5910-25-8

Basic information

• Product Name: 3-Phenyl-2,4-pentanedione
• Synonyms: 3-PHENYL-2,4-PENTANEDIONE;3-phenylpentane-2,4-dione;3-PHENYLACETYLACETONE;Phenylpentanedione;3-PHENYL-2,4-PENTANEDIONE 98+%
• CAS NO: 5910-25-8
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• Product Categories: Environmentally-friendly Oxidation;Ligands (Environmentally-friendly Oxidation);Synthetic Organic Chemistry
• Mol File: 5910-25-8.mol
• Article Data: 26

Chemical Properties

• Melting Point: 56°C
• Boiling Point: 126-128°C 15mm
• Flash Point: 94.4 °C
• Appearance: /
• Density: 1.056 g/cm³
• Vapor Pressure: 0.0156mmHg at 25°C
• Refractive Index: 1.508
• Solubility: soluble in Methanol
• PKA: 9.54±0.46(Predicted)
• CAS DataBase Reference: 3-Phenyl-2,4-pentanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-2,4-pentanedione(5910-25-8)
• EPA Substance Registry System: 3-Phenyl-2,4-pentanedione(5910-25-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 5910-25-8(Hazardous Substances Data)

Usage

General Description

3-Phenyl-2,4-pentanedione, also known as acetylacetone or acac, is a chemical compound commonly used in the synthesis of other compounds. This pale yellow liquid has a sweet and pleasant smell, and it is primarily noted for its ability to act as a bidentate ligand with metals, forming metal acetylacetonates. This acetylacetonates are very useful in various industrial applications, such as catalysis and materials science. It is relatively stable due to its resonance stabilization. However, just like with many other chemicals, 3-Phenyl-2,4-pentanedione needs to be handled with care as it can cause irritation on contact or inhalation. It is toxic if ingested and it's flammable, thus safety measures should be implemented during storage and its usage.

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

Upstream product

• 108-24-7 acetic anhydride 
• 103-79-7 1-phenyl-acetone 
• 141-78-6 ethyl acetate 
• 52144-59-9 (Z)-(tert-butylsulfanyl)(phenyl)diazene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 123-54-6 acetylacetone 
• 83566-43-2 tetraphenyl-bismuth trifluoroacetate 
• 47252-14-2 triphenylbismuth carbonate 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 
• 1007-32-5 benzyl ethyl ketone 
• 103-80-0 phenylacetyl chloride 
• 108-86-1 bromobenzene 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 4345-49-7 3,5-dimethyl-4-phenyl-1H-pyrazole 
• 50324-02-2 4,6-dimethyl-5-phenyl-1H-pyrimidin-2-one 
• 4345-46-4 3,5-dimethyl-4-phenyl-isoxazole 
• 91951-93-8 3,5-dimethyl-4-phenyl-2H-[1,2,6]thiadiazine 1,1-dioxide 
• 118399-54-5 (E)-<α-(1-Methyl-3-oxo-2-phenyl-1-butenyloxy)benzyliden>propandinitril 
• 118399-55-6 (Z)-<α-(1-Methyl-3-oxo-2-phenyl-1-butenyloxy)benzyliden>propandinitril 
• 118399-56-7 (E)-(1-Methyl-3-oxo-2-phenyl-1-butenyl)-N-cyanbenzimidat 
• 118399-57-8 (Z)-(1-Methyl-3-oxo-2-phenyl-1-butenyl)-N-cyanbenzimidat 
• 155951-02-3 1-(5-Chloro-2-nitro-phenyl)-3,5-dimethyl-4-phenyl-1H-pyrazole 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 53439-91-1 (S)-phenylacetylcarbinol 
• 19275-80-0 (R)-2-oxo-1-phenylpropyl acetate 
• 109050-49-9 (3-phenylacetylacetonate)2Hg 

Relevant articles and documents

Chemoenzymatic Dynamic Kinetic Asymmetric Transformations of β-Hydroxyketones

Herein we report on the development and application of chemoenzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT) of α-substituted β-hydroxyketones (β-HKs), using Candida antartica lipase B (CALB) as transesterification catalyst and a ruthenium complex as epimerization catalyst. An operationally simple protocol allows for an efficient preparation of highly enantiomerically enriched α-substituted β-oxoacetates. The products were obtained in yields up to 95 % with good diastereomeric ratios.

Intramolecular cooperative C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines to give o-(N-Acylamino)aryl ketones and multisubstituted indoles

A copper-catalyzed C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines was developed. In this process, the ortho effect played an important role in the reactivity and a new reaction pathway that involved a (2-aminophenyl)-bis-(1,3-dicarbonyl) copper species was clearly observed by a time-course HRMS analysis of the reaction mixture. Unlike the previous reports, both the nucleophilic and electrophilic parts of the 1,3-dicarbonyl compound were coupled with 2-iodoaniline by C-C bond cleavage to form o-(N-acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.

α-Arylation of β-diketones with aryl halides catalyzed by CuO/aluminosilicate

α-Arylation of β-diketones has been carried out over CuO/aluminosilicate catalyst under ligand-free condition. The reaction conditions were optimized with different solvents, bases, catalyst amounts, and temperatures using acetylacetone and 4-bromobenzaldehyde as a model system. The scope of the catalytic system was extended to include various substituted aryl halides. 27 examples were successfully demonstrated and the yields were ranging from 55% to 94%. C-Br bond was regioselectively activated in the presence of C-Cl bond. Similarly acetylacetone was chemoselectively arylated by 4-bromobenzaldehyde in the presence of dibenzoylacetone. Heterogeneous nature of the catalyst was confirmed by hot-filtration test. The catalyst was also found to be reusable.