4728-04-5

Basic information

• Product Name: 3-(2-Furanylmethylene)-2,4-pentanedione
• Synonyms: 3-(2-Furanylmethylene)-2,4-pentanedione;2,4-Pentanedione, 3-(2-furanylmethylene)-;Einecs 225-227-4
• CAS NO: 4728-04-5
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.19
• EINECS: 225-227-4
• Mol File: 4728-04-5.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 339.4°C at 760 mmHg
• Flash Point: 158.6°C
• Appearance: /
• Density: 1.136g/cm³
• Vapor Pressure: 9.22E-05mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 3-(2-Furanylmethylene)-2,4-pentanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Furanylmethylene)-2,4-pentanedione(4728-04-5)
• EPA Substance Registry System: 3-(2-Furanylmethylene)-2,4-pentanedione(4728-04-5)

Safety Data

• Hazardous Substances Data: 4728-04-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10O3/c1-7(11)10(8(2)12)6-9-4-3-5-13-9/h3-6H,1-2H3

Upstream product

• 98-01-1 furfural 
• 123-54-6 acetylacetone 
• 41002-50-0 4-acetoxy-3-penten-2-one 
• 1522-20-9 acetylacetone 

Downstream Products

• 111203-08-8 5-(5-amino-4-cyano-2-furyl)-2-cyano-2,4-pentadienenitrile 
• 105263-08-9 5-acetyl-2-amino-4-furan-2-yl-6-methyl-4H-pyran-3-carbonitrile 
• 1352788-20-5 3-(2-furyl)-5-N-(2-hydroxyethyl)amino-2-acetyl-4-ethoxycarbonyl-1-methyl-4-cyclohexen-1-ol 
• 848822-05-9 3-(α-furyl)-5-benzylamino-2,4-diacetyl-1-methyl-4-cyclohexen-1-ol 
• 179088-19-8 5-acetyl-3-cyano-6-methyl-4-(2'-furyl)-tetrahydro-2(1H)-pyridine-2-thione 
• 4440-16-8 2-(2-furanylmethylene)-propanedioic acid 
• 98174-93-7 3-((Ξ)-furfurylidene)-pentane-2,4-dione-mono-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Pyridine immobilised on magnetic silica as an efficient solid base catalyst for Knoevenagel condensation of furfural with acetyl acetone

Novel heterogeneous pyridine immobilised magnetic silica (Fe3O4@SiO2-Py) was found to be an efficient, greener and heterogeneous solid base catalyst for the Knoevenagel condensation of furfural with acetylacetone under optimized reaction conditions. The Knoevenagel condensation product 3-(2-furylmethylene)-2,4-pentanedione (FMP), a jet fuel precursor, was produced in high yield of 85% with 94% conversion of furfural at 100 °C within a period of 4 h. Fe3O4@SiO2-Py catalyst showed excellent stability and recyclability without losing its initial activity.

Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation

A new protocol based on lipase-catalyzed tandem reaction toward α,β-enones/enoesters is presented. For the synthesis of the desired products the tandem process based on enzyme-catalyzed hydrolysis and Knoevenagel reaction starting from enol acetates and aldehyde is developed. The relevant impact of the reaction conditions including organic solvent, enzyme type, and temperature on the course of the reaction was revealed. It was shown that controllable release of the active methylene compound from the corresponding enol carboxylate ensured by enzymatic reaction diminishes significantly the formation of the unwanted co-products. Furthermore, this protocol was extended by including a second tandem chemoenzymatic transformation engaging various aldehyde precursors. After a careful optimization of the reaction conditions, the target products were obtained with yields up to 86 % and with excellent E/Z-selectivity.

Cross-linked polystyrene-TiCl4 complex as a reusable Lewis acid catalyst for solvent-free Knoevenagel condensations of 1,3-dicarbonyl compounds with aldehydes

Cross-linked polystyrene copolymer beads with the average particle size in the range of (50–80 mesh size) were prepared by a new method, characterized and functionalized with titanium tetrachloride to afford the corresponding polystyrene?titanium tetrachloride complex in one step reaction and characterized by FT-IR, UV, TGA, DSC, XRD, SEM, BET. This polymer metal complex (PS/TiCl4) was used as a heterogeneous, recoverable, reusable Lewis acid for solvent-free Knoevenagel condensations of 1,3-diketones with aromatic aldehydes under green and mild conditions. The rate of reactions was found to decrease with an increasing percentage of crosslinking and the mesh size of the copolymer beads. This complex showed good stability and catalytic activity in the Knoevenagel reactions.