Methyl 3-cyclopentenecarboxylate Chemical Properties

Boiling point:

74 °C(Press: 24 Torr)

Density 

1.031 g/mL at 25 °C

Flash point:

48°(118°F)

refractive index 

1.4500

storage temp. 

2-8°C

form 

Liquid

color 

Colorless to pale brown

InChI

InChI=1S/C7H10O2/c1-9-7(8)6-4-2-3-5-6/h2-3,6H,4-5H2,1H3

InChIKey

CEOILRYKIJRPBZ-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)CC=CC1

CAS DataBase Reference

58101-60-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-41

Safety Statements 

24/25-36/39

RIDADR 

UN 1993C 3 / PGIII

WGK Germany 

3

HazardClass 

3

HS Code 

2916200090

Methyl 3-cyclopentenecarboxylate Usage And Synthesis

Uses

Methyl 3-Cyclopentene-1-carboxylate has been used as a reactant in the preparation of (silyloxy)methylcyclopentanone as a key intermediate of sphingosine phosphate receptor agonists.

Synthesis

At 0 °C and under nitrogen protection, 3-cyclopentenecarboxylic acid (10 g, 89 mmol) was dissolved in dichloromethane (100 mL), followed by the addition of 1,1'-carbonyl diimidazole (43 g, 267 mmol). The reaction mixture was stirred at room temperature for 4 hours, after which methanol (100 mL) was added. Stirring of the reaction mixture was continued overnight. The solvent was removed by low temperature evaporation to afford methyl 3-cyclopentene-1-carboxylate (11.2 g, 99% yield).

References

[1] Patent: US2007/254952, 2007, A1. Location in patent: Page/Page column 35
[2] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 4-7, p. 661 - 664
[3] ChemMedChem, 2011, vol. 6, # 9, p. 1559 - 1565
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5336 - 5339

Methyl 3-cyclopentenecarboxylate(58101-60-3)Related Product Information

• ethyl cyclopent-3-ene-1-carboxylate
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• Methyl acetate
• Methyl 2-bromobenzoate
• METHYL THIOPHENE-2-CARBOXYLATE
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• Methyl
• 3-CYANOPROPIONIC ACID METHYL ESTER
• Methyl 3-cyclopropyl-3-oxopropionate
• Methyl 3-cyanobenzoate