59288-24-3

Basic information

• Product Name: 2-Furanmethanol, 5-ethenyl-
• Synonyms: 5-Hydroxy-2-vinylfuran;5-trifluoromethyl-2-furanmethanol;5-Trifluormethyl-2-hydroxymethylfuran
• CAS NO: 59288-24-3
• Molecular Formula: C7H8O2
• Molecular Weight: 124.13700
• Mol File: 59288-24-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Furanmethanol, 5-ethenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanmethanol, 5-ethenyl-(59288-24-3)
• EPA Substance Registry System: 2-Furanmethanol, 5-ethenyl-(59288-24-3)

Safety Data

• Hazardous Substances Data: 59288-24-3(Hazardous Substances Data)

Usage

General Description

2-Furanmethanol, 5-ethenyl- is a chemical compound with the molecular formula C5H6O2. It is also known as furyl alcohol and is a colorless to pale yellow liquid with a sweet, bready odor. It is commonly used as a flavor and fragrance ingredient in the food and beverage industry. Additionally, it has applications in the production of pharmaceuticals, pesticides, and other organic compounds. 2-Furanmethanol, 5-ethenyl- is also considered a potential biomass-derived platform chemical, with potential uses in biofuels and renewable energy sources. However, it is important to handle and use this chemical with caution, as it can be harmful if ingested or inhaled, and can cause skin and eye irritation.

Upstream product

• 59288-25-4 5-(acetoxymethyl)-2-vinylfuran 
• 55087-82-6 1-[5-(hydroxymethyl)furan-2-yl]ethan-1-one 
• 153026-71-2 5-ethynylfuran-2-carbaldehyde 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 1067966-63-5 methyltriphenylphosphonium methylcarbonate 
• 470-23-5 D-fructose 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 114430-54-5 2-acetyl-5-(bromomethyl)furan 
• 1009843-50-8 5-acetyl-2-furfuryl acetate 
• 10551-58-3 5-acetoxymethyl-2-furaldehyde 
• 623-17-6 furfurylacetate 
• 1193-79-9 2-acetyl-5-methylfuran 
• 534-22-5 2-methylfuran 

Relevant articles and documents

Diversified upgrading of HMF via acetylation, aldol condensation, carboxymethylation, vinylation and reductive amination reactions

Multiple sustainable methodologies were developed for the chemical upgrading of HMF: i) at 30–90 °C, highly selective base-catalyzed acetylation and carboxymethylation reactions of HMF with nontoxic reagents as isopropenyl acetate (iPAc) and dimethyl carbonate (DMC) were achieved to prepare the corresponding ester and carbonate products, (5-formylfuran-2-yl)methyl acetate (5-formylfuran-2-yl) methyl carbonate, respectively; ii) based on the combined use of iPAc/DMC with acetone, a tandem protocol of acetylation/transcarbonation and aldol condensation was designed to synthesize a variety of HMF-derived α,β-unsaturated carbonyl compounds; iii) in water as a solvent, a chemoselective Pd-catalysed reductive amination of HMF with amino-alcohols also including glycerol derivatives, was developed using H2 at atmospheric pressure; iv) finally, both HMF and its ester and carbonate products successfully underwent Wittig vinylation reactions promoted by a methyl carbonate phosphonium salt ( [Ph3PCH3] [CH3OCO2]), to obtain the corresponding olefins. The vinylation reagent (the salt) was a DMC derivative. In all cases i-iv), not only processes occurred under mild conditions, but post-reaction procedures (work-up and purification) were optimized to isolate final products in high yields of 85–98%.

5-Hydroxymethyl-2-vinylfuran: A biomass-based solvent-free adhesive

5-Hydroxymethylfurfural (HMF) is an important platform chemical derived from biomass. Tremendous efforts have been made to transform HMF into valuable chemicals for applications in biofuels, materials science, and pharmaceuticals. Here we report the conversion of HMF into 5-hydroxymethyl-2-vinylfuran (HMVF), a versatile adhesive. HMVF can bond to a variety of substrates, e.g. metal, glass, plastics and rubber, under heating or acid treatment at room temperature. Mechanistic studies show that the vinyl group undergoes free radical polymerization and the hydroxyl group dehydrates to form an ether linkage to crosslink HMVF under either heating or acid treatment. The bonding strength (τ) of HMVF cured by heating (h-HMVF) is close to that of Krazy Glue (Loctite 401, cyanoacrylate) and higher than that of white glue (Pattex No. 710, PVA) and Pattex PKME15C epoxy glue. The outstanding adhesive performance of HMVF is attributed both to the interaction of hydroxyl groups with substrates and crosslinking by etherification between hydroxyl groups. Similar to Krazy Glue, HMVF is also used in its monomer form, which eliminates the use of solvents. Cells show good adhesion on crosslinked HMVF, which makes HMVF a potential bio-adhesive.