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2,4-Pentanedione is used as a precursor to acetylacetonate, a common bidentate and a raw material for the synthesis of heterocyclic compounds. It is used in pharmaceuticals, organic intermediates for solvents, analytical reagents, tungsten and molybdenum in aluminum extraction agent.
A simple procedure for the synthesis of methyl ketones involves alkylation at the 3-position with an alkyl halide using K2CO3 in EtOH, with in situ acetyl cleavage: Org. Synth. Coll., 5, 767 (1973). Knoevenagel condensation with aldehydes in THF in the presence of K2CO3 also occurs with acetyl cleavage, providing a simple route to alkenyl ketones: Chem. Lett., 1325 (1978). With K2CO3 and TBAB, selective one-pot monoalkylation or dialkylation with different alkyl groups can be achieved: Synthesis, 688 (1989). 3-Arylation with aryl bromides takes place in the presence of Cu(I) or Cu(II) salts in DMF: Chem. Lett., 597 (1982); Org. Synth. Coll., 6, 36 (1988).
Strong bases, e.g. NaNH2, form the dianion which reacts with electrophiles, e.g. alkyl halides, esters, acyl halides, Michael acceptors, etc., at the less-stabilized terminal carbon: J. Org. Chem., 26, 1716 (1961); Tetrahedron Lett., 357 (1970); J. Org. Chem., 39, 2289 (1974); Org. Synth. Coll., 5, 848 (1973). For arylation at the 1-position, see Diphenyliodonium chloride, A15149. For reviews of dimetallation, see: Org. React., 17, 155 (1969); Synthesis, 509 (1977)./n
Freeman, F. Mechanisms of Reactions of Sulfur Hydride Hydroxide: Tautomerism, Condensations, and C-Sulfenylation and O-Sulfenylation of 2,4-Pentanedione. J. Phys. Chem. A 2015, 119 (14), 3500-3517.
Freeman, F. Mechanisms of Reactions of Sulfur Hydride Hydroxide: Tautomerism, Condensations, and C-Sulfenylation and O-Sulfenylation of 2, 4-Pentanedione. J. Phys. Chem. A 2015, 199 (14), 3500-3517.
Hazard Statements: H226-H302-H311-H331
Flammable liquid and vapour. Harmful if swallowed. Toxic in contact with skin. Toxic if inhaled.
Precautionary Statements: P210-P261-P280-P303+P361+P353-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.