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2-Methyloxolane is an organic compound with the molecular formula C5H10O.
2-Methyloxolane is a highly flammable, mobile liquid.
2-Methyloxolane is mainly used as a replacement for Tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations.
CAS Number: 96-47-9
EC Number: 202-507-4
IUPAC Name: 2-Methyloxolane
Chemical Formula: C5H10O
Other names: 96-47-9, 2-Methyloxolane, Methyltetrahydrofuran, Tetrahydro-2-methylfuran, Tetrahydrosylvan, Furan, tetrahydro-2-methyl-, Furan, 2-methyl-tetrahydro-, Furan, tetrahydromethyl-, 25265-68-3, methyl tetrahydrofuran, FCD0VD8ALF, UNII-FCD0VD8ALF, NSC 2115, 2-Methylfuranidine, EINECS 202-507-4, BRN 0102448, CCRIS 8717, DTXSID9030258, AI3-25425, NSC-2115, EINECS 246-769-8, UN2536, Tetrahydrofuran, 2-methyl-, DTXCID7010258, EC 202-507-4, 5-17-01-00078 (Beilstein Handbook Reference), 2-METHYLTETRAHYDROFURAN [MI], 2Methyloxolane, Tetrahydro2methylfuran, Furan, 2methyltetrahydro, Furan, tetrahydro2methyl, (+-)-2-METHYLTETRAHYDROFURAN, 246-769-8, jwujqdfvadabey-uhfffaoysa-n, 2-MeTHF, Tetrahydrosilvan, MFCD00005367, 2-methyl tetrahydrofuran, 2-methyl-tetrahydrofuran, 2-methyl-tetrahydro-furan, MeTHF, (+/-)-2-Methyltetrahydrofuran; MTHF; NSC 2115; Tetrahydro-2-methylfuran; Tetrahydrosylvan; 2-Me-THF, methyl-tetrahydrofuran, Me-THF, Methyl tetrahydrofurane, 2-methyltetrahyrdofuran, 2-methyltetrahydrofurane, 2-methyl tetrahydrofurane, 2-methyl-tetrahydrofurane, Tetrahydrosylvan;Methy THF, WLN: T5OTJ B1, (2S)-2-methyltetrahydrofuran, CHEMBL1580503, NSC2115, BCP16203, STR08776, Tox21_200383, AKOS009157664, FM14741, (+/-)-2-METHYLTETRAHYDROFURAN, CAS-96-47-9, NCGC00090914-01, NCGC00090914-02, NCGC00257937-01, 2-Methyltetrahydrofuran, analytical standard, DB-015964, CS-0010107, M0437, NS00007944, 2-Methyltetrahydrofuran (stabilized with BHT), 2-Methyltetrahydrofuran - Stabilized with BHT, EN300-60207, E80342, 2-Methyltetrahydrofuran, purum, >=97.0% (GC), Q209444, Methyltetrahydrofuran [UN2536] [Flammable liquid], 2-Methyltetrahydrofuran, anhydrous, >=99%, Inhibitor-free, 2-Methyltetrahydrofuran, absolute, stored over molecular sieve, 2-Methyltetrahydrofuran, stabilized, anhydrous, water Max 20ppm, 2-Methyltetrahydrofuran, anhydrous, >=99.0%, contains 250 ppm BHT as stabilizer, 2-Methyltetrahydrofuran, ReagentPlus(R), >=99.5%, contains 150-400 ppm BHT as stabilizer, 2-Methyltetrahydrofuran, anhydrous, contains 250 ppm BHT as stabilizer, ZerO2(TM), >=99.0%
2-Methyloxolane is derived from sugars via furfural and is occasionally touted as a biofuel.
2-Methyltetrahydrofuran is inversely soluble in water.
2-Methyloxolanes solubility decreases with increasing temperature, which is a rare property.
2-Methyloxolane can act as a Lewis base in organometallic reactions.
2-Methyloxolane is usually produced as a racemic mixture.
2-Methyloxolane is usually synthesized by catalytic hydrogenation of furfural.
2-Methyloxolane is produced by the acid-catalyzed digestion of pentosan sugars, C5 polysaccharides, in biomass.
Thus, the raw materials of 2-Methyloxolane are renewable biomass rich with cellulose, hemicelluloses, and lignin, such as corncobs or bagasse and other plant and agricultural waste.
