Pinacolone
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| 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) |
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| 1209331 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.000.838 | ||
| EC Number |
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| MeSH | Pinacolone | ||
PubChem CID |
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| RTECS number |
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| UNII | |||
| UN number | 1224 | ||
CompTox Dashboard (EPA) |
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| 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 | |||
| GHS labelling: | |||
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| 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) | |||
| 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).
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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.[2] It is also a controlled export in Australia Group member states.[3]
Preparation
[edit]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]
Isoamylene is another starting point for the synthesis of pinacolone.[6]
Uses
[edit]Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides. Some derivatives include:
- Tebuconazole aka Elite®.
- Vibunazole[7] & Bay-i 19139 [55362-18-0].
- It is also used to prepare pinacidil, as well as naminidil.
- Stiripentol[8][9]
- Tribuzone[10]
- Pivaloylacetonitrile is used in the synthesis of Doramapimod.[11]
- Triadimefon[12] & Triadimenol[13] & Nexinhib 20.
- Bitertanol[13]
- Paclobutrazol & Diclobutrazole
- Valconazole
- Thiofanox
- Metribuzin.
See also
[edit]References
[edit]- ↑ "Pinacolone | C6H12O | ChemSpider".
- ↑ Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 24 August 2007. ISBN 9780849314346.
- ↑ "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; Collected Volumes, vol. 1, p. 462.
- ↑ Siegel, Hardo; Eggersdorfer, Manfred (2012). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. 5. Vol. 20. doi:10.1002/14356007.a15_077. ISBN 9783527306732.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Astoin, J. et al, Eur. J. Med. Chem.-Chim. Ther., 1978, 13, 41.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- 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.