6263-84-9

Basic information

• Product Name: 1,3,5-TRIPHENYL-1,5-PENTANEDIONE
• Synonyms: TIMTEC-BB SBB008072;AKOS BB-2957;1,3,5-TRIPHENYL-1,5-PENTANEDIONE;1,3,5-Triphenylpentane-1,5-dione;1,3,5-Triphenyl-1,5-pentadione
• CAS NO: 6263-84-9
• Molecular Formula: C₂₃H₂₀O₂
• Molecular Weight: 328.4
• Mol File: 6263-84-9.mol

Chemical Properties

• Melting Point: 85 °C
• Boiling Point: 509.4°C at 760 mmHg
• Flash Point: 188.1°C
• Appearance: /
• Density: 1.127g/cm³
• Vapor Pressure: 1.7E-10mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 1,3,5-TRIPHENYL-1,5-PENTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRIPHENYL-1,5-PENTANEDIONE(6263-84-9)
• EPA Substance Registry System: 1,3,5-TRIPHENYL-1,5-PENTANEDIONE(6263-84-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 6263-84-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3,5-TRIPHENYL-1,5-PENTANEDIONE is used as a chelating agent for the synthesis of various organic compounds, which can be further utilized in the development of new drugs and pharmaceutical products. Its antimicrobial properties also make it a promising candidate for the development of antimicrobial agents.
Used in Cosmetics Industry:
1,3,5-TRIPHENYL-1,5-PENTANEDIONE is used as a chelating agent in the production of perfumes, where it helps to stabilize and enhance the fragrance of the perfumes.
Used in Food Industry:
1,3,5-TRIPHENYL-1,5-PENTANEDIONE is used as a flavoring agent in the food industry, where it imparts unique flavors and enhances the taste of various food products.
Used in Antioxidant Applications:
1,3,5-TRIPHENYL-1,5-PENTANEDIONE is being investigated for its potential antioxidant properties, which can be utilized in various industries to prevent oxidation and extend the shelf life of products.
Used in Anti-cancer Applications:
1,3,5-TRIPHENYL-1,5-PENTANEDIONE is being studied for its potential anti-cancer properties, which can be employed in the development of new cancer treatments and therapies.

InChI:InChI=1/C23H20O2/c24-22(19-12-6-2-7-13-19)16-21(18-10-4-1-5-11-18)17-23(25)20-14-8-3-9-15-20/h1-15,21H,16-17H2

Upstream product

• 17393-17-8 1,2-dibenzoyl-3-phenylcyclopropane 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 94-41-7 benzalacetophenone 
• 73108-83-5 1-butoxy-1-oxo-2,4,6-triphenyl-1λ⁵-phosphinane-2,6-diol 
• 2128-90-7 6-phenyl-2H-pyran-2-one 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 82572-06-3 P,P-diphenyl-N-(1-phenylethylidene)phosphinic amide 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 1667-01-2 2,4,6-Trimethylacetophenone 
• 1896-62-4 (E)-benzalacetone 
• 94-41-7 (Z)-chalcone 
• 7196-01-2 4-(1-phenylvinyl)morpholine 
• 64-17-5 ethanol 

Downstream Products

• 67209-28-3 1,2,4-triphenylcyclopentane-1,2-diol 
• 580-35-8 2,4,6-triphenylpyridine 
• 54608-05-8 1,3,5-triphenyl-pentane-1,5-dione dioxime 
• 7149-37-3 4-benzoyl-1,3,5,7-tetraphenylheptane-1,7-dione 
• 854659-42-0 5-imino-1,3,5-triphenyl-pentan-1-one 
• 94055-33-1 1,3,5-triphenyl-2-bromo-1,5-pentanedione 
• 94055-32-0 2,4-dibromo-1,3,5-triphenyl-pentane-1,5-dione 
• 94-41-7 benzalacetophenone 
• 98-86-2 acetophenone 
• 103400-36-8 2,4-dibenzoyl-1-chloro-1,3,5-triphenyl-cyclopentane 
• 38047-69-7 2,4,6-triphenyl-piperidine 
• 860544-24-7 1,1,3,5,5-pentaphenyl-pentane-1,5-diol 
• 39659-25-1 3-Phenyl-2,4-dibenzoylpentane 
• 73108-83-5 1-butoxy-1-oxo-2,4,6-triphenyl-1λ⁵-phosphinane-2,6-diol 

Relevant articles and documents

Preparation, spectral studies and X-ray crystal structure of 1,3,5-triphenyl-1,5-pentanedione, C23H20O2

1,3,5-triphenyl-1,5-pentanedione, C23H20O2, has been prepared and characterized by spectroscopic methods and single crystal X-ray analysis.Crystals are monoclinic, space group P21/n, a = 28.124(4), b = 5.997(1), c = 10.434(1) Angstroem, β = 98.42(1) deg, Z = 4.The structure has been refined to a final R-value of 0.040 for 1625 reflections with Fo > 3?(Fo).The compound contains the two carbonyl groups in a mutually cis arrangement.KEY WORDS: C23H20O2, diketone, cis arrangement.

