Dimethyl carbate

Not to be confused with Dimethyl carbonate.
Dimethyl carbate
Names
IUPAC name
Dimethyl (1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
Other names
Dimethyl cis-5-norbornene-2,3-dicarboxylate; Dimalone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+
    Key: VGQLNJWOULYVFV-SPJNRGJMSA-N
  • InChI=1/C11H14O4/c1-14-10(12)8-6-3-4-7(5-6)9(8)11(13)15-2/h3-4,6-9H,5H2,1-2H3/t6-,7+,8-,9+
    Key: VGQLNJWOULYVFV-SPJNRGJMBT
  • O=C(OC)[C@@H]2[C@H](C(=O)OC)[C@H]\1C[C@@H]2/C=C/1
Properties
C11H14O4
Molar mass 210.229 g·mol−1
Density 1.4852 g/cm3[1]
Melting point 38 °C (100 °F; 311 K)[1]
Pharmacology
P03BX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dimethyl carbate is an insect repellent. It can be prepared by the Diels–Alder reaction of dimethyl maleate and cyclopentadiene.[2]

  1. ^ a b Merck Index, 11th Edition, 3230
  2. ^ Inukai, Takashi; Kojima, Takeshi (1966). "Aluminum chloride catalyzed diene condensation. II. Stronger adherence to the Alder endo rule". Journal of Organic Chemistry. 31: 2032–2033. doi:10.1021/jo01344a543. ISSN 0022-3263.