Ethyl 2-oxocyclopentanecarboxylate
[CAS# 611-10-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl 2-oxocyclopentanecarboxylate
• Synonyms: 2-Carbethoxycyclopentanone; 2-(Ethoxycarbonyl)cyclopentanone
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.18
• CAS Registry Number: 611-10-9
• EC Number: 210-253-0
• SMILES: CCOC(=O)C1CCCC1=O

Properties

• Density: 1.054
• Boiling point: 102-104 °C (11 mmHg)
• Refractive index: 1.45-1.454
• Flash point: 77 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H227-H315-H319-H335
• Safety Statements: P210-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-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
Eye irritation	Eye Irrit.	2A	H319
Flammable liquids	Flam. Liq.	4	H227
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Ethyl 2-oxocyclopentanecarboxylate is an important compound with important applications in the field of organic synthesis. It is a widely used intermediate that plays an important role in the synthesis of various drugs and fine chemicals.

Ethyl 2-oxocyclopentanecarboxylate is a derivative of cyclopentanone, a compound that has been known to chemists for more than a century. Ethyl 2-oxocyclopentanecarboxylate is formed by the esterification of cyclopentanone with ethanol under acidic conditions. The compound is characterized by the presence of ketone and ester functional groups, which makes it highly reactive and can be used in various synthetic pathways.

The chemical formula of ethyl 2-oxocyclopentanecarboxylate is C8H12O3 and its molecular weight is 156.18 g/mol. It is a colorless to pale yellow liquid with a characteristic odor. The compound is soluble in organic solvents such as ethanol, ether and chloroform. Its structure consists of a five-membered cyclopentanone ring with an ester group attached to the second carbon position, making it a valuable intermediate for further chemical transformations.

The main application of ethyl 2-oxocyclopentanecarboxylate is as a synthetic pharmaceutical intermediate. It is used as a key building block in the production of various drugs, especially those involving complex cyclic structures. The reactivity of this compound allows the introduction of different functional groups, thereby facilitating the creation of various pharmacologically active molecules. Ethyl 2-oxocyclopentanecarboxylate is used in the synthesis of antiviral and antibacterial agents. These compounds are essential for the treatment of infections caused by viruses and bacteria, and intermediates play a key role in the construction of the active ingredients of these drugs.

In the agricultural sector, ethyl 2-oxocyclopentanecarboxylate is used in the synthesis of certain pesticides and herbicides. Its role as a synthetic intermediate helps in the development of chemicals that protect crops from pests and weeds, thereby increasing agricultural productivity.

Ethyl 2-oxocyclopentanecarboxylate is widely used as a synthetic intermediate in organic chemistry. It participates in a variety of chemical reactions, including condensation, reduction, and substitution reactions. This versatility makes it an essential reagent in the organic chemist's toolkit. The compound is also used in the synthesis of cyclopentane derivatives, which are important in the production of flavors, fragrances, and other fine chemicals. These derivatives often require specific functional groups that can be introduced through reactions involving ethyl 2-oxocyclopentanecarboxylate.

In the field of materials science, ethyl 2-oxocyclopentanecarboxylate can be used as a precursor for the synthesis of polymers and resins. These materials are used in coatings, adhesives, and a variety of industrial products that require specific properties such as durability and flexibility.

Ongoing research continues to explore new applications and synthetic methods for ethyl 2-oxocyclopentanecarboxylate. Advances in green chemistry could lead to more sustainable and environmentally friendly production methods for this compound. In addition, its potential role in the synthesis of new pharmaceuticals and agrochemicals remains a promising area of ​​research.

References

2019. alpha-Alkylation of 1,3-Dicarbonyls and Formation of Quaternary Stereocenters. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-232-00130

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).
DOI: 10.1007/s10904-019-01424-5

2020. Recent Developments in Highly Stereoselective Michael Addition Reactions Catalyzed by Metal Complexes. Synthesis, 52(06).
DOI: 10.1055/s-0039-1690044