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673277

Sigma-Aldrich

2-Methyltetrahydrofuran

greener alternative

BioRenewable, anhydrous, ≥99%, Inhibitor-free

Synonym(s):

2-MeTHF, Tetrahydro-2-methylfuran, Tetrahydrosilvan

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About This Item

Empirical Formula (Hill Notation):
C5H10O
CAS Number:
Molecular Weight:
86.13
Beilstein:
102448
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.21

grade

anhydrous

Quality Level

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.

sustainability

Greener Alternative Product

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

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 a 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

Organic Solar Cells

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

Features and Benefits

Greener alternative for THF, DCM, DMSO, and MTBE

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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

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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
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
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
Enzyme-catalyzed C-C bond formation using 2-methyltetrahydrofuran (2-MTHF) as (co) solvent: efficient and bio-based alternative to DMSO and MTBE.
Shanmuganathan S, et al.
Green Chemistry, 12(12), 2240-2245 (2010)
Efficient chemoselective addition of Grignard reagents to carbonyl compounds in 2-methyltetrahydrofuran.
Zhong W, et al.
J. Chem. Res. (M), 2009(6), 370-373 (2009)

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