637-64-9

Basic information

• Product Name: TETRAHYDROFURFURYL ACETATE
• Synonyms: FEMA 3055;2-(ACETOXYMETHYL)OXOLANE;2-(ACETOXYMETHYL)TETRAHYDROFURAN;TETRAHYDROFURFURYL ACETATE;Tetrahydro-2-furanmethanol acetate;TETRAHYDROFURFURYL ACETATE 97+%;Tetrahydrofurfurylacetate,98%;2-Furanmethanol, tetrahydro-, acetate
• CAS NO: 637-64-9
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.17
• EINECS: 211-296-8
• Product Categories: ester Flavor;Building Blocks;C4 to C7;Chemical Synthesis;Furans;Heterocyclic Building Blocks
• Mol File: 637-64-9.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 194-195 °C753 mm Hg(lit.)
• Flash Point: 184 °F
• Appearance: /
• Density: 1.061 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.249mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 383629
• CAS DataBase Reference: TETRAHYDROFURFURYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAHYDROFURFURYL ACETATE(637-64-9)
• EPA Substance Registry System: TETRAHYDROFURFURYL ACETATE(637-64-9)

Safety Data

• Safety Statements: S23:Do not inhale gas/fumes/vapour/spray.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 637-64-9(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 637-64-9 differently. You can refer to the following data:
1. Colorless liquid. Soluble in water, alcohol, ether, and chloroform. Combustible.
2. Tetrahydrofurfuryl acetate has a faint, fruity, ethereal odor, somewhat similar to acetic acid (reminiscent of methyl formate). It has a sweet, ethereal, deep, fruit-like flavor.

Uses

Tetrahydrofurfuryl Acetate is a synthetic flavoring agent that is a stable, colorless liquid of slightly fruity odor. it should be stored in glass or tin containers. it is used in fruit flavors for application in candy and baked goods at 2–20 ppm.

Preparation

By acetylation of the corresponding alcohol with acetic anhydride, acetyl chloride, or acetic acid and mineral acids.

Taste threshold values

Taste characteristics at 100 ppm: sweet, brown, caramel-like with nutty, rummy nuances.

General Description

The radical-chain racemisation of (R)-tetrahydrofurfuryl acetate has been studied.

InChI:InChI=1/C7H12O3/c1-6(8)10-5-7-3-2-4-9-7/h7H,2-5H2,1H3/t7-/m0/s1

Synthetic route

Tetrahydrofurfuryl alcohol (97-99-4) + acetic anhydride (108-24-7) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With phosphoric acid In acetonitrile at 50℃; for 3h;	99%
With zirconium sulfophenyl phosphonate In dichloromethane at 20℃; for 3h; Acetylation;	97%
With aluminum triflate at 20℃; for 0.00555556h;	96%

n-Pent-4-enyl alcohol (821-09-0) + acetic acid (64-19-7) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With dihydrogen peroxide; potassium iodide at 20℃; for 4h;	87%

Tetrahydrofurfuryl alcohol (97-99-4) + acetyl chloride (75-36-5) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With pyridine In chloroform for 2h; Ambient temperature;	86%
durch Veresterung;

Tetrahydrofurfuryl alcohol (97-99-4) + acetic acid (64-19-7) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With iron(III) chloride at 20℃; for 9h; Esterification;	85%
With sulfuric acid durch Veresterung;
With hydrogenchloride durch Veresterung;
With molecular sieve at 120℃; for 8h;

ethyl acetate (141-78-6) + 2-Methoxymethoxymethyl-tetrahydro-furan (161617-56-7) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With indium (III) iodide for 16h; Heating;	85%

tetrahydrofurfuryl tetrahydropyranyl ether (710-14-5) + acetyl chloride (75-36-5) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With sodium iodide In acetonitrile for 6h; Ambient temperature;	84%

n-Pent-4-enyl alcohol (821-09-0) + thallium(III) triacetate (2570-63-0) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
In benzene Ambient temperature;	83%
In benzene Mechanism; Heating; intramolecular cyclization of other unsaturated alcohols;	83%

