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538329

Sigma-Aldrich

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

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About This Item

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

vapor density

6.1 (vs air)

Assay

≥99.5%

autoignition temp.

843 °F

mp

83-88 °C (lit.)

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

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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Synthesis and characterisation of Cu (II), Ni (II), Mn (II), Zn (II) and VO (II) Schiff base complexes derived fromo-phenylenediamine and acetoacetanilide
Raman N, et al.
Journal of Chemical Sciences (Bangalore), 113.3 , 183-189 (2001)
Effect of swift heavy ion (SHI) irradiation on dielectric properties of acetoacetanilide crystals
Prabhu SG, et al.
Nuclear Instruments & Methods in Physics Research. Section B, Beam Interactions With Materials and Atoms null
On the kinetics and initiation mechanism of acrylamide polymerization using the ceric ion/acetoacetanilide system as initiator
Dong JH, et al.
Macromolecular Chemistry and Physics, 195.3, 823-831 (1994)
Synthesis, spectral, redox and antimicrobial activities of Schiff base complexes derived from 1-phenyl-2, 3-dimethyl-4-aminopyrazol-5-one and acetoacetanilide
Raman N, et al.
Transition Metal Chemistry, 26.1-2, 131-135 (2001)
Formation of 6-aryl-2-methyl-4-oxo-N, N?-diphenyl-2-cyclohexene-1, 3-dicarboxamides from acetoacetanilide and aromatic aldehydes catalyzed by a mixture of aryl amines and iodine
Gein VL, et al.
Russ. J. Gen. Chem., 86.1, 58-61 (2016)
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