2-Butanone, 3-methyl-

• Formula: C₅H₁₀O
• Molecular weight: 86.1323
• IUPAC Standard InChI: InChI=1S/C5H10O/c1-4(2)5(3)6/h4H,1-3H3 Copy

  
• IUPAC Standard InChIKey: SYBYTAAJFKOIEJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 563-80-4
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Isopropyl methyl ketone; Ketone, isopropyl methyl; Methyl butanone-2; Methyl isopropyl ketone; 3-Methyl-2-butanone; iso-C3H7COCH3; 2-Acetylpropane; 3-Methylbutan-2-one; MIPK; UN 2397; 2-Methylbutan-3-one; NSC 9379; methylbutanone; 3-Methyl-2-butanoate; 3-methylbutanone
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, UV/Visible spectrum, Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

Kovats' RI, non-polar column, temperature ramp

View large format table.

Kovats' RI, polar column, isothermal

View large format table.

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Van Den Dool and Kratz RI, polar column, custom temperature program

View large format table.

Normal alkane RI, non-polar column, isothermal

View large format table.

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Normal alkane RI, polar column, temperature ramp

View large format table.

Normal alkane RI, polar column, custom temperature program

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Harrop, Head, et al., 1970
Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 22. Enthalpies of combustion of some aliphatic ketones, J. Chem. Thermodyn., 1970, 2, 203-210. [all data]

Hales J.L., 1967
Hales J.L., Thermodynamic properties of organic oxygen compounds. Part 18. Vapor heat capacities and heats of vaporization of ethyl ketone, ethyl propyl ketone, methyl isopropyl ketone, and methyl phenyl ether, Trans. Faraday Soc., 1967, 63, 1876-1879. [all data]

Rogers, 1947
Rogers, M.T., The electric moments and ultraviolet absorption spectras of some derivatives of cyclopropane and of ethylene oxide, J. Am. Chem. Soc., 1947, 69, 2544-2548. [all data]

Hu, Lu, et al., 2006
Hu, X.-F.; Lu, C.-H.; Yin, C.-S., Modeling Gas Chromatographic Retention Indices of Oxygen-containing Compounds by Novel Atom-type Topological Indices, Chinese Journal of Chemical Physics, 2006, 19, 3, 243-247, https://doi.org/10.1360/cjcp2006.19(3).243.5 . [all data]

Héberger, Görgényi, et al., 2002
Héberger, K.; Görgényi, M.; Kowalska, T., Temperature dependence of Kováts indices in gas chromatography revisited, J. Chromatogr. A, 2002, 973, 1-2, 135-142, https://doi.org/10.1016/S0021-9673(02)01198-6 . [all data]

Héberger and Görgényi, 1999
Héberger, K.; Görgényi, M., Principal component analysis of Kováts indices for carbonyl compounds in capillary gas chromatography, J. Chromatogr., 1999, 845, 1-2, 21-31, https://doi.org/10.1016/S0021-9673(99)00323-4 . [all data]

Winskowski, 1983
Winskowski, J., Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren, Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041 . [all data]

Wehrli and Kováts, 1959
Wehrli, A.; Kováts, E., Gas-chromatographische Charakterisierung ogranischer Verbindungen. Teil 3: Berechnung der Retentionsindices aliphatischer, alicyclischer und aromatischer Verbindungen, Helv. Chim. Acta, 1959, 7, 7, 2709-2736, https://doi.org/10.1002/hlca.19590420745 . [all data]

Ohnishi and Shibamoto, 1984
Ohnishi, S.; Shibamoto, T., Volatile compounds from heated beef fat and beef fat with glycine, J. Agric. Food Chem., 1984, 32, 5, 987-992, https://doi.org/10.1021/jf00125a008 . [all data]

Censullo, Jones, et al., 2003
Censullo, A.C.; Jones, D.R.; Wills, M.T., Speciation of the volatile organic compounds (VOCs) in solventborne aerosol coatings by solid phase microextraction-gas chromatography, J. Coat. Technol., 2003, 75, 936, 47-53, https://doi.org/10.1007/BF02697922 . [all data]

Kim, 2001
Kim, J.S., Einfluss der Temperatur beim Rösten von Sesam auf Aroma und antioxidative Eigenschaften des Öls, PhD Thesis, Technischen Universität Berlin zur Erlangung des akademischen Grades, Berlin, 2001, 151. [all data]

Owens J.D., Allagheny N., et al., 1997
Owens J.D.; Allagheny N.; Kipping G.; Ames J.M., Formation of volatile compounds during Bacillus subtilis fermentation of soya beans, J. Sci. Food Agric., 1997, 74, 1, 132-140, https://doi.org/10.1002/(SICI)1097-0010(199705)74:1<132::AID-JSFA779>3.0.CO;2-8 . [all data]

Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y., Headspace gas analysis of fish sauce, J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u . [all data]

Shimoda, Shiratsuchi, et al., 1996
Shimoda, M.; Shiratsuchi, H.; Nakada, Y.; Wu, Y.; Osajima, Y., Identification and sensory characterization of volatile flavor compounds in sesame seed oil, J. Agric. Food Chem., 1996, 44, 12, 3909-3912, https://doi.org/10.1021/jf960115f . [all data]

Tanchotikul and Hsieh, 1989
Tanchotikul, U.; Hsieh, T.C.-Y., Volatile Flavor Components in Crayfish Waste, J. Food Sci., 1989, 54, 6, 1515-1520, https://doi.org/10.1111/j.1365-2621.1989.tb05149.x . [all data]

Radovic, Careri, et al., 2001
Radovic, B.S.; Careri, M.; Mangia, A.; Musci, M.; Gerboles, M.; Anklam, E., Analytical, nutritional, and clinical methods section. Contribution of dynamic headspace GC-MS analysis of aroma compounds to authenticity testing of honey, Food Chem., 2001, 72, 4, 511-520, https://doi.org/10.1016/S0308-8146(00)00263-6 . [all data]

Amboni, Junkes, et al., 2002
Amboni, R.D.DeM.C.; Junkes, B. daS.; Yunes, R.A.; Heinzen, V.E.F., Quantitative structure-property relationships study of chromatographic retention indices and normal boiling points for oxo compounds using the semi-empirical topological method, J. Mol. Struct. (Theochem), 2002, 586, 1-3, 71-80, https://doi.org/10.1016/S0166-1280(02)00062-3 . [all data]

Kurdina, Markovich, et al., 1969
Kurdina, Z.G.; Markovich, V.E.; Sakharov, V.M., Gas chromatography of cyclic O-containing compounds in Gas chromatography, Issue # 10, NIITEKhim, Moscow, 1969, 128-133. [all data]

Zenkevich, Eliseenkov, et al., 2011
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N.; Zhakovskaya, Z.A.; Khoroshko, L.O., Gas chromatographic identification of chlorination products of aliphatic ketones, J. Chromatogr., 2011, 1218, 21, 3291-3299, https://doi.org/10.1016/j.chroma.2010.12.056 . [all data]

Sivadier, Ratel, et al., 2009
Sivadier, G.; Ratel, J.; Engel, E., Latency and persistence of diet volatile biomarkers in lamb fats, J. Agric. Food Chem., 2009, 57, 2, 645-652, https://doi.org/10.1021/jf802467q . [all data]

Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D., Volatile constituents of Perique tobacco, Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]

Ngassoum, Jirovetz, et al., 2001
Ngassoum, M.B.; Jirovetz, L.; Buchbauer, G., SPME/GC/MS analysis of headspace aroma compounds of the Cameroonian fruit Tetrapleura tetraptera (Thonn.) Taub., Eur. Food Res. Technol., 2001, 213, 1, 18-21, https://doi.org/10.1007/s002170100330 . [all data]

Chen and Ho, 1999
Chen, J.; Ho, C.-T., Comparison of volatile generation in serine/threonine/glutamine-ribose/glucose/fructose model systems, J. Agric. Food Chem., 1999, 47, 2, 643-647, https://doi.org/10.1021/jf980771a . [all data]

Lu, Yu, et al., 1997
Lu, G.; Yu, T.-H.; Ho, C.-T., Generation of flavor compounds by the reaction of 2-deoxyglucose with selected amino acids, J. Agric. Food Chem., 1997, 45, 1, 233-236, https://doi.org/10.1021/jf960609c . [all data]

Larsen and Frisvad, 1995
Larsen, T.O.; Frisvad, J.C., Characterization of volatile metabolites from 47 Penicillium taxa, Mycol. Res., 1995, 99, 10, 1153-1166, https://doi.org/10.1016/S0953-7562(09)80271-2 . [all data]

Misharina, Golovnya, et al., 1991
Misharina, T.A.; Golovnya, R.V.; Charnomskii, V.V., Volatile components of boiled shrimp funchalia woodwardi and crab geryon maritae, Zh. Anal. Khim., 1991, 46, 1421-1429. [all data]

Habu, Flath, et al., 1985
Habu, T.; Flath, R.A.; Mon, T.R.; Morton, J.F., Volatile components of Rooibos tea (Aspalathus linearis), J. Agric. Food Chem., 1985, 33, 2, 249-254, https://doi.org/10.1021/jf00062a024 . [all data]

del Rosario, de Lumen, et al., 1984
del Rosario, R.; de Lumen, B.O.; Habu, T.; Flath, R.A.; Mon, T.R.; Teranishi, R., Comparison of headspace volatiles from winged beans and soybeans, J. Agric. Food Chem., 1984, 32, 5, 1011-1015, https://doi.org/10.1021/jf00125a015 . [all data]

