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623-17-6

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623-17-6 Usage

Description

Furfuryl acetate is the ester formed by the esterification between furfuryl alcohol and acetate. It can be used as a food spices and flavoring ingredient. It can also be used as the intermediate of dye, resin and spices. It is found in alcoholic beverage. Furfuryl acetate is present in wheat bread, crisp bread, roasted onion, pork liver, beer, rum, cocoa and coffee.

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).

Chemical Properties

Furfuryl acetate is a colorless to light yellow liquid with a ethereal foral fruity odor.

Occurrence

Reported found in roasted almonds, beer, white bread, cocoa, coffee, roasted flberts, roasted onion, roasted peanuts, cooked pork liver, wheaten and crispbread, oats, rum, beer, licorice, dried bonito, sukiyaki and Bourbon vanilla

Uses

Furfuryl acetate is a flavoring ingredient. It was used in the synthesis of 5-acetoxymethyl-2-vinylfuran and 5-hydroxymethyl-2-vinylfuran via Vilsmeier-Haack and Wittig reactions.

General Description

Colorless to clear yellow or orange liquid with a pungent odor.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 623-17-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 3 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 623-17:
(5*6)+(4*2)+(3*3)+(2*1)+(1*7)=56
56 % 10 = 6
So 623-17-6 is a valid CAS Registry Number.

623-17-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A15285)  Furfuryl acetate, 97%   

  • 623-17-6

  • 25g

  • 326.0CNY

  • Detail
  • Alfa Aesar

  • (A15285)  Furfuryl acetate, 97%   

  • 623-17-6

  • 100g

  • 972.0CNY

  • Detail
  • Alfa Aesar

  • (A15285)  Furfuryl acetate, 97%   

  • 623-17-6

  • 500g

  • 4352.0CNY

  • Detail
  • Aldrich

  • (166200)  Furfurylacetate  99%

  • 623-17-6

  • 166200-25G

  • 269.10CNY

  • Detail

623-17-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Furfuryl acetate

1.2 Other means of identification

Product number -
Other names furan-2-ylmethyl acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:623-17-6 SDS

623-17-6Synthetic route

furfurylacetate
623-17-6

furfurylacetate

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

(E)-(5-(3-oxo-3-phenylprop-1-enyl)furan-2-yl)methyl acetate
1440662-73-6

(E)-(5-(3-oxo-3-phenylprop-1-enyl)furan-2-yl)methyl acetate

Conditions
ConditionsYield
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

furfurylacetate

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
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

furfurylacetate

2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

4-(furan-2-ylmethyl)-2,6-dimethylphenol

4-(furan-2-ylmethyl)-2,6-dimethylphenol

Conditions
ConditionsYield
With Montmorillonite In dichloromethane at 60℃; Sealed tube;35%
maleic anhydride
108-31-6

maleic anhydride

furfurylacetate
623-17-6

furfurylacetate

(+/-)-(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

(+/-)-(1RS,2SR,6RS,7SR)-(3,5-dioxo-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-1-yl)methyl acetate

Conditions
ConditionsYield
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

furfurylacetate

methoxybenzene
100-66-3

methoxybenzene

2<(4-Methoxylphenyl)methyl>furan

2<(4-Methoxylphenyl)methyl>furan

Conditions
ConditionsYield
With bis(trifluoromethanesulfonyl)amide In dichloromethane at 20℃; for 0.333333h;70 %Chromat.
furfurylacetate
623-17-6

furfurylacetate

A

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

B

1,2-pentanediol
5343-92-0

1,2-pentanediol

C

pentan-1-ol

pentan-1-ol

Conditions
ConditionsYield
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

furfurylacetate

methyl phosphite

methyl phosphite

acetic acid 5-(dimethoxy-phosphoryl)-furan-2-ylmethyl ester

acetic acid 5-(dimethoxy-phosphoryl)-furan-2-ylmethyl ester

Conditions
ConditionsYield
With manganese triacetate In acetic acid at 80℃; for 3h;86%
furfurylacetate
623-17-6

furfurylacetate

bis(pinacol)diborane

bis(pinacol)diborane

(CH3)4C2O2BCH2C4H3O

(CH3)4C2O2BCH2C4H3O

Conditions
ConditionsYield
With gold-nanoparticles supported on TiO2 In 1,4-dioxane at 60℃; for 2h;53%
furfurylacetate
623-17-6

furfurylacetate

anthranilic acid
118-92-3

anthranilic acid

1-acetoxymethyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene
117078-27-0

1-acetoxymethyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene

Conditions
ConditionsYield
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-dimethoxyethane45.8%
furfurylacetate
623-17-6

furfurylacetate

3-tert-butyl-3-methylcycloprop-1-ene
137073-16-6

3-tert-butyl-3-methylcycloprop-1-ene

(3E,5E,7E)-8,9,9-trimethyl-2-oxodeca-3,5,7-trienyl acetate
1268380-58-0

(3E,5E,7E)-8,9,9-trimethyl-2-oxodeca-3,5,7-trienyl acetate

Conditions
ConditionsYield
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

methanol

furfurylacetate
623-17-6

furfurylacetate

2,5-dimethoxy-2,5-dihydrofurfuryl acetate
41991-02-0

2,5-dimethoxy-2,5-dihydrofurfuryl acetate

Conditions
ConditionsYield
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

furfurylacetate

N-acetyl-L-lysine methyl ester

N-acetyl-L-lysine methyl ester

methyl (S)-2-acetamido-6-(2-methylene-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

methyl (S)-2-acetamido-6-(2-methylene-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

Conditions
ConditionsYield
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%

623-17-6Relevant articles and documents

ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS

-

Paragraph 0013; 0028, (2021/01/29)

An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.

Preparation method of furfuryl alcohol ester

-

Paragraph 0028-0029; 0036-0037, (2021/02/10)

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.

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot

Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir

supporting information, p. 16702 - 16707 (2020/10/27)

A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is

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