Methyl acetoacetate

An ester, C5H8O3, 116.116 g/mol. Boiling point 171.7 °C, melting point -80 °C, as published.

verified recordOrganic — ester9 measured properties

Identifiers

Molecular formula: C₅H₈O₃
Molecular weight: 116.116 g/mol
Exact mass: 116.047344 g/mol
IUPAC name: methyl 3-oxobutanoate
SMILES: COC(=O)CC(C)=O
InChI: InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3
InChIKey: WRQNANDWMGAFTP-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: 336 to 338 °F at 760 mmHg (USCG, 1999)measured · CAMEO Chemicals; 171.7 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: -112 °F (USCG, 1999)measured · CAMEO Chemicals; -80 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.076 (USCG, 1999) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.0762 g/cu cm at 20 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility: Soluble in 2 parts water; miscible with alcohol and ethermeasured · Hazardous Substances Data Bank (HSDB); SOLUBILITY IN WATER: 38 G/100 MLmeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 0.89 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases; 0.892 mm Hg at 25 °C /Extrapolated/measured · Hazardous Substances Data Bank (HSDB)
LogP: log Kow = -0.69 /Estimated/measured · Hazardous Substances Data Bank (HSDB); -0.26measured · ILO-WHO International Chemical Safety Cards (ICSCs)
Flash Point: 158 °F (USCG, 1999)measured · CAMEO Chemicals; 170 °F (77 °C) (open cup)measured · Hazardous Substances Data Bank (HSDB)
Viscosity: 1.704 cPa at 20 °Cmeasured · Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V21 389 (1983)
Refractive Index: Index of refraction: 1.4184 at 20 °C/Dmeasured · Lide, DR (ed.). CRC Handbook of Chemistry and Physics. 81st Edition. CRC Press LLC, Boca Raton: FL 2000, p. 3-99

Calculated properties

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

Molecular weight: 116.11 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 116.047344113 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0calculated · 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: 106calculated · 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: 0.1385calculated · 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: 2calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 27.314 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.6calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.3804calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon5 atoms · 51.7% by mass
O Oxygen3 atoms · 41.3% by mass
H Hydrogen8 atoms · 6.9% 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: 8
Total atoms, hydrogen included: 16
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 Methyl acetoacetate yet.

Other names for it

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

The sources also call it Methyl 3-oxobutanoate, Methylacetoacetate, Methyl acetylacetate, Acetoacetic acid methyl ester, Methyl 3-oxobutyrate, 3-Oxobutanoic acid methyl ester, Methyl acetylacetonate, Butanoic acid, 3-oxo-, methyl ester, Acetoacetic methyl ester, 1-Methoxybutane-1,3-dione, Acetoacetic acid, methyl ester.

Structurally related

Nothing structurally close to Methyl acetoacetate has a page here yet.

Where these values came from

reference compound database7757
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.