23464-17-7

Usage

Physical state

Yellow crystalline solid

Solubility

Soluble in organic solvents, insoluble in water

Uses

a. Precursor in the synthesis of pharmaceuticals and organic compounds
b. Reagent in organic chemistry reactions
c. Synthesis of heterocyclic compounds and polymer materials

Odor

Characteristic smell

Toxicity

Moderately toxic when ingested or inhaled in large amounts

Hazards

Potential skin and eye irritant upon contact

Upstream product

• 60-29-7 diethyl ether 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 412282-58-7 4-benzoyl-3-phenyl-oxetan-2-one 
• 5411-12-1 chalcone epoxide 
• 132938-26-2 Acetic acid (E)-1-benzoyl-2-phenyl-vinyl ester 
• 556-64-9 methyl thiocyanate 
• 5411-12-1 cis-1,3-Diphenyl-2,3-epoxypropan-1-one 
• 7570-85-6 trans-2,3-epoxy-1,3-diphenyl-1-propanone 
• 7664-93-9 sulfuric acid 
• 6281-88-5 1,3-diphenyl-2,3-dipiperidino-propan-1-one 
• 7726-95-6 bromine 
• 94-41-7 benzalacetophenone 
• 54519-12-9 2-hydroxychalcone 
• 60999-92-0 β-benzoyl-β-nitrostyrene 

Downstream Products

• 106571-30-6 (6-benzoyl-2,5-diphenyl-3,4-dihydro-2H-pyran-2-yl)-phenyl-ethanedione 
• 108012-69-7 1-phenyl-2-benzyl-glyoxale-1-oxime 
• 812673-60-2 3-bromo-1,3-diphenyl-propane-1,2-dione 
• 114564-42-0 4-Benzyl-5-phenyl-1,3-dioxol-2-on 
• 120211-45-2 2,2-Diethoxy-4-phenyl-5-[1-phenyl-meth-(E)-ylidene]-2,5-dihydro-furan 
• 1083-30-3 dihydrochalcone 
• 69897-44-5 trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one 
• 5381-80-6 anti-1,2-dihydroxy-1,3-diphenylpropane 
• 5381-80-6 rac-(1R,2R)-1,3-diphenylpropane-1,2-diol 
• 41049-36-9 1-hydroxy-1,3-diphenylacetone 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 103-82-2 phenylacetic acid 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

High-valent metalloporphyrin, Fe(tpp)OTf, catalyzed rearrangement of α,β-epoxy ketones into 1,2-diketones

Iron(III) tetraphenylporphyrin triflate, Fe(tpp)OTf, works as an efficient and characteristic Lewis acid catalyst in the selective rearrangement of α,β-epoxy ketones into 1,2-diketones.

Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones

A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.

Efficient epoxide isomerization within a self-assembled hexameric organic capsule

The isomerization of epoxides to the corresponding carbonyl compounds is efficiently catalyzed by the supramolecular organic nano-capsule formed by the self-assembly of six resorcin[4]arene units. The capsule provides a combination of weak Br?nsted acidity and a suitable nano-environment that favors the metal-free isomerization reaction.

Enantioselective aerobic oxidation of α-hydroxy-ketones catalyzed by oxidovanadium(V) methoxides bearing chiral, N-salicylidene- tert -butylglycinates

Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N- salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (krel).

Facile preparation of 1,2-diketones

Easily accessible lead-like libraries of heterocyclic molecules useful for high-throughput screening are of continuous interest to the pharmaceutical industry. A number of drug-like libraries are derived from aromatic 1,2-diketones; however, nonsymmetrical 1,2-diketones are challenging to prepare. This communication describes a simple and practical synthesis of 1,2-diketones based on a controlled cross benzoin-like condensation reaction. Copyright Taylor & Francis Group, LLC.

Synthesis of 1,2-diketones by the transition metal-catalyst-free reaction of α-oxo acid chlorides or oxalyl chloride with organostannanes

(Chemical Equation Presented) The reaction of an α-oxo acid chloride with an organostannane proceeds transition metal-catalyst-free to afford a 1,2-diketone in an excellent yield. In addition, a sequence comprising pretreatment of oxalyl chloride with an

Silica gel catalysed rearrangement of α-epoxyketones to 1,2-diketones

A convenient and simple method for the preparation of diphenylpropane-1,2-diones is described. The process involves rearrangement of α-epoxyketones on silica gel; an unusual migration of a proton instead of the more common benzoyl migration.

DICHLORODIISOPROPOXYTITANIUM - A CONVENIENT REAGENT FOR THE SELECTIVE TRANSFORMATIONS OF α,β-EPOXYCARBONYL COMPOUNDS

Depending on the structure and the reaction conditions, α,β-epoxycarbonyl compounds isomerize selectively in the presence of dichlorodiisopropoxytitanium to α-diketones or undergo nucleophilic cleavage with the formation of the corresponding hydroxychloro ketones.

Synthesis of α-diketones from α,β-dihydroxy ketones

Treatment of α,β-dihydroxy ketones with carbonyldiimidazole resulted in the formation of α-diketones based on the elimination of the cyclic carbonates formed in situ.