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Methylchloracetat
methyl 2-chloroacetate · MONO METHYL CHLORO ACETATE · METHYL MONOCHLOROACETATE · IHT-FC MCA · Chloroacetic acid methyl · CHLOROACETIC ACID METHYL ESTER · ClH2CCOOCH3 · AKOS BBS-00004061
Identifikatoren & physikalische Daten
| CAS No. | 96-34-4 |
|---|---|
| Summenformel | C3H5ClO2 |
| Durchschnittliche Molmasse | 108,52 g/mol |
| Monoisotopische Masse | 107,99780708 g/mol |
| SMILES | COC(=O)CCl |
| InChIKey | QABLOFMHHSOFRJ-UHFFFAOYSA-N |
| PubChem CID | 7295 |
| EC No. | 202-501-1 |
| DTXSID | DTXSID9041576 |
| Lokaler Name | Methylchloracetat |
Chemische & physikalische Eigenschaften
| XLogP | 0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 52,8 |
| Stoffklassen | Other Classes -> Chloroacetic Acid DerivativesCorrosives |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | 0.76 (calculated) |
| Geruch | Sweet pungent odor |
| Dichte | 1.2337 at 68 °F (USCG, 1999) - Denser than waterwill sink1.236 g/cu cm at 20 °C1.2 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.021.238 g/mL at 25 °C(lit.) |
| Viscosity | 2.95X10-3 Pa.s at 241.03 K |
| Color/Form | LiquidColorless liquid |
| Löslichkeit | In water, 4.6X10+4 mg/L at 20 °CIn water, 5.2 g/100 mL at 19.8 °C (5.2X10+4 mg/L)Miscible with alcohol, etherVery soluble in acetone, benzene, ethyl ether, ethanolMiscible with oxygenated solventsSolubility in water, g/100ml at 19.8 °C: 5.251.6g/l (slow decomposition)28 g/L (20 ºC) |
| Corrosivity | Corrosive |
| Flammpunkt | 125 °F (USCG, 1999)57 °C135 °F (57 °C) (open cup)57 °C o.c. |
| Siedepunkt | 266 °F at 760 mmHg (USCG, 1999)130 °CBP: 130-132 °C129.5 °C130 °C740 mm Hg(lit.) |
| Decomposition | Hazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen chloride gasWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/. |
| Schmelzpunkt | -33 °C |
| Dampfdichte | 3.8 (vs air) |
| Dampfdruck | 10 mm Hg ( 25 °C) |
| Brechungsindex | n20/D 1.422(lit.) |
| Lagerbedingungen | Store at <= 20°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| pH | 4.6 (28g/l, H2O, 20℃) |
| Explosionsgrenze | 4.6-18.5%(V) |
| Merck | 14,6042 |
| BRN | 506255 |
| Henry-Konstante | 4.9×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 12.9(20℃) |
| InChI | 1S/C3H5ClO2/c1-6-3(5)2-4/h2H2,1H3 |
| InChIKey | QABLOFMHHSOFRJ-UHFFFAOYSA-N |
| SMILES | ClCC(=O)OC |
| LogP (Verteilungskoeffizient) | 0.63 at 20℃ |
| CAS Datenbank | 96-34-4(CAS DataBase Reference) |
| NIST chemische Informationen | Acetic acid, chloro-, methyl ester(96-34-4) |
| EPA chemische Informationen | Acetic acid, 2-chloro-, methyl ester (96-34-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.6% (1 of 159) of reports.H226 (99.4%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, chloro-, methyl esterAcetic acid, 2-chloro-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-chloro-, methyl ester 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: 10-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13502Methyl chloroacetate: HSNO Approval: HSR003022 Approved with controlsThe 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 | Poison Flammable Liquid |
| Brandgefahren | Special Hazards of Combustion Products: Toxic fumes of hydrogen chloride (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 57 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable when exposed to heat or flame ... |
| Gesundheitsgefahren | Extremely corrosive to the eyes, skin, nose, throat, and upper respiratory tract. 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 include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| Gefahrenübersicht | Corrosive to skinSevere eye irritantRespiratory tract irritantMay be absorbed through skin[ICSC] Toxic by inhalation and ingestion[eChemPortal: ESIS] Danger of skin sensitization[MAK] Inhalation may induce upper and lower airway inflammation and edema[CHRIS] Oral LD50 (mouse) = 240 mg/kg[RTECS] An irritant[MSDSonline] |
| DOT-Nummer und Handbuch | 2295 131 |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| EG-Einstufung | Symbol: TR: 10-23/25-37/38-41S: (1/2)-26-37/39-45 |
| UN-Einstufung | UN Hazard Class: 6.1UN Subsidiary Risks: 3UN Pack Group: I |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | METHYL CHLOROACETATE is a halogenated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. |
