Methyl vinyl ketone

Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2.

Similarly it is prepared by the Mannich reaction involving diethylammonium chloride and acetone, which produces the Mannich adduct:[2][3] Heating this ammonium salt releases the ammonium chloride and the MVK:[3] MVK can act as an alkylating agent because it is an effective Michael acceptor.

It gained early attention for its use in the Robinson annulation, a method useful in the preparation of steroids: Its alkylating ability is both the source of its high toxicity and the feature that makes it a useful intermediate in organic synthesis.

[2] MVK is an intermediate in the synthesis of some pharmaceutical drugs including etorphine, buprenorphine, tolquinzole, butaclamol, and etretinate.

MVK is extremely hazardous upon inhalation causing coughing, wheezing and shortness of breath even at low concentrations.

Skeletal formula of methyl vinyl ketone
Ball-and-stick model of the methyl vinyl ketone molecule
NFPA 704 four-colored diamond Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorus Special hazards (white): no code
Robinson annulation reaction
Robinson annulation reaction
Vinclozolin is a commercial fungicide prepared using MVK.