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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:
Molecular Weight:
177.20
Beilstein:
473419
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

6.1 (vs air)

Quality Level

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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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
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)
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 and photoluminescent properties of lanthanides acetoacetanilide complexes
Souza, E. R., et al.
Journal of Fluorescence, 23.5, 939-946 (2013)
Crystal structures of azo pigments derived from acetoacetanilide
Whitaker, A.
Journal of the Society of Dyers and Colourists, 104.7-8 , 294-300 (1988)

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