Acetoacetanilide

Title: Acetoacetanilide
CAS Registry Number: 102-01-2
CAS Name: 3-Oxo-N-phenylbutanamide
Additional Names: a-acetylacetanilide; acetoacetic anilide; b-ketobutyranilide
Molecular Formula: C10H11NO2
Molecular Weight: 177.20
Percent Composition: C 67.78%, H 6.26%, N 7.90%, O 18.06%
Line Formula: C6H5NHCOCH2COCH3
Literature References: Prepd by the reaction of ketene dimer with aniline: Chick, Wilsmore, J. Chem. Soc. 1908, 946; Boese, Ind. Eng. Chem. 32, 16 (1940); Williams, Krynitsky, Org. Synth. coll. vol. III, 10 (1955). By the reaction of aniline with ethyl acetoacetate: Knorr, Ann. 26, 69 (1886); Roos, Ber. 21, 624 (1883); Knorr, Reuter, Ber. 27, 1169 (1894). Enol form (unstable) prepd by pouring an alkaline soln of the keto form in cold, dilute H2SO4.
Derivative Type: Ketone Form
Properties: Leaflets from dilute alcohol, mp 85°. Slightly soluble in water; sol in alcohol, chloroform, ether, hot benzene, hot petr ether, acids, or alkali hydroxide solns. Gives a violet color with ferric chloride.
Melting point: mp 85°
Use: Manuf of yellow dyes, such as Hansa and benzidine yellows. In rubber compounding. In organic syntheses.
Acetoacetic Acid Acetobromglucose Acetochlor Acetohexamide Acetohydroxamic Acid

Acetoacetanilide
Acetoacetanilide.png
Identifiers
CAS number 102-01-2 YesY
PubChem 7592
ChemSpider 7311
Jmol-3D images Image 1
Properties
Molecular formula C10H11NO2
Molar mass 177.20 g mol−1
Appearance Colourless solid
Melting point 83 to 88 °C; 181 to 190 °F; 356 to 361 K
Solubility in water low
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.