Acetoacetanilide

Acetoacetanilide is an organic compound with the formula CH3C(O)CH2C(O)NHC6H5. It is the acetoacetamide derivative of aniline. It is a white solid that is poorly soluble in water. It and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows.

Acetoacetanilide
Names
Preferred IUPAC name
3-Oxo-N-phenylbutanamide
Other names
Acetoacetylaminobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.725
EC Number
  • 202-996-4
UNII
Properties
C10H11NO2
Molar mass 177.203 g·mol−1
Appearance Colourless solid
Melting point 83 to 88 °C (181 to 190 °F; 356 to 361 K)
low
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H302, H312, H332, H373
P260, P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P314, P322, P330, P363, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity (yellow): no hazard code
1
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation and reactions

Acetoacetanilide is prepared by acetoacetylation of aniline using diketene.

To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".[1]

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See also

References
  1. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
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