Acetone

Acetone^[1]
Names
	IUPAC name Acetone
	Preferred IUPAC name Propan-2-one
	Systematic IUPAC name 2-Propanone
	Other names Acetonum (Latin pronunciation: [aˈkeːtonum]); Dimethyl ketone; Dimethyl carbonyl; Ketone propane; β-Ketopropane; Propanone; 2-Propanone; Pyroacetic spirit (archaic); Spirit of Saturn (archaic);
Identifiers
CAS Number	67-64-1 ;
3D model (JSmol)	Interactive image;
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 ;
	InChI InChI=1S/C3H6O/c1-3(2)4/h1-2H3 Key: CSCPPACGZOOCGX-UHFFFAOYSA-N ; InChI=1/C3H6O/c1-3(2)4/h1-2H3 Key: CSCPPACGZOOCGX-UHFFFAOYAF;
	SMILES CC(=O)C;
Properties
Chemical formula	C3H6O
Molar mass	58.080 g·mol−1
Appearance	Colourless liquid
Odor	Pungent, fruity
Density	0.7845 g/cm3 (25 °C)
Melting point	−94.9 °C (−138.8 °F; 178.2 K)
Boiling point	56.08 °C (132.94 °F; 329.23 K)
Solubility in water	Miscible
Solubility	Miscible in benzene, diethyl ether, methanol, chloroform, ethanol
log P	−0.24
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)	−33.8·10−6 cm3/mol
Thermal conductivity	0.161 W/(m·K) (25 °C)
Refractive index (nD)	1.3588 (20 °C)
Viscosity	0.306 mPa·s (25 °C)
Structure
Coordination geometry	Trigonal planar at C2
Molecular shape	Dihedral at C2
Dipole moment	2.88 D
Thermochemistry
Heat capacity (C)	126.3 J/(mol·K)
Std molar; entropy (S⦵298)	199.8 J/(mol·K)
Std enthalpy of; formation (ΔfH⦵298)	−248.4 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−1.79 MJ/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, 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	2.5–12.8%
Threshold limit value (TLV)	250 ppm (STEL), 500 ppm (C)
	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; Formaldehyde; Urea; Carbonic acid;
Supplementary data page
	Acetone (data page)
	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 (2-propanone or dimethyl ketone) is an organic compound with the formula (CH₃)₂CO.^[22] It is the simplest and smallest ketone (R−C(=O)−R'). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odor.^[23]

Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.^[24]^[25] It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.^[26]

Acetone is produced and disposed of in the human body through normal metabolic processes. Small quantities of it are present naturally in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Medical ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to suppress epileptic attacks in children with treatment-resistant epilepsy.^[27]

^ The Merck Index, 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription required)
^ ^a ^b ^c ^d 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)
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0004". National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp. 4–6. ISBN 978-0-313-08057-9.
^ Cite error: The named reference gorman1962 was invoked but never defined (see the help page).
^ ChemSpider lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.
^ 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.
^ Cite error: The named reference smell was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f Haynes, p. 3.4
^ Haynes, p. 5.173
^ 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. doi:10.1021/ar00156a004. S2CID 26624076.
^ Haynes, p. 3.576
^ Haynes, p. 6.254
^ Haynes, p. 6.243
^ Haynes, p. 9.60
^ Haynes, pp. 5.3, 5.67
^ ^a ^b ^c Haynes, p. 15.13
^ ^a ^b Haynes, p. 16.34
^ ^a ^b ^c "Acetone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Allen, P .W.; Bowen, H. J. M.; Sutton, L. E.; Bastiansen, O. (1952). "The molecular structure of acetone". Transactions of the Faraday Society. 48: 991. doi:10.1039/TF9524800991.
^ Myers, Richard Leroy (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood Press. p. 4-6. ISBN 9780313337581.
^ Acetone, World Petrochemicals report, January 2010
^ Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
^ "Update: U.S. EPA Exempt Volatile Organic Compounds". American Coatings Association. 2018-01-30. Archived from the original on 2021-02-08. Retrieved 2019-03-20.
^ Freeman, JM; Kossoff, EH; Hartman, AL (Mar 2007). "The ketogenic diet: one decade later". Pediatrics. 119 (3): 535–43. doi:10.1542/peds.2006-2447. PMID 17332207. S2CID 26629499.

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

[nist-2] 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)

[NIOSH-3] NIOSH Pocket Guide to Chemical Hazards. "#0004". National Institute for Occupational Safety and Health (NIOSH).

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

[gorman1962-6] Cite error: The named reference gorman1962 was invoked but never defined (see the help page).

[7] ChemSpider lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.

[iupac2013-8] 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.

[smell-9] Cite error: The named reference smell was invoked but never defined (see the help page).

[h1-10] ^ ^a ^b ^c ^d ^e ^f Haynes, p. 3.4

[11] Haynes, p. 5.173

[12] 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-13] Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004. S2CID 26624076.

[14] Haynes, p. 3.576

[15] Haynes, p. 6.254

[16] Haynes, p. 6.243

[17] Haynes, p. 9.60

[18] Haynes, pp. 5.3, 5.67

[ig-19] Haynes, p. 15.13

[da-20] Haynes, p. 16.34

[IDLH-21] "Acetone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[22] Allen, P .W.; Bowen, H. J. M.; Sutton, L. E.; Bastiansen, O. (1952). "The molecular structure of acetone". Transactions of the Faraday Society. 48: 991. doi:10.1039/TF9524800991.

[Myers-23] Myers, Richard Leroy (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood Press. p. 4-6. ISBN 9780313337581.

[r1-24] Acetone, World Petrochemicals report, January 2010

[Ullmann-25] Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.

[26] "Update: U.S. EPA Exempt Volatile Organic Compounds". American Coatings Association. 2018-01-30. Archived from the original on 2021-02-08. Retrieved 2019-03-20.

[Freeman2007-27] Freeman, JM; Kossoff, EH; Hartman, AL (Mar 2007). "The ketogenic diet: one decade later". Pediatrics. 119 (3): 535–43. doi:10.1542/peds.2006-2447. PMID 17332207. S2CID 26629499.

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