Dimethyl carbate

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
CAS Number	39589-98-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:136029;
ChemSpider	10430159;
PubChem CID	10921747;
UNII	BN2PH0TQOD ;
CompTox Dashboard (EPA)	DTXSID701032069 ;
	InChI 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;
	SMILES O=C(OC)[C@@H]2[C@H](C(=O)OC)[C@H]\1C[C@@H]2/C=C/1;
Properties
Chemical formula	C11H14O4
Molar mass	210.229 g·mol−1
Density	1.4852 g/cm3
Melting point	38 °C (100 °F; 311 K)
Pharmacology
ATC code	P03BX05 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

References

^ ^a ^b Merck Index, 11th Edition, 3230
^ 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.

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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
CAS Number	39589-98-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:136029
ChemSpider	10430159
PubChem CID	10921747
UNII	BN2PH0TQOD^Y
CompTox Dashboard (EPA)	DTXSID701032069
InChI 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
SMILES O=C(OC)[C@@H]2[C@H](C(=O)OC)[C@H]\1C[C@@H]2/C=C/1
Properties
Chemical formula	C₁₁H₁₄O₄
Molar mass	210.229 g·mol⁻¹
Density	1.4852 g/cm³^[1]
Melting point	38 °C (100 °F; 311 K)^[1]
Pharmacology
ATC code	P03BX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references