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Merck
CN

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

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About This Item

Linear Formula:
CH3COCH2CONHC6H5
CAS Number:
102-01-2
Molecular Weight:
177.20
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24878321
EC Number:
202-996-4
Beilstein/REAXYS Number:
473419
MDL number:
MFCD00008780

Key Documents

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Product Name

Acetoacetanilide, ≥99.5%

InChI key

DYRDKSSFIWVSNM-UHFFFAOYSA-N

InChI

1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13)

SMILES string

CC(=O)CC(=O)Nc1ccccc1

vapor density

6.1 (vs air)

assay

≥99.5%

autoignition temp.

843 °F

mp

83-88 °C (lit.)

functional group

amide
ketone

Quality Level

100

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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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN2031
MKCM7115
MKCL5325
MKCH4921
MKCG4054

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