Pinacolone

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]

Pinacolone
Names
IUPAC name
3,3-Dimethyl-2-butanone
Other names
t-Butyl methyl ketone
1,1,1-Trimethylacetone
Identifiers
3D model (JSmol)
1209331
ChemSpider
ECHA InfoCard 100.000.838
EC Number
  • 200-920-4
MeSH Pinacolone
RTECS number
  • EL7700000
UNII
UN number 1224
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance Colorless liquid
Density 0.801 g cm−3
Melting point −52[1] °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
Safety data sheet External MSDS
F Xn
R-phrases (outdated) R11, R22
S-phrases (outdated) S9, S16, S29, S33
NFPA 704 (fire diamond)
Flammability code 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. propaneHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Flash point 5 °C (41 °F; 278 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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
gollark: Not exactly.
gollark: No.
gollark: They're like oranges in a spacesuit.
gollark: "Easy things are also often pretty hard"
gollark: Technically, that's not natural numbers but integers.

See also

References
  1. "Pinacolone | C6H12O | ChemSpider".
  2. Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 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.; Collective Volume, 1, p. 462
  5. Siegel, H; Eggersdorfer (2012). Ketones. Ullman's Encyclopedia of Chemistry. 5. 20. doi:10.1002/14356007.a15_077. ISBN 9783527306732.
  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.
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