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673277

Sigma-Aldrich

2-Methyltetrahydrofuran

greener alternative

BioRenewable, anhydrous, ≥99%, Inhibitor-free

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

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.)

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 (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.

Packaging

100, 12×100 mL in Sure/Seal™
1, 2 L in Sure/Seal™
200 L in Pure-Pac™ 2

Features and Benefits

Greener alternative for THF, DCM, DMSO, and MTBE

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

WGK 2

Flash Point(F)

14.0 °F - closed cup

Flash Point(C)

-10.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Tatsuya Higaki et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(27), 13215-13220 (2019-06-19)
Research on plasmons of gold nanoparticles has gained broad interest in nanoscience. However, ultrasmall sizes near the metal-to-nonmetal transition regime have not been explored until recently due to major synthetic difficulties. Herein, intriguing electron dynamics in this size regime is...
Dennis Weidener et al.
Molecules (Basel, Switzerland), 25(15) (2020-07-28)
Fractionation of lignocellulose into its three main components, lignin, hemicelluloses, and cellulose, is a common approach in modern biorefinery concepts. Whereas the valorization of hemicelluloses and cellulose sugars has been widely discussed in literature, lignin utilization is still challenging. Due...
2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry.
Pace V, et al.
ChemSusChem, 5(8), 1369-1379 (2012)
Weiwei Cheng et al.
Journal of agricultural and food chemistry, 67(8), 2321-2330 (2019-02-06)
A facile and two-step strategy was employed to synthesize a series of novel aspartic-acid-based ampholytic amphiphiles from sustainable and commercially viable substances as starting materials. The molecular structures of the synthetic compounds were well-identified by mass spectrometry and 1H/13C nuclear...
Renxi Jin et al.
Nanoscale, 9(48), 19183-19190 (2017-12-01)
Doping metal nanoclusters with a second type of metal is a powerful method for tuning the physicochemical properties of nanoclusters at the atomic level and it also provides opportunities for a fundamental understanding of alloying rules as well as new...

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