2140-49-0

Basic information

• Product Name: 4-Acetyl-3-oxobutanoic Acid
• Synonyms: 3,5-Dioxohexanoic Acid;4-Acetyl-3-oxobutanoic Acid;4-Acetylacetoacetic Acid;Triacetic Acid
• CAS NO: 2140-49-0
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 144.12532
• Mol File: 2140-49-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 277.2°C at 760 mmHg
• Flash Point: 135.7°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 0.000566mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 4-Acetyl-3-oxobutanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetyl-3-oxobutanoic Acid(2140-49-0)
• EPA Substance Registry System: 4-Acetyl-3-oxobutanoic Acid(2140-49-0)

Safety Data

• Hazardous Substances Data: 2140-49-0(Hazardous Substances Data)

Usage

Uses

Triacetic Acid is a metabolite of two species of Penicillium. Triacetic Acid is an intermediate in the fermentation of trihydroxybenzenes to acetate.

Definition

ChEBI: A dioxo monocarboxylic acid comprising hexanoic acid with the two oxo groups placed at the 3- and 5-positions.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1931, 1990 DOI: 10.1080/00397919008053123

InChI:InChI=1/C6H8O4/c1-4(7)2-5(8)3-6(9)10/h2-3,8-10H,1H3/b5-2-

Upstream product

• 19841-57-7 ethyl 3,5-dioxohexanoate 
• 124-38-9 carbon dioxide 
• 123-54-6 acetylacetone 
• 26567-75-9 acetylacetone enol 
• 23652-85-9 (Z)-4-(methylamino)-3-penten-2-one 

Downstream Products

• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 541-50-4 2-acetoacetic acid 
• 64-19-7 acetic acid 

Relevant articles and documents

Photocatalytic carboxylation of organic substrates with carbon dioxide at zinc sulfide with deposited ruthenium nanoparticles

Photocatalytic carboxylation of acetylacetone with carbon dioxide has been performed by using ZnS-based photocatalysts. The formation of two isomeric carboxylic acids, as proven by IR and 13C NMR spectroscopy, was observed. The reaction yield was enhanced after deposition of ruthenium nanoparticles on ZnS. The reaction encompasses ruthenium-mediated one-electron reduction of CO2 to CO2.- with electrons from the conduction band of ZnS and one-hole oxidation of acetylacetone to the relevant radical. Coupling of photogenerated radicals leads to the formation of carboxylic acids. Generation of CO2.- has been confirmed by spin-trapping EPR measurements. The process described herein may find applications for the solar-light-driven green synthesis of Cn+1 carboxylic compounds from Cn substrates by utilising carbon dioxide. Dropping acid: Zinc sulfide with deposited ruthenium(0) nanoparticles photocatalyzes the carboxylation of acetylacetone with carbon dioxide as a substrate (see picture). The reaction proceeds through coupling of photogenerated R. and CO2.- radicals. Copyright

An Improved Method for γ-Carboxylation of β-Diketones. Synthesis of 4-Alkyl-3,5-dioxohexanoic Acids and 5-Alkyl Derivatives of Triacetic Acid Lactone

γ-Carboxylation of β-diketones, 1, can be improved using samples containing 100percent of ketoenol tautomers, 3, prepared by mild hydrolysis of the corresponding copper(II) complexes 2.Cyclization of the so formed 4-alkyl-3,5-dioxohexanoic acids, 4, affords 5-alkyl-4-hydroxy-6-methyl-2-pyrones, 5.