Acetoacetanilide

Acetoacetanilide

Names
Other names Acetoacetylaminobenzene
Identifiers
CAS Registry Number	102-01-2 Y
ChemSpider	7311
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
Jmol-3D images	Image
PubChem	7592
SMILES CC(=O)CC(=O)NC1=CC=CC=C1
Properties
Molecular formula	C10H11NO2
Molar mass	177.20 g·mol−1
Appearance	Colourless solid
Melting point	83 °C (181 °F; 356 K)
Solubility in water	low
Except where noted otherwise, data is 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