2,4-Pentanedione

• Catalog No.: A14117
• CAS Number: 123-54-6
• M. F.: C5H8O2
• M. W.: 100.11582
• Purity: 99%

SYNONYMS

• Title: 2,4-戊烷二酮
• IUPAC name: pentane-2,4-dione
• IUPAC Traditional name: acetylacetone
• Synonyms: Acetylacetone; AcAc

DATABASE IDS

• MDL Number: MFCD00008787
• EC Number: 204-634-0
• Beilstein Number: 741937
• CAS Number: 123-54-6
• Merck Index: 1481

PROPERTIES

• Purity: 99%
• Boiling Point: 140-141°C
• Density: 0.973
• Flash Point: 34°C(93°F)
• Melting Point: -23°C
• Refractive Index: 1.4520
• GHS Hazard statements: H226-H302
• European Hazard Symbols: X
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Risk Statements: 10-22
• RTECS: SA1925000
• Safety Statements: 21-23-24/25
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN2310
• Packing Group: III

REFERENCES

• 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).