5-(Hydroxymethyl)-2-furaldehyde
Structural Formula Vector Image
Title: 5-(Hydroxymethyl)-2-furaldehyde
CAS Registry Number: 67-47-0
CAS Name: 5-(Hydroxymethyl)-2-furancarboxaldehyde
Additional Names: 5-(hydroxymethyl)-2-furancarbonal; 5-(hydroxymethyl)-2-furfural; HMF; 5-hydroxymethyl-2-formylfuran
Molecular Formula: C6H6O3
Molecular Weight: 126.11
Percent Composition: C 57.14%, H 4.80%, O 38.06%
Literature References: Prepn from the fructose portion of the sugar molecule in 57% yield: Haworth, Jones, J. Chem. Soc. 1944, 667; Haworth, Wiggins, GB 591858 (1947); GB 600871 (1948). Improved process: Garber, Jones, US 2929823 (1960 to Merck & Co.). Purification: Jones, Lange, US 2994645 (1961 to Merck & Co.). Outline of process using cornstarch, glucose and sucrose as raw materials: Medwick, Chem. Eng. News 75 (Sept. 11, 1961). Prepn from molasses: Jones, Lange, US 3066150 (1962 to Merck & Co.); Hales et al., US 3071599 (1963 to Atlas Chem.).
Properties: Needles from ether + petr ether, mp 31.5°. Avoid contact with eyes. Produces harmless yellow stains on skin. Odor of chamomile flowers. Very slightly volatile with steam (as compared with furfural). d425 1.2062. bp0.02 110°. nD18 1.5627. uv max: 283 nm. Heat of combustion: 665 kcal/mol. Freely sol in water, methanol, ethanol, acetone, ethyl acetate, dimethylformamide. Sol in ether, benzene, chloroform. Less sol in carbon tetrachloride. Sparingly sol in petr ether. Keep protected from light and air.
Melting point: mp 31.5°
Boiling point: bp0.02 110°
Index of refraction: nD18 1.5627
Absorption maximum: uv max: 283 nm
Density: d425 1.2062
Use: In the synthesis of dialdehydes, glycols, ethers, aminoalcohols, acetals. Aq acid catalyzes ring opening.

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