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414247

Sigma-Aldrich

2-Methyltetrahydrofuran

greener alternative

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

Synonyme(s) :

Tétrahydro-2-méthylfurane

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About This Item

Formule empirique (notation de Hill):
C5H10O
Numéro CAS:
Poids moléculaire :
86.13
Numéro Beilstein :
102448
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352005
ID de substance PubChem :
Nomenclature NACRES :
NA.07

Qualité

anhydrous

Niveau de qualité

Pureté

≥99.0%

Forme

liquid

Contient

250 ppm BHT as stabilizer

Limite d'explosivité

0.34-6.3 %

Caractéristiques du produit alternatif plus écologique

Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

Impuretés

<0.002% water
<0.005% water (100 mL pkg)

Résidus d'évap.

<0.0003%

Indice de réfraction

n20/D 1.406 (lit.)

Point d'ébullition

78-80 °C (lit.)

Pf

-136 °C

Densité

0.86 g/mL at 25 °C (lit.)

Autre catégorie plus écologique

Chaîne SMILES 

CC1CCCO1

InChI

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

Clé InChI

JWUJQDFVADABEY-UHFFFAOYSA-N

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Description générale

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

Caractéristiques et avantages

Greener alternative for THF, DCM, DMSO, and MTBE

Conditionnement

Autres remarques

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

Informations légales

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

Pictogrammes

FlameCorrosionExclamation mark

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Risques supp

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

14.0 °F - closed cup

Point d'éclair (°C)

-10.0 °C - closed cup

Équipement de protection individuelle

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


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Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
Biorenewable Solvents for High-Performance Organic Solar Cells
Panidi J, et al.
ACS Energy Letters, 8, 3038-3047 (2023)
2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry.
Pace V, et al.
ChemSusChem, 5(8), 1369-1379 (2012)
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

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