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.
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Preferred IUPAC name
3-Oxo-N-phenylbutanamide | |
Other names
Acetoacetylaminobenzene | |
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ChemSpider | |
ECHA InfoCard | 100.002.725 |
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CompTox Dashboard (EPA) |
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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) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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]
See also
References
- 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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