623-30-3

Basic information

• Product Name: 2-Furanacrolein
• Synonyms: B-(2-FURFURYLIDENE)ACETALDEHYDE;B-(2-FURYL)ACROLEIN;BETA-(2-FURYLACROLEIN) TRANS-ISOMER;(E)-3-FURAN-2-YL-PROPENAL;FURAN-2-ACROLEIN;FURYL ACROLEIN;FEMA 2494;AKOS BBS-00003241
• CAS NO: 623-30-3
• Molecular Formula: C₇H₆O₂
• Molecular Weight: 122.12
• EINECS: 210-785-3
• Product Categories: Heterocycles;Furan&Benzofuran;aldehyde Flavor;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 623-30-3.mol
• Article Data: 26

Chemical Properties

• Melting Point: 49-55 °C(lit.)
• Boiling Point: 143 °C37 mm Hg(lit.)
• Flash Point: 211 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.1483 (rough estimate)
• Vapor Pressure: 0.0351mmHg at 25°C
• Refractive Index: 1.5286 (estimate)
• Storage Temp.: 0-10°C
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 107570
• CAS DataBase Reference: 2-Furanacrolein(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanacrolein(623-30-3)
• EPA Substance Registry System: 2-Furanacrolein(623-30-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45-24/25
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• RTECS: LT8528500
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 623-30-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 623-30-3 differently. You can refer to the following data:
1. Colorless to light yellow liqui
2. 3(2-Furyl)acrolein has a cooked spicy-herb odor and taste.

Occurrence

Reported found in ground and roasted coffee and rum

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 2517, 1993 DOI: 10.1021/jo00061a027

General Description

Light brown powder. Cinnamon odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Furanacrolein is an aldehyde. May become involved in exothermic self-condensation or polymerization reactions that are often catalyzed by acid. May generate flammable and/or toxic gases with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. 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). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Fire Hazard

Flash point data are not available for 2-Furanacrolein, but 2-Furanacrolein is probably combustible.

InChI:InChI=1/C7H6O2/c8-5-1-3-7-4-2-6-9-7/h1-6H

Synthetic route

furfural (98-01-1) + triethylamine (121-44-8) → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With chloro-trimethyl-silane; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0 - 20℃; for 24h; Sealed tube; Inert atmosphere;	93%

C19H30O2S → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With triethylsilane In tetrahydrofuran for 1h; Reagent/catalyst; Fukuyama Reduction;	79%

(E)-3-(2-furanyl)-2-propen-1-ol (27393-97-1, 79380-02-2) → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With p-benzoquinone In diethylene glycol dimethyl ether at 120℃; for 19h;	65%

3-(2-furyl)acrylic acid p-tosylhydrazide → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With sodium carbonate In ethylene glycol at 160℃; for 0.0166667h;	60%

furfural (98-01-1) + ethanol (64-17-5) → 3-furan-2-yl-propenal (623-30-3) + Ethyl 2-furoate (614-99-3)

Conditions	Yield
With oxygen; sodium carbonate at 100℃; under 4500.45 Torr; for 24h; Catalytic behavior; Autoclave;	A 36% B 17%
With oxygen; potassium carbonate at 140℃; under 2250.23 Torr; for 4h; Reagent/catalyst; Autoclave;
With oxygen; potassium carbonate at 140℃; under 2250.23 Torr; for 4h; Autoclave; Sealed tube;

furfural (98-01-1) + ethanol (64-17-5) → 3-furan-2-yl-propenal (623-30-3) + 2-furoic acid methyl ester (611-13-2)

Conditions	Yield
With oxygen; potassium carbonate at 140℃; under 2250.23 Torr; for 4h; Reagent/catalyst;	A 21% B n/a
With oxygen at 140℃; under 2250.23 Torr; for 4h; Reagent/catalyst; Autoclave;	A 61.6 %Chromat. B 37 %Chromat.

furfural (98-01-1) + acetaldehyde (75-07-0) + furan-2,3,5(4H)-trione pyridine (1:1) → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
at 0℃;

furfural (98-01-1) + acetaldehyde (75-07-0) → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With sodium hydroxide; water at 40℃;
With sodium hydroxide
With sodium hydroxide In ethanol; water at 0 - 20℃; for 11h;
Stage #1: furfural With sodium hydroxide In ethanol; water at 0℃; for 0.166667h; Stage #2: acetaldehyde In ethanol; water at 0 - 20℃; for 11h;

furfural (98-01-1) + acetaldehyde (75-07-0) → 3-furan-2-yl-propenal (623-30-3) + 5-(furan-2-yl)-penta-2,4-dienal (5916-94-9)

Conditions	Yield
With sodium hydroxide In water at 40℃; for 0.0833333h;	A 10 g B 6.2 g
With sodium hydroxide at 20℃;

3-ethoxy-3-[2]furyl-propionaldehyde diethylacetal (91976-43-1) + sodium acetate (127-09-3) + acetic acid (64-19-7) → 3-furan-2-yl-propenal (623-30-3)

3-(2-furyl)acryloylimidazole (2172-16-9) → 1H-imidazole (288-32-4) + 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With α-chymotrypsin In water Thermodynamic data; enthalpy changes for base (nonenzymatic) and enzymatic (α-chymotrypsin) hydrolysis;

furfural (98-01-1) + acetylaldehyde → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With sodium hydroxide

furfural (98-01-1) + acetaldehyde (75-07-0) + furan-2,3,5(4H)-trione pyridine (1:1) → 3-furan-2-yl-propenal (623-30-3) + 1--pentadien-(1.3)-al-(5) + 1--heptatrien-(1.3.5)-al-(7)

