2-Methyltetrahydrofuran

Description

2-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 properties

Colorless liquid; ether-like odor. Solubility in waterincreases with a decrease in temperature. Freelysoluble in most organic solvents.

The Uses of 2-Methyltetrahydrofuran

2-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.

The Uses of 2-Methyltetrahydrofuran

To a solution of the SM (2.92 g, 9.89 mmol) in 2-methyl tetrahydrofuran (115 mL) was added DIEA (13.8 mL, 39.5 mmol) and cyclopropylamine (2.77 mL, 39.5 mmol). The resulting mixture was heated to 70 C and T3P (50% weight solution in DCE) (17.3 mL, 59.3 mmol) was added. The reaction mixture was heated at 70 C for 16 h and then diluted with EtOAc (200 mL). The mixture was then washed sequentially with sat aq Na2CO3 (100 mL), 10% aq citric acid (100 mL), and saturated aq Na2CO3 (100 mL). The combined org extracts were dried (MgSO4) and concentrated in vacuo to give an oil. The crude was purified by column chromatography (eluting with 50% EtOAc/heptane) to give a solid which was recrystallized with IPA to provide the product as a white solid. [2.46 g, 74%]

The Uses of 2-Methyltetrahydrofuran

2-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.

The Uses of 2-Methyltetrahydrofuran

ZerO₂ products?are rigorously degassed with highly pure inert gas providing solvents and solutions?(anhydrous if specified)?with very low residual oxygen content.

What are the applications of Application

2-Methyltetrahydrofuran is a biomass-derived organic chemistry solvent

General Description

This 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.

Hazard

Flammable, dangerous fire risk.

Flammability and Explosibility

Highly flammable

Potential Exposure

Used as a chemical intermediate and asolvent.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with methyltetrahydrofuran you should betrained on its proper handling and storage. Store in tightlyclosed containers in a cool, well-ventilated area. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must beequipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers ofthis chemical. Wherever this chemical is used, handled,manufactured, or stored, use explosion-proof electricalequipment and fittings.

Shipping

Methyltetrahydrofuran requires a shipping labelof “FLAMMABLE LIQUID.” It falls in Hazard Class 3 andPacking Group II.

Purification Methods

Likely 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.

Incompatibilities

Strong oxidizers may cause fire andexplosion