Methyl 2-cyclopentanonecarboxylate
[CAS# 10472-24-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
• Name: Methyl 2-cyclopentanonecarboxylate
• Synonyms: Methyl 2-oxocyclopentanecarboxylate; 2-Methoxycarbonylcyclopentanone; Carbomethoxycyclopentanone
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• CAS Registry Number: 10472-24-9
• EC Number: 233-962-7
• SMILES: COC(=O)C1CCCC1=O

Properties

• Density: 1.054
• Boiling point: 102-104 °C (11 mmHg)
• Refractive index: 1.455-1.457
• Flash point: 79 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H227-H302-H315-H319-H335
• Safety Statements: P210-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P370+P378-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Flammable liquids	Flam. Liq.	4	H227
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Methyl 2-cyclopentanonecarboxylate is a versatile compound with a wide range of applications in organic synthesis and pharmaceuticals due to its unique structure. The synthesis and characterization of methyl 2-cyclopentanonecarboxylate was first reported in the mid-20th century by researchers studying cyclopentanone derivatives. The compound is synthesized by esterification of 2-cyclopentanonecarboxylic acid using methanol and an acid catalyst.

Methyl 2-cyclopentanonecarboxylate has the molecular formula C7H10O3 and features a cyclopentanone ring and a carboxylate group at the 2-position. This structural motif gives it a unique reactivity that makes it valuable in a variety of chemical transformations.

The compound is a key intermediate in organic synthesis. Its reactive carbonyl group allows for a range of chemical modifications, including nucleophilic addition, condensation, and reduction. It is often used to synthesize complex organic molecules, including natural products and pharmaceuticals.

Methyl 2-cyclopentanonecarboxylate is used in the development of pharmaceutical compounds. Its versatile structure allows for the creation of novel drug candidates with potential therapeutic applications. Researchers have explored its use in the synthesis of anti-inflammatory, analgesic, and antibacterial compounds.

The compound is also used in the flavor and fragrance industry. Its pleasant odor makes it a valuable ingredient in perfume and flavor formulations. It helps create complex smell and taste profiles in a variety of consumer products.

Current research aims to expand the application of methyl 2-cyclopentanonecarboxylate in new areas. Efforts are being made to develop more efficient synthetic routes, optimize its reactivity for specific applications, and explore its potential in emerging fields such as green chemistry and sustainable materials.

References

1961. beta-Dicarbonyl compounds. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 10(11), 6146.
DOI: 10.1007/bf00906146

2021. Applications of the Horner-Wadsworth-Emmons Olefination in Modern Natural Product Synthesis. Synthesis, 53(22), 6331.
DOI: 10.1055/a-1493-6331

2019. Michael Addition of 1,3-Dicarbonyl Derivatives in the Presence of Zeolite Y as an Heterogeneous Catalyst. Journal of Inorganic and Organometallic Polymers and Materials, 30(7), 1424.
DOI: 10.1007/s10904-019-01424-5