• USA Home
  • 414247 - 2-Methyltetrahydrofuran

EMAIL THIS PAGE TO A FRIEND
414247 Sigma-Aldrich

2-Methyltetrahydrofuran

Green Alternative

BioRenewable, anhydrous, ≥99.0%, contains 250 ppm BHT as stabilizer

Synonym: 2-MeTHF, Tetrahydro-2-methylfuran, Tetrahydrosilvan

  • CAS Number 96-47-9

  • Empirical Formula (Hill Notation) C5H10O

  • Molecular Weight 86.13

  •  Beilstein/REAXYS Number 102448

  •  EC Number 202-507-4

  •  MDL number MFCD00005367

  •  PubChem Substance ID 57650057

Purchase

Properties

Related Categories 12 Principles Aligned Products, Anhydrous Solvents, Bio-based Greener Alternatives, BioRenewable, Chemical Synthesis,
Quality Level   100
grade   anhydrous
assay   ≥99.0%
contains   250 ppm BHT as stabilizer
expl. lim.   0.34-6.3 %
greener alternative product characteristics   Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.
impurities   <0.002% water
  <0.005% water (100 mL pkg)
evapn. residue   <0.0003%
refractive index   n20/D 1.406 (lit.)
bp   78-80 °C (lit.)
mp   -136 °C
density   0.86 g/mL at 25 °C (lit.)
SMILES string   CC1CCCO1
InChI   1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3
InChI key   JWUJQDFVADABEY-UHFFFAOYSA-N

Description

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is a biorenewable and thus aligns with "Safer Solvents and Auxiliaries" and "Use of Renewable Feedstocks". Click here for more information.
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.

Application

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.

Green Alternatives to DCM and THF from Renewable resources

2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

Packaging

1, 6×1, 2, 4×2 L in Sure/Seal™

View returnable container options.

100, 12×100 mL in Sure/Seal™

200 L in Pure-Pac™ 2

Features and Benefits

Greener alternative for THF, DCM, DMSO, and MTBE

Other Notes

Pure-Pac® II containers require the Micromatic MacroValve coupler for dispensing solvents, Z560723.

Legal Information

Pure-Pac is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
EUH019
RIDADR 
UN 2536 3 / PGII
WGK Germany 
WGK 2
RTECS 
LU2800000
Flash Point(F) 
14.0 °F - closed cup
Flash Point(C) 
-10.0 °C - closed cup

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number
Protocols & Articles

Articles

Anhydrous Solvents for Coupling Reactions

Due to the sensitivity to air and moisture, coupling reactions often require relatively low air and water conditions to initiate the reaction. Therefore, the use of anhydrous solvents is highly recom...
Keywords: Coupling reactions, Cross couplings, Negishi Coupling, Solvents

Anhydrous Solvents for Organic and Organometallic Chemistry

Many well-known reactions require water-free conditions to initiate or complete the reaction. Failure to include anhydrous solvents can result in low product yield or reaction failure. As the market ...
Keywords: Acylations, Alkylations, Electrophilic aromatic substitution, Formylations, Grignard Reaction, Solvents, Substitutions, Vilsmeier-Haack reaction

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

Related Content

Greener Alternatives Four Categories

A new icon has been added to identify our Greener alternative products. Products with this icon fulfill one of the four criteria.
Keywords: Alternative energy, Environmental, Green chemistry, PAGE, Solvents, Substitutions

Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?