Acetoacetanilide

Acetoacetanilide

Names
Other names Acetoacetylaminobenzene
Identifiers
CAS Number	102-01-2
3D model (Jmol)	Interactive image
ChemSpider	7311
ECHA InfoCard	100.002.725
PubChem	7592
InChI InChI=1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13) Key: DYRDKSSFIWVSNM-UHFFFAOYSA-N InChI=1/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13) Key: DYRDKSSFIWVSNM-UHFFFAOYAR
SMILES CC(=O)CC(=O)NC1=CC=CC=C1
Properties
Chemical 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 otherwise noted, 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.

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]

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