Acetoacetanilide

Acetoacetanilide
Names
	Preferred IUPAC name 3-Oxo-N-phenylbutanamide
	Other names Acetoacetylaminobenzene
Identifiers
CAS Number	102-01-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1604429;
ChemSpider	7311;
ECHA InfoCard	100.002.725
EC Number	202-996-4;
PubChem CID	7592;
UNII	W35JB9PY3X ;
CompTox Dashboard (EPA)	DTXSID0024397 ;
	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	177.203 g·mol−1
Appearance	Colourless solid
Melting point	83 to 88 °C (181 to 190 °F; 356 to 361 K)
Solubility in water	low
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H373
Precautionary statements	P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P322, P330, P363, P501
NFPA 704 (fire diamond)	2 1 0
	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. This chemical and many related compounds (prepared from various aniline derivatives) are used in the production of organic pigments called arylide yellows. Acetoacetanilides usually exist as the keto-amide tautomer according to X-ray crystallography.^[1]

Preparation and reactions

Acetoacetanilide is prepared by acetoacetylation of aniline using diketene.^[2] Many analogues have been prepared.^[3]

To make the dyes, acetoacetanilides are coupled to diazonium salts, "azo coupling".^[4]

Acetoacetylation with diketene followed by diazo coupling.

In the presence of sulfuric acid, acetoacetanilide dehydrates to give 4-methyl-2-quinolone.^[5]

References

^ Gilli, Paola; Bertolasi, Valerio; Ferretti, Valeria; Gilli, Gastone (2000). "Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation". Journal of the American Chemical Society. 122 (42). doi:10.1021/ja000921+.
^ Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide". Organic Syntheses. 21: 4. doi:10.15227/orgsyn.021.0004.
^ Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.
^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
^ Lauer, W. M.; Kaslow, C. E. (1944). "4-Methylcarbostyril". Organic Syntheses. 24: 68. doi:10.15227/orgsyn.024.0068.

[1] Gilli, Paola; Bertolasi, Valerio; Ferretti, Valeria; Gilli, Gastone (2000). "Evidence for Intramolecular N−H···O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation". Journal of the American Chemical Society. 122 (42). doi:10.1021/ja000921+.

[2] Williams, Jonathan W.; Krynitsky, John A. (1941). "Acetoacetanilide". Organic Syntheses. 21: 4. doi:10.15227/orgsyn.021.0004.

[3] Jaffe, Edward E. (2004). "Pigments, Organic". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.151807011001060605.a01.pub2. ISBN 978-0-471-48494-3.

[Ullmann1-4] K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371

[5] Lauer, W. M.; Kaslow, C. E. (1944). "4-Methylcarbostyril". Organic Syntheses. 24: 68. doi:10.15227/orgsyn.024.0068.

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[5]

Preparation and reactions

See also

References