ChemicalBook--->CAS DataBase List--->58101-60-3

58101-60-3

58101-60-3 Structure

58101-60-3 Structure
IdentificationMore
[Name]

Methyl 3-cyclopentenecarboxylate
[CAS]

58101-60-3
[Synonyms]

METHYL 3-CYCLOPENTENECARBOXYLATE
Methyl-3-cyclopentene-1-carboxylate
3-Cyclopentene CarboxylicAcid Methyl Ester
3-Cyclopentene-1-Carboxylic AcidMethyl Ester
Methyl3-Cyclopentene-1-CarBonate
[Molecular Formula]

C7H10O2
[MDL Number]

MFCD04038661
[Molecular Weight]

126.15
[MOL File]

58101-60-3.mol
Chemical PropertiesBack Directory
[Boiling point ]

74 °C(Press: 24 Torr)
[density ]

1.031 g/mL at 25 °C
[Fp ]

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 DataBack Directory
[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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Methanol-->N,N-Dimethylformamide-->Thionyl chloride-->Potassium hydroxide-->Sodium hydride-->Sodium ethoxide-->Dimethyl malonate-->Lithium chloride-->Calcium hydride-->cis-1,4-Dichloro-2-butene-->cis-2,3-dichlorobut-2-ene-->3-Cyclopentene-1-carbonyl chloride-->DIALLYL GLUTARATE-->3-Cyclopentene-1-carboxylic acid-->Dimethyl 3-Cyclopentene-1,1-dicarboxylate
Hazard InformationBack Directory
[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]

Methanol

67-56-1

3-Cyclopentene-1-carboxylic acid

7686-77-3

Methyl 3-cyclopentenecarboxylate

58101-60-3

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
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl 3-cyclopentenecarboxylate(58101-60-3)1HNMR
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