10318. 2-Methyltetrahydrofuran

Nomenclature

CAS number: 96-47-9
Tetrahydro-2-methylfuran; tetrahydrosylvan; 2-MeTHF; MeTHF.
C5H10O; mol wt 86.13.
C 69.72%, H 11.70%, O 18.58%.

Description and references

Environmentally friendly organic solvent derived from renewable biomass. Alternative to tetrahydrofuran for organometallic reactions and dichloromethane for biphasic reactions. Prepn: A. Lipp, Ber. 22, 2567 (1889); and physical properties: E. V. Whitehead et al., J. Am. Chem. Soc. 73, 3632 (1951) DOI. Prepn by catalytic hydrogenation of biomass containing furfural: I. Ahmed, WO 0234697; US 7064222 (2002, 2006 both to Pure Energy Corp.). Review of green chemistry properties: B. Comanita, Spec. Chem. 26, 44-45 (2006); of solvent applications in organic synthesis: D. F. Aycock, Org. Process Res. Dev. 11, 156-159 (2007) DOI.

Chemical structure

Properties

Colorless liquid. Flammable. bp 79.9-80.1°; bp716 77-78°. fp 137.2°. d20 0.8604. nD20 1.4063. Dielectric constant at 25°: 7. Flash pt, closed cup: 10.4°F (12°C). Ignition pt: 270°C. Vaporization energy: 89.7 kcal/kg. Forms azeotrope with water (10.6%), bp 71°. Limited miscibility with water. Very stable to basic conditions; stable to acid concentrations of most synthetic processes.

Use

Solvent in synthetic organic chemistry.