2-Butanone, 3,3-dimethyl-

• Formula: C₆H₁₂O
• Molecular weight: 100.1589
• IUPAC Standard InChI: InChI=1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 Copy

  
• IUPAC Standard InChIKey: PJGSXYOJTGTZAV-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-97-8
• 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: tert-Butyl methyl ketone; Methyl tert-butyl ketone; Pinacolin; Pinacoline; Pinacolone; 2,2-Dimethyl-3-butanone; 2,2-Dimethylbutanone; 3,3-Dimethyl-2-butanone; 3,3-Dimethylbutanone; tert-C4H9COCH3; Ketone, tert-butyl methyl; 1,1,1-Trimethylacetone; t-Butyl methyl ketone; Ketone, t-butyl methyl; Methyl t-butyl ketone; Pinakolin; 1,1-Dimethylethyl methyl ketone; 3,3-Dimethyl-butan-2-one; NSC 935
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

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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

Condensed phase thermochemistry data

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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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

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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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

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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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₆H₁₁O^- +  =

By formula: C₆H₁₁O^- + H⁺ = C₆H₁₂O

 +  = 2 + 

By formula: C₈H₁₈O₂ + H₂O = 2CH₄O + C₆H₁₂O

IR Spectrum

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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

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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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

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

von Geiseler G., 1973
von Geiseler G., The heat capacity and the heat of vaporization of isomeric butylmethylketones and propylacetates, Z. Phys. Chem. (Leipzig), 1973, 252, 170-176. [all data]

Andon, Counsell, et al., 1970
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part XXIII. Low-temperature heat capacity and entropy of C₆, C₇, and C9 ketones, 1970, J. [all data]

Vorontsova and Vlasov, 1987
Vorontsova, N.A.; Vlasov, O.N., Determination of saturated vapor pressure of Bayletone and its semiproducts, Deposited Doc. ONIITEkhim Cherkassy, 1987, Doc. No. 1423 khp - 87, 1987. [all data]

Hill and Kropa, 1933
Hill, G.A.; Kropa, E.L., Some Halogented Pinacalones, J. Am. Chem. Soc., 1933, 55, 2509. [all data]

Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F., Freezing points of orgainic substances VI. New experimental determinations., Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]

Andon, Counsell, et al., 1970, 2
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F., Thermodynamic Properties of Organic Oxygen Compounds Part XXIII. Low- temperature Heat Capacity and Entropy of C6, C7, and C9 Ketones, J. Chem. Soc. A, 1970, 1970, 833. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Lees, E.B.; Sprake, C.H.S.; Townsend, R., Thermodynamic properties of organic oxygen compounds XXXVIII. Vapour pressures of some aliphatic ketones, The Journal of Chemical Thermodynamics, 1975, 7, 5, 453-472, https://doi.org/10.1016/0021-9614(75)90275-X . [all data]

Svoboda, Kubes, et al., 1992
Svoboda, V.; Kubes, V.; Basarova, P., Enthalpies of vaporization and cohesive energies of hexan-2-one, 2-methylpentan-4-one, 2,2-dimethylbutan-3-one, 2,6-dimethylheptan-4-one and cyclohexanone, J. Chem. Thermodynam., 1992, 24, 333-336. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Geiseler, Quitzsch, et al., 1973
Geiseler, G.; Quitzsch, K.; Hofmann, H.-P.; Pfestorf, R.Z., Z. Phys. Chem. (Leipzig), 1973, 252, 170. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects, J. Am. Chem. Soc., 1979, 101, 5512-5515. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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