2-Methyltetrahydrofuran

2-Methyltetrahydrofuran Basic information
Product Name:2-Methyltetrahydrofuran
Synonyms:2-Methyltetrahydrofuran,For Grignard reaction,anhydrous, stabilized;2-Methyltetrahydrofuran,99+%,Extra Dry,Stabilized;2-Methyltetrahydrofuran,99+%,Extra Dry over Molecular Sieve,Stabilized;2-Methyltetrahydrofuran,99+%,Extra Dry,stabilizer free;2-Methyltetrahydrofuran ,99% [stabilized with BHT];2-Methyltetrahydrofuran,Tetrahydro-2-methylfuran, Tetrahydrosilvan;2-Methyltetrahydrofu;2-Methyltetrahydrofuran, Stabilized, AcroSeal, Extra Dry over Molecular Sieve, 99+%
CAS:96-47-9
MF:C5H10O
MW:86.13
EINECS:202-507-4
Product Categories:Greener Solvent Alternatives;organic solvent;Chemical Synthesis;Furans;fine chemical;pharm intermediate;ACS and Reagent Grade Solvents;Amber Glass Bottles;Anhydrous Solvents;Building Blocks;C4 to C7;Heterocyclic Building Blocks;Sure/Seal Bottles;5L,10L,50L,500L,1T,10T,100T;ReagentPlus;ReagentPlus Solvent Grade Products;Solvent Bottles;Solvent by Application;Solvent by Type;Solvent Packaging Options;Solvents;bc0001
Mol File:96-47-9.mol
2-Methyltetrahydrofuran Structure
2-Methyltetrahydrofuran Chemical Properties
Melting point -136 °C
Boiling point 78-80 °C(lit.)
density 0.86 g/mL at 25 °C(lit.)
vapor pressure 136 hPa (20 °C)
refractive index n20/D 1.406(lit.)
Fp 10.4 °F
storage temp. Store below +30°C.
solubility 150g/l
form Liquid
color Clear colorless
explosive limit1.2-5.7%(V)
Water Solubility 15 g/100 mL (25 C)
FreezingPoint -136℃
BRN 102448
Dielectric constant6.97
Stability:Stable, but highly flammable. Incompatible with oxidizing agents, strong acids, strong bases. May form explosive peroxides in storage, so often supplied with an inhibitor added.
LogP1.1 at 20℃
CAS DataBase Reference96-47-9(CAS DataBase Reference)
NIST Chemistry ReferenceFuran, tetrahydro-2-methyl-(96-47-9)
EPA Substance Registry SystemFuran, tetrahydro-2-methyl- (96-47-9)
Safety Information
Hazard Codes F,Xi
Risk Statements 11-19-36/37-2017/11/19
Safety Statements 16-23-39-33-26
RIDADR UN 2536 3/PG 2
WGK Germany 2
RTECS LU2800000
Autoignition Temperature270 °C
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29321900
ToxicityLD50 orally in Rabbit: > 300 - 2000 mg/kg LD50 dermal Rat > 2000 mg/kg
MSDS Information
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Tetrahydro-2-methylfuran English
SigmaAldrich English
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2-Methyltetrahydrofuran Usage And Synthesis
Description2-Methyltetrahydrofuran (MeTHF or 2-MTHF) 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. It is a potential greener solvent alternative for organic synthesis. It shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries. Its polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether. The ring opening reaction of 2-MTHF has been studied using acid chloride and iodide.
Chemical PropertiesColorless liquid; ether-like odor. Solubility in waterincreases with a decrease in temperature. Freelysoluble in most organic solvents.
Uses2-Methyltetrahydrofuran acts as a solvent in organic synthesis. It is considered as a replacement for terahydrofuran due to its higher reaction temperature and easy separation after reaction. It is also useful in the electrolyte formulation for secondary lithium electrodes and as a component in alternative fuels. Further, it is used as a solvent for spectroscopic studies at -1960C. It also acts as a solvent for Grignard reagent in organometallic reactions. In addition to this, it plays an important role as a motor fuel.
Uses2-Methyltetrahydrofuran may be used as solvent for phosphatidylserine synthesis.
