acetoacetanilide
Sign in to saveAcetoacetanilide 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, one example being Pigment Yellow 74.
Wikidata facts
- Subclass of
- anilides
- Mass
- 177.079
Show 5 more facts
- canonical SMILES
- CC(=O)CC(=O)NC1=CC=CC=C1
- chemical formula
- C₁₀H₁₁NO₂
- isomeric SMILES
- CC(=O)C/C(=N\C1=CC=CC=C1)/O
- melting point
- 85
- Commons category
- Acetoacetanilide
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Encyclopedic overview
4 sectionsContents
- Structure
- Preparation and reactions
- Related compounds
- 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, one example being Pigment Yellow 74.
==Structure== Acetoacetanilide crystallizes as the keto-amide tautomer according to X-ray crystallography. The molecules are linked by intermolecular hydrogen bonds, which allows the benzoyl ketone to rotate out of the plane of the amide. For the general case of substituted acetoanilides, substituents on the aryl ring affect the balance of intra- vs intermolecular hydrogen bonding. The situation is illustrated by the 2' vs. 3' vs. 4' fluoro-substituted acetoacetanilides.
Excerpted from Wikipedia’s “acetoacetanilide” article, available under the CC BY-SA 4.0 licence.