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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
Chemical data
- Formula
- C6H12O
- Molecular weight
- 100.16 g/mol
- IUPAC name
- 3,3-dimethylbutan-2-one
- SMILES
- CC(=O)C(C)(C)C
- InChIKey
- PJGSXYOJTGTZAV-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
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
Excerpted from Wikipedia’s “pinacolone” article, available under the CC BY-SA 4.0 licence.