9212. 2,5-Tetrahydrofurandimethanol

Nomenclature

CAS number: 104-80-3
THF glycol; 2,5-bis(hydroxymethyl)tetrahydrofuran.
C6H12O3; mol wt 132.16.
C 54.53%, H 9.15%, O 36.32%.

Description and references

Prepd from diallyl by oxidation with perbenzoic acid in chloroform, boiling with dil sulfuric acid and hydrolyzing the reaction product with KOH soln: B"oeseken, 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.

Chemical structure

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.

Caution

Highly irritating to eyes, skin, mucous membranes.

Use

Solvent, softener, humectant. In the synthesis of plasticizers, resins, surfactants, agricultural chemicals.