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

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

Uses

Used in Chemical Synthesis:
3-Phenyl-2,4-pentanedione is used as a key intermediate in the synthesis of other compounds, making it an essential component in the production of various chemical products.
Used in Catalyst Production:
3-Phenyl-2,4-pentanedione is used as a bidentate ligand in the formation of metal acetylacetonates, which are valuable catalysts in numerous chemical reactions. These catalysts are employed in various industries to enhance the efficiency and selectivity of chemical processes.
Used in Materials Science:
3-Phenyl-2,4-pentanedione is used in the development of new materials, such as advanced coatings and composites, due to the unique properties imparted by metal acetylacetonates formed from 3-Phenyl-2,4-pentanedione.
Used in Safety Measures:
3-Phenyl-2,4-pentanedione is used as a reminder of the importance of safety precautions during its storage and usage, as it can cause irritation, is toxic if ingested, and is flammable. Proper handling and storage protocols are necessary to minimize risks associated with 3-Phenyl-2,4-pentanedione.

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 
• 15435-71-9 sodium acetylacetonate 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 52144-59-9 (Z)-(tert-butylsulfanyl)(phenyl)diazene 
• 591-50-4 iodobenzene 
• 123-54-6 acetylacetone 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 624-31-7 4-tolyl iodide 
• 62-53-3 aniline 
• 753-53-7 borontrifluoride acetic acid 
• 104-15-4 toluene-4-sulfonic acid 

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 
• 4541-60-0 Acetyl-phenyl-aceton-dioxim 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 53439-91-1 (S)-phenylacetylcarbinol 
• 19275-80-0 (R)-2-oxo-1-phenylpropyl acetate 
• 155951-13-6 4,5-dihydro-3-phenylpyrazolo<1,5-a>quinoxalin-4-one 
• 155951-14-7 8-Chloro-3-phenyl-5H-pyrazolo[1,5-a]quinoxalin-4-one 
• 155951-15-8 7-Methoxy-3-phenyl-5H-pyrazolo[1,5-a]quinoxalin-4-one 
• 155951-10-3 4,5-dihydro-3-phenyl-4-oxopyrazolo<1,5-a>quinoxalin-2-carboxylic acid 
• 155951-11-4 8-Chloro-4-oxo-3-phenyl-4,5-dihydro-pyrazolo[1,5-a]quinoxaline-2-carboxylic acid 
• 155951-12-5 7-Methoxy-4-oxo-3-phenyl-4,5-dihydro-pyrazolo[1,5-a]quinoxaline-2-carboxylic acid 

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.

Direct α-arylation of ketones efficiently catalyzed by Cu-MOF-74

The activity and reusability of Cu-MOF-74 as heterogeneous catalyst were studied in the Cu-catalyzed C[sbnd]C cross-coupling reaction of 4-iodotoluene (4-IT) with acetylacetone (AcAc) to direct synthesis of α-aryl-ketones. Cu-MOF-74 is characterized by having unsaturated copper sites into its highly porous metal-organic framework that can play a crucial role in catalytic applications. The influence of critical reaction variables such as solvent, reaction temperature, AcAc/4-IT ratio, catalyst concentration and basic agent (type and concentration) were evaluated. High conversions were achieved at 140 °C, 5 mol % of catalyst, AcAc/4-IT ratio of 2:1, DMF as solvent and 1.5 equivalent of Cs2CO3 base. The C-arylation between 4-IT and AcAc proceeded only in the presence of Cu-MOF-74 material, being very low the transformation in absence of the solid catalyst. Cu-MOF-74 material displayed a remarkable structural stability, regarding its XRD patterns and solid recovery degree after several reaction cycles, which was also complemented by the negligible amount of copper leached in the reaction media. This catalyst showed promising results in comparison to other homogeneous and heterogeneous Cu-based catalysts. This work evidences the great potential of MOF materials as heterogeneous catalysts in fine chemistry applications.

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.

Superparamagnetic copper ferrite nanoparticles as an efficient heterogeneous catalyst for the α-arylation of 1,3-diketones with C-C cleavage

Superparamagnetic CuFe2O4 nanoparticles were synthesized from CuCl2 and FeCl3 by a co-precipitation method in ethylene glycol and characterized by several techniques, which included vibrating sample magnetometry, XRD, SEM, TEM, atomic absorption spectrometry, and nitrogen physisorption measurements. The CuFe 2O4 nanoparticles could be used as a solid catalyst for the α-arylation reaction of acetylacetone with iodobenzene to form phenylacetone as the principal product and 3-phenyl-2,4-pentanedione as the byproduct. The reaction that used the CuFe2O4 nanoparticles as catalyst could proceed to completion with 95 % selectivity to phenylacetone. The CuFe2O4 nanoparticles could be separated easily from the reaction mixture by magnetic decantation and could be reused several times for the α-arylation reaction without a significant degradation in catalytic activity. Magnetic attraction: Superparamagnetic CuFe2O4 nanoparticles are synthesized from CuCl 2 and FeCl3 by a co-precipitation method. The CuFe 2O4 nanoparticles are used as a solid catalyst for the α-arylation reaction of acetylacetone with iodobenzene to form phenylacetone as the principal product and 3-phenyl-2,4-pentanedione as the byproduct.

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.

Cu-catalyzed reaction of 1,2-dihalobenzenes with 1,3-cyclohexanediones for the synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones

The Cu(I)-catalyzed reaction of 1-bromo-2- iodobenzenes and other 1,2-dihalobenzenes with 1,3-cyclohexanediones in DMF at 130 °C using Cs 2CO3 as a base and pivalic acid as an additive selectively delivers 3,4- dihydrodibenzo[b,d]fur

Anion-induced enantioselective cyclization of diynamides to pyrrolidines catalyzed by cationic gold complexes

Only chiral anions do the job! Optically active gold complexes derived from substituted binol hydrogen phosphate catalyze the desymmetrizing cyclization of 1,4-diynamides. This reaction provides access to synthetically useful, chiral methylene pyrrolidine

Copper(II) and 1,1′-trimethylene-2,2′-biimidazole-promoted arylation of acetylacetone with aryl iodides

A new and efficient way was developed to carry out the reaction of acetylacetone with aryl iodides under the assistance of Cu(II) and 1,1′-trimethylene-2,2′-biimidazole at 100°C. 3-Aryl-2,4-pentanediones were obtained in excellent yields. Copyright

Reversal of selectivity in gold-catalyzed cyclizations of 3,3-disubstituted 1,4-diynes

A general synthetic access to 3,3-disubstituted 1,4-diynes bearing a quaternary carbon center from acetylacetone was developed. The compounds were cyclized to the corresponding enol ethers by cationic gold complexes. The reactions occur in complete exo-se

Deacylative allylation: Allylic alkylation via retro-Claisen activation

A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of "deacylative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond. In comparison to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.