Catalog Number
ACMA00016961
Product Name
Ethyl acetoacetate
Description
Ethyl acetoacetate appears as a colorless liquid with a fruity odor. Flash point 185°F. Boiling point 365°F. May cause adverse health effects if ingested or inhaled. May irritate to skin, eyes and mucous membranes. Used in organic synthesis and in lacquers and paints.;Liquid;Liquid;Liquid;COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.;clear, colourless to yellow mobile liquid; fruity taste; fruity, sweet, and rum-like odour
IUPAC Name
ethyl 3-oxobutanoate
Molecular Weight
130.14g/mol
Molecular Formula
C6H10O3;CH3COCH2COOC2H5;C6H10O3
Canonical SMILES
CCOC(=O)CC(=O)C
InChI
InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChI Key
XYIBRDXRRQCHLP-UHFFFAOYSA-N
Boiling Point
363 °F at 760 mm Hg (USCG, 1999);180.8 °C;180.8 °C AT 760 MM HG;180.8 °C
Melting Point
less than -112 °F (USCG, 1999);-45.0 °C;-45 °C;-45 °C;-45°C;-45 °C
Flash Point
135 °F (USCG, 1999);184 °F CC (84.4 °C);70 °C c.c.
Density
1.028 at 68 °F (USCG, 1999);d20 1.03;1.0282 AT 20 °C/4 °C;Relative density (water = 1): 1.021;1.022-1.027
Solubility
110 mg/mL at 17 °C;SOL IN ABOUT 35 PARTS WATER;SOL IN BENZENE, & CHLOROFORM; MISCIBLE WITH ETHER, & ACETONE;water solubility = 1.11X10+5 mg/l @ 17 °C;110 mg/mL at 17 °C;Solubility in water, g/100ml at 20 °C: 2.86;miscible in alcohol, ether, ethyl acetate, 1 ml in 12 ml water
Application
Ethyl acetoacetate, a colorless liquid with a sweet, fruity aroma reminiscent of green apples, serves multiple roles across various industries due to its versatile properties. Primarily, it acts as a chemical intermediate, facilitating the production of a diverse array of compounds such as amino acids, antibiotics, analgesics, and antimalarial agents, among others. Additionally, it is integral to the manufacture of dyes, inks, perfumes, plastics, and flavoring agents. The compound also plays a crucial role in organic synthesis, aiding in the creation of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine, and coumarin derivatives. Beyond its industrial applications, ethyl acetoacetate is used as a fragrance component in feminine fine fragrances, leveraging its fresh, fruity top notes. It finds use as a flavoring agent in food, a formaldehyde scavenger, and even as a bio-based diluent to enhance the cold flow properties of biodiesel. The compound also engages in reactions to form complex organic structures, showcasing its importance in the synthesis of vitamins, pharmaceuticals, and other specialized chemicals.
Color/Form
COLORLESS LIQUID
Covalently-Bonded Unit Count
1
Exact Mass
130.062994g/mol
Log P
0.25 (LogP);0.25;log Kow = 0.25;0.25;0.27
MeSH Entry Terms
ethyl 3-oxobutanoate;ethyl acetoacetate;ethyl acetoacetate, 1,2-(14)C-labeled;ethyl acetoacetate, 1,3-(14)C-labeled;ethyl acetoacetate, 14C4-labeled;ethyl acetoacetate, 2,4-(14)C-labeled;ethyl acetoacetate, 2-(14)C-labeled;ethyl acetoacetate, 3-(14)C-labeled;ethyl beta-ketobutyrate
Monoisotopic Mass
130.062994g/mol
Odor
PLEASANT GREEN, FRUITY, RUM ODOR
Other Experimental
CONVERSION FACTOR: 5.31 MG/CU M IS EQUIVALENT TO 1 PPM;CONVERSION FACTOR: 1 MG/L IS EQUIVALENT TO 188 PPM;THIS COMPD IS A TAUTOMER AT ROOM TEMP CONSISTING OF ABOUT 93% KETO FORM & 7% ENOL FORM; COEFFICIENT OF EXPANSION 0.00101/DEG C; FP (ENOL) -80 °C; FP (KETO) -39 °C;MAX ABSORPTION (VAPOR): 238.5 NM (LOG E= 4.21); DENSITY 1.0119 @ 10 °C; INDEX OF REFRACTION 1.4432 @ 20 °C /ENOL FORM/;MAX ABSORPTION (VAPOR): 263 NM (LOG E= 2.47); DENSITY 1.0368 AT 10 °C/4 °C; INDEX OF REFRACTION: 1.4171 AT 20 °C /KETO FORM/;CAN REACT WITH OXIDIZING MATERIALS;IR: 32 (Sadtler Research Laboratories IR Grating Collection) /Ethyl acetoacetate (keto form)/;UV: 40 (Sadtler Research Laboratories Spectral Collection) /Ethyl acetoacetate (keto form)/;NMR: 10321 (Sadtler Research Laboratories Spectral Collection) /Ethyl acetoacetate (keto form)/;MASS: 590 (Atlas of Mass Spectral Data, John Wiley & Sons, New York) /Ethyl acetoacetate (keto form)/
Refractive Index
n20D 1.4190;MAX ABSORPTION (ALCOHOL): 248 NM (LOG E= 3.2); INDEX OF REFRACTION: 1.4194 AT 20 °C/D; SADTLER REFERENCE NUMBER: 101 (IR, PRISM);1.418-1.421
Vapor Density
4.48;Relative vapor density (air = 1): 4.48
Vapor Pressure
0.78 mmHg;0.78 MM HG AT 25 °C;Vapor pressure, kPa at 20 °C: 0.1
