| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name 3,3-Dimethylbutan-2-one | |||
| Other names t-Butyl methyl ketone 1,1,1-Trimethylacetone | |||
| Identifiers | |||
| |||
3D model (JSmol) | |||
| 1209331 | |||
| ChEBI | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.000.838 | ||
| EC Number |
| ||
| MeSH | Pinacolone | ||
| RTECS number |
| ||
| 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 | |||
| GHS labelling: | |||
  | |||
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Pinacolone (3,3-dimethyl-2-butanone) is an importantketone inorganic chemistry. It is a colorless liquid with a slight peppermint or camphor odor. It is a precursor totriazolylpinacolone in the synthesis of the fungicidetriadimefon and in synthesis of the herbicidemetribuzin. The molecule is an unsymmetricalketone. 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 topinacolyl alcohol, which is used in the production ofsoman.[2] It is also a controlled export inAustralia Group member states.[3]
Most famously, at least in the classroom, pinacolone arises by thepinacol rearrangement, which occurs by protonation ofpinacol (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 thePrins reaction. It also is generated byketonization ofpivalic 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. Some derivatives include:
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