Butanedione

A ketone, C4H6O2, 86.09 g/mol. Boiling point 87.5 °C, melting point -1.2 °C, as published.

verified recordOrganic — ketone8 measured properties

Identifiers

Molecular formula: C₄H₆O₂
Molecular weight: 86.09 g/mol
Exact mass: 86.036779 g/mol
IUPAC name: butane-2,3-dione
SMILES: CC(=O)C(C)=O
InChI: InChI=1S/C4H6O2/c1-3(5)4(2)6/h1-2H3
InChIKey: QSJXEFYPDANLFS-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: 190 °F at 760 mmHg (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 87.5 °Cmeasured · Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-76; 87.00 to 88.00 °C. @ 760.00 mm Hgmeasured · The Good Scents Company Information System; 88 °Cmeasured · reference compound database; 87-88 °Cmeasured · reference compound database; 190 °Fmeasured · reference compound database; 88 °C @760 [mm Hg]measured · reference compound database
Melting Point: 27.7 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; -1.2 °Cmeasured · Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-76; -2.4 °Cmeasured · reference compound database; -2.4 °Cmeasured · reference compound database; 27.7 °Fmeasured · reference compound database
Flash Point: 80 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 7 °C (45 °F) - closed cupmeasured · Sigma-Aldrich; Safety Data Sheet for 2,3-Butanedione. Product Number: B85307, Version 4.9 (Revision Date 02/05/2016). Available from, as of April 28, 2016: https://www.sigmaaldrich.com/safety-center.html; 80 °F (27 °C) (closed cup)measured · National Fire Protection Association; Fire Protection Guide to Hazardous Materials. 14TH Edition, Quincy, MA 2010, p. 325-21; 6 °C c.c.measured · reference compound database; 80 °Fmeasured · reference compound database
Solubility: greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; In water, 200 g/L at 20 °Cmeasured · Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 94; Soluble in about 4 parts watermeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 537; Readily soluble in all important organic solventsmeasured · Siegel H, Eggersdorfer M; Ketones. Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2016). New York, NY: John Wiley & Sons. Online Posting Date: June 15, 2000.; Miscible with ethermeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 537; For more Solubility (Complete) data for DIACETYL (8 total), please visit the HSDB record page.measured · reference compound database; 200 mg/mL at 15 °Cmeasured · reference compound database; Solubility in water, g/100ml at 25 °C: 20measured · reference compound database; soluble in glycerol and water; miscible with alcohol, propylene glycol, and most fixed oilsmeasured · reference compound database; (in ethanol)measured · reference compound database
Density: 0.99 at 59 °F (NTP, 1992) - Less dense than water; will floatmeasured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 0.990 at 15 °C/15 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 537; Relative density (water = 1): 1.1measured · reference compound database; 0.975-0.990measured · reference compound database; 0.99 at 59 °Fmeasured · reference compound database; 0.990 @ 15°Cmeasured · reference compound database
Vapor Pressure: 56.8 [mmHg]measured · reference compound database; 56.8 mm Hg at 25 °Cmeasured · Boublik, T., Fried, V., and Hala, E., The Vapour Pressures of Pure Substances. Second Revised Edition. Amsterdam: Elsevier, 1984.; Vapor pressure, kPa at 25 °C: 7.6measured · reference compound database; 56.8 [mm Hg] @25 °Cmeasured · reference compound database
LogP: log Kow = -1.34measured · Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 9; -1.34measured · HANSCH,C ET AL. (1995); -1.34measured · reference compound database; -1.34measured · reference compound database
Refractive Index: Index of refraction: 1.3951 at 20 °C.measured · Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-76; 1.393-1.397measured · reference compound database

Calculated properties

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

Molecular weight: 86.09 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 86.03677943 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: -1.3calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 34.1 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 71calculated · 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: 0.1644calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 34.14 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: 1calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 21.362 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0.5calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.4259calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon4 atoms · 55.8% by mass
O Oxygen2 atoms · 37.2% by mass
H Hydrogen6 atoms · 7.0% 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: 12
Rings: 0
Aromatic rings: 0
Stereocentres: 0
Formal charge: 0

Functional groups

Ketone
A carbonyl bonded to 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 Butanedione yet.

Other names for it

The systematic name on this record is butane-2,3-dione.

The sources also call it 2,3-butanedione, diacetyl, biacetyl, Butane-2,3-dione, dimethylglyoxal, dimethyl diketone, Dimethyl glyoxal, 2,3-diketobutane, 2,3-dioxobutane, 2,3-Butadione, Glyoxal, dimethyl-.

Structurally related

Nothing structurally close to Butanedione has a page here yet.

Where these values came from

reference compound database650
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.