623-15-4

Basic information

• Product Name: 4-(2-FURYL)-3-BUTEN-2-ONE
• Synonyms: (3E)-4-(2-Furyl)-3-buten-2-one;1-(2-Furyl)but-2-en-3-one;2-furfurylideneacetone;3-Buten-2-one, 4-(2-furyl)-;3-Butene-2-one, 4-(2-furanyl)-;4-(2-furanyl)-3-buten-2-on;4-(2-furanyl)-3-buten-2-one;4-(2-furyl)-3-buten-2-on
• CAS NO: 623-15-4
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.15
• EINECS: 210-774-3
• Product Categories: Industrial/Fine Chemicals
• Mol File: 623-15-4.mol
• Article Data: 115

Chemical Properties

• Melting Point: 34-41 °C(lit.)
• Boiling Point: 112-115°C 10mm
• Flash Point: 220 °F
• Appearance: reddish crystalline powder
• Density: 1.0496
• Vapor Pressure: 0.0786mmHg at 25°C
• Refractive Index: n20/D 1.565(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive: Light Sensitive
• Stability: Flammable. Incompatible with strong oxidizing agents.
• BRN: 109696
• CAS DataBase Reference: 4-(2-FURYL)-3-BUTEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-FURYL)-3-BUTEN-2-ONE(623-15-4)
• EPA Substance Registry System: 4-(2-FURYL)-3-BUTEN-2-ONE(623-15-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• WGK Germany: 3
• RTECS: EM9939000
• TSCA: Yes
• Hazardous Substances Data: 623-15-4(Hazardous Substances Data)

Usage

Chemical Properties

4-(2-Furyl)-3-buten-2-one has a sweet spicy odor and taste It is useful in nut favors.

Occurrence

Reported found in coffee and rum

Uses

4-(2-Furyl)-3-buten-2-one, can be used in technical or engineered material industyr. It has shown to have the durability need in composites.

Taste threshold values

Taste characteristics at 20 ppm: sweet, nutty, powdery, vanilla and coumarin creamy.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 6735, 1984 DOI: 10.1021/ja00334a044The Journal of Organic Chemistry, 52, p. 4855, 1987 DOI: 10.1021/jo00231a006

General Description

Reddish crystalline solid.

Air & Water Reactions

Slightly water soluble.

Reactivity Profile

An aldehyde and a ketone. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

4-(2-FURYL)-3-BUTEN-2-ONE is flammable.

InChI:InChI=1/C8H8O2/c1-7(9)4-5-8-3-2-6-10-8/h2-6H,1H3/b5-4+

Upstream product

• 98-00-0 (2-furyl)methyl alcohol 
• 67-64-1 acetone 
• 98-01-1 furfural 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 56-23-5 tetrachloromethane 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 7732-18-5 water 
• 6502-39-2 4-furan-2-yl-but-3-en-2-one oxime 
• 513-88-2 1,1-Dichloroacetone 
• 110-00-9 furan 
• 78-94-4 methyl vinyl ketone 
• 1423-60-5 methyl ethynyl ketone 
• 876-27-7 4-chlorophenyl acetate 
• 79380-04-4 3-(2-furyl)-1-methylallyl alcohol 

Downstream Products

• 4280-89-1 1-(α-furyl)-5-phenylpenta-1,4-dien-3-one 
• 57337-21-0 4-furan-2-yl-but-3-en-2-one phenylhydrazone 
• 1004-29-1 2-butanyltetrahydrofuran 
• 3208-43-3 4-tetrahydrofuran-2-yl-butan-2-ol 
• 5451-15-0 2-methyl-1,6-dioxa-spiro[4.4]nonane 
• 699-17-2 4-(furan-2-yl)butan-2-one 
• 13599-33-2 3-methyl-5-(2-furyl)-4,5-dihydro-1H-pyrazole 
• 20577-46-2 4,7-dioxooctanoic acid 
• 539-47-9 3-(fur-2-yl)crotonic acid 
• 87351-05-1 4-(furan-2-yl)-4-phenylbutan-2-one 
• 75491-25-7 1-((1R,2S)-2-Furan-2-yl-cyclopropyl)-ethanone 
• 75491-25-7 1-((1S,2S)-2-Furan-2-yl-cyclopropyl)-ethanone 
• 627539-50-8 (S)-4-(2-furyl)-2-butanol 
• 6963-39-9 4-(furan-2-yl)butan-2-ol 

Relevant articles and documents

Aldol condensation of furfural and acetone on layered double hydroxides

The Aldol condensation of furfural (Fur) with acetone (Ac) to 4-(2-Furyl)-3-buten-2-one (FAc) is one of the most important processes in the aqueous-reforming of oxygen-containing biomass derivatives and has been carried out in the presence of solid-base catalysts, calcined-rehydrated Layered Double Hydroxides (LDH). The Mg-Al Layered Double Hydroxides has been prepared by the coprecipitation, calcination and regeneration from mixed oxides by rehydration. The catalyst prepared with different Mg/Al molar ratios showed different catalytic performance and the best catalyst was with the Mg/Al molar ratio of 2.5. Phenol adsorption showed that the best catalyst had the largest numbers of accessible basic sites. The appropriate rehydration temperature and time for mixed oxides obtained by calcination were also investigated. The Mg-Al LDH catalysts can be regenerated by calcination at 773 K and rehydration in decarbonate water, but the regeneration is complex and incomplete. In addition, the catalyst calcined at high temperature also had activity, which was attributed to the formation of the Mg-Al spinels.

Aldol condensation of furfural and acetone on zeolites

Zeolites of different structural types were used as catalysts for aldol condensation of furfural and acetone in batch reaction conditions at T = 20-100 C and time 0-24 h. To establish a relation between physico-chemical and catalytic properties of microporous materials, the samples were characterized by SEM, N2 adsorption, FTIR and TGA. It was found that the acidic solids possessed appreciable activity in the reaction and resulted in a formation of products of aldehyde-ketone interaction. Nevertheless, furfural conversion decreased rapidly due to coke formation inside zeolite pores. Simultaneously with a general route of the reaction observed for basic catalysts, dimerization of the condensation product on acidic sites occurred. It was supposed that catalytic behavior of zeolites considerably affected by their both structural and textural properties. Experiments with re-used samples showed that zeolites totally restored their activity and selectivity after calcination at 530 C.

Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones

Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.

Production of liquid fuel intermediates from furfural via aldol condensation over La2O2CO3-ZnO-Al2O3 catalyst

Aldol condensation of furfural with acetone over basic catalysts allows the production of furanic adducts 4-(2-furyl)-3-buten-2-one (FAc, C8) and 1,5-di-2-furanyl-1,4-pentadien-3-one (F2Ac, C13)) that can be transformed into high-quality diesel