Rotsatschakul, Visesanguan, et al., 2009
Rotsatschakul, P.; Visesanguan, W.; Smitinont, T.; Chaiseri, S., Changes in volatile compounds during fermentation of nham (Thai fermented sausage), Int. Food Res. J., 2009, 16, 391-414. [all data]

Feng and Mu, 2007
Feng, H.; Mu, L.-L., Quantitative structure-retention relationships for alkane and its derivatives based on electrotopological state index and molecular shape index, Chem. Ind. Engineering (Chinese), 2007, 24, 2, 161-168. [all data]

Thierry, Maillard, et al., 2005
Thierry, A.; Maillard, M.-B.; Bonnarme, P.; Roussel, E., The addition of Propionibacterium freudenreichii to raclette cheese induces biochemical changes and enhances flavor development, J. Agric. Food Chem., 2005, 53, 10, 4157-4165, https://doi.org/10.1021/jf0481195 . [all data]

Junkes, Amboni, et al., 2004
Junkes, B.S.; Amboni, R.D.M.C.; Yunes, R.A.; Heinzen, V.E.F., Application of the semi-empirical topological index in quantitative structure-chromatographic retention relationship (QSRR) studies of aliphatic ketones and aldehydes on stationary phases of different polarity, J. Braz. Chem. Soc., 2004, 15, 2, 183-189, https://doi.org/10.1590/S0103-50532004000200005 . [all data]

Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F., Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies, Internet Electronic Journal of Molecular Design, 2003, 2, 1, 33-49. [all data]

Estrada and Gutierrez, 1999
Estrada, E.; Gutierrez, Y., Modeling chromatographic parameters by a novel graph theoretical sub-structural approach, J. Chromatogr. A, 1999, 858, 2, 187-199, https://doi.org/10.1016/S0021-9673(99)00808-0 . [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R., Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas, Eur Commission EUR, 1994, 549-568. [all data]

Ciccioli, Brancaleoni, et al., 1993
Ciccioli, P.; Brancaleoni, E.; Cecinato, A.; Sparapani, R.; Frattoni, M., Identification and determination of biogenic and anthropogenic volatile organic compounds in forest areas of Northern and Southern Europe and a remote site of the Himalaya region by high-resolution gas chromatography-mass spectrometry, J. Chromatogr., 1993, 643, 1-2, 55-69, https://doi.org/10.1016/0021-9673(93)80541-F . [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

P'yanova, Zvereva, et al., 1987
P'yanova, V.P.; Zvereva, M.N.; Tsypysheva, LG.; Portnova, T.V.; Kruglov, E.A., Investigating the products of thiophane synthesis, Abstr. IX All-Union Conference on Gas Chromatography, Kuibyshev State University, Kuibyshev, 1987, 308. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Choi, 2004
Choi, H.-S., Aroma evaluation of an aquatic herb, changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME, J. Agric. Food Chem., 2004, 52, 26, 8099-8104, https://doi.org/10.1021/jf040239p . [all data]

Tanaka, Yamauchi, et al., 2003
Tanaka, T.; Yamauchi, T.; Katsumata, R.; Kiuchi, K., Comparison of volatile components in commercial Itohiki-Natto by solid phase microextraction and gas chromatography, Nippon Shokuhin Kagaku Kogaku Kaishi, 2003, 50, 6, 278-285, https://doi.org/10.3136/nskkk.50.278 . [all data]

Girard and Durance, 2000
Girard, B.; Durance, T., Headspace volatiles of sockeye and pink salmon as affected by retort process, Food Chem. Toxicol., 2000, 65, 1, 34-39. [all data]

Hwan and Chou, 1999
Hwan, C.-H.; Chou, C.-C., Volatile components of the Chinese fermented soya bean curd as affected by the addition of ethanol in ageing solution, J. Sci. Food Agric., 1999, 79, 2, 243-248, https://doi.org/10.1002/(SICI)1097-0010(199902)79:2<243::AID-JSFA179>3.0.CO;2-I . [all data]

Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F., Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS), J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x . [all data]

Gyawalia, Seo, et al., 2006
Gyawalia, R.; Seo, H.-Y.; Lee, H.-J.; Song, H.-P.; Kim, D.-H.; Byun, M.-W.; Kim, K.-S., Effect of γ-irradiation on volatile compounds of dried Welsh onion (Allium fistulosum L.), Radiat. Phys. Chem., 2006, 75, 2, 322-328, https://doi.org/10.1016/j.radphyschem.2005.07.001 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.