Diketene

An ester, C4H4O2, 84.074 g/mol. Boiling point 127 °C, melting point -6.5 °C, as published.

verified recordOrganic — ester8 measured properties

Identifiers

Molecular formula: C₄H₄O₂
Molecular weight: 84.074 g/mol
Exact mass: 84.021129 g/mol
IUPAC name: 4-methylideneoxetan-2-one
SMILES: C=C1CC(=O)O1
InChI: InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
InChIKey: WASQWSOJHCZDFK-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: 127 °Cmeasured · Hazardous Substances Data Bank (HSDB); 127 °Cmeasured · ILO-WHO International Chemical Safety Cards (ICSCs)
Melting Point: -6.5 °Cmeasured · Hazardous Substances Data Bank (HSDB); Heat of Fusion at Melting Point = 1.44X10+7 Joules kmolmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.0877 g/cu cm at 20 °Cmeasured · Hazardous Substances Data Bank (HSDB); Density (at 20 °C): 1.09 g/cm³measured · ILO-WHO International Chemical Safety Cards (ICSCs)
Solubility: Very slightly soluble in water in which it decomposes slowlymeasured · Hazardous Substances Data Bank (HSDB); Miscible with most organic solvents. Miscible with hexanemeasured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 10.7 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases; VP: 1.07 kPa at 20 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Flash Point: 93 °F (NFPA, 2010)measured · CAMEO Chemicals; 90 °Fmeasured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
Viscosity: 0.88 mPa.smeasured · Miller R et al; Ketenes. Ullmann's Encyclopedia of Industrial Chemistry. (1999-2018). New York, NY: John Wiley & Sons. Online Posting Date: 15 Sept 2001
Refractive Index: Index of refraction: 1.4342 at 23 °C/Dmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 582; Index of refraction: 1.439 at 20 °C/Dmeasured · Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-196

Calculated properties

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

Molecular weight: 84.07 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 84.021129366 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0.3calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 26.3 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 104calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 0calculated · reference compound database
H-bond acceptors: 2calculated · reference compound database
logP: 0.447calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 26.3 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: 2calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 19.849 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.25calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.3981calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon4 atoms · 57.1% by mass
O Oxygen2 atoms · 38.1% by mass
H Hydrogen4 atoms · 4.8% 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: 6
Total atoms, hydrogen included: 10
Rings: 1
Aromatic rings: 0
Stereocentres: 0
Formal charge: 0

Functional groups

Ester
A carbonyl bonded to an oxygen that links to another carbon.
Ether
An oxygen bridging two carbons.
Alkene
A carbon–carbon double bond.

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 Diketene yet.

Other names for it

The systematic name on this record is 4-methylideneoxetan-2-one.

The sources also call it 4-Methylene-2-oxetanone, 2-Oxetanone, 4-methylene-, Ketene, dimer, 3-Buteno-beta-lactone, Vinylaceto-beta-lactone, 0DZ97C3Z7D, 3-Butenoic acid, 3-hydroxy-, beta-lactone, NSC-93783, DTXSID9027289, RefChem:134103, DTXCID107289.

Structurally related

Nothing structurally close to Diketene has a page here yet.

Where these values came from

reference compound database12661
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.