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Merck

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:
102448
Número CE:
Número MDL:
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
NACRES:
NA.07

grado

anhydrous

Nivel de calidad

Análisis

≥99.0%

formulario

liquid

contiene

250 ppm BHT as stabilizer

lim. expl.

0.34-6.3 %

características de los productos alternativos más sostenibles

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

sustainability

Greener Alternative Product

impurezas

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

residuo de evap.

<0.0003%

índice de refracción

n20/D 1.406 (lit.)

bp

78-80 °C (lit.)

mp

-136 °C

densidad

0.86 g/mL at 25 °C (lit.)

categoría alternativa más sostenible

cadena SMILES

CC1CCCO1

InChI

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

Clave InChI

JWUJQDFVADABEY-UHFFFAOYSA-N

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Descripción general

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.

Aplicación

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

Características y beneficios

Greener alternative for THF, DCM, DMSO, and MTBE

Otras notas

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

Información legal

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

Producto relacionado

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

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

Riesgos supl.

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

14.0 °F - closed cup

Punto de inflamabilidad (°C)

-10.0 °C - closed cup

Equipo de protección personal

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


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Certificados de análisis (COA)

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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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