Ethylacetoacetat
ETHYL 3-OXOBUTANOATE · ACE · EAA · ACETOACETIC ESTER · Ethyl acetyl acetate · Ethyl acetoacetate, 99%, pure · Ethyl acetoacetate, extra pure · ETHYL ACETOACETATE, 99%ETHYL ACETOACETATE, 99%ETHYL ACETOACETATE, 99%ETHYL ACETOACETATE, 99%
Identifikatoren & physikalische Daten
| CAS No. | 141-97-9 |
|---|---|
| Summenformel | C6H10O3 |
| Durchschnittliche Molmasse | 130,14 g/mol |
| Monoisotopische Masse | 130,06299418 g/mol |
| SMILES | CCOC(=O)CC(C)=O |
| InChIKey | XYIBRDXRRQCHLP-UHFFFAOYSA-N |
| PubChem CID | 8868 |
| ChEMBL | CHEMBL169176 |
| ChEBI | CHEBI:4893 |
| EC No. | 205-516-1 |
| DTXSID | DTXSID2027092 |
| Lokaler Name | Ethylacetoacetat |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 117 |
| LogP (Verteilungskoeffizient) | log Kow = 0.250.27 |
| Geruch | PLEASANT GREEN, FRUITY, RUM ODOR |
| Geschmack | RIPE FRUIT TASTE |
| Dichte | 1.028 at 68 °F (USCG, 1999) - Denser than waterwill sink1.0282 AT 20 °C/4 °CRelative density (water = 1): 1.0211.022-1.0271.0282 @ 20°C1.029 g/mL at 20 °C(lit.) |
| Color/Form | COLORLESS LIQUID |
| Löslichkeit | SOL IN ABOUT 35 PARTS WATERSOL IN BENZENE, & CHLOROFORMMISCIBLE WITH ETHER, & ACETONEwater solubility = 1.11X10+5 mg/l @ 17 °C110 mg/mL at 17 °CSolubility in water, g/100ml at 20 °C: 2.86miscible in alcohol, ether, ethyl acetate, 1 ml in 12 ml water116 g/L (20°C)116 g/L (20 ºC) |
| Flammpunkt | 135 °F (USCG, 1999)184 °F CC (84.4 °C)70 °C c.c.185 °F |
| Siedepunkt | 363 °F at 760 mmHg (USCG, 1999)180.8 °C AT 760 MM HG180.00 to 181.00 °C. @ 760.00 mm Hg181 °C180.8 °C @760 [mm Hg]181 °C(lit.) |
| Schmelzpunkt | less than -112 °F (USCG, 1999)-45 °C−43 °C(lit.) |
| Dampfdichte | 4.48Relative vapor density (air = 1): 4.484.48 (vs air) |
| Dampfdruck | 0.78 [mmHg]0.78 MM HG AT 25 °CVapor pressure, kPa at 20 °C: 0.10.78 [mm Hg] @25 °C1 mm Hg ( 28.5 °C) |
| Brechungsindex | MAX ABSORPTION (ALCOHOL): 248 NM (LOG E= 3.2)INDEX OF REFRACTION: 1.4194 AT 20 °C/DSADTLER REFERENCE NUMBER: 101 (IR, PRISM)1.418-1.421n20/D 1.419 |
| FEMA | 2415 | ETHYL ACETOACETATE |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 11(at 25℃) |
| Aggregatzustand | Liquid |
| Farbe | APHA: ≤15 |
| Wichte | 1.027~1.035 (20/4℃) |
| Geruch | Agreeable, fruity. |
| pH | 4.0 (110g/l, H2O, 20℃) |
| Explosionsgrenze | 1.0-54%(V) |
| Biologische Quelle | synthetic |
| Geruchsart | fruity |
| Spezifische Wärmekapazität | Cp(liquid): 1.91 J/(g·K), at 25℃ |
| JECFA Number | 595 |
| Merck | 14,3758 |
| BRN | 385838 |
| Henry-Konstante | 9.0×100 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 15.0(Ambient) |
| Stabilität | Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible. |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3 |
| InChIKey | XYIBRDXRRQCHLP-UHFFFAOYSA-N |
| SMILES | CCOC(=O)CC(C)=O |
| LogP (Verteilungskoeffizient) | 0.8 at 20℃ |
| Oberflächenspannung | 31.93mN/m at 298.15K |
| CAS Datenbank | 141-97-9(CAS DataBase Reference) |
| NIST chemische Informationen | Butanoic acid, 3-oxo-, ethyl ester(141-97-9) |
| EPA chemische Informationen | Ethyl acetoacetate (141-97-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 76.8% (1836 of 2392) of all reports.WarningH319 (17.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 2392 reports by companies from 13 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 1836 of 2392 reports by companies.There are 9 notifications provided by 556 of 2392 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: Butanoic acid, 3-oxo-, ethyl esterRegulation (EC) No 1831/2003 (amended)Butanoic acid, 3-oxo-, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanoic acid, 3-oxo-, 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: 12-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1965Ethyl acetoacetate: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion or sodium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2024) |
Anwendungen & Verwendung
Beschreibung
Acetessigsäure-ethylester bildet eine farblose angenehm riechende Flüssigkeit, die bei 180 ℃ siedet. In Wasser ist der Ester kaum löslich, während er mit Alkohol und Ether mischbar ist. Die acide Methylen-Gruppe im Molekül lässt sich alkylieren, acylieren oder halogenieren. Acetessigsäure-ethylester ist ein wichtiges Zwischenprodukte für die Herstellung von Heterocyclen, insbesondere Arzneimitteln, Pestizide und Farbstoffen.
Beschreibung
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and amino pyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.
Occurrence
Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread.
Herstellung & Synthese
synthetische
Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol. The preparation of ethyl acetoacetate is a classic laboratory procedure . It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.