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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, Tetrahydro-2-methylfuran, Tetrahydrosilvan

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About This Item

Empirical Formula (Hill Notation):
C5H10O
CAS Number:
96-47-9
Molecular Weight:
86.13
Beilstein:
102448
EC Number:
202-507-4
MDL number:
MFCD00005367
UNSPSC Code:
12352103
PubChem Substance ID:
329750937
NACRES:
NA.21

Quality Level

100

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.

sustainability

Greener Alternative Product

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,

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 biorenewable and thus it 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, environmentally favorable solvent alternative to tetrahydrofuran (THF), 1,4 Dioxane (Dioxane) and dichloromethane (DCM) for most industrial applications. Its polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether. It is a potential greener solvent alternative for organic synthesis and shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries.

Application

2-Methyltetrahydrofuran may be used as an alternative solvent to:
THF in organometallic reactions
  • Grignard
  • Reformantsky
  • Lithiation
  • Hydride Reduction
  • Metal-Catalyzed Coupling (Heck, Stile, Suzuki)




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

Features and Benefits

  • Made from Renewable Resource - furfural derived from agricultural byproducts
  • High boiling point
  • Clean organic-water phase separation
  • Reduced energy to recover

Other Notes

To see other BioRenewable or Greener Solvents

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Statements

H225,H302,H315,H318

Hazard Classifications

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

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

14.0 °F - closed cup

Flash Point(C)

-10.0 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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