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2-methyltetrahydrofuran
Sign in to save2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C5H10O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations (as, unlike THF, it is not miscible with water). It is derived from sugars via furfural and is occasionally touted as a biofuel.
Chemical data
- Formula
- C5H10O
- Molecular weight
- 86.13 g/mol
- IUPAC name
- 2-methyloxolane
- SMILES
- CC1CCCO1
- InChIKey
- JWUJQDFVADABEY-UHFFFAOYSA-N
- XLogP
- 1
- Polar surface area
- 9.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 86.073
Show 5 more facts
- Commons category
- Methyltetrahydrofuran
- chemical formula
- C₅H₁₀O
- canonical SMILES
- CC1CCCO1
- melting point
- -136.0
- found in taxon
- cacao
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Structures and properties
- Preparation
- Applications
- References
- Further reading
2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C5H10O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations (as, unlike THF, it is not miscible with water). It is derived from sugars via furfural and is occasionally touted as a biofuel.
==Structures and properties== 2-Methyltetrahydrofuran is "inversely soluble" in water. That is, its solubility decreases with increasing temperature, which is a rare property. The solubility of water in 2-methyltetrahydrofuran is reported to be 14.4 g/ 100 g at 23 °C. Much like tetrahydrofuran, 2-methyltetrahydrofuran can act as a Lewis base in organometallic reactions. 2-Methyltetrahydrofuran is usually produced as a racemic mixture.
Excerpted from Wikipedia’s “2-methyltetrahydrofuran” article, available under the CC BY-SA 4.0 licence.