| Brandbekämpfung | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:Use water spray, dry powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. 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. Do NOT induce vomiting. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | Call a physician.General First Aid: |
| Sichere Lagerung | Fireproof. Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).1.0 [ppm] |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. |
| Freisetung ohne Brand | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: |
| Entsorgungsverfahren | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in covered plastic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Ökotoxizitätswerte | EC50Species: Daphnia magna (Water flea)Conditions: freshwater, staticConcentration: 84 mg/L for 24 hrEffect: behavior, equilibrium /formulation/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl chloroacetate is expected to have very high mobility in soil(SRC). Volatilization of methyl chloroacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 7.63 mm Hg at 25 °C(3), and water solubility, 4600 mg/L(4). Methyl chloroacetate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 45-95% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl chloroacetate is not 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 2.4X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 7.63 mm Hg(4), and water solubility, 4.6X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 16 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.63(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 45-95% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is an important environmental fate process in water(SRC). A measured base-catalyzed hydrolysis rate constant of 140 L/mole-sec at 25 °C was reported with corresponding hydrolysis half-lives of 140 to 0.14 hrs at pH values of 6-9(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl chloroacetate, which has a vapor pressure of 7.63 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl chloroacetate 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 65 days(SRC), calculated from its rate constant of 2.5X10-13 cu cm/molecule-sec at 25 °C(3). Methyl chloroacetate 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 | Dermatotoxin - Skin burns. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Methyl chloroacetate (MCA) is a colorless liquid. It is used as a solvent and intermediate. HUMAN STUDIES: In man, delayed occurrence of irritation of the conjunctiva is observed after exposure to the vapor. It was suggested that cross reactivity to MCA may occur in an industrial situation. ANIMAL STUDIES: In guinea-pigs MCA induced sensitization. Cross-sensitization with chloroacetic acid ethyl ester has been observed in this species. MCA is corrosive to rabbit skin and is absorbed through the skin (0.5 mL undiluted substance/rabbit leads to death). The substance is severely irritating to the rabbit eye. In rats MCA produced pronounced eye and respiratory tract irritation at concentrations as low as 250 ppmsome animals exposed to this concentration died within a few days. After repeated inhalation exposure to MCA for 28 days at concentrations of 10, 33 or 100 ppm, adverse effects on the breathing (irregular breathing) and on movement (uncoordinated gait) as well as irritant effects (closing together of the eyelids, sneezing, increased frequency of cleaning) and an increase in relative lung weight occurred in rats at the highest concentration. No increase in the incidence of lung tumors has been established after intraperitoneal administration to strain A mice. MCA was not mutagenic in the Salmonella/microsome test in five strains of Salmonella typhimurium or in Escherichia coli either with or without metabolic activation. No induction of micronuclei has been observed in the micronucleus test in the mouse. ECOTOXICITY STUDIES: Testing the acute toxicity to the Daphnia resulted in a 24 hr EC0 of 3.2 mg/L and a 24 hr EC50 of 5.5 mg/L for inhibition of the swimming capability. The 48 hr and 96 hr LC0 in the zebra fish was 1.13 mg/L. For the rainbow trout, 48 hr LC0 < 2.5 mg/L and 48 hr LC100 of 6 mg/L are reported. |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ Testing the acute toxicity to the Daphnia resulted in a 24 hr EC0 of 3.2 mg/L and a 24 hr EC50 of 5.5 mg/L for inhibition of the swimming capability. The 48 hr and 96 hr LC0 in the zebra fish was 1.13 mg/L. For the rainbow trout, 48 hr LC0 < 2.5 mg/L and 48 hr LC100 of 6 mg/L are reported. |
