3,5-Pyrazoledicarboxylic acid diethyl ester
[CAS# 37687-24-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Acid ester compound
• Name: 3,5-Pyrazoledicarboxylic acid diethyl ester
• Synonyms: 1H-Pyrazole-3,5-dicarboxylic acid diethyl ester; 3,5-(Diethoxycarbonyl)-1H-pyrazole; Diethyl pyrazole-3,5-dicarboxylate; Diethyl 1H-pyrazole-3,5-dicarboxylate; NSC 97126
• Molecular Formula: C₉H₁₂N₂O₄
• Molecular Weight: 212.20
• CAS Registry Number: 37687-24-4
• EC Number: 609-467-0
• SMILES: CCOC(=O)C1=CC(=NN1)C(=O)OCC

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*, 1.249 g/mL (Expl.)
• Melting point: 55 - 58 ºC (Expl.)
• Boiling point: 362.4±22.0 ºC 760 mmHg (Calc.)^*
• Flash point: 173.0±22.3 ºC (Calc.)^*
• Index of refraction: 1.52 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

3,5-Pyrazoledicarboxylic acid diethyl ester is an organic compound that belongs to the class of pyrazole derivatives, specifically a diethyl ester of pyrazoledicarboxylic acid. This compound contains a pyrazole ring, a five-membered heterocyclic structure with two nitrogen atoms, and two ester functional groups attached to the carboxyl positions at the 3 and 5 positions of the ring. The diethyl ester functionality is significant because it enhances the solubility and reactivity of the compound, making it useful in various chemical syntheses.

The synthesis of 3,5-pyrazoledicarboxylic acid diethyl ester typically involves the esterification of 3,5-pyrazoledicarboxylic acid with ethanol or ethyl alcohol in the presence of a suitable catalyst, such as sulfuric acid or other dehydrating agents. The reaction results in the formation of the ester derivative, which retains the carboxyl functional groups but with improved solubility compared to the parent acid.

This compound is valuable as an intermediate in organic synthesis. The ester groups provide a functional site for further chemical modifications. The pyrazole ring structure is known for its ability to undergo a variety of reactions, including nucleophilic substitution, hydrolysis, and cyclization, which can lead to the formation of more complex molecules with different functional groups. This reactivity makes 3,5-pyrazoledicarboxylic acid diethyl ester an important building block for the synthesis of pyrazole-based compounds with diverse properties.

In pharmaceutical chemistry, pyrazole derivatives are often studied for their potential bioactivities. Pyrazole rings are commonly found in molecules with anti-inflammatory, antimicrobial, and anticancer activities. The introduction of ester groups, such as those in 3,5-pyrazoledicarboxylic acid diethyl ester, may affect the compound's lipophilicity and facilitate its interaction with biological targets. As a result, this compound, or derivatives thereof, could be explored for use in drug development, particularly in the synthesis of novel pyrazole-based bioactive compounds.

Additionally, 3,5-pyrazoledicarboxylic acid diethyl ester has applications in materials science. The pyrazole ring is a versatile structure that can be incorporated into various polymers and materials. Its ability to coordinate with metals allows for its use as a ligand in coordination chemistry. The compound could be utilized in the design of metal-organic frameworks (MOFs) or other coordination compounds with specific structural and functional properties. Furthermore, the compound can serve as a precursor for the synthesis of dyes and pigments, as pyrazole derivatives are known for their ability to impart color to materials.

The compound also holds promise in the field of agrochemicals. The pyrazole ring, combined with the ester groups, could be modified to create new pesticidal agents, such as herbicides or fungicides. The biological activity of pyrazole derivatives in these areas is well-documented, and the presence of ester groups could improve the stability and bioavailability of the resulting compounds, enhancing their effectiveness as crop protection agents.

In conclusion, 3,5-pyrazoledicarboxylic acid diethyl ester is a versatile compound with significant potential in organic synthesis, pharmaceuticals, materials science, and agrochemicals. Its pyrazole ring and ester functional groups provide a platform for further chemical modifications, making it a valuable intermediate for the development of bioactive compounds, specialty materials, and agricultural products. Its reactivity and solubility characteristics position it as a useful tool in the exploration of new chemical properties and applications.

References

2004. Diethyl 1H-pyrazole-3,5-dicarboxylate. Acta Crystallographica Section E Structure Reports Online, 60(3).
DOI: 10.1107/s1600536804001928

2006. The Sodium Salt of Diethyl 1H-pyrazole-3,5-dicarboxylate as an Efficient Amphiphilic Receptor for Dopamine and Amphetamines. Crystal Structure and Solution Studies. Journal of the American Chemical Society, 128(50).
DOI: 10.1021/ja064657h