Tetrahydrofurfuryl alcohol (97-99-4) + N,N-dimethyl acetamide (127-19-5) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With cerium(IV) oxide at 155℃; for 36h; Inert atmosphere; Sealed tube;	82%

n-Pent-4-enyl alcohol (821-09-0) + thallium(III) triacetate (2570-63-0) → tetrahydro-2H-pyran-3-yl acetic acid (3265-65-4) + tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
In acetic acid at 60℃; for 0.333333h;	A 32% B 30%
In acetic acid at 60℃; for 0.333333h; Mechanism; intramolecular cyclization of other unsaturated alcohols;	A 32% B 30%

Tetrahydrofurfuryl alcohol (97-99-4) + sodium acetate (127-09-3) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With acetic acid; benzene

furfural (98-01-1) + acetic anhydride (108-24-7) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With nickel; toluene-4-sulfonic acid Hydrogenation;

furfurylidene diacetate → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With platinum Hydrogenation;

(furan-2-yl)methylene diacetate (613-75-2) + nickel /kieselguhr → 2-methyltetrahydrofuran (96-47-9) + gem-diacetate de tetrahydrofurfural (5331-61-3) + tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
at 160℃; Hydrogenation;

methyl tetrahydrofurfuryl ether (19354-27-9) + acetyl chloride (75-36-5) → tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With bismuth(III) chloride In dichloromethane at 20℃; for 2h;

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With palladium on activated charcoal; hydrogen In Methyl formate at 170℃; under 52505.3 Torr; for 1h; Autoclave;	A 10%Chromat. B 34.7%Spectr.

furfural (98-01-1) → Tetrahydrofurfuryl alcohol (97-99-4) + tetrahydrofuran-2-carbaldehyde (7681-84-7) + tetrahydrofurfuryl acetate (637-64-9)

Conditions	Yield
With palladium on activated charcoal; hydrogen In Methyl formate at 170℃; under 52505.3 Torr; for 1h; Autoclave;	A 34.5%Chromat. B 10.3 %Spectr. C 24.1%Spectr.

tetrahydrofurfuryl acetate (637-64-9) → Tetrahydrofurfuryl alcohol (97-99-4)

Conditions	Yield
With ytterbium(III) triflate In isopropyl alcohol for 8h; Deacetylation; Heating;	95%
With MetProLeuAspGlnProThrAlaAlaPheLeuAspPheLeuArgSerSerGlyGlyLysProLeuTyrGluLeuProLeuAlaGluAlaArgAlaAlaMetAlaMetGlySerGlnLeuGlyAlaProProAlaAspValGlyArgIleValAspArgSerIleAspValProGlyGlyAlaValAlaLeuArgIleTyrThrProAlaThrThrLysAlaGlyGlyLeuLeuProAlaIleLeuGlnTyrHisGlyGlyGlyPheValLeuGlyAsnLeuAspThrHisGluSerIleAlaArgPheTyrCysAlaHisAlaGlyAlaValValIleSerValAspTyrArgLeuAlaProGluHisArgPheProThrGlnValGluAspSerPheAlaAlaLeuThrTrpValSerGluHisAlaSerGluLeuGlyValAspProAlaArgValAlaValAlaGlyAspSerAlaGlyGlyAsnLeuAlaThrValMetCysLeuLeuAlaLysAlaArgGlyGlyProArgIleAlaCysGlnAlaLeuLeuTyrProValAlaAspPheArgProGluGlnValTyrAlaSerHisAlaGlnPheGlyAspGlySerTyrPheLeuSerSerLysAspMetAspTrpPheArgAlaSerTyrPheThrAspValAlaSerGlnAlaAlaGluProThrAlaSerProMetAlaThrThrAspLeuSerGlyLeuProProAlaLeuValThrThrAlaGlyCysAspProLeuLeuAspGluGlyArgAlaTyrAlaAspArgLeuLysAlaAlaGlyValProValAspTyrArgCysPheGluThrThrIleHisAlaCysAlaSerPheAlaGlyThrIleProAlaGlyLeuAspMetLeuGlyPheValAlaAspTrpLeuAlaAlaHisThrLys In aq. phosphate buffer at 37℃; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;

acetyl chloride (75-36-5) + tetrahydrofurfuryl acetate (637-64-9) → 1,2-diacetoxy-5-iodopentane

