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673277 Sigma-Aldrich

2-Methyltetrahydrofuran

Green Alternative

BioRenewable, anhydrous, ≥99%, Inhibitor-free

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 57652076

  •  NACRES NA.21

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Properties

Related Categories 12 Principles Aligned Products, Anhydrous Solvents, Bio-based Greener Alternatives, BioRenewable, Building Blocks,
Quality Level   100
grade   anhydrous
assay   ≥99%
form   liquid
expl. lim.   0.34-6.3 % (lit.)
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 (lit.)
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 tetrahydrofuran, 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.

Application

2-Methyltetrahydrofuran may be used as solvent for phosphatidylserine synthesis.
It may be used as an alternative solvent to:
• Dimethyl sulfoxide (DMSO) or methyl tert-butyl ether (MTBE) in the C-C bond forming reactions catalyzed by lyase enzyme.
• Tetrahydrofuran (THF) in the reaction between Grignard reagents and carbonyl compounds.
• Methylene chloride in some biphasic 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, 2 L in Sure/Seal™

100, 12×100 mL in Sure/Seal™

200 L in Pure-Pac™ 2

Features and Benefits

Greener alternative for THF, DCM, DMSO, and MTBE

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)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles

Articles

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...

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The aim of green chemistry is to reduce chemical related impact on human health and virtually eliminate contamination of the environment through dedicated, sustainable prevention programs. Green chem...
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Peer-Reviewed Papers
15

References

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