Ethyl Acetoacetate

An ester, C6H10O3, 130.143 g/mol. Boiling point 180.8 °C AT 760 MM HG, melting point -45 °C, as published.

verified recordOrganic — ester7 measured properties

Identifiers

Molecular formula: C₆H₁₀O₃
Molecular weight: 130.143 g/mol
Exact mass: 130.062994 g/mol
IUPAC name: ethyl 3-oxobutanoate
SMILES: CCOC(=O)CC(C)=O
InChI: InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3
InChIKey: XYIBRDXRRQCHLP-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 363 °F at 760 mmHg (USCG, 1999)measured · CAMEO Chemicals; 180.8 °C AT 760 MM HGmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: less than -112 °F (USCG, 1999)measured · CAMEO Chemicals; -45 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.028 at 68 °F (USCG, 1999) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.0282 AT 20 °C/4 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: SOL IN ABOUT 35 PARTS WATERmeasured · Hazardous Substances Data Bank (HSDB); SOL IN BENZENE, & CHLOROFORM; MISCIBLE WITH ETHER, & ACETONEmeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 0.78 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases; 0.78 MM HG AT 25 °Cmeasured · Hazardous Substances Data Bank (HSDB)
LogP: log Kow = 0.25measured · Hazardous Substances Data Bank (HSDB); 0.25measured · Human Metabolome Database (HMDB)
Flash Point: 135 °F (USCG, 1999)measured · CAMEO Chemicals; 184 °F CC (84.4 °C)measured · Hazardous Substances Data Bank (HSDB)

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 130.14 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 130.062994177 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0.2calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 43.4 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 117calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 0calculated · reference compound database
H-bond acceptors: 3calculated · reference compound database
logP: 0.5286calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 43.37 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 3calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 3calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 31.931 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.6667calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.4131calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon6 atoms · 55.4% by mass
O Oxygen3 atoms · 36.9% by mass
H Hydrogen10 atoms · 7.7% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 9
Total atoms, hydrogen included: 19
Rings: 0
Aromatic rings: 0
Stereocentres: 0
Formal charge: 0

Functional groups

Ester
A carbonyl bonded to an oxygen that links to another carbon.
Ketone
A carbonyl bonded to two carbons.
Ether
An oxygen bridging two carbons.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Ethyl Acetoacetate yet.

Other names for it

The systematic name on this record is ethyl 3-oxobutanoate.

The sources also call it ethyl 3-oxobutanoate, ethyl acetylacetate, ethyl 3-oxobutyrate, diacetic ether, Butanoic acid, 3-oxo-, ethyl ester, Acetoacetic ester, acetoacetic acid, ethyl ester, ethyl acetylacetonate, 3-oxobutanoic acid ethyl ester, active acetyl acetate, Active acetylacetate.

Structurally related

Nothing structurally close to Ethyl Acetoacetate has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Ethyl Acetoacetate. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

(-)-alpha-Amino-3-(azidomethyl)-4-hydroxybenzeneacetic acid

used as a reactant

C₉H₁₀N₄O₃, 222.204 g/mol.

Where these values came from

reference compound database8868
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.