1917-15-3

Basic information

• Product Name: 5-Methyl-2-furoic acid
• Synonyms: ASINEX-REAG BAS 02788557;ASISCHEM D13359;AKOS B000090;5-METHYL-2-FURANCARBOXYLIC ACID;5-METHYL-2-FUROIC ACID;5-METHYL-FURAN-2-CARBOXYLIC ACID;RARECHEM AL BO 1465;TIMTEC-BB SBB005609
• CAS NO: 1917-15-3
• Molecular Formula: C₆H₆O₃
• Molecular Weight: 126.11
• Product Categories: Furans
• Mol File: 1917-15-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 136-137°C
• Boiling Point: 194.21°C (rough estimate)
• Flash Point: 97.062 °C
• Appearance: /
• Density: 1.2653 (rough estimate)
• Vapor Pressure: 0.0253mmHg at 25°C
• Refractive Index: 1.4676 (estimate)
• Storage Temp.: 2-8°C
• PKA: 3.41±0.10(Predicted)
• CAS DataBase Reference: 5-Methyl-2-furoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-2-furoic acid(1917-15-3)
• EPA Substance Registry System: 5-Methyl-2-furoic acid(1917-15-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• WGK Germany: 1
• HazardClass: IRRITANT
• Hazardous Substances Data: 1917-15-3(Hazardous Substances Data)

Usage

General Description

5-Methyl-2-furoic acid is a chemical compound with the formula C6H6O3. It is a furan carboxylic acid derivative that contains a furan ring with a carboxylic acid group. The compound is a colorless to pale yellow solid with a sweet, caramel-like odor. 5-Methyl-2-furoic acid is used as a flavoring agent in the food industry, providing a burnt caramel or sweet, nutty flavor to various products. It is also used in the production of pharmaceuticals and as an intermediate in organic synthesis. Additionally, this compound has potential applications in the development of new materials and is being studied for its potential pharmacological and biological activities.

InChI:InChI=1/C6H6O3/c1-4-2-3-5(9-4)6(7)8/h2-3H,1H3,(H,7,8)/p-1

Upstream product

• 13529-17-4 5-Formyl-2-furancarboxylic acid 
• 3238-40-2 furan-2,5-dicarboxylic acid 
• 88-14-2 2-furanoic acid 
• 74-88-4 methyl iodide 
• 3857-25-8 2-hydroxymethyl-5-methylfuran 
• 620-02-0 5-Methylfurfural 
• 2527-96-0 methyl 5-methyl-2-furancarboxylate 

Downstream Products

• 6132-37-2 ethyl 5-bromofuran-2-carboxylate 
• 20842-19-7 5-methyl-furan-2-carboxylic acid hydrazide 
• 13679-43-1 2',2-methylenebis-(5-methylfuran) 
• 1120-21-4 n-Undecane 
• 534-22-5 2-methylfuran 
• 13678-51-8 furan 2-(2-furanylmethyl)-5-methyl 
• 81103-70-0 5-Phenethyl-furan-2-carboxylic acid 
• 81103-71-1 5-(1-Hydroxy-cyclohexylmethyl)-furan-2-carboxylic acid 
• 848057-98-7 5-methyl-N-[2-(morpholin-4-yl)-5-(trifluoromethyl)phenyl]furan-2-carboxamide 

Relevant articles and documents

Catalytic Aerial Oxidation of Biomass-Derived Furans to Furan Carboxylic Acids in Water over Bimetallic Nickel–Palladium Alloy Nanoparticles

Bimetallic Ni1?xPdx (0.10≤x≤0.75) alloy nanoparticle catalysts were synthesised and successfully employed for the catalytic aerial oxidation of biomass-derived furans, such as 2-furfuraldehyde (furfural), 2-furfuryl alcohol (furfuryl alcohol), 5-hydroxymethyl-2-furfural (5-HMF), 5-methyl-2-furfural (MF) and 5-methyl-2-furfuryl alcohol (MFA), to selectively afford the corresponding furan carboxylic acids (2-furoic acid, furan-2,5-dicarboxylic acid (FDCA) and 5-methyl-2-furoic acid (MFCA)) in water at 80 °C. Among the studied Ni1?xPdx nanoparticle catalysts, Ni0.90Pd0.10 nanoparticle catalyst outperformed the others, achieving high yields of the corresponding furan carboxylic acid products. The presence of Ni in the Ni1?xPdx nanoparticle catalysts was advantageous, because it not only enhanced the catalytic activity for the facile oxidation of biomass-derived furans using aerial oxygen to achieve high catalytic turnover, but also provided excellent stability to the Ni0.90Pd0.10 nanoparticle catalyst towards air and water and thus significantly enhanced its recyclability (up to 10 catalytic runs). The experiments revealed that the catalytic oxidation of 5-HMF proceeded by the initial oxidation of the formyl group to carboxylic acid, and, subsequently, the conversion of alcohol to carboxylic acid via the formyl group to form FDCA. Moreover, the one-pot direct transformation of fructose to furan carboxylic acid products (such as FDCA) was also achieved by using the Ni0.90Pd0.10 nanoparticle catalyst.

Solvent-free mechanochemical oxidation and reduction of biomass-derived 5-hydroxymethyl furfural

The simultaneous synthesis of 5-hydroxymethyl-2-furoic acid and 2,5-hydroxymethylfuran from biomass-derived 5-hydroxymethyl furan was developed using a solvent-free mechanochemical approach. The results obtained for the Cannizzaro disproportionation reaction show quantitative conversions of the starting materials with reaction times of only 5 min. Employing solvent-free conditions allows for a more sustainable synthetic approach that is reflected in an Efactor 7 times smaller than that in previous reports. Additionally, initial results of the use of a sacrificial reagent, with the same solvent-free mechanochemical approach, for the selective reduction and oxidation of HMF are presented.

PROCESS FOR THE PREPARATION OF A PURIFIED ACID COMPOSITION

A purified acid composition comprising 2,5-furandicarboxylic acid is prepared by a process comprising a) providing an acid composition solution of a crude acid composition in a polar solvent, the crude acid composition comprising 2,5-furandicarboxylic acid (FDCA) and 2-formyl-furan-5- carboxylic acid (FFCA); b) contacting the acid composition solution with hydrogen in the presence of a hydrogenation catalyst to hydrogenate FFCA to hydrogenation products, such that the hydrogenation products contain a minor amount of 2-methyl-furan-5-carboxylic acid (MFA) or no MFA, yielding a hydrogenated solution; c) separating at least a portion of the FDCA from the hydrogenated solution by crystallization.