Half-sandwich Ru(II)-thioamide complexes as catalysts for one pot synthesis of aromatic 1,5-diketones

Four Ru(II)-arene thioamide complexes of the type [(η6-cymene)Ru(PPh3)(L)]+ (L = bidentate monoanionic thioamide ligand) have been synthesized and isolated as their hexafluorophosphate salts. All these complexes are fully

Synthesis method of polyphenylpyridine nitrate

The invention belongs to the technical field of organic synthesis, and relates to a synthesis method of polyphenylpyridine nitrate. The synthesis method comprises the following steps of: (1) synthesizing 2, 4, 6-triphenylpyran perchlorate; (2) synthesizing 1, 3, 5-triphenyl-2-pentane-1,5-dione (3) synthesizing 2, 4, 6-triphenylpyran nitrate; and (4) synthesizing the 1, 2, 4, 6-tetraphenylpyridine nitrate. By utilizing the synthesis method of the polyphenylpyridine nitrate, the polyphenylpyridine nitrate can be efficiently synthesized by adopting a method of cyclizing aminobenzene and diketone through reaction, the selectivity is strong, the side reaction is less, the yield is higher, the process conditions are relatively mild, and the adopted raw materials are simple and easy to obtain.

Catalytic activity of Mg-Al hydrotalcites and derived mixed oxides for imination reactionsviaan oxidative-dehydrogenation mechanism

The catalytic activities of Mg-Al hydrotalcites and derived Mg-Al mixed oxides were studied for the imination of benzylic substrates (benzyl amine and benzyl alcohol), with aniline as a model reaction, to establish a green and cost-effective catalytic (precious metal free) process for imination and tandem reactions utilizing alcohols as reagents. The Mg-Al mixed oxide (Mg/Al ratio = 3.0) was found to be an efficient catalyst for imination reactions to synthesize cross-imines with high selectivity as well as for tandem reactions of alcohols. Basic sites of catalysts adsorb benzylic substrates through the hydrogen of their functional groups (-NH2/-OH) and activate (weaken) benzylic C-H bonds for hydride elimination. Thus, basic sites catalyze the reaction by activating benzylic substrates for oxidative-dehydrogenation (i.e., deprotonation followed by hydride elimination with the help of oxygen) to produce reactive imine/carbonyl intermediates, which undergo subsequent nucleophilic reactions with amine.

Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones

Enantioselective diverse synthesis of a small-molecule collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asymmetric preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of N-heterocycle-containing scaffolds with functional group, and stereochemical diversity. Herein, we report a breakthrough toward this end via an initial diastereo- A nd enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations. Chiral N,N′-dioxide-earth metal complexes enable the generation of optically active tetrahydroindolizines in situ, across the strong background reaction for racemate-formation. In connection with deliberate sequential transformations, involving convenient rearomatic oxidation, and light-active aza-Norrish II rearrangement, the tetrahydroindolizine intermediates were converted into the final library including 3-arylindolizine derivatives and dicarbofunctionalized 1,5-dicarbonyl compounds. More importantly, the stereochemistry of four-stereogenic centered tetrahydroindolizine intermediates could be efficiently transferred into axial chirality in 3-arylindolizines and vicinal pyridyl and aryl substituted 1,5-diketones. In addition, densely functionalized cyclopropanes and bridged cyclic compounds were also discovered depending on the nature of the pyridinium ylides. Mechanism studies were involved to explain the stereochemistry during the reaction processes.

Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow

A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.

Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina

The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO2-Al2O3 was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.

Synthesis, optical spectroscopy and laser potential of pyrylium tosylates

Safe and inexpensive methods for synthesis of a series of four substituted 2,4,6-triphenylyrylium tosylate salts with different substituents are reported. The synthesis methods use p-toluenesulfonic acid monohydrate instead of conventional acid catalysts

In situ formed acetals facilitated direct Michael addition of unactivated ketones

TfOH-promoted synthesis of 1,5-diketones by the Michael reaction of unactivated ketones with chalcones has been described. Acetals formed under HC(OMe)3/TfOH conditions generate the required enol-equivalents for a smooth Michael reaction. A wide array of symmetrical and unsymmetrical 1,5-diketones has been synthesised.

N-Heterocyclic Carbene-Catalysed Mukaiyama-Michael Reaction and Mukaiyama Aldol/Mukaiyama-Michael Three-Component Coupling Reaction

An N-heterocyclic carbene-catalysed Mukaiyama-Michael addition between several trimethylsilyl (TMS) enol ethers and chalcone derivatives has been discovered. In addition, a related reaction cascade involving dehydrative Mukaiyama aldol followed by a Mukaiyama-Michael addition process has been developed. The later reaction can also be achieved as a three-component coupling reaction. The enantioselective variant of these reactions has been examined with homochiral catalysts. Though these catalysts were active, they fail to achieve enantioinduction.