CAS 1191-99-7: 2,3-Dihydrofuran

2,3-Dihydrofuran is a compound that belongs to the class of organic compounds called heterocycles. It is prepared by the palladium-catalyzed coupling of malonic acid with 2-iodobenzoic acid. This reaction can be conducted in either solution or on the surface of a solid support and isolated with high yield. The reaction mechanism is shown below: H+ + HO - HO H2O HO - Pd + HO - PdO HO H2O The structure of 2,3-dihydrofuran has been elucidated through an NMR spectroscopic analysis. Hydroxide solution was used as a reaction solution for this analysis. The chemical shifts observed in the spectrum indicate that the hydroxide ion is coordinated to one oxygen atom and three hydrogen atoms on the two carbon atoms adjacent to the double bond.

2,3-Dihydrofuran

2,3-Dihydrofuran is a versatile reagent used in lanthanide-catalyzed Diels-Alder reactions with 2-pyrones and in Rh(II)-stabilized cycloadditions with vinylcarbenoids. It is applied for alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenyl­phosphine)­palladium(II). It is also used in the preparation of biologically active compounds such as antitumor agents. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications 2,3-Dihydrofuran is a dehydration product of tetrahydrofuran (THF). 2,3-Dihydrofuran is also used in the preparation of niologically active compounds such as antitumor agents. References Kohlweyer, U. et al.: FEMS Microbiol. Lett., 186, 301 (2000); Li, J. et al.: Lett. Drug Design Disc., 9, 379 (2012);

2, 3-Dihydrofuran, a heterocyclic compound, is one of the simplest enol ethers.

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.