2,5-Tetrahydrofurandimethanol
Title: 2,5-Tetrahydrofurandimethanol
CAS Registry Number: 104-80-3
CAS Name: THF glycol
Additional Names: 2,5-bis(hydroxymethyl)tetrahydrofuran
Molecular Formula: C6H12O3
Molecular Weight: 132.16
Percent Composition: C 54.53%, H 9.15%, O 36.32%
Literature References: Prepd from diallyl by oxidation with perbenzoic acid in chloroform, boiling with dil sulfuric acid and hydrolyzing the reaction product with KOH soln: Böeseken, Rec. Trav. Chim. 45, 838 (1926); by Raney nickel reduction of 5-hydroxymethylfurfural or of dimethyl furan-2,5-dicarboxylate: Cope, Baxter, J. Am. Chem. Soc. 77, 393 (1955). The usual form obtained is the cis form, described here.
Properties: Hygroscopic liquid. Faint odor. Avoid contact with eyes. d40 1.1719; d425 1.1542; d450 1.1359. mp below -50°. bp760 265°; bp96 200°; bp11 155°; bp0.25 105°. nD25 1.4766. Viscosity (cP): 1926 at 0°; 225 at 25°; 51.9 at 50°. Coefficient of expansion: 0.00063 per °C at 25°. Specific heat 0.5 cal/g/°C. Heat of vaporization 115 cal/g. Miscible with water, methanol, ethanol, acetone, benzene, methyl acetate, methyl ethyl ketone, chloroform. Moderately sol in ether, toluene. Almost insol in heptane, methylcyclohexane.
Melting point: mp below -50°
Boiling point: bp760 265°; bp96 200°; bp11 155°; bp0.25 105°
Index of refraction: nD25 1.4766
Density: d40 1.1719; d425 1.1542; d450 1.1359
CAUTION: Highly irritating to eyes, skin, mucous membranes.
Use: Solvent, softener, humectant. In the synthesis of plasticizers, resins, surfactants, agricultural chemicals.

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