Pinacolone

Pinacolone is an organic ketone with the molecular formula C6H12O. It is commonly known as tert-butyl methyl ketone and also named 3,3-dimethyl-2-butanone. In structure, it consists of a carbonyl group bonded to a methyl group on one side and a tert-butyl group on the other, giving the formula CH3-CO-C(CH3)3. It is typically a colorless liquid at room temperature and is soluble in many organic solvents, with limited miscibility in water.

The compound’s name and structure reflect its origin in the pinacol rearrangement. Pinacolone is the principal product of acid-catalyzed rearrangement of pinacol (2,3-dimethyl-2,3-butanediol). Under acidic conditions, pinacol undergoes protonation, dehydration, and a hydride shift to yield pinacolone.

Industrial and laboratory significance centers on pinacolone as a versatile synthetic intermediate. It is used in the preparation of various organic compounds, including fragrances and pharmaceutical intermediates. As a relatively simple, highly reactive ketone, it participates in nucleophilic additions and other standard ketone reactions, enabling diverse downstream syntheses.

Safety and handling considerations for pinacolone include its classification as a flammable liquid and its potential to cause irritation to skin, eyes, and the respiratory tract. It should be handled in a well-ventilated area, with appropriate personal protective equipment, and kept away from heat sources and oxidizers. Storage is typically in tightly closed containers under appropriate laboratory or industrial guidelines.

See also: Pinacol rearrangement, tert-butyl methyl ketone.