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Sigma-Aldrich

2-Methyltetrahydrofuran

greener alternative

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

Sinônimo(s):

2-MeTHF, Tetrahydro-2-methylfuran, Tetrahydrosilvan

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About This Item

Fórmula empírica (Notação de Hill):
C5H10O
Número CAS:
Peso molecular:
86.13
Beilstein:
102448
Número CE:
Número MDL:
Código UNSPSC:
12352005
ID de substância PubChem:
NACRES:
NA.07

grau

anhydrous

Nível de qualidade

Ensaio

≥99.0%

forma

liquid

contém

250 ppm BHT as stabilizer

Lim. expl.

0.34-6.3 %

características do produto alternativo mais ecológico

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)

resíduo de evaporação

<0.0003%

índice de refração

n20/D 1.406 (lit.)

pb

78-80 °C (lit.)

pf

-136 °C

densidade

0.86 g/mL at 25 °C (lit.)

categoria alternativa mais ecológica

cadeia de caracteres SMILES

CC1CCCO1

InChI

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

chave InChI

JWUJQDFVADABEY-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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 e benefícios

Greener alternative for THF, DCM, DMSO, and MTBE

Outras notas

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

Informações legais

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

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

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

Perigos de suplementos

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

14.0 °F - closed cup

Ponto de fulgor (°C)

-10.0 °C - closed cup

Equipamento de proteção individual

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


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Os clientes também visualizaram

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)
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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