| Signs and Symptoms | Cough. Shortness of breath. Sore throat.MAY BE ABSORBED! Redness. Pain. Skin burns.Redness. Pain. Blurred vision.Abdominal pain. Nausea. Vomiting. Diarrhoea. |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of methyl chloroacetate can be estimated to be 6(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl chloroacetate is expected to have very high mobility in soil(SRC). |
| TSCA Test Submissions | Methyl chloroacetate (CAS# 96-34-4) was evaluated for acute inhalation toxicity in male and female rats at dose levels of 1.75, 4.26, and 4.44 mg/L for one-hour. Mortality ratios were 0/5 M, 0/5 F2/5 M, 3/5 Fand 4/5 M, 4/5 F, respectively. The estimated LC50 value was 3.69 mg/L (831 ppm). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ A 23 year old chemical laboratory technician presented with erythema and small blisters on the dorsum of his right hand and forearm. The reaction resulted from a spill of monochloroacetic-acid (MCA). The solution contained 1.5 molar MCA in 94 percent ethanol. He attempted to wash the spill from his arm using water for 10 minutes. After 10 days, the lesions healed, leaving small scars. These scars, after 14 days, became the sites of itchy vesicles. A patch test was performed on day 28, at which time, the patient gave a positive result to the MCA solution at 1 percent in 70 percent methanol. Since it was not considered likely that MCA was the active agent, possible sensitivity to monochloroacetic-acid-ethyl-ester (EMCA) was examined. Strong positive reactions were observed to patch tests with EMCA, whereas the MCA tests were negative. Because plans were underway to use EMCA in a large production process, a guinea-pig maximization test was initiated. Five of the 20 animals tested reacted to EMCA, indicating that this compound is at least a moderate sensitizer. All animals reacted to monochloroacetic-acid-methyl-ester (MMCA). The authors suggest that cross reactivity to MMCA may occur in an industrial situation./SIGNS AND SYMPTOMS/ In man, delayed occurrence of irritation of the conjunctiva is observed after exposure to the vapor. |
| Artificial Pollution Sources | Methyl chloroacetate's production and use as an intermediate and solvent(1) may result in its release to the environment through various waste streams(SRC). |
| F | 19 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2295 |
| Zollcode | 2915 40 00 |
| RTECS-Nr. | AF9500000 |
| R-Sätze (R) | 10-23/25-37/38-41-40-36/37/38-38 |
| Toxizität | LD50 orally in Rabbit: 107 mg/kg |
| Gefahrensymbole | T,Xi,F |
| Sicherheitshinweise (S) | 26-37/39-45-36-16 |
| Gefahrenklasse | 6.1Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | I |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 96-34-4(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 869 °F |
Anwendungen & Verwendung
Verwenden
Methyl chloroacetate is used as a solvent and chemical intermediate. It acts as a precursor in the preparation of (carboxymethyl) trimethylammonium chloride esters. Further, it is used in the preparation of octakis-(carbethoxymethoxy)calix[8]arene. It is employed as an extraction solvent during the separation of neutral compounds. In addition to this, it is used in the synthesis of dimethyl carbonate.
Herstellung & Synthese
synthetische
Methyl chloroacetate is prepared by esterification of chloroacetic acid with methanol. Reaction: Methanol and chloroacetic acid are uniformly mixed in a weight ratio of 0.366:1, heated with stirring, and the esterification reaction is carried out at 105-110 °C. In the reaction process, the ternary azeotrope of methyl chloroacetate, water and methanol is continuously steamed, layered through the ester separator, the separated methanol and water are returned to the reaction pot, and the separated crude ester is made of sodium carbonate. neutralize. The neutralized crude ester is firstly cut out the 130°C fraction by atmospheric distillation, and then subjected to vacuum distillation to collect the 65°C (8kPa) fraction, which is the finished product of methyl chloroacetate. The yield is about 96%.