623-17-6

Basic information

• Product Name: Furfuryl acetate
• Synonyms: FEMA 2490;FURFURYL ACETATE;2-(ACETOXYMETHYL)FURAN;2-furanmethanol acetate;2-FURANMETHYL ACETATE;ACETIC ACID FURFURYL ESTER;2-furfurylacetate;2-Furfuryl-acetate
• CAS NO: 623-17-6
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.14
• EINECS: 210-775-9
• Product Categories: Heterocycles;Furans, Benzofurans & Dihydrobenzofurans;ester Flavor;Furans, Benzofurans & Dihydrobenzofurans;Alphabetical Listings;E-F;Flavors and Fragrances;Certified Natural ProductsFlavors and Fragrances;Building Blocks;Furans;Heterocyclic Building Blocks
• Mol File: 623-17-6.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 175-177 °C(lit.)
• Flash Point: 150 °F
• Appearance: colorless/
• Density: 1.118 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.06mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: 0.5-1.0 g/100 mL at 23 ºC
• BRN: 116128
• CAS DataBase Reference: Furfuryl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Furfuryl acetate(623-17-6)
• EPA Substance Registry System: Furfuryl acetate(623-17-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• RTECS: LU9120000
• TSCA: Yes
• Hazardous Substances Data: 623-17-6(Hazardous Substances Data)

Usage

Description

Furfuryl acetate, also known as the ester formed by the esterification between furfuryl alcohol and acetate, is a colorless to clear yellow or orange liquid with a pungent, ethereal, and fruity odor. It is commonly found in various food items and alcoholic beverages, contributing to their distinct flavors and aromas.

Uses

Used in Flavor and Fragrance Industry:
Furfuryl acetate is used as a flavoring ingredient for its distinct fruity odor, enhancing the taste and aroma of various food products. It is particularly favored for its ability to add a unique flavor profile to the products it is used in.
Used in Synthesis:
Furfuryl acetate serves as an intermediate in the synthesis of various compounds, such as 5-acetoxymethyl-2-vinylfuran and 5-hydroxymethyl-2-vinylfuran, through Vilsmeier-Haack and Wittig reactions. These synthesized compounds have potential applications in the chemical and pharmaceutical industries.
Used in Alcoholic Beverages:
Furfuryl acetate is used in the alcoholic beverage industry to add a unique and pleasant aroma to drinks like beer and rum, contributing to their overall sensory experience.
Used in the Food Industry:
Furfuryl acetate is used as a flavoring ingredient in the food industry, particularly in products like roasted almonds, white bread, cocoa, coffee, roasted flberts, roasted onion, roasted peanuts, cooked pork liver, wheaten and crispbread, oats, licorice, dried bonito, sukiyaki, and Bourbon vanilla. Its presence in these products enhances their taste and aroma, making them more appealing to consumers.

References

Kim, You Sun, S. S. Lee, and M. W. Oh. "Halogen Containing Heterocyclic Compounds (Part III) Chlorination of Furfuryl Acetate in Presence of Acid and Lewis Acids." Soil Biology & Biochemistry 924.1(1970):263-270. Harayama, Koichi, F. Hayase, and H. Kato. "Contribution to Stale Flavor of 2-Furfuryl Ethyl Ether and Its Formation Mechanism in Beer." Bioscience Biotechnology & Biochemistry 59.6(1995):1144-1146. Antón, Víctor, et al. "Thermophysical Characterization of Furfuryl Esters: Experimental and Modeling." Energy & Fuels (2017).

Air & Water Reactions

Slightly water soluble.

Reactivity Profile

Furfuryl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Furfuryl acetate reacts with strong oxidizing agents, strong acids, strong bases and strong reducing agents. Furfuryl acetate reacts violently with cyanoacetic acid, formic acid, mineral acids, nitric acid and (nitric acid + N204 + sulfuric acid).

Fire Hazard

Furfuryl acetate is combustible.

