Acetone

Acetone^[1]
Names
	Preferred IUPAC name Propan-2-one
	Other names Acetone; Dimethyl ketone; Dimethyl carbonyl; β-Ketopropane; Propanone; 2-Propanone; Dimethyl formaldehyde; Pyroacetic spirit (archaic); Ketone propane;
Identifiers
CAS number	67-64-1
PubChem	180
EC number	200-662-2
KEGG	D02311
MeSH	Acetone
ChEBI	CHEBI:15347
RTECS number	AL3150000
SMILES	CC(=O)C
	InChI
Beilstein Reference	635680
Gmelin Reference	1466
3DMet	B00058
Properties
Molecular formula	C3H6O
Molar mass	58.07 g mol-1
Appearance	Colorless liquid
Odor	Pungent, irritating, floral, cucumber like
Density	0.7845 g/cm3 (25 °C)
Melting point	−94.7 °C, 178 K, -138 °F
Boiling point
Solubility in water	Miscible
Solubility	Miscible in benzene, diethyl ether, methanol, chloroform, ethanol
log P	-0.16
Vapor pressure	9.39 kPa (0 °C); 30.6 kPa (25 °C); 374 kPa (100 °C); 2.8 MPa (200 °C);
Acidity (pKa)	19.16 (H2O); 26.5 (DMSO);
Magnetic susceptibility (χ)	−33.78·10−6 cm3/mol
Refractive index (nD)	1.3588 (VD = 54.46)
Viscosity	0.295 mPa·s (25 °C)
Structure
Coordination; geometry	Trigonal planar at C2
Molecular shape	Dihedral at C2
Dipole moment	2.91 D
Thermochemistry
Std enthalpy of; formation ΔfHo298	(−250.03) – (−248.77) kJ/mol
Std enthalpy of; combustion ΔcHo298	−1.772 MJ/mol
Standard molar; entropy So298	200.4 J/(mol·K)
Specific heat capacity, C	125.45 J/(mol·K)
Hazards
NFPA 704	3 1 0
Explosive limits	2.6–12.8%
U.S. Permissible; exposure limit (PEL)	1000 ppm (2400 mg/m3)

Acetone, or propanone, is an organic compound with the chemical formula (CH
3)
2CO. This clear, mobile, easy-to-burn liquid is the simplest example of the ketones. Acetone can be mixed with water. It is an important solvent, often to clean things in the laboratory. Common uses of acetone in the home are as the active ingredient in nail polish remover and as paint thinner. It is a common building block in organic chemistry.

Related compounds

Like most ketones, acetone is a tautomer of an enol, 2-propenol. When mixed with water, it can also form a geminal diol hydrate, 2,2-propanediol. These compounds are much less stable than acetone, with less than 0.1% of chemical species being in the enol or diol form in most solutions.

Acetone Media

Overview of the cumene process
Keto-Enol-Tautomerie von Aceton

Sources

↑ The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription needed)
↑ ^2.0 ^2.1 ^2.2 ^2.3 Acetone in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-11)
↑ Klamt, Andreas. COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design (2005)Elsevier. p. 92–94. ISBN 978-0-444-51994-8.
↑ Ash, Michael. Handbook of preservatives (2004)Synapse Information Resources, Inc.. p. 369. ISBN 1-890595-66-7.
↑ Myers, Richard L.. The 100 Most Important Chemical Compounds: A Reference Guide (2007)Greenwood. p. 4–6. ISBN 978-0-313-08057-9.
↑ ^6.0 ^6.1 NIOSH Pocket Guide to Chemical Hazards. #0260National Institute for Occupational Safety and Health (NIOSH).
↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) (2014). Cambridge: The Royal Society of Chemistry. p. 723. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
↑ ^8.0 ^8.1 Properties of substance: acetone. chemister.ru.
↑ acetone. ChemSrc. Retrieved 2018-04-13.
↑ Chiang, Yvonne. The pKa and keto-enol equilibrium constant of acetone in aqueous solution. Journal of the American Chemical Society 106 (2) (1984). p. 460–462. doi:10.1021/ja00314a055.
↑ Bordwell, Frederick G.. Equilibrium acidities in dimethyl sulfoxide solution. Accounts of Chemical Research 21 (12) (1988). p. 456–463. doi:10.1021/ar00156a004.
↑ Working with modern hydrocarbon and oxygenated solvents: a guide to flammability (January 2008)American Chemistry Council Solvents Industry Group. p. 7.

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[1] The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription needed)

[nist-2] 2.0 ^2.1 ^2.2 ^2.3 Acetone in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-11)

[3] Klamt, Andreas. COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design (2005)Elsevier. p. 92–94. ISBN 978-0-444-51994-8.

[4] Ash, Michael. Handbook of preservatives (2004)Synapse Information Resources, Inc.. p. 369. ISBN 1-890595-66-7.

[5] Myers, Richard L.. The 100 Most Important Chemical Compounds: A Reference Guide (2007)Greenwood. p. 4–6. ISBN 978-0-313-08057-9.

[NIOSH-6] 6.0 ^6.1 NIOSH Pocket Guide to Chemical Hazards. #0260National Institute for Occupational Safety and Health (NIOSH).

[iupac2013-7] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) (2014). Cambridge: The Royal Society of Chemistry. p. 723. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.

[chemister-8] 8.0 ^8.1 Properties of substance: acetone. chemister.ru.

[chemsrc-9] acetone. ChemSrc. Retrieved 2018-04-13.

[10] Chiang, Yvonne. The pKa and keto-enol equilibrium constant of acetone in aqueous solution. Journal of the American Chemical Society 106 (2) (1984). p. 460–462. doi:10.1021/ja00314a055.

[Bordwell-11] Bordwell, Frederick G.. Equilibrium acidities in dimethyl sulfoxide solution. Accounts of Chemical Research 21 (12) (1988). p. 456–463. doi:10.1021/ar00156a004.

[12] Working with modern hydrocarbon and oxygenated solvents: a guide to flammability (January 2008)American Chemistry Council Solvents Industry Group. p. 7.

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