2-Methyltetrahydrofuran

Base Information

• Chemical Name: 2-Methyltetrahydrofuran
• CAS No.: 96-47-9
• Deprecated CAS: 74069-67-3
• Molecular Formula: C5H10O
• Molecular Weight: 86.1338
• Hs Code.: 29321900
• European Community (EC) Number: 202-507-4,246-769-8
• NSC Number: 2115
• UN Number: 2536
• UNII: FCD0VD8ALF
• DSSTox Substance ID: DTXSID9030258
• Nikkaji Number: J49.588C
• Wikipedia: 2-Methyltetrahydrofuran
• Wikidata: Q209444
• ChEMBL ID: CHEMBL1580503
• Mol file: 96-47-9.mol

Synonyms:Furan, 2-methyl-tetrahydro-;(2R)-2-methyloxolane;2-Methyloxolane;Tetrahydrosylvan;(2S)-2-methyloxolane;74069-67-3;Furan, tetrahydro-2-methyl-;Tetrahydro-2-methyl-furan;

Chemical Property of 2-Methyltetrahydrofuran

Chemical Property:

• Appearance/Colour: Clear,colorless liquid
• Vapor Pressure: 96.8mmHg at 25°C
• Melting Point: -136 °C
• Refractive Index: n20/D 1.406(lit.)
• Boiling Point: 79.9 °C at 760 mmHg
• Flash Point: 10.4°F
• PSA: 9.23000
• Density: 0.863 g/cm³
• LogP: 1.18530
• Storage Temp.: Flammables area
• Solubility.: 150g/l
• Water Solubility.: 15 g/100 mL (25 C)
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 86.073164938
• Heavy Atom Count: 6
• Complexity: 43.2
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% , ^*data from raw suppliers

2-Methyltetrahydrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-19-36/37-2017/11/19
• Safety Statements: 16-23-39-33-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ethers (
• Canonical SMILES: CC1CCCO1
• 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.
• 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. 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. ZerO2 products?are rigorously degassed with highly pure inert gas providing solvents and solutions?(anhydrous if specified)?with very low residual oxygen content.

Technology Process of 2-Methyltetrahydrofuran

There total 291 articles about 2-Methyltetrahydrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.3%

furfural (98-01-1) → 2-methyltetrahydrofuran (96-47-9) + 2-methylfuran (534-22-5)

Guidance literature:

furfural; With hydrogen; at 200 ℃; under 760.051 Torr; Flow reactor;

With hydrogen; at 100 ℃; under 760.051 Torr; Temperature; Flow reactor;

DOI:10.1016/j.catcom.2019.105836

Reference yield: 51.4%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + diazomethane (186581-53-3,908094-01-9,334-88-3) → TETRAHYDROPYRANE (142-68-7) + 3-methyltetrahydrofuran (13423-15-9) + 2-methyltetrahydrofuran (96-47-9)

Guidance literature:

Product distribution; Mechanism; Ambient temperature; Irradiation;

DOI:10.1021/jo00186a007

Reference yield: 49.9%

tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + diazomethane-d2 (14621-84-2) → 3-methyltetrahydrofuran (13423-15-9) + 2-methyltetrahydrofuran (96-47-9)

Guidance literature:

Product distribution; Mechanism; Ambient temperature; Irradiation;

DOI:10.1021/jo00186a007

upstream raw materials:

tetrahydrofuran

diazomethane

methylene

2-methylfuran

Downstream raw materials:

2-(α-Chlorbenzyl)-2-methyltetrahydrofuran

n-Pent-4-enyl alcohol

Trimethyl-((2R,5R)-5-methyl-tetrahydro-furan-2-yl)-silane

Trimethyl-((2R,5S)-5-methyl-tetrahydro-furan-2-yl)-silane

Refernces

• 1、 Courtneidge,Lusztyk,Page. "Alkoxyl radicals from alcohols. Spectroscopic detection of intermediate alkyl and acyl hypoiodites in the Suarez and Beebe reactions". . p. 1003 - 1006. Retrieved 1994.
• 2、 Sendler,Beech. "-". . p. 1455. Retrieved 1960.
• 3、 Varila, Toni,M?kel?, Eveliina,Kupila, Riikka,Romar, Henrik,Hu, Tao,Karinen, Reetta,Puurunen, Riikka L.,Lassi, Ulla. "Conversion of furfural to 2-methylfuran over CuNi catalysts supported on biobased carbon foams". . p. 16 - 27. Retrieved 2020/12/28.
• 4、 Hua, Manli,Song, Jinliang,Huang, Xin,Hou, Minqiang,Fan, Honglei,Zhang, Zhaofu,Wu, Tianbin,Han, Buxing. "Support Effect of Ru Catalysts for Efficient Conversion of Biomass-Derived 2,5-Hexanedione to Different Products". . p. 7685 - 7693. Retrieved 2021/06/30.