pinacolone
Sign in to saveAlso known as 3,3-dimethylbutan-2-one
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. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. 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
Wikidata facts
- Mass
- 100.089
Show 6 more facts
- chemical formula
- C₆H₁₂O
- canonical SMILES
- CC(=O)C(C)(C)C
- melting point
- -52.5
- Commons category
- Pinacolone
- boiling point
- 106.1
- ionization energy
- 9.11
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Article
4 sectionsContents
- Preparation
- Uses
- See also
- References
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. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. 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. It is also a controlled export in Australia Group member states.
==Preparation== 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). 580px