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Pinacolone

1,1,1-Trimethylacetone | NFPA-H = 1 | NFPA-F = 4 | NFPA-R = 0

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. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. 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).

:[[File:800px-Pinacol rearragement.png|580px]]

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.

Uses

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

  • retrosynthetic analysis of vibunazole showed that it was derived from pinacolone.
  • It is also used to prepare pinacidil, as well as naminidil.
  • Stiripentol
  • Tribuzone
  • Pivaloylacetonitrile is used in the synthesis of Doramapimod.
  • Triadimefon
  • Diclobutrazole
  • Paclobutrazol
  • Valconazole
  • Diethylstilbestrol pinacolone [18922-13-9].
  • Some kind of Bisphenol A derivative also
  • Thiofanox

References

References

  1. "Pinacolone | C6H12O | ChemSpider".
  2. (24 August 2007). "Handbook of chemical and biological warfare agents". CRC Press.
  3. "Export Control List: Chemical Weapons Precursors". australiagroup.net.
  4. G. A. Hill and E. W. Flosdorf. (1941). "Pinacolone".
  5. (2012). "Ullmann's Encyclopedia of Industrial Chemistry".
  6. (July 1993). "Inhibition of DNA topoisomerase I activity by diethylstilbestrol and its analogues.". Biological & Pharmaceutical Bulletin.
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hexanones tert-butyl-compounds nerve-agent-precursors
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