Acetone

Acetone^[1]
Full structural formula of acetone with dimensions	Skeletal formula of acetone
Ball-and-stick model of acetone	Space-filling model of acetone
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 ;
3D model (JSmol)	Interactive image;
3DMet	B00058;
Beilstein Reference	635680
ChEBI	CHEBI:15347 ;
ChEMBL	ChEMBL14253 ;
ChemSpider	175 ;
ECHA InfoCard	100.000.602
EC Number	200-662-2;
Gmelin Reference	1466
KEGG	D02311 ;
MeSH	Acetone
PubChem CID	180;
RTECS number	AL3150000;
UNII	1364PS73AF ;
UN number	1090
CompTox Dashboard (EPA)	DTXSID8021482 ;
	SMILES CC(=O)C;
Properties
Chemical formula	C3H6O
Molar mass	58.08 g·mol−1
Appearance	Colorless liquid
Odor	Pungent, irritating, floral, cucumber like
Density	0.7845 g/cm3 (25 °C)
Melting point	−94.7 °C (−138.5 °F; 178.5 K)
Boiling point	56.05 °C (132.89 °F; 329.20 K)
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
	GHS labelling:
Pictograms	Template:GHS02
Signal word	Danger
Hazard statements	H225, H319, H336, H373
Precautionary statements	P210, P235, P260, P305+P351+P338
NFPA 704 (fire diamond)	1 3 0
Flash point	−20 °C (−4 °F; 253 K)
Autoignition; temperature	465 °C (869 °F; 738 K)
Explosive limits	2.6–12.8%
Threshold limit value (TLV)	1185 mg/m3 (TWA), 2375 mg/m3 (STEL)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	5800 mg/kg (rat, oral); 3000 mg/kg (mouse, oral); 5340 mg/kg (rabbit, oral);
LC50 (median concentration)	20,702 ppm (rat, 8 h)
LCLo (lowest published)	45,455 ppm (mouse, 1 h)
	NIOSH (US health exposure limits):
PEL (Permissible)	1000 ppm (2400 mg/m3)
REL (Recommended)	TWA 250 ppm (590 mg/m3)
IDLH (Immediate danger)	2500 ppm
Related compounds
Related compounds	Butanone; Isopropyl alcohol; Urea; Carbonic acid; Carbonyl fluoride;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Acetone, or propanone, is an organic compound with the chemical formula (CH₃)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.^[source?]

Sources

↑ The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription required)
↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
1 2 3 4 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 (2005). COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design. Elsevier. pp. 92–94. ISBN 978-0-444-51994-8.
↑ Ash, Michael; Ash, Irene (2004). Handbook of preservatives. Synapse Information Resources, Inc. p. 369. ISBN 1-890595-66-7.
↑ Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp. 4–6. ISBN 978-0-313-08057-9.
1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0260". National Institute for Occupational Safety and Health (NIOSH).
1 2 Lide, David R. (ed) (2003). CRC Handbook of Chemistry and Physics, 84th Edition. CRC Press. Boca Raton, Florida; Section 3, Physical Constants of Organic Compounds.
1 2 Properties of substance: acetone. chemister.ru.
↑ "acetone". ChemSrc. Retrieved 2018-04-13.
↑ Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S.; Wirz, Jakob (1984). "The pKa and keto-enol equilibrium constant of acetone in aqueous solution". Journal of the American Chemical Society. 106 (2): 460–462. Bibcode:1984JAChS.106..460C. doi:10.1021/ja00314a055.
↑ Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. Bibcode:1988AcChR..21..456B. doi:10.1021/ar00156a004. S2CID 26624076.
↑ "Working with modern hydrocarbon and oxygenated solvents: a guide to flammability". American Chemistry Council Solvents Industry Group. January 2008. p. 7. Archived from the original on 2009-06-01.
1 2 3 "Acetone". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.

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

[iupac2013-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 723. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[nist-3] 1 2 3 4 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)

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

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

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

[NIOSH-7] 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0260". National Institute for Occupational Safety and Health (NIOSH).

[CRC-8] 1 2 Lide, David R. (ed) (2003). CRC Handbook of Chemistry and Physics, 84th Edition. CRC Press. Boca Raton, Florida; Section 3, Physical Constants of Organic Compounds.

[chemister-9] 1 2 Properties of substance: acetone. chemister.ru.

[chemsrc-10] "acetone". ChemSrc. Retrieved 2018-04-13.

[11] Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S.; Wirz, Jakob (1984). "The pKa and keto-enol equilibrium constant of acetone in aqueous solution". Journal of the American Chemical Society. 106 (2): 460–462. Bibcode:1984JAChS.106..460C. doi:10.1021/ja00314a055.

[Bordwell-12] Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. Bibcode:1988AcChR..21..456B. doi:10.1021/ar00156a004. S2CID 26624076.

[13] "Working with modern hydrocarbon and oxygenated solvents: a guide to flammability". American Chemistry Council Solvents Industry Group. January 2008. p. 7. Archived from the original on 2009-06-01.

[IDLH-14] 1 2 3 "Acetone". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.

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