1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
[CAS# 113100-53-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
• Molecular Formula: C₆H₅F₃N₂O₂
• Molecular Weight: 194.11
• CAS Registry Number: 113100-53-1
• EC Number: 601-232-0
• SMILES: CN1C=C(C(=N1)C(F)(F)F)C(=O)O

Properties

• Melting point: 200-204 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, with the chemical formula C₆H₅F₃N₂O₂, is a heterocyclic compound characterized by the substitution of the pyrazole ring with a methyl group at the 1-position, a trifluoromethyl group at the 3-position, and a carboxylic acid group at the 4-position. The compound has unique chemical properties that make it valuable in pharmaceutical and agrochemical research.

The synthesis and discovery of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid stems from the exploration of the potential biological activities of fluorinated heterocyclic compounds. Researchers have attempted to improve the bioavailability and metabolic stability of pyrazole derivatives by introducing a trifluoromethyl group, which is known to improve pharmacological properties. The introduction of a carboxylic acid group further enhances the utility of the compound in various chemical transformations.

1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid can be synthesized by a variety of methods, usually involving cyclization of appropriate precursors followed by functionalization. A common synthetic route starts with a methylhydrazine derivative and a trifluoromethylated ketone, which forms the pyrazole ring via a cyclization reaction. The resulting pyrazole compound is then carboxylated to introduce a carboxylic acid functional group at the 4-position. This synthetic approach yields 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, which can be isolated and purified for further applications.

Trifluoromethylated pyrazolecarboxylic acid derivatives are of particular interest in pharmaceutical research. They are promising scaffolds for the development of new drugs with enhanced potency and selectivity. The trifluoromethyl group can modulate the physicochemical properties of the compound, affecting its solubility, lipophilicity, and metabolic stability. These derivatives are widely studied as anti-inflammatory, antibacterial, and antiviral agents.

In the agrochemical sector, derivatives of 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid are incorporated into herbicides and fungicides for their insecticidal activity to improve efficacy against specific pests and pathogens while minimizing environmental impact. The trifluoromethyl group enhances herbicidal and fungicidal properties, making these derivatives valuable tools in modern agriculture.

This compound and its derivatives are used in chemical research to explore structure-activity relationships and develop new synthetic approaches. Researchers study various substitution patterns on the pyrazole ring to optimize bioactivity and pharmacokinetic characteristics. The versatility of these compounds allows for the exploration of a variety of chemical transformations and applications.

As with all compounds, proper handling and safety precautions should be followed when synthesizing, handling, and applying 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid and its derivatives. Regulatory guidelines ensure their safe use in pharmaceutical, agrochemical, and other industries.

References

113100-53-1|1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid|2019. New relevant pesticide transformation products in groundwater detected using target and suspect screening for agricultural and urban micropollutants with LC-HRMS. Water Research, 165.
DOI: 10.1016/j.watres.2019.114972

2016. Synthesis and in vivo nematocidal evaluation of novel 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives. Frontiers of Chemical Science and Engineering, 11(1).
DOI: 10.1007/s11705-016-1595-x

2009. Synthesis of potential fungicides based on N-(3-furanyl)pyrrolecarboxamides and N-(3-furanyl)pyrazolecarboxamides. Monatshefte für Chemie - Chemical Monthly, 140(12).
DOI: 10.1007/s00706-009-0187-6