Pinacolone

Pinacolone

Pinacolone

Chemical compound

Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid and has a slight peppermint- or camphor- odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. The molecule is an unsymmetrical 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.[2] It is also a controlled export in Australia Group member states.[3]

Quick Facts Names, Identifiers ...

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).[4]

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.[5]

Drug Uses

Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides.

  1. retrosynthetic analysis of vibunazole showed that it was derived from pinacolone.
  2. It is also used to prepare pinacidil, as well as naminidil.
  3. Stiripentol
  4. Tribuzone
  5. Pivaloylacetonitrile is used in the synthesis of Doramapimod.
  6. Triadimefon
  7. Diclobutrazole
  8. Paclobutrazol
  9. Valconazole
  10. Diethylstilbestrol pinacolone [18922-13-9].[6]
  11. Some kind of Bisphenol A derivative also U.S. patent 4,599,463
  12. Thiofanox

See also

References

  1. [1]
    "Pinacolone | C6H12O | ChemSpider".
  2. [2]
    Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 24 August 2007. ISBN 9780849314346.
  3. [3]
    "Export Control List: Chemical Weapons Precursors". Australia Group. australiagroup.net. Retrieved 7 April 2017.
  4. [4]
    G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses; Collected Volumes, vol. 1, p. 462.
  5. [5]
    Siegel, H; Eggersdorfer (2012). Ketones. 5. Vol. 20. doi:10.1002/14356007.a15_077. ISBN 9783527306732. {{cite book}}: |journal= ignored (help)
  6. [6]
    Oda, T; Sato, Y; Kodama, M; Kaneko, M (July 1993). "Inhibition of DNA topoisomerase I activity by diethylstilbestrol and its analogues". Biological & Pharmaceutical Bulletin. 16 (7): 708–10. doi:10.1248/bpb.16.708. PMID 8401407.
Share this article:

This article uses material from the Wikipedia article Pinacolone, and is written by contributors. Text is available under a CC BY-SA 4.0 International License; additional terms may apply. Images, videos and audio are available under their respective licenses.