Pinacolone

Pinacolone
Skeletal formula of pinacolone
Skeletal formula of pinacolone
Names
Preferred IUPAC name
3,3-Dimethylbutan-2-one
Other names
t-Butyl methyl ketone
1,1,1-Trimethylacetone
t-BuAc
Identifiers
3D model (JSmol)
1209331
ChEBI
ChemSpider
ECHA InfoCard 100.000.838 Edit this at Wikidata
EC Number
  • 200-920-4
MeSH Pinacolone
RTECS number
  • EL7700000
UNII
UN number 1224
  • InChI=1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 checkY
    Key: PJGSXYOJTGTZAV-UHFFFAOYSA-N checkY
  • CC(=O)C(C)(C)C
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance Colorless liquid
Density 0.801 g cm−3
Melting point −52 °C (−62 °F; 221 K)
Boiling point 103 to 106 °C (217 to 223 °F; 376 to 379 K)
−69.86·10−6 cm3/mol
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H302, H315, H319, H332, H335, H412
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
4
0
Flash point 5 °C (41 °F; 278 K)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid with a slight peppermint or camphor odor. The molecule is an asymmetrical ketone. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions (hydrogenation, reductive amination, etc.). It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to pinacolyl alcohol, which is used in the production of soman. It is also a controlled export in Australia Group member states.

Preparation

Most famously, at least in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol).

Industrially, pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-dioxane, which is the product of isoprene and formaldehyde via the Prins reaction. It also is generated by ketonization of pivalic acid and acetic acid or acetone over metal oxide catalysts. 3-Methylbutanal is a starting material for 2,3-dimethyl-2-butene, which in turn is converted to pinacolone. Pinacolone can also be produced from 2-methy-2-butanol when reacted with C5 alcohols.

Isoamylene is another starting point for the synthesis of pinacolone.

Uses

Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides. Some derivatives include:

See also

References

  1. ↑ "Pinacolone | C6H12O | ChemSpider".
  2. ↑ Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 24 August 2007. ISBN 9780849314346.
  3. ↑ "Export Control List: Chemical Weapons Precursors". Australia Group. australiagroup.net. Retrieved 7 April 2017.
  4. ↑ G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses; Collected Volumes, vol. 1, p. 462.
  5. ↑ Siegel, Hardo; Eggersdorfer, Manfred (2012). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. 5. Vol. 20. doi:10.1002/14356007.a15_077. ISBN 9783527306732.
  6. ↑ Gao, Z., Tian, Y., Liu, P., Jiang, L., Gao, L., Du, L., Zhu, J. (21 June 2023). "Scale-Up of Synthesizing 3,3-Dimethyl-2-butyl Ketone (Pinacolone) from 2-Methyl-2-butene (β-Isoamylene) and Its Kinetic Study". Industrial & Engineering Chemistry Research. 62 (24): 9453–9462. doi:10.1021/acs.iecr.3c00908.
  7. ↑ Castañer, J., Fromtling, R. A. (1984). "BAY-N-7133". Drugs of the Future. 9 (6): 404. doi:10.1358/dof.1984.009.06.67103. ISSN 0377-8282. Retrieved 27 August 2026.
  8. ↑ Castañer, J., Hillier, K. (1980). "Stiripentol". Drugs of the Future. 5 (8): 413. doi:10.1358/dof.1980.005.08.70107. ISSN 0377-8282. Retrieved 27 August 2026.
  9. ↑ Astoin, J. et al, Eur. J. Med. Chem.-Chim. Ther., 1978, 13, 41.
  10. ↑ Fišnerová, L., Němeček, O., Musil, V. (1968). "Über ein neues Darstellungsverfahren von 1,2-Diphenyl-3,5-dioxypyrazolidin-, 1,3-Dimethyl- und 1,3-Diphenylbarbitursäure-Derivaten". Collection of Czechoslovak Chemical Communications. 33 (8): 2681–2689. doi:10.1135/cccc19682681. Retrieved 27 August 2026.
  11. ↑ Regan, J., Breitfelder, S., Cirillo, P., Gilmore, T., Graham, A. G., Hickey, E., Klaus, B., Madwed, J., Moriak, M., Moss, N., Pargellis, C., Pav, S., Proto, A., Swinamer, A., Tong, L., Torcellini, C. (1 July 2002). "Pyrazole Urea-Based Inhibitors of p38 MAP Kinase: From Lead Compound to Clinical Candidate". Journal of Medicinal Chemistry. 45 (14): 2994–3008. doi:10.1021/jm020057r. Retrieved 27 August 2026.
  12. ↑ Rouchaud, J., Meyer, J. (January 1982). "Synthesis of the fungicide [ 14 C]triadimefon". Journal of Labelled Compounds and Radiopharmaceuticals. 19 (1): 111–116. doi:10.1002/jlcr.2580190113. Retrieved 27 August 2026.
  13. 1 2 Reuther, W., Ruland, A., Baus, U. (14 March 1988). "Eine einfache Synthese von Keten‐O,N‐ und Keten‐O,O‐acetalen durch Tosylat‐Eliminierung". Liebigs Annalen der Chemie. 1988 (3): 235–240. doi:10.1002/jlac.198819880310. Retrieved 27 August 2026.