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155810

Sigma-Aldrich

2-Methyltetrahydrofuran

greener alternative

BioRenewable, ReagentPlus®, ≥99.5%, contains 150-400 ppm BHT as stabilizer

Synonym(s):
2-MeTHF, Tetrahydrosilvan, Tetrahydro-2-methylfuran
Empirical Formula (Hill Notation):
C5H10O
CAS Number:
Molecular Weight:
86.13
Beilstein:
102448
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

product line

ReagentPlus®

assay

≥99.5%

form

liquid

contains

150-400 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

≤1.0% water (coulometr.)
≤100 ppm peroxide (as H2O2)

refractive index

n20/D 1.406 (lit.)

bp

78-80 °C (lit.)

mp

-136 °C

density

0.86 g/mL at 25 °C (lit.)

greener alternative category

Aligned, Aligned

SMILES string

CC1CCCO1

InChI

1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3

InChI key

JWUJQDFVADABEY-UHFFFAOYSA-N

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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 is an environmentally favorable alternative to tetrahydrofuran (THF), 1,4 Dioxane (Dioxane) and dichloromethane (DCM) for most industrial applications.
Many of its benefits include:
  • High boiling point
  • Clean organic-water phase separation
  • Reduced energy to recover

Application

Alternative for THF in Organometallic reactions:
  • Grignard
  • Reformantsky
  • Lithiation
  • Hydride Reduction
  • Metal-Catalyzed Coupling (Heck, Stile, Suzuki)

Alternative to Dichloromethane for Biphasic Reactions:
  • Alkylation
  • Amidation
  • Nucleophilic Substitution

Forms organic (non-crystalline) glass for low temperature (-196°C) spectroscopic studies.

Packaging

100, 500 mL in glass bottle
2.5, 4×4 L in glass bottle
18, 200 L in steel drum

Features and Benefits

BioRenewable
Replacement for THF, DCM, MTBE and DMSO

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Irrit. 2

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK Germany

WGK 2

Flash Point(F)

14.0 °F - closed cup

Flash Point(C)

-10.0 °C - closed cup

Certificate of Analysis

Certificate of Origin

Mari Merce Cascant et al.
Analytical and bioanalytical chemistry, 409(14), 3527-3539 (2017-04-09)
There is a great interest in finding alternatives and green solvents in extraction processes to replace petroleum based solvents. In order to investigate these possibilities, computational methods, as Hansen solubility parameters (HSP) and conductor-like screening model for real solvent (COSMO-RS)...
V R Koch et al.
Science (New York, N.Y.), 204(4392), 499-501 (1979-05-04)
Rechargeable, high energy density lithium batteries require an efficient lithium electrode. Earlier work with electrolytes based on propylene carbonate, methyl acetate, and tetrahydrofuran yielded poor lithium electrode cycling efficiencies because of electrolyte reduction by lithium. Solutions of lithium hexafluoroarsenate in...
Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions.
Aycock DF.
Organic Process Research & Development, 11(1), 156-159 (2007)
Axel Kahnt et al.
Journal of the American Chemical Society, 133(25), 9863-9871 (2011-05-21)
Electron-transfer reactions are fundamental to many practical devices, but because of their complexity, it is often very difficult to interpret measurements done on the complete device. Therefore, studies of model systems are crucial. Here the rates of charge separation and...
Tony W T Bristow et al.
Journal of the American Society for Mass Spectrometry, 25(10), 1794-1802 (2014-08-12)
For on-line monitoring of chemical reactions (batch or continuous flow), mass spectrometry (MS) can provide data to (1) determine the fate of starting materials and reagents, (2) confirm the presence of the desired product, (3) identify intermediates and impurities, (4)...

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