Names | |
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IUPAC name
3,3-Dimethyl-2-butanone
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Other names
t-Butyl methyl ketone
1,1,1-Trimethylacetone |
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Identifiers | |
75-97-8 | |
3D model (Jmol) | Interactive image |
1209331 | |
ChemSpider | 6176 |
ECHA InfoCard | 100.000.838 |
EC Number | 200-920-4 |
MeSH | Pinacolone |
PubChem | 6416 |
RTECS number | EL7700000 |
UN number | 1224 |
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Properties | |
C6H12O | |
Molar mass | 100.16 g·mol−1 |
Appearance | Colorless liquid |
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) |
-69.86·10−6 cm3/mol | |
Hazards | |
Safety data sheet | External MSDS |
EU classification (DSD)
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F Xn |
R-phrases | R11, R22 |
S-phrases | S9, S16, S29, S33 |
NFPA 704 | |
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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what is ?) | (|
Infobox references | |
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.).
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).
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.(specify which ones)
It is also used to prepare pinacidil, as well as naminidil.