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MilliporeSigma

414247

Sigma-Aldrich

2-Methyltetrahydrofuran

greener alternative

BioRenewable, anhydrous, ≥99.0%, contains 250 ppm BHT as stabilizer

Sinónimos:

2-MeTHF, Tetrahydro-2-methylfuran, Tetrahydrosilvan

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About This Item

Fórmula empírica (notación de Hill):
C5H10O
Número de CAS:
Peso molecular:
86.13
Beilstein/REAXYS Number:
102448
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.07

grade

anhydrous

Quality Level

assay

≥99.0%

form

liquid

contains

250 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

<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

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 tetrahdrofuran, 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 to form secondary chlorides and primary iodides respectively. On long term storage, tetrahydrofuran forms organic peroxides. This process can be suppressed by adding butylated hydroxytoluene (BHT) as a stabilizer. BHT removes the free radicals required for the peroxide formation.

Application

2-Methyltetrahydrofuran may be used as solvent for phosphatidylserine synthesis.
It may be used as an alternative solvent to:
  • DMSO (dimethyl sulfoxide) or MTBE (methyl tertiary butyl ether) in the C-C bond forming reactions catalyzed by lyase enzyme.
  • THF in the reaction between Grignard reagents and carbonyl compounds.
  • Methylene chloride in some biphase 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

Other Notes

Pure-Pac® II containers require the Micromatic MacroValve coupler for dispensing solvents, Z560723.

Legal Information

Pure-Pac is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

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

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

14.0 °F - closed cup

flash_point_c

-10.0 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Visite la Librería de documentos

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)
2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry.
Pace V, et al.
ChemSusChem, 5(8), 1369-1379 (2012)
2-Methyltetrahydrofuran as an alternative to dichloromethane in 2-phase reactions.
Ripin DHB and Vetelino M.
Synlett, 15, 2353-2353 (2003)
Regiocontrolled ring opening of 2-methyltetrahydrofuran with acid chlorides and iodides.
Mimero P, et al.
Tetrahedron Letters, 35(10), 1553-1556 (1994)

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