2-Methylfuran

2-Methylfuran Basic information
Description Chemical Properties Uses Preparation References
Product Name:2-Methylfuran
Synonyms:Sylvan;SILVAN;2-methyl-fura;2-methyloxole;-Methylfuran;FEMA 4179;5-METHYLFURAN;ALPHA-METHYLFURAN
CAS:534-22-5
MF:C5H6O
MW:82.1
EINECS:208-594-5
Product Categories:Furan;Intermediate;Isotope Labeled Compounds
Mol File:534-22-5.mol
2-Methylfuran Structure
2-Methylfuran Chemical Properties
Melting point -88.7 °C
Boiling point 63-66 °C (lit.)
density 0.91 g/mL at 25 °C (lit.)
vapor density 2.8 (vs air)
vapor pressure 139 mm Hg ( 20 °C)
refractive index n20/D 1.433(lit.)
FEMA 4179 | 2-METHYLFURAN
Fp −8 °F
storage temp. Store below +30°C.
solubility 3000mg/l
form Liquid
color Clear yellow
Odorat 1.00 % in propylene glycol. ethereal acetone chocolate
Odor Typechocolate
Water Solubility 0.3 g/100 mL (20 ºC)
FreezingPoint -88.68℃
JECFA Number1487
BRN 103733
Stability:Volatile
InChIKeyVQKFNUFAXTZWDK-UHFFFAOYSA-N
LogP1.79
CAS DataBase Reference534-22-5(CAS DataBase Reference)
NIST Chemistry ReferenceFuran, 2-methyl-(534-22-5)
EPA Substance Registry System2-Methylfuran (534-22-5)
Safety Information
Hazard Codes F,T
Risk Statements 11-23-23/24/25-2017/11/23
Safety Statements 16-33-45-7/9-9
RIDADR UN 2301 3/PG 2
WGK Germany 1
RTECS LU2625000
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29321900
ToxicityLD50 orally in Rabbit: 167 mg/kg
MSDS Information
ProviderLanguage
2-Methylfuran English
SigmaAldrich English
ACROS English
ALFA English
2-Methylfuran Usage And Synthesis
Description2-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.
2-Methylfuran
Chemical Properties2-Methylfuran is a flammable, water-soluble liquid with a chocolate odor, found naturally in Myrtle and Dutch Lavender used as a FEMA GRAS (Generally Recognized As Safe) flavoring substance, with the potential for use in alternative fuels. 2-Methylfuran is expected to gain traction in the near future as it is primarily used in pharmaceuticals industry. It is a light yellowish green volatile organic compound with an ethereal odor and is also known as sylvan. 2-Methylfuran changes its shading to black or yellow when exposed to sunlight. It is highly flammable and hence is stored in a ventilated, cool dry place far from heat & fire.
Uses2-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.
Preparation2-Methylfuran is an article of commerce (chemical intermediate) and is normally manufactured by catalytic hydrogenolysis of furfural alcohol or via a hydrogenation-hydrogenolysis sequence from furfural in the vapor phase.
ReferencesWang, Chongming, et al. "Combustion characteristics and emissions of 2-methylfuran compared to 2, 5-dimethylfuran, gasoline and ethanol in a DISI engine." Fuel 103 (2013): 200-211.
Ma, Xiao, et al. "Laminar burning characteristics of 2-methylfuran and isooctane blend fuels." Fuel 116 (2014): 281-291.
Chemical Properties2-Methylfuran is a cyclic diene possessing ether-like properties. It is highly reactive with many inorganic and organic compounds yielding a variety of new derivatives which await exploration for the development of commercial applications.
Chemical PropertiesColorless liquid; spicy, smoky aroma
OccurrenceReported found in cooked beef, bread, butter, chicken, cocoa, coffee, currant, mint, tea and tomato.
Uses2-Methylfuran is a volatile organic compound (VOCs) used as a potential non-intrusive tool for screening of lung cancer.
Uses2-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.
DefinitionChEBI: 2-methylfuran is a member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a methyl group. It has a role as a human urinary metabolite, a hepatotoxic agent, a fuel, a flavouring agent and a plant metabolite. It is a member of furans and a volatile organic compound.
Aroma threshold valuesMedium strength odor, chocolate type; recommend smelling in a 1.00% solution or less
General DescriptionA clear colorless liquid with an ethereal odor. Flash point -22°F. Less dense than water and insoluble in water. Hence floats on water. Vapors heavier than air.
Air & Water ReactionsHighly flammable. Insoluble in water.
Reactivity Profile2-Methylfuran is incompatible with strong acids and strong bases. May react vigorously with oxidizing materials .
HazardHighly flammable, dangerous fire andexplosion risk. Irritant.
Health HazardInhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Safety ProfilePoison by ingestion. Moderately toxic by inhalation. An eye irritant. Mutation data reported. Very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
Purification MethodsWash it with acidified saturated ferrous sulfate solution (to remove peroxides), separate, dry with CaSO4 or CaCl2, and fractionally distil it from KOH immediately before use. To reduce the possibility of spontaneous polymerisation, addition of about one-third of its volume of heavy mineral oil to 2-methylfuran prior to distillation has been recommended. [Beilstein 17 H 36, 17 I 18, 17 II 39, 17 III/IV 265.]
Nitrofurazone ETHYL 2-FUROATE 2-Furaldehyde diethyl acetal 5-(5-Methylfuran-2-yl)-nicotinic acid,2-(5-Methylfuran-2-yl)-isonicotinic acid,5-(5-Methylfuran-2-yl)-nicotinic acid,2-(5-Methylfuran-2-yl)-isonicotinic acid Furil FURFURYL ALCOHOL RESIN 5-Nitrofurfural Tiglic aldehyde Potassium 5-methylfuran-2-trifluoroborate,Potassium 5-methylfuran-2-trifluoroborate 3-(5-Methylfuran-2-yl)-1H-pyrazole-5-carbohydrazide ,97% 5-methylfuran-2-carboxamidine,5-methylfuran-2-carboxamidine 2-METHYLFURAN-2-CARBONYL CHLORIDE 97%,2-METHYLFURAN-2-CARBONYL CHLORIDE 97% 3-methylfuran-2-carbohydrazide,3-methylfuran-2-carbohydrazide Ethyl 3-(5-methylfuran-2-yl)-1H-pyrazole-5-carboxylate ,97% 5-FORMYL-2-FURANSULFONIC ACID SODIUM SALT HYDRATE (2-METHYL-PYRIDIN-3-YL)-METHANOL AKOS B004245 METHYL FUROATE

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