It may be used as an alternative solvent to:
  • DMSO (dimethyl sulfoxide) or MTBE (methyl tertiary butyl ether) in the C-C bond forming reactions catalyzed by lyase enzyme.
  • THF in the reaction between Grignard reagents and carbonyl compounds.
  • Methylene chloride in some biphase reactions.
UsesZerO2 products?are rigorously degassed with highly pure inert gas providing solvents and solutions?(anhydrous if specified)?with very low residual oxygen content.
General DescriptionThis product is a biorenewable and thus aligns with "Safer Solvents and Auxiliaries" and "Use of Renewable Feedstocks".
2-Methyltetrahydrofuran (2-MTHF), a 2-methyl substituted tetrahdrofuran, is a biomass derived solvent. It is a potential greener solvent alternative for organic synthesis. It shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries. Its polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether. The ring opening reaction of 2-MTHF has been studied using acid chloride and iodide to form secondary chlorides and primary iodides respectively. On long term storage, tetrahydrofuran forms organic peroxides. This process can be suppressed by adding butylated hydroxytoluene (BHT) as a stabilizer. BHT removes the free radicals required for the peroxide formation.
HazardFlammable, dangerous fire risk.
Flammability and ExplosibilityHighlyflammable
Purification MethodsLikely impurities are 2-methylfuran, methyldihydrofurans and hydroquinone (stabiliser, which is removed by distillation under reduced pressures). It is washed with 10% aqueous NaOH, dried, vacuum distilled from CaH2, passed through freshly activated alumina under nitrogen, and refluxed over sodium metal under vacuum. Store it over sodium. [Ling & Kevan J Phys Chem 80 592 1976.] Distil it from sodium under vacuum, and store it with sodium-potassium alloy (this treatment removes water and prevents the formation of peroxides). Alternatively, it can be freed from peroxides by treatment with ferrous sulfate and sodium bisulfate, then solid KOH, followed by drying with, and distilling from, sodium, or type 4A molecular sieves under argon. It may be difficult to remove *benzene if it is present as an impurity (can be readily detected by its ultraviolet absorption in the 249-268nm region). [Ichikawa & Yoshida J Phys Chem 88 3199 1984.] It has also been purifed by percolating through Al2O3 and fractionated collecting fraction b 79.5-80o. After degassing, the material is distilled onto degassed molecular sieves, then distilled onto anthracene and a sodium mirror. The solvent is then distilled from the green solution onto potassium mirror or sodium-potassium alloy, from which it is distilled again. [Mohammad & Kosower J Am Chem Soc 93 2713 1971.] It should be stored in the presence of 0.1% of hydroquinone or 2,6-di-tert-butyl –p-cresol as stabiliser. The R(+)-enantiomer has b 78-80o/atm and []D +27.5o (neat), and the S(-)-enantiomer has b 86o/atm and [] D -27.0o (neat) [Iffland & Davis J Org Chem 42 4150 1977, Gagnaire & Butt Bull Soc Chim Fr 312 1961, Beilstein 17 III/IV 60, 17/1 V 78.] HARMFUL VAPOURS.
D-RIBULOSE Tetrahydrofurfuryl bromide Tetrahydro 2,2'-Cyclouridine Span 60 Span 20 beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate POLY(TETRAHYDROFURAN) STANDARD 20000 D-GLUCOHEPTONO-1,4-LACTONE 2-Methylfuran D-RIBOFURANOSE-5-PHOSPHORIC ACID SODIUM SALT 3-METHYLTETRAHYDROFURAN,3-METHYLTETRAHYDROFURAN,1-METHYLTETRAHYDROFURAN,1-METHYLTETRAHYDROFURAN,3-METHYLTETRAHYDROFURAN 95+%,3-METHYLTETRAHYDROFURAN 95+% Tetrahydrofurfuryl alcohol Tetrahydrofuran ALPHA-BROMO-GAMMA-VALEROLACTONE TETRAHYDRO-3-FURANMETHANOL 2-Methyltetrahydrofuran 2-Methyltetrahydrofuran-3-one

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