Groundwater and soil from 91 waste sites at 18 Department of Energy (DOE) facilities were analyzed2,4-dimethylphenol was found at one of the facilities in groundwater, concn not quantified(5).2,4-Dimethylphenol was found in six effluents in an EPA survey (4000 samples) of effluents covering 46 industrial categories(1). Industries with positive levels of 2,4-dimethylphenol included iron and steel manufacturing, petroleum refining, organics and plastics, rubber processing, organic chemicals, and publicly owned treatment works(1). 2,4-Dimethylphenol was detected in 3.4% of 1321 effluent samples reported in STORET, EPA's water quality data base (1975-82)(2) and, in two out of five effluents of hazardous waste incinerators(3) and at 10 ug/l in urban runoff in Washington, DC(4). This constituted a 2% frequency of detection in the National Urban Runoff Program, which examined 86 runoff samples from 15 USA cities(4). The final effluent of Los Angeles County Municipal Wastewater Treatment Plant was found to contain 5 and <10 ppb 2,4-dimethylphenol in July 1978 and Nov 1980, respectively(5). Of 18 advanced water treatment effluents analyzed, 2,4-dimethylphenol was found in effluents at Lake Tahoe, CA (2 ng/l) and Blue Plains, WA (1 and 8.9 ng/l)(6). |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur in fish. |
| EPA IRIS Information | 2,4-DimethylphenolHematologic2 x 10 ^-2 mg/kg-day |
| 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 Clean Water Act and is subject to effluent limitations.Sufficient data are not available for 2,4-dimethylphenol to derive a level which would protect against the potential toxicity of this compound. Using available organoleptic data, for controlling undesirable taste and odor quality of ambient water, the estimated level for 2,4-dimethylphenol is 400 ug/l. It should be recognized that organoleptic data as a basis for establishing a water quality criterion have limitations and have no demonstrated relationship to potential adverse human health effects. |
| Landesrichtlinien für Trinkwasser | (CA) CALIFORNIA 100 ug/l(FL) FLORIDA 400 ug/l(MN) MINNESOTA 100 ug/l |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2261 6.1/PG 2 |
| Zollcode | 29071400 |
| RTECS-Nr. | ZE5600000 |
| R-Sätze (R) | 24/25-34-51/53-39/23/24/25-23/24/25-11 |
| Toxizität | Acute oral LD50 for mice 809 mg/kg, rats 3,200 mg/kg (quoted, RTECS, 1985). |
| Gefahrensymbole | T,N,F |
| Sicherheitshinweise (S) | 26-36/37/39-45-61-36/37-16-7 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralAquatic Chronic 2Eye Dam. 1Skin Corr. 1BSkin Sens. 1B |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Gefahrstoffdaten | 105-67-9(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 480 °C |
Anwendungen & Verwendung
Verwenden
2,4-dimethylphenol is a fungicide and disinfectant with a variety of agricultural uses. It is also used in making wetting agent; dyestuffs; phenolic antioxidants; pharmaceuticals; rubber chemicals; lubricant ; gasoline additive and plasticizers.
Herstellung & Synthese
synthetische
synthesis of 2,4-dimethylphenol: 2,4-Dimethylphenol is obtained by sulfonation, salting out, alkali melting and acidification of m-xylene.