2-Methylfuran

Base Information

• Chemical Name: 2-Methylfuran
• CAS No.: 534-22-5
• Molecular Formula: C5H6O
• Molecular Weight: 82.102
• Hs Code.: 29321900
• European Community (EC) Number: 248-253-8,208-594-5
• NSC Number: 5211,3707
• UN Number: 2301
• UNII: 51O3BGW3F2
• DSSTox Substance ID: DTXSID9025611
• Nikkaji Number: J6.337A
• Wikipedia: 2-Methylfuran
• Wikidata: Q209438
• Metabolomics Workbench ID: 42490
• ChEMBL ID: CHEMBL1445555
• Mol file: 534-22-5.mol

Synonyms:2-methylfuran;Silvan;Sylvan

Chemical Property of 2-Methylfuran

Chemical Property:

• Appearance/Colour: Colorless to pale yellow green clear liquid
• Vapor Pressure: 139 mm Hg ( 20 °C)
• Melting Point: -88.7 °C
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 64.536 °C at 760 mmHg
• Flash Point: -26 °C
• PSA: 13.14000
• Density: 0.928 g/cm³
• LogP: 1.58800
• Storage Temp.: Flammables area
• Solubility.: 3000mg/l
• Water Solubility.: 0.3 g/100 mL (20 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 82.041864811
• Heavy Atom Count: 6
• Complexity: 43.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2-Methylfuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23-23/24/25-2017/11/23
• Safety Statements: 16-33-45-7/9-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Ethers, Other
• Canonical SMILES: CC1=CC=CO1
• Description: 2-methylfuran is a flammable, water soluble liquid with the potential to be used as an alternative biofuel. It has become very attractive and promising due to the recent breakthrough in its production method through dehydration and hydrogenolysis of fructose or cellulose. This indicates the prospect of industrial mass production of 2-methylfuran and its derivative 2, 5-dimethylfuran. The 2-methylfuran and 2, 5-dimethylfuran have now been considered as a potential choice of alternative fuel pathway for spark ignition (SI) engines because of their similarities to gasoline. Therefore, as an alternative bio-fuels, it presents a potential way to provide sustainable-renewable sources and tackle the severe issue of fossil fuel depletion and global warming.
• Uses: 2-Methylfuran is widely used in manufacturing of drugs like atropine, sodium acetate, furadantine, anisodamine and thiamine furan. In pharmaceuticals industry, synthesis of vitamin B1 is done using 2-Methylfuran. It is less dense than water but its vapors are heavier when contrastedwith air. 2-Methylfuran also finds application as a tool for screening of lung cancer and production of anti-malarial drug like chloroquine. It is also used to produce methyl furfural, aliphatic compounds and sulfur and nitrogen heterocycles. Moreover, 2-Methylfuran is also used for making pesticides, flavors or fragrances and has narcotic effect. 2-Methylfuran may be used in the synthesis of exo-cis-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride via Diels-Alder reaction with maleic anhydride. 2-Methylfuran is a volatile organic compound (VOCs) used as a potential non-intrusive tool for screening of lung cancer.

Technology Process of 2-Methylfuran

There total 267 articles about 2-Methylfuran 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: 52.57%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → furan (110-00-9) + 2-methylfuran (534-22-5) + 2,2'-difurylmethane (1197-40-6) + 2,2-[oxybis(methylene)]bis-furan (4437-22-3)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,3,5-trimethyl-benzene; at 164 ℃; for 20h; Inert atmosphere;

Reference yield: 30.4%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2-methylfuran (534-22-5) + 2,5-dimethylfuran (625-86-5) + 5-Methylfurfural (620-02-0) + 2,5-bis-(hydroxymethyl)furan (1883-75-6) + 2-hydroxymethyl-5-methylfuran (3857-25-8)

Guidance literature:

With hydrogen; In tetrahydrofuran; at 220 ℃; for 1h; under 11251.1 Torr;

Reference yield:

benzyl 2-methyl-2,5-dihydrofuran-2-carboxylate (162104-79-2) → 2-methylfuran (534-22-5) + benzyl bromide (100-39-0)

Guidance literature:

With N-Bromosuccinimide; (PhCO₂)2O; In tetrachloromethane; for 16h; Heating;

DOI:10.1039/c39950000027

upstream raw materials:

furfural

(2-furyl)methyl alcohol

(E)-(furan-2-ylmethylene)hydrazine

sodium ethanolate

Downstream raw materials:

(1R,2S)-2-[Methyl-(5-methyl-furan-2-ylmethyl)-amino]-1-phenyl-propan-1-ol

4-methyl-4-(5-methylfuran-2-yl)pentan-2-one

4,4-dimethylnonane-2,5,8-trione

1-phenyl-1,6-dioxo-hepta-2,4-(E,E)-diene

Refernces

Promotion effect of Ce or Zn oxides for improving furfuryl alcohol yield in the furfural hydrogenation using inexpensive Cu-based catalysts

10.1016/j.mcat.2018.06.001

This study investigated the use of cerium or zinc oxides as promoters to improve the yield of furfuryl alcohol in the hydrogenation of furfural using an inexpensive copper-based catalyst supported on a mixed layer of cerolite/magnesium-montmorillonite. It was found that high copper loadings (15-30 wt.% copper) maintained high furfural conversions above 80 mol% after 5 h at 210 °C, while the addition of cerium oxide (CeO) or zinc oxide (ZnO) as promoters, while reducing furfural conversion, significantly improved the selectivity of furfuryl alcohol, reaching a maximum yield of above 80% after 5 h at 190 °C. The effects of copper content and the presence of promoters on the catalytic performance were also investigated, with the results indicating that moderate copper loadings favored the formation of 2-methylfuran, while higher loadings and the addition of cerium oxide (CeO) or zinc oxide (ZnO) improved the selectivity of furfuryl alcohol. The study concluded that the addition of CeO2 or ZnO changes the electron density of the active phase, thereby improving the selectivity of furfuryl alcohol and reducing the deactivation due to carbonaceous deposition.