14086-08-9

Usage

Uses

Used in Foundry Industry:
Furfuryl alcohol is utilized as a key component in the production of furan resins, which are extensively used in the foundry industry for manufacturing foundry sand. These resins provide superior bonding properties, enhancing the strength and durability of sand molds and cores in metal casting processes.
Used in Wood Adhesives:
In the woodworking industry, furfuryl alcohol-based furan resins serve as effective adhesives. They offer excellent adhesion, water resistance, and heat resistance, making them ideal for various applications such as plywood, particleboard, and fiberboard production.
Used as a Flavoring Agent in the Food Industry:
Furfuryl alcohol is employed as a flavoring agent in the food industry, imparting unique taste and aroma characteristics to various food products. Its use is carefully regulated to ensure safety and quality standards are met.
Used as a Solvent in Printing Inks and Coatings:
In the printing and coatings industry, furfuryl alcohol functions as a solvent, aiding in the application and drying of inks and coatings. Its solvent properties contribute to improved performance and durability of the final product.
Used as a Preservative in the Synthesis of Varnishes:
Furfuryl alcohol is used as a preservative in the synthesis of varnishes, enhancing their shelf life and protecting them from degradation. This ensures the varnishes maintain their quality and performance over time.
However, it is important to note that exposure to furfuryl alcohol has been associated with certain health risks, including irritation to the skin, eyes, and respiratory system, as well as potential carcinogenic effects. Therefore, proper safety measures and precautions should be taken during its handling and use.

Upstream product

• 13265-84-4 D-glucal 
• 17678-19-2 2-(2-hydroxyacetyl)furan 
• 21193-75-9 D-galactal 
• 98-01-1 furfural 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 1487-18-9 (furan-2-yl)ethylene 
• 19377-75-4 1-(furan-2-yl)ethane-1,2-diol 
• 100-52-7 benzaldehyde 
• 58394-31-3 1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose 
• 58238-40-7 (1R,2R,4R,6R)-3,7,9-trioxatricyclo[4.2.1.0^2,4]nonan-5-one 
• 37112-31-5 levoglucosenone 
• 1040427-99-3 (R)-furan-2-yl-hydroxyacetic acid butyl ester 
• 1578-26-3 1-(2'-furyl)-2-trimethylsilanylethan-1-ol 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 33647-74-4 6-hydroxy-(2R)-2-hydroxymethyl-2H-pyran-3(6H)-one 
• 14086-10-3 C₂₀H₁₆O₅ 
• 139545-83-8 2-<1,2-bis-(tert-butyldiphenylsiloxy)ethyl>furan 
• 124067-17-0 (2R) 1-<(t-butyldiphenylsilyl)oxy>-2-furanylethanol 
• 222986-42-7 (2S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate 
• 222986-44-9 (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate 
• 222986-50-7 (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-ethoxycarbonyloxy-5,6-dihydro-2H-pyran-2-yl benzoate 
• 222986-52-9 1-O-benzoyl-6-O-tert-butyldimethylsilyl-3-O-ethoxycarbonyl-α-D-mannopyranose 
• 260426-00-4 (2S,6R)-6-(pivaloyloxymethyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl benzoate 
• 301806-03-1 (2S,5S,6R)-6-(pivaloyloxymethyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl benzoate 
• 260426-01-5 (2S,5S,6R)-6-(pivaloyloxymethyl)-5-pivaloyloxy-5,6-dihydro-2H-pyran-2-yl benzoate 
• 260425-94-3 (2S,5S,6R)-6-(tert-butyldimethylsilanyloxymethyl)-5-(tert-butyldimethylsilanyloxy)-5,6-dihydro-2H-pyran-2-yl benzoate 
• 301806-05-3 4-nitro-benzoic acid 2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(2,2-dimethyl-propionyloxy)-3,6-dihydro-2H-pyran-3-yl ester 
• 27948-61-4 (R)-(+)-1-(2-furyl)ethanol 

Relevant academic research and scientific papers

Efficient and rapid experimental procedure for the synthesis of furan diol from d-glucal using ionic liquid

A new efficient and rapid experimental method and product isolation procedure as well as easy recyclable reaction media is expected to contribute to the development of a green strategy for the synthesis of furan diol from d-glucal. We determine the best conditions of reaction, minimizing the toxicity and finding an environmentally more acceptable process, using [Bmim][MSO4]/InCl3·3H2O as a new solvent system under extremely mild conditions, providing high yields with a dramatic enhancement of reaction rate.

Metal-catalyzed transformation of D-glucal to optically active furan diol

The treatment of D-glucal with a catalytic amount of Sm(OTf)3 or RuCl2(PPh3)3 in the presence of 1 equiv. of H2O afforded optically active furan diol in good yield under mild conditions.

Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses

The enantioselective syntheses of C-6 O-TBS- and N-Cbz-protected 2-deoxy- and 2,3-dideoxysugars have been achieved in 6-8 steps from furfural. A combination of chemo-, regio-, and diastereoselective oxidation and reduction reactions produced deoxysugars w

Montmorillonite clay catalyzed synthesis of enantiomerically pure 1,2,3,4-tetrahydroquinolines

Arylamines undergo smooth cyclization with 2-deoxy-D-ribose on the surface of montmorillonite KSF clay under mild conditions to afford the corresponding sugar-derived chiral tetrahydroquinolines in high yields with moderate diastereoselectivity. The assignment of the stereochemistry of the product was achieved by various NMR studies. Georg Thieme Verlag Stuttgart.

Kinetic resolution of racemic 2-(2-furyl)-2-hydroxyethyl acetate in the presence of PS lipase

Kinetic resolution of racemic 2-(2-furyl)-2-hydroxyethyl acetate by transesterification with vinyl acetate in the presence of Amano PS lipase, yielding (1R)-1-(2-furyl)ethane-1,2-diol diacetate with 98% ee and (2S)-2-(2-furyl)-2-hydroxyethyl acetate with

Diastereoselective Weitz-Scheffer epoxidation of levoglucosenone for the synthesis of isolevoglucosenone and derivatives

High-yielding epoxidation conditions for the cellulose pyrolysis product (?)-levoglucosenone (LGO) and 3-aryl derivatives of LGO have been developed. The reaction of LGO with hydrogen peroxide/base is known to give a Baeyer-Villiger reaction, however, it was found that the reactions of LGO or derivatives with tert-butylhydroperoxide/base affords solely epoxides through the Weitz-Scheffer reaction. A critical parameter in the successful isolation of the epoxide from LGO was to avoid all contact with water or alcohols during the reaction and workup. The epoxide products were reacted under Wharton conditions affording allylic alcohols and subsequent oxidation led to isolevoglucosenone or 3-arylisolevoglucosenone derivatives. Previously unreported reactions on isolevoglucosenone were then investigated.

Kinetic Resolution of 1,2-Diols via NHC-Catalyzed Site-Selective Esterification

A kinetic resolution of 1,2-diols bearing both a secondary and a primary alcohol motif through an N-heterocyclic carbene-catalyzed oxidative acylation reaction has been developed. A site- and enantioselective esterification reaction is involved for this process. Both the monoacylated diols obtained and the remaining enantioenriched 1,2-diols are versatile building blocks for the preparation of functional molecules with proven biological activities.

Synthesis of (-)-muricatacin from tri- O -acetyl- d -glucal

The total synthesis of (-)-muricatacin is achieved using commercially available tri-O-acetyl-d-glucal as the starting material. The structure of the intermediate chiral butenolide is established unambiguously by X-ray crystallographic analysis, which consequently leads to correction of a previous structural misassignment. Georg Thieme Verlag Stuttgart. New York.

Synthesis of carba analogs of 6-O-(benzyl)-d-allal- and -d-galactal-derived allyl epoxides and evaluation of the regio- and stereoselective behavior in nucleophilic addition reactions

The new racemic diastereoisomeric epoxides 6α and 6β, the carba analogs of the corresponding d-galactal- and d-allal-derived allyl epoxides have been synthesized and their regio- and stereoselective behavior examined in addition reactions with model O-, C-, N-, and S-nucleophiles. The results have indicated that epoxide 6β has a pronounced tendency toward anti-1,2-addition, whereas epoxide 6α shows interesting levels of syn- and/or anti-1,4-addition processes. A chiral recognition process found with epoxide 6β, turned out to be consistently reduced in epoxide 6α. All the results have been rationalized on the basis of conformational, steric, and stereoelectronic effects.

Developing a diastereoselective intramolecular [4 + 3] cycloaddition of nitrogen-stabilized oxyallyl cations derived from N-sulfonyl-substituted allenamides

Efforts toward achieving a practical and diastereoselective intramolecular [4 + 3] cycloaddition of nitrogen-stabilized oxyallyl cations with tethered dienes are described. Epoxidation of N-sulfonyl substituted allenamides with dimethyldioxirane (DMDO) generates nitrogen-stabilized oxyallyl cations that readily undergo stereoselective [4 + 3] cycloaddition with dienes. Selectivity is found to depend on the tethering length as well as the stability of the oxyallyl cation intermediate, whether generated from N-carbamoyl- or N-sulfonyl-substituted allenamides. The use of chiral N-sulfonyl-substituted allenamides provided minimal diastereoselectivity in the cycloaddition, while high diastereoselectivity can be achieved with a stereocenter present on the tether. These studies provide further support for the synthetic utility of allenamides.