5910-22-5

Usage

Physical state

Colorless or pale yellow liquid

Odor

Fruity

Functional groups

Beta-diketone (two ketone groups separated by a single carbon atom)

Chelating properties

Strong (used as a ligand in coordination chemistry)

Applications

a. Precursor in the synthesis of various organic compounds
b. Solvent in organic synthesis
c. Reagent in organic synthesis
d. Component in industrial processes
e. Production of polymer resins
f. Catalyst in chemical reactions

Upstream product

• 1192-62-7 1-(2-furyl)-1-ethanone 
• 611-13-2 2-furoic acid methyl ester 
• 527-69-5 2-furancarbonyl chloride 
• 1107549-20-1 cis-1,2-bis(2-furyl)-1,2-bis(trimethylsilyloxy)cyclopropane 
• 75-11-6 diiodomethane 
• 614-99-3 Ethyl 2-furoate 
• 31729-70-1 bis(iodozinc)methane 

Downstream Products

• 492-94-4 furil 
• 1449389-03-0 C₂₂H₁₇F₃O₆ 
• 1449389-02-9 C₂₁H₁₈O₆ 

Relevant academic research and scientific papers

Red organic electroluminescent devices based on novel furan-contained Eu complex as an emitting layer

A novel europium complex, Eu(DFP)3(phen) (DFP=1,3-Di-(2-furyl)-1,3-propanedione, phen=1,10-phenanthroline), was synthesized and used as an emitting material in organic eletroluminescent (EL) devices. The structure of fabricated EL devices is composed of ITO / TPD / Eu(DFP)3(phen) / AlLi(99:1). The double layered EL device emitted red light originating from Eu(DFP)3(phen) with a maximum luminance of 34.3 cd/m2 at 12 V and 25.7 mA/cm2.

Br?nsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines

A Br?nsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.

Steady state and laser photolysis studies of keto-enol tautomerizations in 2-alkyl-1,3-diketones having five-membered rings in acetonitrile: Temporal UV-A sunscreen

Keto-enol tautomerization in 2-alkyl-1,3-diketons having five-membered rings was studied using steady state and laser flash photolysis techniques in solution. The alkyl keto-diketones undergo photoinduced tautomerization mainly in the triplet state to the enol in acetonitrile. The alkyl enol-diketones, thus formed, undergo thermal tautomerization to the original keto forms in a few days. The alkyl enol-diketones show fast internal conversion from the excited singlet state to the ground state without yielding the corresponding isomeric forms (rotamer). Based on the computation for state energies of the keto, enol and isomer forms, a schematic energy diagram for the tautomerization was drawn.

Synthesis of Furanyl β-Diketone-based Heteroleptic Iridium(III) Complexes and Studies of Their Photo-Luminescence Properties

Four iridium complexes containing furan moieties were synthesized and characterized. The positioning of the furan unit had a strong effect on the optical properties of the complexes. The synthetic methodologies developed pave the way for the introduction of oligofuran compounds in IrIII heteroleptic complexes for OLED applications.

Diastereoselective nucleophilic cyclopropanation of 1,2-diketones and α-ketoimines with bis(iodozincio)methane

A reaction of 1,2-diketones and α-ketoimines with bis(iodozincio)methane gave cyclopropan-1,2-diol and 2-aminocyclopropanol respectively via nucleophilic [2+1]cycloaddition. The reaction proceeded via a sequential nucleophilic attack of the dizinc reagent to vicinal two carbonyl group. The reaction showed high diastereoselectivity to give cis-isomer via a face-to-face coordination between the substrate and bis(iodozincio)methane.

Structure and reactivity of bis(iodozincio)methane solution

Bis(iodozincio)methane, which has been shown to be an efficient reagent for organic synthesis, is obtained as THF solution. The structural information about the reagent as THF solution was corrected by small angle neutron scattering and by anomalous X-ray scattering. Those scattering experiments implied that the prepared bis(iodozincio)methane exists without forming any oligomer or aggregate. A coordination of tetrahydrothiophene to bis(iodozincio)methane enhances the nucleophilicity of the reagent and stabilizes its monomeric structure in the solution.

Structure and reactivity of bis(iodozincio)methane in tetrahydrothiophene

Addition of tetrahydrothiophene (THT) to a THF solution of bis(iodozincio)methane modified the stability and reactivity: EXAFS analysis indicated that THT stabilizes bis(iodozincio)methane in a monomeric structure; the species reacts with acyl chlorides to give 1,3-diketones.