Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate
[CAS# 141573-95-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate
• Molecular Formula: C₈H₁₀F₂N₂O₂
• Molecular Weight: 204.17
• CAS Registry Number: 141573-95-7
• EC Number: 619-510-5
• SMILES: CCOC(=O)C1=CN(N=C1C(F)F)C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: 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-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is synthesized through a series of organic reactions involving the condensation of ethyl esters with difluoromethylhydrazine derivatives under controlled conditions. The synthetic route produces a crystalline solid with a specific molecular arrangement characterized by the substitution of pyrazole rings with ethyl ester groups and difluoromethyl groups at strategic positions. The discovery of this compound marks a breakthrough in medicinal chemistry, providing new avenues for drug development and agricultural innovation.

From a chemical perspective, ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is characterized by its pyrazole core structure, including difluoromethyl (-CF2H) and ethyl ester groups (-COOEt). These structural elements give it unique physical and chemical properties, such as solubility, stability, and bioactivity, which are essential for its application in various chemical processes.

The compound is a key intermediate in the synthesis of pharmaceutical compounds, especially those targeting central nervous system diseases and infectious diseases. Its structural modification potential can enhance drug potency, bioavailability, and metabolic stability, contributing to improved therapeutic efficacy.

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate is widely used as a precursor in the development of herbicides and fungicides. Its selective activity against specific plant pathogens and weeds supports sustainable agricultural practices, ensuring crop protection and yield optimization.

The versatile reactivity of this compound enables its application in organic synthesis for the preparation of a wide range of chemical intermediates and fine chemicals. Its incorporation enhances the functional and performance characteristics of the products and is essential for specialty chemical manufacturing.

The ongoing research program focuses on exploring the potential of ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate in the following areas: studying its pharmacological properties and therapeutic applications through structure-activity relationship studies and bioassays, aiming to develop novel drug candidates with improved efficacy and safety; enhancing its formulation and delivery systems to optimize efficacy, minimize environmental impact, and meet regulatory standards for sustainable agricultural practices; exploring its role in materials science applications, including functional coatings, polymers, and nanomaterials, leveraging its unique chemistry for the design and development of advanced materials.

Studies on the safety and regulatory compliance of ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate ensure its responsible handling and use in industrial applications. The regulatory framework involves environmental impact assessments, occupational health guidelines, and product stewardship to mitigate potential risks associated with its manufacture and use.

References

none