6668-24-2

Usage

Uses

Used in Organic Synthesis:
Acetylacetone is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the formation of complex organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, acetylacetone is used as a building block for the synthesis of various drugs, contributing to the development of new medicinal compounds.
Used in Pesticide and Fragrance Production:
Acetylacetone is employed in the production of pesticides and fragrances, where its chemical properties are harnessed to create effective and aromatic products.
Used as a Metal Chelator in Catalyst and Material Production:
Acetylacetone is used as a metal chelator, forming stable complexes with metal ions, which is crucial in the production of metal-based catalysts and materials, enhancing their performance and stability.
Used in Analytical Chemistry:
In the field of analytical chemistry, acetylacetone is utilized for its solvent properties, aiding in the analysis and identification of various chemical compounds.
Used in Industrial Processes as a Solvent:
Acetylacetone is employed as a solvent in a range of industrial processes, where its unique properties contribute to the efficiency and effectiveness of these processes.

InChI:InChI=1/C11H12O2/c1-8(9(2)12)11(13)10-6-4-3-5-7-10/h3-8H,1-2H3

Upstream product

• 141-78-6 ethyl acetate 
• 93-55-0 1-phenyl-propan-1-one 
• 74-88-4 methyl iodide 
• 37559-20-9 1-phenyl-2-methylenebutane-1,3-dione 
• 13809-02-4 4-(but-2-en-2-yl)morpholine 
• 98-88-4 benzoyl chloride 
• 93-91-4 1-phenylbutan-1,3-dione 
• 768-90-1 1-Adamantyl bromide 
• 77-78-1 dimethyl sulfate 
• 1901-26-4 3-methyl-4-phenyl-3-buten-2-one 
• 26954-42-7 Ethyl-(α-ethyl-benzylidenamino)-aluminiumchlorid 
• 75-05-8 acetonitrile 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 75-36-5 acetyl chloride 

Downstream Products

• 60433-18-3 2-benzyl-2-methyl-1-phenyl-butane-1,3-dione 
• 57205-21-7 2-Methyl-1-phenyl-2-phenylseleno-1,3-butandion 
• 1528-39-8 3-phenyl-2-pentanone 
• 28871-03-6 2,3-dimethyl-4-phenyl-thiopyrano[2,3-b]indole 
• 13954-46-6 1-Phenyl-2-methyl-butan-1,3-dion-bis- 
• 3815-34-7 2,2-dimethyl-1-phenyl-1,3-butanedione 
• 111239-38-4 (+)-1-phenyl-2-methyl-2-allylbutane-1,3-dione 
• 111239-47-5 (-)-1-phenyl-2-methyl-2-allylbutane-1,3-dione 
• 111239-47-5 (R)-2-Allyl-2-methyl-1-phenyl-butane-1,3-dione 
• 111239-38-4 (S)-2-Allyl-2-methyl-1-phenyl-butane-1,3-dione 
• 149046-48-0 3,5-dioxo-4-methyl-5-phenylpentanoic acid 
• 132713-76-9 2-bromo-2-methyl-1-phenylbutane-1,3-dione 
• 118365-05-2 2-(9-fluorenyl)-1-phenylbutane-1,3-dione 

Relevant academic research and scientific papers

Synthesis of β-oxo carbonyl and thiocarbonyl compounds via basic sulfur abstraction

Sulfur abstraction from suitable thioesters represents a mild method for the formation of carbon-carbon bonds and the formation of 1,3-dicarbonyl compounds. A study of the scope and limitations of this reaction for the synthesis of these or mixed 1,3-carbonyl/thiocarbonyl compounds by a base promoted sulfur abstraction rearrangement is described. These reactions were typically very clean and the products were obtained in good yield (65–95%) in just 30 min. This method is particularly efficient for the introduction of thiocarbonyl containing groups. Thus, it constitutes a synthetic strategy for the generation of a new carbon-carbon bond and the regioselective preparation of mixed β-dicarbonyl compounds.

Synthesis, electrochemical, structural and theoretical study of new derivatives of O[sbnd]B[sbnd]N and O[sbnd]B[sbnd]O heterocycles

Three new oxazaborine and two boron diketonate derivatives containing different structural motifs were synthesized and studied using NMR, electrochemistry (CV, RDV, and dc-polarography), UV–Vis spectra and X-ray structure analysis. The experimental data were correlated with quantum chemical calculations. The main attention was focused on determination of the first oxidation and the first reduction potentials, their relationship to the calculated HOMO and LUMO energies and to their UV–Vis spectra. The electrochemical data reflect the structure–redox properties relationship depending on location of oxidation and reduction center.

