Ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate
[CAS# 5932-31-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate
• Synonyms: 2,4,5,6-Tetrahydro-cyclopentapyrazole-3-carboxylic acid ethyl ester
• Molecular Formula: C₉H₁₂N₂O₂
• Molecular Weight: 180.20
• CAS Registry Number: 5932-31-0
• EC Number: 696-180-9
• SMILES: CCOC(=O)C1=NNC2=C1CCC2

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.569, Calc.^*
• Boiling Point: 384.1±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 186.1±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H332
• Safety Statements: P261-P264-P270-P271-P280-P301+P317-P302+P352-P304+P340-P317-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

Ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate is a heterocyclic compound of interest in organic chemistry, particularly in drug discovery and medicinal chemistry. Its structure consists of a pyrazole ring fused to a cyclopentane ring, with an ethyl ester group at the 3-position of the pyrazole ring. This unique molecular framework imparts specific chemical properties, making the compound useful in various synthetic applications and as a potential building block for pharmacologically active molecules.

The discovery of ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate likely originated from efforts to explore fused heterocyclic systems, as such structures often exhibit interesting biological activity. Fused pyrazole systems, in particular, have attracted attention due to their prevalence in natural products and their roles as key scaffolds in drug design. Researchers have synthesized derivatives of pyrazoles to examine their potential as inhibitors, anti-inflammatory agents, and other therapeutic roles.

One of the main applications of ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate is its role as an intermediate in the synthesis of more complex molecules. In medicinal chemistry, it serves as a versatile scaffold for the development of new pharmaceutical compounds. The fusion of the pyrazole and cyclopentane rings introduces conformational rigidity, which is often desirable in drug design because it can improve the binding affinity of molecules to their biological targets. This rigidity can also enhance selectivity, reducing the likelihood of off-target effects.

Moreover, the ester group in the compound provides a reactive site for further functionalization, allowing chemists to modify the molecule’s properties, such as solubility, lipophilicity, or reactivity. This makes ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate an important starting material for synthesizing various derivatives aimed at optimizing pharmacological properties.

In addition to its use in drug development, the compound has potential applications in agrochemicals and material sciences, where heterocyclic compounds play roles as functional additives or as components in complex organic molecules.

The exploration of ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate highlights the importance of fused heterocyclic systems in organic synthesis and their broad utility in both pharmaceutical and industrial contexts. As synthetic methods continue to evolve, this compound is likely to remain a valuable component in chemical research, contributing to the development of new materials and bioactive compounds.

References

2011. Synthesis of 3-Aminomethyl-Substituted Pyrazoles and Isoxazoles. *Russian Journal of Organic Chemistry*, 47(8). DOI: 10.1134/s1070428011080136