Ethyl-chloracetat
CHLOROACETIC ACID ETHYL ESTER · Ethyl chloroacetat · Ethyl monochloracetate · ETHYL MONO CHLORO ACETATE · NSC 8833 · Chloricacidester · ethylchloracetate · 2-chlorobutanoate
Identifikatoren & physikalische Daten
| CAS No. | 105-39-5 |
|---|---|
| Summenformel | C4H7ClO2 |
| Durchschnittliche Molmasse | 122,55 g/mol |
| Monoisotopische Masse | 122,01345714 g/mol |
| SMILES | CCOC(=O)CCl |
| InChIKey | VEUUMBGHMNQHGO-UHFFFAOYSA-N |
| PubChem CID | 7751 |
| ChEMBL | CHEMBL3186148 |
| EC No. | 203-294-0 |
| DTXSID | DTXSID4026715 |
| Lokaler Name | Ethyl-chloracetat |
Chemische & physikalische Eigenschaften
| XLogP | 0,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 62,7 |
| Stoffklassen | Other Classes -> Chloroacetic Acid DerivativesFlammable agents - 2nd degree |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 0.94(calculated) |
| Geruch | Fruity pungent odor |
| Dichte | 1.15 at 68 °F (USCG, 1999) - Denser than waterwill sink1.1498 @ 20 °C/4 °C1.15 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.011.145 @25 °C1.145 g/mL at 25 °C (lit.) |
| Viscosity | 2.93X10-3 Pa.s @ 247.15 K |
| Color/Form | Water-white mobile liqLiquid |
| Löslichkeit | Insol in watermiscible with alc, etherSol in benzeneInsoluble in water, miscible in ethanol, acetone and ethyl etherMiscible in oxygenated solventsSolubility in water, g/100ml at 20 °C: 1.2312.3g/l20 g/L (20 ºC) |
| Flammpunkt | 100 °F (USCG, 1999)53 °C147 °F (64 °C) (OPEN CUP)53 °C c.c.150 °F |
| Siedepunkt | 289 °F at 760 mmHg (USCG, 1999)144-146 °C144.2 °C144 °C @760 [mm Hg]143 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES OF /HYDROGEN CHLORIDE/. |
| Schmelzpunkt | -15 °F (USCG, 1999)-26 °C-27 °C-26 °C (lit.) |
| Dampfdichte | 4.23 (vs air) |
| Dampfdruck | 10 mm Hg ( 38 °C) |
| Brechungsindex | n20/D 1.421(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| Geruch | Extremely irritatingfruitypungent |
| Explosionsgrenze | 2.6%(V) |
| Merck | 14,3783 |
| BRN | 506455 |
| Henry-Konstante | 2.6×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 11.6(20℃) |
| Stabilität | Stable. Incompatible with acids, bases, oxidizing agents, reducing agents. Flammable. |
| InChI | 1S/C4H7ClO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
| InChIKey | VEUUMBGHMNQHGO-UHFFFAOYSA-N |
| SMILES | CCOC(=O)CCl |
| LogP (Verteilungskoeffizient) | 0.940 |
| CAS Datenbank | 105-39-5(CAS DataBase Reference) |
| NIST chemische Informationen | Ethyl chloroacetate(105-39-5) |
| EPA chemische Informationen | Ethyl chloroacetate (105-39-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H226 (80%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, chloro-, ethyl esterAcetic acid, 2-chloro-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-chloro-, ethyl 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: 24-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/16030Acetic acid, chloro-, ethyl ester: HSNO Approval: HSR001147 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: Irritating, toxic hydrogen chloride and phosgene may be generated in fires. (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 53 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | FLAMMABLE LIQUIDA DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME ... |
| Gesundheitsgefahren | Inhalation causes irritation of mucous membrane, headache, and nausea. Contact with liquid causes extreme eye irritation and conjunctivitisirritates skin if not removed at once. Ingestion causes irritation of mouth and stomach. (USCG, 1999) |
Anwendungen & Verwendung
Verwenden
Ethyl chloroacetate is a reagent used in the preparation of 5 member heterocycles. It is used as pharmaceutical and organic intermediate. It is used as a solvent for organic synthesis and the production of pesticides (such as sodium fluoroacetate).
Herstellung & Synthese
synthetische
Ethyl chloroacetate is synthesized by esterification of chloroacetic acid and ethanol under the catalysis of sulfuric acid. The reaction equation is as follows:ClCH2COOH+C2H5OH[H2SO4]→ClCH2COOC2H5+H2OReaction: Add chloroacetic acid, ethanol and benzene into the esterification pot, turn on the stirrer, slowly add sulfuric acid, heat to reflux, continuously steam out the benzene-water azeotrope, and de-esterify the water generated by condensation and separator layering, Benzene is refluxed into the esterification pot, cooled and discharged when there is no more water to steam out, the crude ester is washed with saturated sodium bicarbonate solution and water to neutrality, dried with anhydrous calcium chloride, distilled, and collected The fraction at 144-146°C is the finished product of ethyl chloroacetate, the content is ≥99.0%, and the yield is 85%.