538329

Acetoacetanilide

≥99.5%

• Synonym(s): 1-(Phenylamino)-1,3-butanedione, 1-(Phenylcarbamoyl)-2-propanone, 3-Oxo-N-phenylbutanamide, 3-Oxo-N-phenylbutyramide, 4-(Phenylamino)-2,4-butanedione, Acetoacetamidobenzene
• Linear Formula: CH₃COCH₂CONHC₆H₅
• CAS Number: 102-01-2
• Molecular Weight: 177.20
• Beilstein: 473419
• EC Number: 202-996-4
• MDL number: MFCD00008780
• UNSPSC Code: 12352100
• PubChem Substance ID: 24878321
• NACRES: NA.22

Properties

• vapor density: 6.1 (vs air)
• Assay: ≥99.5%
• autoignition temp.: 843 °F
• mp: 83-88 °C (lit.)
• functional group: amide; ketone
• SMILES string: CC(=O)CC(=O)Nc1ccccc1
• InChI: 1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13)
• InChI key: DYRDKSSFIWVSNM-UHFFFAOYSA-N

Description

General description

Acetoacetanilide (N-phenyl-3-oxobutanamide) undergoes condensation reaction with o-phenylenediamine to afford a Schiff base. Dielectric constant of acetoacetanilide crystals were found to increase on exposure to 120MeV Ag¹³⁺ ions due to increase in number of defects. Acetoacetanilide/Ce⁴⁺ system serves as an initiator during the polymerization of vinyl monomers.

Application

Acetoacetanilide may be used to synthesize:

• azo pigments
• acetoacetanilido-4-aminoantipyrine (Schiff base)
• 6-aryl-2-methyl-4-oxo-N,N′-diphenyl-2-cyclohexene-1,3-dicarboxamides
• photoluminescent lanthanide complexes

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3