Tetrahydrofurfuryl acetate

Base Information

• Chemical Name: Tetrahydrofurfuryl acetate
• CAS No.: 637-64-9
• Deprecated CAS: 52630-61-2
• Molecular Formula: C7H12O3
• Molecular Weight: 144.17
• Hs Code.: 2932190090
• European Community (EC) Number: 211-296-8
• NSC Number: 4872
• UNII: I1PIW4REZU
• DSSTox Substance ID: DTXSID30862335
• Nikkaji Number: J101.366A
• Wikipedia: Tetrahydrofurfuryl_acetate
• Wikidata: Q27280260
• Metabolomics Workbench ID: 44725
• ChEMBL ID: CHEMBL2287522
• Mol file: 637-64-9.mol

Synonyms:TETRAHYDROFURFURYL ACETATE;637-64-9;oxolan-2-ylmethyl acetate;2-Acetoxymethyloxolane;(Tetrahydrofuran-2-yl)methyl acetate;2-Furanmethanol, tetrahydro-, acetate;2-(Acetoxymethyl)tetrahydrofuran;Furfuryl alcohol, tetrahydro-, acetate;Tetrahydro-2-furanmethyl acetate;Tetrahydro-2-furanmethanol acetate;FEMA No. 3055;2-Furanmethanol, tetrahydro-, 2-acetate;Tetrahydro-2-furylmethyl acetate;I1PIW4REZU;UNII-I1PIW4REZU;NSC 4872;EINECS 211-296-8;(oxolan-2-yl)methyl acetate;AI3-21209;NSC-4872;MFCD00022478;TETRAHYDROFURFURYLACETATE;SCHEMBL118897;2-(ACETOXYMETHYL)OXOLANE;CHEMBL2287522;AAQDYYFAFXGBFZ-UHFFFAOYSA-;FEMA 3055;Tetrahydrofurfuryl acetate, 97%;DTXSID30862335;NSC4872;CHEBI:169190;Tetrahydro-2-furanylmethyl acetate;Tetrahydro-2-furanylmethyl acetate #;AKOS005206826;2-Furanmethanol,tetrahydro-, 2-acetate;TETRAHYDROFURFURYL ACETATE [INCI];Tetrahydrofurfuryl acetate, >=97%, FG;(+/-)-TETRAHYDROFURFURYL ACETATE;AS-62668;SY036811;TETRAHYDROFURFURYL ACETATE, [FHFI];CS-0155423;FT-0657839;T0105;TETRAHYDROFURFURYL ACETATE, (+/-)-;Furfuryl alcohol, tetrahydro-, acetate (8CI);F16574;A834517;Q27280260

Chemical Property of Tetrahydrofurfuryl acetate

Chemical Property:

• Vapor Pressure: 0.249mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Boiling Point: 194-195 °C753 mm Hg(lit.)
• Flash Point: 184 °F
• PSA: 35.53000
• Density: 1.061 g/mL at 25 °C(lit.)
• LogP: 0.72850
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

98% ^*data from raw suppliers

Tetrahydrofurfuryl acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: S23:Do not inhale gas/fumes/vapour/spray.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=O)OCC1CCCO1
• Chemical Characteristics: Reacts with polarity-reversal catalysts to undergo radical-chain racemization.
• Uses: Tetrahydrofurfuryl acetate serves as a versatile compound in food flavoring and cosmetics, imparting distinctive fruity ethereal flavors. Generally accepted as safe in the USA. Typical usage levels are 2 ppm in drinks, 8 ppm in ice cream, and 20 ppm in baked products and confectionery.
• Production Methods: Produced by reacting tetrahydrofurfuryl alcohol with acetic anhydride.
• References: [1] Radical-chain racemisation of tetrahydrofurfuryl acetate under conditions of polarity-reversal catalysis: possible implications for the radical-induced strand cleavage of DNA; DOI 10.1039/A801381K; [2] Thermophilic lactic acid bacteria affect the characteristics of sourdough and whole-grain wheat bread; DOI 10.1016/j.fbio.2020.100791

Technology Process of Tetrahydrofurfuryl acetate

There total 17 articles about Tetrahydrofurfuryl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

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

Guidance literature:

With phosphoric acid; In acetonitrile; at 50 ℃; for 3h;

DOI:10.1021/acs.joc.1c00102

Reference yield: 87.0%

n-Pent-4-enyl alcohol (821-09-0) + acetic acid (64-19-7,77671-22-8) → tetrahydrofurfuryl acetate (637-64-9)

Guidance literature:

With dihydrogen peroxide; potassium iodide; at 20 ℃; for 4h;

DOI:10.3184/174751915X14399788140213

Reference yield: 86.0%

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

Guidance literature:

With pyridine; In chloroform; for 2h; Ambient temperature;

DOI:10.1021/jo00220a034

upstream raw materials:

Tetrahydrofurfuryl alcohol

sodium acetate

acetic anhydride

acetic acid

Downstream raw materials:

Methyl-5-O-acetyl-2,3-dideoxy-pentofuranosid

succinaldehyde bis(dimethyl acetal)

Acetic acid 2-methoxy-tetrahydro-furan-2-ylmethyl ester

Tetrahydrofurfuryl alcohol

Refernces

• 1、 Hayashi, Hiroyuki,Yasukochi, Shotaro,Sakamoto, Tatsuhiro,Hatano, Manabu,Ishihara, Kazuaki. "Insight into the Mechanism of the Acylation of Alcohols with Acid Anhydrides Catalyzed by Phosphoric Acid Derivatives". . p. 5197 - 5212. Retrieved 2021/04/12.
• 2、 Hu, Xun,Kadarwati, Sri,Song, Yao,Li, Chun-Zhu. "Simultaneous hydrogenation and acid-catalyzed conversion of the biomass-derived furans in solvents with distinct polarities". . p. 4647 - 4656. Retrieved 2016/01/29.