Conditions	Yield
With sodium iodide In acetonitrile for 24h; Ambient temperature;	88%

tetrahydrofurfuryl acetate (637-64-9) → 2,5-Dibromo-1-pentanol acetate (30727-26-5)

Conditions	Yield
With trimethylsilyl bromide for 48h; Heating;	87%

isoquinoline (119-65-3) + tetrahydrofurfuryl acetate (637-64-9) → (5-(isoquinolin-1-yl)tetrahydrofuran-2-yl)methyl acetate

Conditions	Yield
With sodium persulfate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid In water at 23℃; for 2h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; regioselective reaction;	77%
With ammonium persulfate; 1-hydroxy-pyrrolidine-2,5-dione In water at 40℃; for 24h; Green chemistry;	70%
With ethanol; bis-[(trifluoroacetoxy)iodo]benzene In dimethyl sulfoxide; 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; diastereoselective reaction;	60%

methanol (67-56-1) + tetrahydrofurfuryl acetate (637-64-9) → Methyl-5-O-acetyl-2,3-dideoxy-pentofuranosid (14152-75-1, 26528-66-5) + Acetic acid 2-methoxy-tetrahydro-furan-2-ylmethyl ester (112570-93-1)

Conditions	Yield
In acetic acid for 5.4h; electrolysis: platinum-plate anode, carbon-rod cathode, Et4NOTs, 30 F/mol, 0.5 A, 20 V;	A 73% B 20%

pivaloyl chloride (3282-30-2) + tetrahydrofurfuryl acetate (637-64-9) → 2,2-Dimethyl-propionic acid 1-acetoxymethyl-4-iodo-butyl ester (82131-14-4)

Conditions	Yield
With copper; sodium iodide In acetonitrile for 24h; Ambient temperature;	73%

tetrahydrofurfuryl acetate (637-64-9) → acetoxy-2 diiodo-1,5 pentane (113401-57-3)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 3h;	73%

pivaloyl chloride (3282-30-2) + tetrahydrofurfuryl acetate (637-64-9) + sodium iodide → 2,2-Dimethyl-propionic acid 1-acetoxymethyl-4-iodo-butyl ester (82131-14-4)

Conditions	Yield
In acetonitrile for 23h; Ambient temperature;	71%

tetrahydrofurfuryl acetate (637-64-9) → (5-oxotetrahydrofuran-2-yl)methyl acetate (5904-80-3, 79580-69-1, 112607-21-3, 112709-12-3)

Conditions	Yield
Stage #1: tetrahydrofurfuryl acetate With [bis(acetoxy)iodo]benzene In nitromethane at 0℃; Stage #2: With tert.-butylhydroperoxide In decane; nitromethane at 0 - 25℃; for 12h; Solvent;	65%
With iron(II) triflate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen at 60℃; under 760.051 Torr; for 48h; Catalytic behavior; Green chemistry; chemoselective reaction;	5.4%

toluene-4-sulfonamide (70-55-3) + tetrahydrofurfuryl acetate (637-64-9) → C14H19NO5S + C14H19NO5S

Conditions	Yield
With [bis(acetoxy)iodo]benzene; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 40℃; for 4h;	A 40% B 30%

methanol (67-56-1) + tetrahydrofurfuryl acetate (637-64-9) → Methyl-5-O-acetyl-2,3-dideoxy-pentofuranosid (14152-75-1, 26528-66-5) + succinaldehyde bis(dimethyl acetal) (6922-39-0) + Acetic acid 2-methoxy-tetrahydro-furan-2-ylmethyl ester (112570-93-1)

