25856-02-4

Usage

Common Uses

Organic synthesis, pharmaceutical research, intermediate in drug production, reagent in organic chemistry, potential biological activity, flavoring agent (limited use)

Type of Compound

Diketone

Chemical Reactions

Ability to undergo various chemical reactions and form complex organic compounds

Therapeutic Applications

Considered an important building block in the synthesis of organic molecules with potential therapeutic applications

Safety Concerns

Limited use as a flavoring agent in the food industry due to safety concerns

Upstream product

• 25856-04-6 3-(3-bromophenyl)-1-phenyl-2,3-dibromopropanone 
• 3132-99-8 m-bromobenzoic aldehyde 
• 98-86-2 acetophenone 
• 93-89-0 benzoic acid ethyl ester 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 93-58-3 benzoic acid methyl ester 
• 53692-59-4 1-(3-bromophenyl)-3-phenylprop-2-yn-1-one 
• 932-90-1 Benzaldoxime 
• 618-89-3 methyl 3-bromobenzoate 
• 29816-74-8 (E)-3-(3-bromophenyl)-1-phenyl-2-propen-1-one 

Downstream Products

• 1340475-96-8 2-benzoyl-4-(3-bromobenzoyl)-1-(3-bromophenyl)-5-phenylpentane-1,5-dione 
• 6277-67-4 4-nitro-1,3-diphenyl-butan-1-one 
• 40396-54-1 1-(3-bromophenyl)-2-phenylethane-1,2-dione 

Relevant academic research and scientific papers

Simultaneous observation of triplet and singlet cyclopentane-1,3-diyl diradicals in the intersystem crossing process

Intersystem crossing is an important chemical process. In this study, the rate constant of intersystem crossing, kISC ～3×107s-1, for cyclopentane-1,3-diyl diradicals was unequivocally determined by the simultaneous observation of the decay process of the

An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources

An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.

Transition-metal-free formal decarboxylative coupling of ?±-oxocarboxylates with ?±-bromoketones under neutral conditions: A simple access to 1,3-diketones

A transition-metal-free formal decarboxylative coupling reaction between ?±-oxocarboxylates and ?±-bromoketones to synthesize 1,3-diketone derivatives is presented. In this reaction, a broad scope of substrates can be employed, and neither a metal-based reagent nor an additional base is required. DFT calculations reveal that this reaction proceeds through a coupling followed by decarboxylation mechanism and the ?±-bromoketone unprecedentedly serves as a nucleophile under neutral conditions. The rate-determining step is an unusual hydrogen-bond-assisted enolate formation by thermolysis.

2-Hydroxylation of 1,3-Diketones with Atmospheric Oxygen

An efficient method for the 2-hydroxylation of 1,3-diketones by using atmospheric oxygen as an oxidant under transition-metal-free condition is described. The protocol has the advantages of using an inexpensive and stable oxidant, producing high yields, and requiring ecofriendly conditions.

Asymmetric transfer hydrogenation of unsymmetrical benzils

In this paper, the asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40°C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating (R = CH3, OCH3) and electron-withdrawing groups (R = F, Cl, CF3) resulted in poor yields (0% to 31.2%), even at 40°C for 72 h. These products had inefficient diastereoselectivities (syn/anti = 1.5 to 5.0/1) caused by steric effects. Furthermore, the results of a dynamic-kinetic study were used to propose a plausible reaction pathway of unsymmetrical benzil using 3-methoxy-1,2-diphenyl ethanedione as an example.

Process for preparing vinyl substituted beta-diketones

A process for preparing vinyl substituted beta-diketones includes reacting a halogen-containing beta-diketone with an olefin in a reaction zone under Heck coupling reaction conditions in the presence of a catalyst, a base, and an organic phosphine to provide a vinyl substituted beta-diketone product.

Synthesis of vinyl-substituted β-diketones for polymerizable metal complexes

Polymerizable β-diketones for application to metal ion coordination have been prepared and characterized. Bromine-substituted β-diketones were synthesized under Claisen-Schmidt-type condensation conditions. Vinyl groups were substituted for the halide by