10262. Cyclopentyl Methyl Ether

Nomenclature

CAS number: 5614-37-9
Methoxycyclopentane; CPME.
C6H12O; mol wt 100.16.
C 71.95%, H 12.08%, O 15.97%.

Description and references

Ethereal solvent with high resistance to peroxide formation, high boiling point, and narrow explosion range; alternative to THF, MTBE, and 1,4-dioxane, q.q.v., for attaining green, sustainable processes. Prepn: J. Loevenich et al., Ber. 62, 3084 (1929); W. T. Olson et al., J. Am. Chem. Soc. 69, 2451 (1947) DOI. Improved prepn: H. C. Brown et al., J. Org. Chem. 50, 1171 (1985) DOI. Synthetic applications: Y. Sawada et al., Org. Lett. 6, 2277 (2004) DOI PubMed; T. Ooi et al., J. Am. Chem. Soc. 127, 5073 (2005) DOI PubMed; H. Tokimoto et al., Tetrahedron: Asymmetry 16, 441 (2005) DOI. Review of properties as a process solvent in organic synthesis: K. Watanabe et al., Org. Process Res. Dev. 11, 251-258 (2007) DOI.

Chemical structure

Properties

Colorless liquid. bp 106°. mp 134.75°. d20 0.86. Flammable; irritant. Vapor specific gravity (air = 1): 3.45. Viscosity (20°): 0.55 cP. Surface tension (20°): 25.17 mN/m. nD20 1.4189. Dielectric constant (25°): 4.76. Soly in water (23°): 1.1 g/100 g. Flash pt: 1°C (30°F). Ignition pt: 180°. Log P (octanol/water): 1.59. Explosion range: 1.1-9.9 vol%. Vaporization energy: 69.2 kcal/kg. Forms azeotrope with water (16.3%), bp 83°. Relatively stable to acidic and basic conditions.

Caution

Irritating to eyes and skin.

Use

Solvent in organic synthesis.