Conditions	Yield
for 5.4h; electrolysis: platinum-plate anode, carbon-rod cathode, Et4NOTs, 50 F/mol, 0.5 A, 20 V;	A 18% B 23% C 5%

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2) + tetrahydrofurfuryl acetate (637-64-9) → 8-(5-acetoxymethyl-tetrahydro-furan-2-yl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione (51015-47-5)

Conditions	Yield
With di-tert-butyl peroxide In water for 24h; Irradiation;

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2) + tetrahydrofurfuryl acetate (637-64-9) → 8-(2-acetoxymethyl-tetrahydro-furan-2-yl)-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione (51015-48-6)

Conditions	Yield
With di-tert-butyl peroxide In water for 24h; Irradiation;

Acetyl bromide (506-96-7) + tetrahydrofurfuryl acetate (637-64-9) → 1,2-diacetoxypentane (81947-72-0, 155667-35-9, 155667-36-0)

Conditions	Yield
(i) ZnCl2, (ii) LiAlH4, iPr2O, (iii) Ac2O; Multistep reaction;

diethylamine (109-89-7) + acetyl chloride (75-36-5) + tetrahydrofurfuryl acetate (637-64-9) → 1,2-diacetoxy-5-diethylamino-pentane (20473-83-0)

Conditions	Yield
(i), (ii) /BRN= 605268/; Multistep reaction;

Upstream product

• 97-99-4 Tetrahydrofurfuryl alcohol 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 710-14-5 tetrahydrofurfuryl tetrahydropyranyl ether 
• 98-01-1 furfural 
• 127-19-5 N,N-dimethyl acetamide 
• 141-78-6 ethyl acetate 
• 161617-56-7 2-Methoxymethoxymethyl-tetrahydro-furan 
• 613-75-2 (furan-2-yl)methylene diacetate 
• 821-09-0 n-Pent-4-enyl alcohol 
• 2570-63-0 thallium(III) triacetate 
• 19354-27-9 methyl tetrahydrofurfuryl ether 

Downstream Products

• 14152-75-1 Methyl-5-O-acetyl-2,3-dideoxy-pentofuranosid 
• 6922-39-0 succinaldehyde bis(dimethyl acetal) 
• 112570-93-1 Acetic acid 2-methoxy-tetrahydro-furan-2-ylmethyl ester 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 81947-72-0 1,2-diacetoxypentane 

Relevant articles and documents

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Esterification of Tertiary Amides by Alcohols Through C?N Bond Cleavage over CeO2

CeO2 has been found to promote ester forming alcoholysis reactions of tertiary amides. The present catalytic system is operationally simple, recyclable, and it does not require additives. The esterification process displays a wide substrate scope (>45 examples; up to 93 % isolated yield). Results of a density functional theory (DFT) study combined with in situ FT-IR observations indicate that the process proceeds through rate limiting addition of a CeO2 lattice oxygen to the carbonyl group of the adsorbed acetamide species with energy barrier of 17.0 kcal/mol. This value matches well with experimental value (17.9 kcal/mol) obtained from analysis of the Arrhenius plot. Further studies by in situ FT-IR and temperature programmed desorption using probe molecules demonstrate that both acidic and basic properties are important, and consequently, CeO2 showed the best performance for the C?N bond cleavage reaction.

Oxidative acetoxylactonisation of alkenoic acids using H2O2 in acetic acid catalysed by KI

In the presence of a catalytic amount of KI in combination with H2O2, a convenient catalytic procedure has been developed for the direct preparation of acetoxylactones from alkenoic acids in acetic acid at room temperature which provides the corresponding cyclic products in good yields. This novel methodology mediated by an in situ generated hypervalent iodine intermediate extends the catalytic application of KI in organic synthesis.