CHEBI:14750 - acetylacetone

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ChEBI Name acetylacetone ChEBI ID CHEBI:14750 Definition A β-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ChemicalBook:CB2179401, eMolecules:474637, ZINC000004720638 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Acetylacetone is an organic compound with the chemical formula CH3−C(=O)−CH2−C(=O)−CH3. It is classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3−C(=O)−CH=C(−OH)−CH3. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. Acetylacetone is a building block for the synthesis of many coordination complexes as well as heterocyclic compounds. Read full article at Wikipedia Formula C5H8O2 Net Charge 0 Average Mass 100.11582 Monoisotopic Mass 100.05243 InChI InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3 InChIKey YRKCREAYFQTBPV-UHFFFAOYSA-N SMILES CC(=O)CC(C)=O ChEBI Ontology Outgoing acetylacetone (CHEBI:14750) is a β-diketone (CHEBI:67265) acetylacetone (CHEBI:14750) is conjugate acid of acetylacetonate (CHEBI:30395) Incoming acetylacetonate (CHEBI:30395) is conjugate base of acetylacetone (CHEBI:14750) IUPAC Name pentane-2,4-dione Synonyms Sources 2,4-dioxopentane ChemIDplus 2,4-Dioxopentane KEGG COMPOUND 2,4-pentadione NIST Chemistry WebBook 2,4-pentanedione ChemIDplus ACAC NIST Chemistry WebBook acetoacetone ChemIDplus acetyl 2-propanone ChemIDplus acetylacetone IUPAC acetylacetone UniProt Acetylacetone KEGG COMPOUND CH3‒CO‒CH2‒CO‒CH3 IUPAC Hacac IUPAC pentan-2,4-dione NIST Chemistry WebBook Manual Xrefs Databases Acetylacetone Wikipedia C15499 KEGG COMPOUND CPD-8879 MetaCyc HMDB0031648 HMDB View more database links Registry Numbers Types Sources 123-54-6 CAS Registry Number ChemIDplus 123-54-6 CAS Registry Number NIST Chemistry WebBook 2537 Gmelin Registry Number Gmelin 741937 Reaxys Registry Number Reaxys Citation Darwish ES, Fattah AM, Attaby FA, Al-Shayea ON (2014) Synthesis and antimicrobial evaluation of some novel thiazole, pyridone, pyrazole, chromene, hydrazone derivatives bearing a biologically active sulfonamide moiety. International journal of molecular sciences 15, 1237-1254 [PubMed:24445259] [show Abstract] This study aimed for the synthesis of new heterocyclic compounds incorporating sulfamoyl moiety suitable for use as antimicrobial agents via a versatile, readily accessible N-[4-(aminosulfonyl)phenyl]-2-cyanoacetamide (3). The 2-pyridone derivatives were obtained via reaction of cyanoacetamide with acetylacetone or arylidenes malononitrile. Cycloaddition reaction of cyanoacetamide with salicyaldehyde furnished chromene derivatives. Diazotization of 3 with the desired diazonium chloride gave the hydrazone derivatives 13a-e. Also, the reactivity of the hydrazone towards hydrazine hydrate to give Pyrazole derivatives was studied. In addition, treatment of 3 with elemental sulfur and phenyl isothiocyanate or malononitrile furnished thiazole and thiophene derivatives respectively. Reaction of 3 with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt 17 which reacted in situ with 3-(2-bromoacetyl)-2H-chromen-2-one and methyl iodide afforded the thiazole and ketene N,S-acetal derivatives respectively. Finally, reaction of 3 with carbon disulfide and 1,3-dibromopropane afforded the N-[4-(aminosulfonyl) phenyl]-2-cyano-2-(1,3-dithian-2-ylidene)acetamide product 22. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. The compounds were evaluated for both their in vitro antibacterial and antifungal activities and showed promising results. Last Modified 12 August 2015