2-Methyltetrahydrofuran is mainly used as a higher boiling substitute for tetrahydrofuran as a specialty solvent.
2-Methyloxolane is a valued solvent for low-temperature reactions.
2-Methyltetrahydrofuran forms a glass, which does not crystallize, and is frequently used as a solvent for spectroscopic studies at −196 °C.
Other common uses of 2-methyltetrahydrofuran is as a solvent for reagents used in organometallic and biphasic chemical processes, because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent, or to azeotropically dry products.
The use of 2-methyltetrahydrofuran provides very clean organic water phase separations.
2-Methyloxolane is a popular, but costlier substitute for tetrahydrofuran.
2-Methyloxolane is approved by the United States Department of Energy as an additive to gasoline.
2-Methyloxolane and other furyl compounds (furfuryl alcohol, methylfuran, tetrahydrofufuryl alcohol) have a tendency to polymerize and are quite volatile.
2-Methyltetrahydrofuran itself, however, is more stable and less volatile, and thus is suitable for use as a motor fuel.
2-Methyltetrahydrofuran has been promoted as an ecologically-friendly alternative to THF.
Whereas 2-Methyloxolane is more expensive, 2-Methyloxolane may provide for greater overall process economy.
2-Methyloxolane has solvating properties that are intermediate between diethyl ether and THF, has limited water miscibility, and forms an azeotrope with water on distillation.
2-Methyloxolanes lower melting point makes it useful for lower temperature reactions, and 2-Methyloxolanes higher boiling point allows procedures under reflux at higher temperatures (relative to THF).
2-Methyloxolane is a natural product.
2-Methyloxolane appears as a colorless liquid with an ether-like odor.
2-Methyloxolane has less dense than water.
2-Methyloxolane vapors heavier than air.
2-Methyloxolane is used to make other chemicals and as a solvent.
2-Methyloxolane is a clear, colorless liquid.
2-Methyloxolane is used as a specialty solvent, mainly as a higher boiling substitute for Tetrahydrofuran.
2-Methyloxolane is a commercially available solvent that is produced from renewable resources.
The properties of 2-Methyloxolane place it between tetrahydrofuran (THF) and diethyl ether in solvent polarity and Lewis base strength.
In many cases, 2-Methyloxolane can replace THF in organometallic reactions.
The formation and reaction of reagents in 2-Methyloxolane and THF are similar.
2-Methyloxolane can be used as a solvent for low-temperature lithiation, for lithium aluminum hydride reductions, for the Reformatsky reaction, and for metal-catalyzed coupling reactions.
2-Methyloxolane is also a good substitute for dichloromethane in biphasic reactions.
2-Methyloxolane is a bio-based solvent that is recognized as the most favorable of ether solvents.
The relatively high boiling point (80˚C) and low melting point (-137˚C) provide a broad temperature range for a myriad of processing conditions.
2-Methyloxolane has a favorable azeotrope with water providing easy options for recycling due to its low (4%) water solubility.
2-Methyloxolane also eliminates the need for an extraction solvent during process work up, as Viridisol® M separates cleanly from water, allowing for easy recovery to an anhydrous form for recycle, all of which minimizes production costs and reduces waste.
2-Methyloxolane has an enhanced stability in the presence of a strong base such as organolithium and is known to stabilize organometallic reagents in hydrocarbon solvents.
2-Methyloxolane has been demonstrated to increase process yields in certain chemical reactions, particularly.
2-Methyloxolane is a highly flammable mobile liquid.
2-Methyloxolane is mainly used as a replacement for THF in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations.
2-Methyloxolane is derived from furfural and is usable as a biofuel.
2-Methyloxolane has been promoted as a more ecologically-friendly alternative to THF.
Whereas 2-Methyloxolane is more expensive, 2-Methyloxolane may provide for greater overall process economy.
2-Methyloxolane has solvating properties that are intermediate between diethyl ether and THF, has limited water miscibility, and forms an azeotrope with water on distillation.
2-Methyloxolanes lower melting point makes it useful for lower temperature reactions, and its higher boiling point allows procedures under reflux at higher temperatures (relative to THF).
2-Methyloxolane has become a broadly used (biogenic) solvent in organic synthesis, particularly with promising applications in biocatalysis, due to its excellent behaviour and favourable properties.
