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2-Methyltetrahydrofuran

2-Methyltetrahydrofuran Structure
CAS No.
96-47-9
Chemical Name:
2-Methyltetrahydrofuran
Synonyms
2-MeTHF;METHF;METHYLTETRAHYDROFURAN;Furan, tetrahydro-2-methyl-;2-Methyloxolane;2-Methyltetrahydrofu;TETRAHYDRO-2-METHYLFURAN;2-Methyltetrahydrofuran,For Grignard reaction,anhydrous, stabilized;2 METHYLE Thf;Tetrahydrosylvan
CBNumber:
CB8854728
Molecular Formula:
C5H10O
Molecular Weight:
86.13
MOL File:
96-47-9.mol
MSDS File:
SDS
Modify Date:
2024/3/14 15:18:29

2-Methyltetrahydrofuran 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.)
Flash point 10.4 °F
storage temp. Store below +30°C.
solubility 150g/l
form Liquid
color Clear colorless
explosive limit 1.2-5.7%(V)
Water Solubility 15 g/100 mL (25 C)
FreezingPoint -136℃
BRN 102448
Dielectric constant 6.97
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.
LogP 1.1 at 20℃
CAS DataBase Reference 96-47-9(CAS DataBase Reference)
NIST Chemistry Reference Furan, tetrahydro-2-methyl-(96-47-9)
EPA Substance Registry System Furan, tetrahydro-2-methyl- (96-47-9)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS05,GHS07
Signal word  Danger
Hazard statements  H225-H302-H315-H318
Precautionary statements  P210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338
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 Temperature 270 °C
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29321900
Toxicity LD50 orally in Rabbit: > 300 - 2000 mg/kg LD50 dermal Rat > 2000 mg/kg
NFPA 704
3
2 0

2-Methyltetrahydrofuran price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 900520 2-Methyltetrahydrofuran anhydrous, contains 250?ppm BHT as stabilizer, ZerO2?, ≥99.0% 96-47-9 4X2ML ₹1970.15 2022-06-14 Buy
Sigma-Aldrich(India) 85488 2-Methyltetrahydrofuran analytical standard 96-47-9 5ML ₹6375.93 2022-06-14 Buy
Sigma-Aldrich(India) 8.21093 2-Methyltetrahydrofuran (stabilised) for synthesis 96-47-9 5ML ₹3930 2022-06-14 Buy
Sigma-Aldrich(India) 85488 2-Methyltetrahydrofuran analytical standard 96-47-9 10ML ₹11496.15 2022-06-14 Buy
Sigma-Aldrich(India) 8.21093 2-Methyltetrahydrofuran (stabilised) for synthesis 96-47-9 250ML ₹11080.01 2022-06-14 Buy
Product number Packaging Price Buy
900520 4X2ML ₹1970.15 Buy
85488 5ML ₹6375.93 Buy
8.21093 5ML ₹3930 Buy
85488 10ML ₹11496.15 Buy
8.21093 250ML ₹11080.01 Buy

2-Methyltetrahydrofuran Chemical Properties,Uses,Production

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.

Uses

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.

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.

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.

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