Dimethyl Carbate
Structural Formula Vector Image
Title: Dimethyl Carbate
CAS Registry Number: 39589-98-5
CAS Name: (endo,endo)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester
Additional Names: cis-3,6-endo-methylene-D4-tetrahydrophthalic acid dimethyl ester; cis-5-norbornene-2,3-dicarboxylic acid dimethyl ester; dimalone
Molecular Formula: C11H14O4
Molecular Weight: 210.23
Percent Composition: C 62.84%, H 6.71%, O 30.44%
Literature 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).
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).
Melting point: mp 38° when very pure
Boiling point: bp12.5 137°; bp9 130°; bp1.5 115°
Index of refraction: nD20 1.4852
Density: d421 1.164
Toxicity data: 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.

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