Conditions	Yield
at 20℃;

3-(2-furyl)propionaldehyde → 3-furan-2-yl-propenal (623-30-3)

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 1h;

Upstream product

• 98-01-1 furfural 
• 75-07-0 acetaldehyde 
• 4543-51-5 3-(2-furyl)propionaldehyde 
• 54829-48-0 2-iodofuran 
• 3054-95-3 acrylaldehyde diethyl acetal 
• 64-17-5 ethanol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 121-44-8 triethylamine 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 20689-54-7 3-furanylacryloyl chloride 
• 27393-97-1 3-(furan-2-yl)prop-2-en-1-ol 
• 2172-16-9 3-(2-furyl)acryloylimidazole 
• 27393-97-1 (E)-3-(2-furanyl)-2-propen-1-ol 
• 91976-43-1 3-ethoxy-3-[2]furyl-propionaldehyde diethylacetal 

Downstream Products

• 121597-17-9 2-furanacrolein phenylhydrazone 
• 90736-46-2 3-[2]furyl-acrylaldehyde-(3-nitro-phenylimine) 
• 4433-34-5 11t-[2]furyl-undeca-2t,4t,6t,8t,10-pentaenal 
• 767-08-8 3-(tetrahydrofuran-2-yl)propan-1-ol 
• 3920-53-4 heptane-1,4,7-triol 
• 26908-23-6 3-furan-2-yl-propan-1-ol 
• 76041-89-9 1,6-dioxa[4,4]spirononane 
• 142-82-5 n-heptane 
• 177852-82-3 3-Furan-2-yl-3-trimethylsilanyl-propionaldehyde 
• 640722-96-9 N-[3-(2-furyl)-2-propenylidene]-2-trifluoromethylaniline 

Relevant articles and documents

Study of the oxidative esterification of furfural catalyzed by Au25(glutathione)18 nanocluster deposited on zirconia

Au/ZrO2 catalyst prepared from Au25(SG)18 nanoclusters (SG stands for glutathione) deposited on ZrO2 has shown to be an efficient system for the oxidative esterification of furfural with methanol. The influence of the supported nanoclusters was studied and showed that partial calcination of the supported nanoclusters at 300 °C was sufficient for a quantitative formation of methyl-2-furoate even in the absence of a base. In the presence of 0.27 mol% of Au, initial activities up to 250 h?1 were obtained at 100 °C under 6 bar of O2. The reactivity was extended to the oxidative esterification of furfuryl alcohol and the formation of various products and intermediates was discussed.

A selective oxidative valorization of biomass-derived furfural and ethanol with the supported gold catalysts

The oxidative upgrading of renewable furfural (FUR) and ethanol is an important way to produce high-quality liquid fuel and value-added furanic derivatives. In this work, a series of supported Au catalysts were prepared using the colloid-immobilization technique, and further employed for catalytic oxidative condensation of FUR with ethanol in the presence of molecular oxygen. It is found that, with Au@CaO as the catalyst, 85.9% conversion of FUR and 81.8% selectivity of the product furan-2-acrolein were achieved in the absence of any homogeneous basic additive. The effects of different reactions such as reaction time, temperature and catalyst amount were explored in detail. Also, the influences of calcination temperature and amount of protective agent during the preparation of catalyst were investigated. According to the characterization results of catalyst, it is concluded that the synergistic effect of metallic Au and basic site of CaO support plays a significant role on the selective oxidative condensation. At last, a possible reaction mechanism is proposed based on the catalytic principle and experimental results.

A regulatable oxidative valorization of furfural with aliphatic alcohols catalyzed by functionalized metal-organic frameworks-supported Au nanoparticles

The oxidative upgrading of furfural (FUR) and aliphatic alcohols is an important way to produce desirable precursor of jet fuel or value-added furanic compound. Therein, developing a highly active catalytic system with switchable product selectivity still remains a challenge. In this work, we report a novel strategy on regulating the oxidative condensation and oxidative esterification of FUR with aliphatic alcohol in the presence of molecular oxygen. Firstly, Au@UiO-66 is prepared using different methods and employed as the catalyst for the oxidative valorization of FUR with methanol. It is found that the impregnation-reduction-H2 (I-H) method is the best where a 100% selectivity of methyl-2-furoate with a complete conversion was obtained using Au@UiO-66 as catalyst. Then, a series of metal-organic frameworks (MOFs) supported Au nanoparticles (Au@UiO-66-X) such as Au@UiO-66, Au@UiO-66-NH2, Au@UiO-66-NO2, Au@UiO-66-COOH and Au@UiO-66-NH3Cl have been prepared with I-H method and employed for oxidative valorization of furfural with ethanol. Experimental results showed that, in “FUR-ethanol-O2” system, the Au@UiO-66-X can efficiently regulate the oxidative condensation and oxidative esterification as two competitive reaction pathways. With Au@UiO-66-COOH as the catalyst, the oxidative condensation process is dominant in which 84.1% selectivity of furan-2-acrolein is attained; Meanwhile, the Au@UiO-66 is beneficial to the occurrence of oxidative esterification and generation of ethyl-2-furoate. At last, based on the catalyst characterization and the numerous control experiments, a possible catalytic reaction mechanism for conversion of FUR is proposed.