t-Butyl methyl ketone
3D model (JSmol)
|Molar mass||100.16 g·mol−1|
|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)|
|Safety data sheet||External MSDS|
|R-phrases (outdated)||R11, R22|
|S-phrases (outdated)||S9, S16, S29, S33|
|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).
|what is ?)(|
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. It is also a controlled export in Australia Group member states.
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.
Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides.
- retrosynthetic analysis of vibunazole showed that it was derived from pinacolone.
- It is also used to prepare pinacidil, as well as naminidil.
- Pivaloylacetonitrile is used in the synthesis of Doramapimod.
- Diethylstilbestrol pinacolone [18922-13-9].
- Some kind of BPA derivative also U.S. Patent 4,599,463
- "Pinacolone | C6H12O | ChemSpider".
- "Export Control List: Chemical Weapons Precursors". Australia Group. australiagroup.net. Retrieved 7 April 2017.
- G. A. Hill and E. W. Flosdorf (1941). "Pinacolone". Organic Syntheses.; Collective Volume, 1, p. 462
- Siegel, H; Eggersdorfer (2012). Ketones. Ullman's Encyclopedia of Chemistry. 5. 20. doi:10.1002/14356007.a15_077. ISBN 9783527306732.
- 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. PMID 8401407.