Synthetic route

furfurylacetate (623-17-6) + 1-phenyl-propan-1-one (93-55-0) → (E)-(5-(3-oxo-3-phenylprop-1-enyl)furan-2-yl)methyl acetate (1440662-73-6)

Conditions	Yield
With silver (II) carbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium acetate; palladium diacetate; tricyclohexylphosphine In 1,2-dimethoxyethane at 100℃; for 24h; Schlenk technique; Inert atmosphere;	56%

furfurylacetate (623-17-6) → (2-furyl)methyl alcohol (98-00-0)

Conditions	Yield
With lipase B from Candida antarctica immobilized on Immobead 150 In aq. phosphate buffer at 40℃; for 0.333333h; pH=7.4;	89%
With methanol; potassium permanganate; trimethylsulphonium iodide at 25℃; under 760.051 Torr; chemoselective reaction;	80%
With methanol; potassium permanganate at 25℃; chemoselective reaction;	78%
With [t-Bu2SnOH(Cl)]2 In methanol at 30℃; for 24h; Deacetylation;	82 % Chromat.
[t-Bu2SnOH(Cl)]2 In methanol at 30℃; for 24h;	82 % Chromat.

furfurylacetate (623-17-6) + 2.6-dimethylphenol (576-26-1) → 4-(furan-2-ylmethyl)-2,6-dimethylphenol

Conditions	Yield
With Montmorillonite In dichloromethane at 60℃; Sealed tube;	35%

maleic anhydride (108-31-6) + furfurylacetate (623-17-6) → (+/-)-(1RS,2SR,6RS,7SR)-(3,5-dioxo-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-1-yl)methyl acetate (6331-95-9, 19308-92-0)

Conditions	Yield
In toluene at 23℃;	86%
In toluene at 23℃; for 97h; Diels-Alder reaction;	74%
In diethyl ether at 25℃; for 168h; Diels-Alder cycloaddition;	34%
With diethyl ether

furfurylacetate (623-17-6) + methoxybenzene (100-66-3) → 2<(4-Methoxylphenyl)methyl>furan

Conditions	Yield
With bis(trifluoromethanesulfonyl)amide In dichloromethane at 20℃; for 0.333333h;	70 %Chromat.

furfurylacetate (623-17-6) → 1 ,5-pentanediol (111-29-5) + 1,2-pentanediol (5343-92-0) + pentan-1-ol

Conditions	Yield
Stage #1: furfurylacetate With 5%-palladium/activated carbon; hydrogen; acetic acid at 100℃; under 7600.51 Torr; for 6h; Autoclave; Stage #2: With methanol; water Reagent/catalyst; Temperature; Pressure; Reflux;	A 24% B 15% C 56%

furfurylacetate (623-17-6) + methyl phosphite → acetic acid 5-(dimethoxy-phosphoryl)-furan-2-ylmethyl ester

Conditions	Yield
With manganese triacetate In acetic acid at 80℃; for 3h;	86%

furfurylacetate (623-17-6) + bis(pinacol)diborane → (CH3)4C2O2BCH2C4H3O

Conditions	Yield
With gold-nanoparticles supported on TiO2 In 1,4-dioxane at 60℃; for 2h;	53%

furfurylacetate (623-17-6) + anthranilic acid (118-92-3) → 1-acetoxymethyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene (117078-27-0)

Conditions	Yield
Stage #1: anthranilic acid With isopentyl nitrite; trichloroacetic acid In tetrahydrofuran at 0 - 20℃; Stage #2: furfurylacetate With methyloxirane In tetrahydrofuran Heating; Further stages.;	75%
With isopentyl nitrite In 1,2-dimethoxyethane	45.8%

furfurylacetate (623-17-6) + 3-tert-butyl-3-methylcycloprop-1-ene (137073-16-6) → (3E,5E,7E)-8,9,9-trimethyl-2-oxodeca-3,5,7-trienyl acetate (1268380-58-0)

Conditions	Yield
Stage #1: furfurylacetate; 3-tert-butyl-3-methylcycloprop-1-ene With C16H26AuNP(1+)*F6Sb(1-) In dichloromethane at 25℃; for 0.25h; Inert atmosphere; Stage #2: With iodine In dichloromethane for 1h; Inert atmosphere;	78%

methanol (67-56-1) + furfurylacetate (623-17-6) → 2,5-dimethoxy-2,5-dihydrofurfuryl acetate (41991-02-0)

