Pinacolone (3,3-dimethyl-2-butanone) is an important ketoneinorganic 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]
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
3,3-Dimethylbutan-2-one | |||
| Other names
t-Butyl methyl ketone | |||
| Identifiers | |||
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3D model (JSmol) |
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| 1209331 | |||
| ChEBI | |||
| ChemSpider |
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| ECHA InfoCard | 100.000.838 
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| 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) | ||
| -69.86·10−6cm3/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). | |||
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 ketonizationofpivalic 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]
Pinacolone is produced in large amounts for use in fungicides, herbicides, and pesticides.
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