O -Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones

A combination of o-iodoxybenzoic acid (IBX) and a catalytic amount of iodine is found to promote a facile one-pot deacylative sulfonylation reaction of 1,3-dicarbonyl compounds with sodium sulfinates to yield β-carbonyl sulfones. The present method provides the target products bearing a wide variety of functional groups in one step and in good yields.

ARYL BETA DIKETONES AND THEIR USE A ODORANTS

The present invention refers to aryl beta diketones of the formula (I) wherein Y, R1, R2 and R3 have the same meaning as given in the description. The invention further refers to fragrance compositions and fragranced articles comprising them.

Method for preparing 2-methyl-1,3-dicarbonyl derivative

The invention discloses a method for preparing a 2-methyl-1,3-dicarbonyl derivative. A 1,3-dicarbonyl derivative serves as an initiator, raw materials are easy to obtain, and a great variety of raw materials are available. The product obtained through the method has high type diversity and can be used directly or used for other further reactions. Besides, only organic peroxides and a catalytic amount of inorganic copper salt are used, so that cost is low. According to the method, a reaction is conducted in air, reaction conditions are mild, pollution is small, reaction time is short, the yield of the target product is high, reaction operation and aftertreatment are easy, and the method is suitable for industrial production.

Regioswitchable Palladium-Catalyzed Decarboxylative Coupling of 1,3-Dicarbonyl Compounds

A palladium-catalyzed chemo- and regioselective coupling of 1,3-dicarbonyl compounds via an allylic linker has been developed. This reaction, which displays broad substrate scope, forms two C-C bonds and installs two all-carbon quaternary centers. The regioselectivity of the reaction can be predictably controlled by utilizing an enol carbonate of one of the coupling partners.

Direct synthesis of 1,3-dicarbonyl compounds via radical coupling of aldehydes with ketones under metal-free conditions

An efficient approach for the synthesis of 1,3-diketones from aldehydes and ketones has been developed using Bu4NI (TBAI) as the catalyst. In the presence of DTBP-TBHP/p-TsOH, aldehydes undergo radical coupling with ketones to provide the desired products in moderate to high yields at 120 °C. Although various substituents on the aromatic ring of aldehydes are well tolerable under the standard reaction conditions, the protocol is limited by the scope of ketones. The method exhibits advantages in terms of the easy access of the starting materials, operational simplicity, functional group tolerance, and the absence of metal catalyst.

Oxidative umpolung ?±-alkylation of ketones

We disclose a hypervalent iodine mediated ?±-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The ?±-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.

Catalytic decarboxylative alkenylation of enolates

A palladium-catalyzed decarboxylative alkenylation of stabilized enolates has been developed, which gives rise to alkenylated dicarbonyl products from enol carbonates regioselectively with concomitant installation of a quaternary all-carbon center. The broad scope of the reaction has been demonstrated by successfully utilizing a range of enolates and external phenol nucleophiles.

Substrate range of the titanium TADDOLate catalyzed asymmetric fluorination of activated carbonyl compounds

The substrate range of the [TiCl2(TADDOLate)] (TADDOL=α,α,α′,α′-tetraaryl-1,3-dioxolane-4, 5-dimethanol)-catalyzed asymmetric α-fluorination of activated β-carbonyl compounds has been investigated. Optimal conditions for catalysis are characterized by using 5 mol-% of TiCl2(naphthalen-1- yl)-TADDOLate) as catalyst in a saturated (0.14 mol/l) MeCN solution of F-TEDA (1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis- [tetrafluoroborate]) at room temperature. A series of α-methylated β-keto esters (3-oxobutanoates, 3-oxopentanoates) with bulky benzyl ester groups (60-90% ee) or phenyl ester (67-88% ee) have been fluorinated readily, whereas α-acyl lactones were also readily fluorinated, but gave lower inductions (13-46% ee). Double stereochemical differentiation in β-keto esters with chiral ester groups raised the stereoselectivity to a diastereomeric ratio (dr) of up to 96.5:3.5. For the first time, β-keto S-thioesters were asymmetrically fluorinated (62-91.5% ee) and chlorinated (83% ee). Lower inductions were observed in fluorinations of 1,3-diketones (up to 40% ee) and β-keto amides (up to 59% ee). General strategies for preparing activated β-carbonyl compounds as important model substrates for asymmetric catalytic α-functionalizations are presented (>60 examples). Copyright