1-phenylbutane-1,3-dione

• ChemBase ID: 76265
• Molecular Formular: C10H10O2
• Molecular Mass: 162.1852
• Monoisotopic Mass: 162.06807956
• SMILES: O=C(c1ccccc1)CC(=O)C
• Canonical SMILES: O=C(c1ccccc1)CC(=O)C
• InChI: InChI=1S/C10H10O2/c1-8(11)7-10(12)9-5-3-2-4-6-9/h2-6H,7H2,1H3
• InChIKey: CVBUKMMMRLOKQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-phenylbutane-1,3-dione
• IUPAC Traditional name: 1,3-butanedione, 1-phenyl-
• Synonyms: 1-phenylbutane-1,3-dione; Benzoylacetone; 1-Phenyl-1,3-butanedione; 1-Phenylbutane-1,3-dione; Benzoylacetone; omega-ACETYLACETOPHENONE; 1-Phenyl-1,3-butanedione; 1-BENZOYLACETONE; Benzoylacetone; 苯甲酰丙酮; 1-苯基-1,3-丁二酮; 苯甲酰丙酮

Database IDs

• CAS Number: 93-91-4
• EC Number: 202-286-4
• MDL Number: MFCD00008786
• Beilstein Number: 742413
• PubChem SID: 162041172; 24891568; 24847841
• PubChem CID: 7166

CALCULATED PROPERTIES

• Acid pKa: 9.147291
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7526495
• LogD (pH = 7.4): 1.7450498
• Log P: 1.7527473
• Molar Refractivity: 46.356 cm^3
• Polarizability: 17.815502 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-56 °C; 54-56 °C(lit.); 54-56°C; 55-60°C
• Boiling Point: 260-262°C
• Density: 1.09 g/mL at 25 °C(lit.); 1.090

Safety Information

• Storage Warning: Irritant
• RTECS: EK3540200
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (GC); 98+%; 99%
• Grade: purum
• Linear Formula: C6H5COCH2COCH3

DETAILS

MP Biomedicals - 02150442

Used with a benzhydryl resin and the N-(2-benzoyl-1-methylvinyl) protecting group for solid phase synthesis under mild conditions.

MP Biomedicals - 05204464

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B11907

Packaging
10, 50, 250 g in poly bottle

REFERENCES

• Dimetallated derivatives react with electrophiles preferentially at the terminal position; e.g. arylation by 2-chloroquinoline: J. Org. Chem., 37, 3199 (1972); J. Am. Chem. Soc., 97, 374 (1975). Reaction with aromatic esters gives 1,3-diaryl-1,3,5-pentanetriones, which can be cyclized with acid to -pyrones: Org. Synth. Coll., 5, 718, 721 (1973):