2-Methyloxolane may be derived from renewable sources such as furfural or levulinic acid and its low water solubility facilitates its complete recovery in reactions in aqueous media, reducing wastes and simplifying the recycling and reuse.
2-Methyloxolane properties typically outperform those of traditional solvents (such as THF), enabling its application in a wide range of chemical and enzymatic synthetic processes.
2-Methyloxolane is an excellent substitute for Tetrahydrofuran (THF) due to its better performance.
2-Methyloxolanes physical and chemical properties make it appealing for applications in syntheses involving organometallics, organocatalysis, and biotransformations or for processing lignocellulosic materials.
The relatively high boiling point (80˚C) and low melting point (-137˚C) provide a broad temperature range for a myriad of reaction conditions.
2-Methyloxolane builds a favorable azeotrope with water, providing easy options for recycling due to its low water solubility.
2-Methyloxolane is inversely soluble.
2-Methyloxolanes solubility decreases with increasing temperature, which is a rare property.
2-Methyloxolane also eliminates the need for an extraction solvent during reaction work up, as 2-MeTHF separates cleanly from water, all of which minimizes production costs and reduces waste.
2-Methyloxolane behaves like THF as a Lewis base in organometallic reactions.
2-Methyloxolane has been promoted as an ecologically friendly alternative to THF.
2-Methyloxolane can be derived from renewable resources (e.g., furfural or levulinic acid) and is a promising alternative solvent in the search for environmentally benign synthesis strategies.
2-Methyloxolane is a readily available, inexpensive, neoteric, bio-based solvent.
2-Methyloxolane has been adopted across a wide range of chemical processes including the batch manufacture of fine chemicals, enzymatic polycondensations and ring opening polymerizations.
2-Methyloxolane is a volatile cyclic ether generated by the chemo-catalytic treatment of biomass and has been touted as the most successful neoteric bio-based solvent.
2-Methyloxolane has been characterised for biological applications and used in several laboratory-scale chemical processes.
2-Methyloxolane can be used as a solvent for low-temperature lithiation, for lithium aluminum hydride reductions, for the Reformatsky reaction, and for metal-catalyzed coupling reactions.
2-Methyloxolane is also a good substitute for dichloromethane in biphasic reactions.
2-Methyloxolane also acts as a solvent for Grignard reagent in organometallic reactions.
In addition to this, 2-Methyloxolane plays an important role as a motor fuel.
2-Methyloxolane may be used as solvent for phosphatidylserine synthesis.
2-Methyloxolane may be used as an alternative solvent.
2-Methyloxolane is a bio-based solvent that is recognized as the most favorable of ether solvents.
The relatively high boiling point (80 C) and low melting point provide a broad temperature range for a myriad of processing conditions.
2-Methyloxolane is a potential greener solvent alternative for organic synthesis.
2-Methyloxolane shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries.
2-Methyloxolanes polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether.
The ring opening reaction of 2-Methyloxolane has been studied using acid chloride and iodide.
2-Methyloxolane acts as a solvent in organic synthesis.
2-Methyloxolane is considered as a replacement for terahydrofuran due to its higher reaction temperature and easy separation after reaction.
2-Methyloxolane is also useful in the electrolyte formulation for secondary lithium electrodes and as a component in alternative fuels.
Further, 2-Methyloxolane is used as a solvent for spectroscopic studies at -1960C.
2-Methyloxolane also acts as a solvent for Grignard reagent in organometallic reactions.
In addition to this, 2-Methyloxolane plays an important role as a motor fuel.
2-Methyloxolane is a biomass derived solvent.
2-Methyloxolane is a potential greener solvent alternative for organic synthesis.
2-Methyloxolane shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries.
2-Methyloxolanes polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether.
The ring opening reaction of 2-Methyloxolane has been studied using acid chloride and iodide to form secondary chlorides and primary iodides respectively.
This process can be suppressed by adding butylated hydroxytoluene as a stabilizer.
2-Methyloxolane removes the free radicals required for the peroxide formation.
USES:
2-Methyloxolane may be used as solvent for phosphatidylserine synthesis.
2-Methyloxolane may be used as an alternative solvent to:
2-Methyloxolane in the C-C bond forming reactions catalyzed by lyase enzyme.
2-Methyloxolane in the reaction between reagents and carbonyl compounds.
Methylene chloride in some biphase reactions.