Conditions	Yield
With ammonium bromide at 5 - 10℃; electrolysis: constant current = 2.5 A, amount of electricity passed = 2 F/mol;	80%
With ammonium bromide; pyrographite at -20℃; Reagens Nr. 4: methanol. Natriummethylat / Elektrolyse und Behandlung des Reaktionsprodukts mit Acetanhydrid und Pyridin;
With bromine; potassium acetate at -7℃;
With bromine; potassium carbonate

furfurylacetate (623-17-6) + N-acetyl-L-lysine methyl ester → methyl (S)-2-acetamido-6-(2-methylene-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

Conditions	Yield
Stage #1: furfurylacetate With N-Bromosuccinimide In tetrahydrofuran; aq. phosphate buffer for 1h; Cooling with ice; Stage #2: N-acetyl-L-lysine methyl ester In tetrahydrofuran; aq. phosphate buffer at 20℃;	69%

Upstream product

• 613-75-2 (furan-2-yl)methylene diacetate 
• 98-00-0 (2-furyl)methyl alcohol 
• 108-05-4 vinyl acetate 
• 10226-94-5 ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate 
• 98-01-1 furfural 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 74-88-4 methyl iodide 
• 108-22-5 Isopropenyl acetate 
• 110-19-0 2-methylpropyl acetate 
• 10343-13-2 benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 2846-62-0 (furan-2-ylmethoxy)trimethylsilane 

Downstream Products

• 96-47-9 2-methyltetrahydrofuran 
• 59-87-0 nitrofurazone 
• 6331-95-9 (+/-)-(1RS,2SR,6RS,7SR)-(3,5-dioxo-4,10-dioxatricyclo[5.2.1.0^2,6]dec-8-en-1-yl)methyl acetate 
• 534-22-5 2-methylfuran 
• 626-95-9 1,4-Pentanediol 
• 96-41-3 Cyclopentanol 
• 1087784-37-9 5-methoxycarbonylmethyl-furan-2-carboxylic acid methyl ester 
• 162337-80-6 methyl 3-methoxycarbonylfuran-2-ylacetate 
• 111-29-5 1 ,5-pentanediol 
• 5343-92-0 1,2-pentanediol 
• 71-41-0 pentan-1-ol 
• 98-01-1 furfural 

Relevant articles and documents

Preparation method of furfuryl alcohol ester

The invention discloses a preparation method of furfuryl alcohol ester. The preparation method comprises the following step: subjecting furfural, a bifunctional catalyst, an acylation reagent and a solvent to reacting under hydrogen pressure to obtain furfuryl alcohol ester. The method provided by the invention has the advantages of high selectivity, few byproducts, mild reaction conditions and certain industrial application prospect.

Conversion of furfural to 2-methylfuran over CuNi catalysts supported on biobased carbon foams

In this study, carbon foams prepared from the by-products of the Finnish forest industry, such as tannic acid and pine bark extracts, were examined as supports for 5/5% Cu/Ni catalysts in the hydrotreatment of furfural to 2-methylfuran (MF). Experiments were conducted in a batch reactor at 503 K and 40 bar H2. Prior to metal impregnation, the carbon foam from tannic acid was activated with steam (S1), and the carbon foam from pine bark extracts was activated with ZnCl2 (S2) and washed with acids (HNO3 or H2SO4). For comparison, a spruce-based activated carbon (AC) catalyst and two commercial AC catalysts as references were investigated. Compressive strength of the foam S2 was 30 times greater than that of S1. The highest MF selectivity of the foam-supported catalysts was 48 % (S2, washed with HNO3) at a conversion of 91 %. According to the results, carbon foams prepared from pine bark extracts can be applied as catalyst supports.

Preparation method of alkyl furfuryl alcohol ester

The invention discloses a preparation method of alkyl furfuryl alcohol ester, which comprises the following step of reacting furfuryl alcohol, an esterification catalyst, an acylation reagent, an acid-binding agent and a solvent to obtain the alkyl furfuryl alcohol ester. The method provided by the invention has the advantages of high selectivity, few byproducts, mild reaction conditions and certain industrial application prospect.