3240. Dimethyl Carbate

Nomenclature

CAS number: 39589-98-5
(endo,endo)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester; cis-3,6-endo-methylene-Δ4-tetrahydrophthalic acid dimethyl ester; cis-5-norbornene-2,3-dicarboxylic acid dimethyl ester; dimalone.
C11H14O4; mol wt 210.23.
C 62.84%, H 6.71%, O 30.44%.

Description and references

Prepd by a Diels-Alder condensation of cyclopentadiene and maleic anhydride, followed by esterification of resulting anhydride: Bode, Ber. 70, 1167 (1937); Morgan et al., J. Am. Chem. Soc. 66, 404 (1944). Toxicology studies: J. H. Draize et al., J. Pharmacol. Exp. Ther. 93, 26 (1948).

Chemical structure

Properties

Crystals, mp 38° when very pure. The usual product is a viscous, syrupy liquid. bp12.5 137°; bp9 130°; bp1.5 115°. d421 1.164. nD20 1.4852. Practically insol in water. Soluble in the usual organic solvents. Solubility in kerosene and mineral oils ≈6%. LD50 in mice, rats (ml/kg): 1.4, 1.0 orally; in rats (ml/kg): 10.0 dermally (Draize).

Caution

Can cause CNS excitation followed by depression.

Use

Insect repellent.