6263-83-8

Basic information

• Product Name: 1,5-DIPHENYL-1,5-PENTANEDIONE
• Synonyms: TIMTEC-BB SBB008576;RARECHEM AQ A2 0032;1,5-diphenyl-5-pentanedione;1,5-DIPHENYL-1,5-PENTANEDIONE;1,3-DIBENZOYLPROPANE;1,5-DIPHENYLPENTANE-1,5-DIONE;1,5-Diphenyl-1,5-pentanedione,99%;1,3-Dibenzoylpropane 98%
• CAS NO: 6263-83-8
• Molecular Formula: C₁₇H₁₆O₂
• Molecular Weight: 252.31
• Product Categories: Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 6263-83-8.mol
• Article Data: 49

Chemical Properties

• Melting Point: 66-68 °C(lit.)
• Boiling Point: 355.49°C (rough estimate)
• Flash Point: 157.7 °C
• Appearance: White to light beige/Crystalline Powder
• Density: 1.0832 (rough estimate)
• Vapor Pressure: 2.56E-07mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• CAS DataBase Reference: 1,5-DIPHENYL-1,5-PENTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIPHENYL-1,5-PENTANEDIONE(6263-83-8)
• EPA Substance Registry System: 1,5-DIPHENYL-1,5-PENTANEDIONE(6263-83-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6263-83-8(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT BEIGE CRYSTALLINE POWDER

Uses

1,3-Dibenzoylpropane may be used in the electrochemical synthesis of cis-1,2-diphenyl-1,2-cyclopentanediol, via reduction in acetonitrile.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 901, 1973 DOI: 10.1021/jo00945a011Tetrahedron Letters, 15, p. 3721, 1974

General Description

1,3-Dibenzoylpropane is a 1,3-diaroylpropane. 1,3-Dibenzoylpropane is formed during hydroxocobalt(III) Schiff base complexes catalyzed selective aldol reaction of dibenzoylmethanes with formaldehyde in methanol.

InChI:InChI=1/C17H16O2/c18-16(14-8-3-1-4-9-14)12-7-13-17(19)15-10-5-2-6-11-15/h1-6,8-11H,7,12-13H2

Upstream product

• 108-55-4 glutaric anhydride, 
• 71-43-2 benzene 
• 98-86-2 acetophenone 
• 3506-36-3 3-dimethylaminopropiophenone 
• 85356-13-4 1,5-Bis(dimethylamino)-1,5-dicyano-1,5-diphenylpentane 
• 50-00-0 formaldehyd 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 13424-80-1 N,N,N′,N′-tetramethylglutaramide 
• 591-51-5 phenyllithium 
• 4727-98-4 1,1,3,3-tetrabenzoylpropane 
• 73258-08-9 1,2-diphenylcyclopentene ozonide 
• 68-12-2 N,N-dimethyl-formamide 
• 27905-65-3 2,6-Diphenyl-1,6-heptadiene 
• 103896-55-5 N-(1-Phenylvinylimino)triphenylphosphorane 

Downstream Products

• 63634-88-8 (1-Hydroxy-5-oxo-1,5-diphenylpentyl)-phosphonige Saeure 
• 63582-98-9 5-(2-Isopropylphenyl)-1.5-diphenyl-4-penten-1-on 
• 67787-57-9 N-methyl-2,6-diphenylpiperidine 
• 1485-98-9 1,2-diphenylcyclopent-1-ene 
• 27905-65-3 2,6-Diphenyl-1,6-heptadiene 
• 98-86-2 acetophenone 
• 768-03-6 Phenyl vinyl ketone 
• 265137-30-2 C₃₁H₂₆Br₂ 
• 1585-03-1 2,4-dimethyl-1,5-diphenylpropan-1,5-dione 
• 56568-43-5 1,5-diphenyl-2,4-dibromo-1,5-pentanedione 
• 65213-66-3 1,2-diphenyl-cyclopentane-1,2-diol 
• 5449-44-5 1,5-diphenyl-pentane-1,5-diol 
• 53484-48-3 cis-1,2-diphenylcyclopentane-1,2-diol 
• 55696-62-3 meso-1,5-diphenyl-pentane-1,5-diol 

Relevant articles and documents

Ruthenium-Catalyzed Alkylation of Cyclopropanols with Sulfoxonium Ylides via C-C Bond Cleavage: Formation of Diverse 1,5-Diketones

A novel ruthenium-catalyzed alkylation of cyclopropanols with sulfoxonium ylides has been developed that affords diverse 1,5-diketones with good efficiency and broad substrate scope. To illustrate the synthetic applications of the obtained 1,5-diketones, aldol and cyclization reactions have been investigated. Preliminary mechanistic studies suggest that this process involves a sequential C C activation and carbene migratory insertion.

Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium ylides and cyclopropanols for δ-diketone synthesis

Previous transition metal-catalyzed synthesis processes of δ-diketones are plagued by the high cost of the rhodium catalyst and harsh reaction conditions. Herein a low-cost, room temperature ruthenium catalytic method is developed based on the coupling of α-keto sulfoxonium ylides with cyclopropanols. The mild protocol features a broad substrate scope (47 examples) and a high product yield (up to 99%). Mechanistic studies argue against a radical pathway and support a cyclopropanol ring opening, sulfoxonium ylide-derived carbenoid formation, migratory insertion C-C bond formation pathway.

Ruthenium-catalyzed alkylation reaction of cyclopropanol and sulfur ylide for synthesis of 1, 5-diketone compounds

The invention relates to a ruthenium-catalyzed alkylation reaction of cyclopropanol and sulfur ylide, and a series of 1, 5-diketone compounds can be synthesized by the method. According to the method,cyclopropanol is catalyzed by ruthenium to generate beta-carbon elimination ring opening, and safe, stable and easy-to-prepare sulfur ylide is used as a carbene precursor, so that the method has goodapplicability in the field of construction of 1, 5-diketone.