1467-40-9

Basic information

• Product Name: 1,5-DIPHENYL-1,3,5-PENTANETRIONE
• Synonyms: 5-pentanetrione,1,5-diphenyl-3;1,5-DIPHENYL-1,3,5-PENTANETRIONE;1,3-DIBENZOYLACETONE;1,5-di(phenyl)pentane-1,3,5-trione;NSC 154656;NSC 631644;1,5-Diphenyl-1,3,5-pentanetrione >=98.0% (T)
• CAS NO: 1467-40-9
• Molecular Formula: C₁₇H₁₄O₃
• Molecular Weight: 266.29
• Product Categories: Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 1467-40-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 107-109 °C
• Boiling Point: 422.7°Cat760mmHg
• Flash Point: 182.6°C
• Appearance: /
• Density: 1.172
• Vapor Pressure: 9.37E-08mmHg at 25°C
• Refractive Index: 1.574
• BRN: 2054189
• CAS DataBase Reference: 1,5-DIPHENYL-1,3,5-PENTANETRIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIPHENYL-1,3,5-PENTANETRIONE(1467-40-9)
• EPA Substance Registry System: 1,5-DIPHENYL-1,3,5-PENTANETRIONE(1467-40-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1467-40-9(Hazardous Substances Data)

Usage

General Description

1,5-Diphenyl-1,3,5-pentanetrione (H2DBA, DBAc) is a symmetrical triketone.1,3,5-triketones are potential tridentate ligands and forms complexes with transition metals, lanthanides and actinides. It acts as ligand and forms binuclear cobalt complex with CoCl2.6H2O. The interaction of two intramolecular hydrogen bonds in 1,5-diphenyl-1,3,5-pentanetrione has been studied. H2DBA can be synthesized by condensation reaction between ethyl benzoate and benzoyl acetone. DBAc arranged in stretched polyethylene (PE) sheets has been investigated by infrared linear dichroism (LD) spectroscopy.

InChI:InChI=1/C17H14O3/c1-12(18)15(16(19)13-8-4-2-5-9-13)17(20)14-10-6-3-7-11-14/h2-11,15H,1H3

Upstream product

• 14547-50-3 1,1-Diethoxy-1,5-diphenyl-pent-3-in-5-on 
• 67-64-1 acetone 
• 93-58-3 benzoic acid methyl ester 
• 14547-48-9 1,1-Diethoxy-1,5-diphenyl-pent-3-in-5-ol 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 98-86-2 acetophenone 
• 105-37-3 Ethyl propionate 
• 67-56-1 methanol 
• 1029-94-3 2,6-diphenyl-pyran-4-one 
• 7732-18-5 water 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 55991-67-8 5-phenylfuran-2,3-dione 
• 93-91-4 1-phenylbutan-1,3-dione 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 133594-61-3 5,7-Dibenzoyl-1,3-dimethyl-2-phenyl-2H-cyclohepta[c]pyrrol-6-one 
• 133594-60-2 5,7-Dibenzoyl-2-butyl-1,3-dimethyl-2H-cyclohepta[c]pyrrol-6-one 
• 22760-83-4 2,4-Bis-diazo-1,5-diphenyl-pentane-1,3,5-trione 
• 10037-16-8 5-benzoyl-6-methyl-2-phenyl-4H-pyranone 
• 59776-74-8 5-benzoyl-2-phenyl-4H-pyran-4-one 
• 35466-35-4 5-benzoyl-2-phenylpyridin-4(1H)-one 

Relevant articles and documents

Synthesis, X-ray crystal structure and DFT study of potential ligands of (2Z)-3-[(2-hydroxyphenyl)amino]-1-phenyl"alk"-2-en-1-one type

The main aim of the study was the synthesis and X-ray and spectroscopic investigations of potential ligands of transition metal complexes. A new compound, (2Z)-3-[(2-hydroxyphenyl)amino]-1-phenylpent-2-en-1-one, was obtained and the detailed experimental results are reported. Theoretical investigations based on the Density Functional Theory (DFT) were also performed for the presented compound as well as for its two analogues. Conformational analysis was done to find minima on the potential energy surface (PES). Analysis of the electrostatic potential (ESP) showed regions in the molecules sensitive to external interactions. Furthermore, topological analysis of the electron density (AIM theory) was applied to confirm the existence of an intramolecular H-bond in the molecules studied. The obtained theoretical results are in good agreement with the available experimental data.

Synthetic studies on a series of functionalized pyrylium salts, 4-chloro- and 4-bromophosphinines

A series of new pyrylium salts that bear sulfonate and phosphonate groups were obtained from the reactions between 2,6-diphenyl-4H-pyran-4-one, sulfonic anhydride, and chlorophosphates, and analyzed spectroscopically. Furthermore, treatment of 2,6-diphenyl-4H-pyran-4-one with phosphoryl chloride or bromide afforded the corresponding 4-chloro- and 4-bromopyrylium tetrafluoroborates in good yield. Subsequently, the synthesis of the corresponding 4-chloro- and 4-bromophosphinines was accomplished by treating the respective chloro- and bromopyrylium tetrafluoroborates with tris(trimethylsilyl)phosphine.

Thermal Cycloaddition of Aroylketene to 1-Aryl-1-trimethylsilyloxyethylene: A Simple Synthesis of 2,6-Diaryl-4H-pyran-4-one

Aroylketene (2) generated by pyrolytic decarbonylation of 5-aryl-2,3-dihydro-2,3-furandione (1) reacted with 1-aryl-1-trimethylsilyloxyethylene (3) in a regioselective manner to give 2,6-diaryl-4H-pyran-4-one (5) and/or 1,5-diarylpentane-1,3,5-trione (6).