Wikipedia

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. 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]

Acetoacetanilide
Names
Preferred IUPAC name
3-Oxo-N-phenylbutanamide
Other names
Acetoacetylaminobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.725 Edit this at Wikidata
EC Number
  • 202-996-4
UNII
  • 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
  • CC(=O)CC(=O)NC1=CC=CC=C1
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)
low
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H302, H312, H332, H373
P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P322, P330, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Preparation and reactions

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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]

See also

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References

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  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.
  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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