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
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• Information on this page:
  • Normal boiling point
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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Normal boiling point

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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

References

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

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]

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

Grove and Walden, 1965
Grove, E.L.; Walden, G.E., Variation of Dielectric Constant with Temperature for SOme Five- and Six-Carbon Ketones, J. Chem. Eng. Data, 1965, 10, 98. [all data]

Wright, 1961
Wright, F.J., Influence of temperature on viscosity of nonassociated liquids, J. Chem. Eng. Data, 1961, 6, 454. [all data]

Wright, 1960
Wright, F.J., Latent Heat of Vaporization and Composition, Recl. Trav. Chim. Pays-Bas, 1960, 79, 784-9. [all data]

Foley, Welch, et al., 1959
Foley, W.M.; Welch, F.J.; La Combe, E.; Mosher, H.S., Asymmetric reductions: vi the action of the grignard reagent from (+)-1- chloro-2-methylbutane on a series of alkyl t-butyl ketones, J. Am. Chem. Soc., 1959, 81, 2779. [all data]

Fitzpatrick and Gettler, 1956
Fitzpatrick, F.W.; Gettler, J.D., J. Am. Chem. Soc., 1956, 78, 530. [all data]

Brewster, Patterson, et al., 1954
Brewster, J.H.; Patterson, J.W.; Fidler, D.A., Reductions at Metal Surfaces III. Clemensen Reduction of Some Sterically- hindered Ketones, J. Am. Chem. Soc., 1954, 76, 6368. [all data]

Hickinbottom and Hogg, 1954
Hickinbottom, W.J.; Hogg, D.R., Reaction of Epoxides with Carboxylic Acids, J. Chem. Soc., 1954, 1954, 4200. [all data]

Cook, 1952
Cook, N.C., , Unpublished, Final Rep. Stand. Proj. on Oxygenated Compounds, Penn. State Univ., College Park, PA, 1952. [all data]

Bridson-Jones and Buckley, 1951
Bridson-Jones, F.S.; Buckley, G.D., Oxidation of organic compounds by nitrous oxide: II tri- and tetra- substituted ethylenes, J. Chem. Soc., 1951, 1951, 3009. [all data]

Elderfield and McCarthy, 1951
Elderfield, R.C.; McCarthy, J.R., The reaction of o-phenylenediamines with carbonyl compounds: II aliphatic ketones, J. Am. Chem. Soc., 1951, 73, 975. [all data]

Miller, Cook, et al., 1950
Miller, A.L.; Cook, N.C.; Whitmore, F.C., The Ketonic Decarboxylation Reaction: The Ketonic Decarboxylation of Trimethylacetic Acid and Isobutyric Acid, J. Am. Chem. Soc., 1950, 72, 2732. [all data]

Lecat, 1949
Lecat, M., Tables Azeotropiques, Vol. 1, 10th ed., Brussels, Belgium, 1949. [all data]

Pomerantz, Mears, et al., 1949
Pomerantz, P.; Mears, T.W.; Howard, F.L., Separation and Identification of the Major C1 to C10 Components of Triptene Residue, J. Res. Natl. Bur. Stand. (U. S.), 1949, 42, 617-32. [all data]

Newman and Smith, 1948
Newman, M.S.; Smith, A.S., J. Org. Chem., 1948, 13, 592. [all data]

Lecat, 1947
Lecat, M., Some azeotropes of which one constituant is heterocyclic nitrogen, Ann. Soc. Sci. Bruxelles, Ser. 1, 1947, 61, 73. [all data]

Rabjohn and Rogier, 1946
Rabjohn, N.; Rogier, E.R., The vapor-phase chlorination of aliphatic ketones, J. Org. Chem., 1946, 11, 781. [all data]

George, 1943
George, R.S., , Ph.D. Thesis, Penn. State Univ., Univ. Park, 1943. [all data]

Allen and Bell, 1942
Allen, C.F.H.; Bell, A., Org. Synth., 1942, 22, 39. [all data]

Ginnings, Plonk, et al., 1940
Ginnings, P.M.; Plonk, D.; Carter, E., Aqueous Solubilities of Some Aliphatic Ketones, J. Am. Chem. Soc., 1940, 62, 1923-1924. [all data]

Whitmore, 1938
Whitmore, F.C., The Reducing Action of Grignard Reagents on Acyl Chlorides, Recl. Trav. Chim. Pays-Bas, 1938, 57, 562. [all data]

Maess and von Muffling, 1937
Maess, L.; von Muffling, L., On the Vapor Pressures of Hydrocarbons and Ketones, Angew. Chem., 1937, 50, 759. [all data]

Gilman and Nelson, 1936
Gilman, H.; Nelson, J.F., Recl. Trav. Chim. Pays-Bas, 1936, 55, 518. [all data]

Kohlraush and Koppl, 1934
Kohlraush, K.W.F.; Koppl, F., Z. Phys. Chem., Abt. B, 1934, 24, 370. [all data]

Sprague and Adkins, 1934
Sprague, J.M.; Adkins, H., Hydrogenation and Hydrogenolysis of 1,3-Diketones., J. Am. Chem. Soc., 1934, 56, 2669. [all data]

Pfeiffer and Adkins, 1931
Pfeiffer, G.J.; Adkins, H., The Relation of the Structure of Ketones to Their Reactivity and Affinity in Acetal Formation II., J. Am. Chem. Soc., 1931, 53, 1043. [all data]

Lecat, 1930
Lecat, M., Azeotropism in Binary Mixtures Containing an Alcohol Mixed with an amine, a nitro derivative, an ether or water., Z. Anorg. Allg. Chem., 1930, 186, 119. [all data]

Carswell and Adkins, 1928
Carswell, H.E.; Adkins, H., The Relation of the Structure of Ketones to their Reactivity and Affinity in Acetal Formation, J. Am. Chem. Soc., 1928, 50, 235. [all data]

Hill and Flosdorf, 1925
Hill; Flosdorf, Org. Synth., 1925, 5, 91. [all data]

Michael, 1919
Michael, A., J. Am. Chem. Soc., 1919, 41, 393. [all data]

Henderson, Henderson, et al., 1914
Henderson, G.G.; Henderson, J.A.R.; Heilbron, I.M., Chem. Ber., 1914, 47, 876. [all data]

Delange, 1908
Delange, Solubility and reactions of pinacolin, Bull. Soc. Chim. Fr., 1908, 3, 910. [all data]

Courtot, 1906
Courtot, A., Bull. Soc. Chim. Fr., 1906, 35, 969. [all data]

Butterow, 1874
Butterow, A., Justus Liebigs Ann. Chem., 1874, 174, 125. [all data]

Fittig, 1860
Fittig, R., Justus Liebigs Ann. Chem., 1860, 114, 54. [all data]

Notes

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• Symbols used in this document:
  

  Tboil

  Boiling point

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