1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol
[CAS# 122431-37-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol
• Synonyms: 5-Hydroxy-1-methyl-3-trifluoromethyl-1H-pyrazole
• Molecular Formula: C₅H₅F₃N₂O
• Molecular Weight: 166.10
• CAS Registry Number: 122431-37-2
• EC Number: 626-417-3
• SMILES: CN1C(=O)C=C(N1)C(F)(F)F

Properties

• Melting point: 177-179 °C

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	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-pyrazol-5-ol, with the chemical formula C₅H₅F₃N₂O, is a heterocyclic compound characterized by a trifluoromethyl group attached to the pyrazole ring and a hydroxyl group at the 5-position. The presence of these functional groups endows it with unique properties that make it valuable in a variety of chemical and industrial applications.

The synthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol can be traced back to the advancement of fluorinated heterocycle research. The impetus for this discovery was the need for novel compounds with potential pharmaceutical and agrochemical applications. Researchers realized that the introduction of a trifluoromethyl group on the pyrazole ring could enhance the stability and biological activity of the compound, leading to the development of efficient synthetic routes.

The synthesis of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol typically involves cyclization of an appropriate precursor with a trifluoromethylating agent. A common method starts with methylhydrazine and trifluoromethylketone, which undergo a cyclization reaction to form a pyrazole ring. The resulting compound is hydroxylated to introduce a hydroxyl group at the 5-position to complete the synthesis. This method provides an efficient route to 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol, which can then be purified for further applications.

The unique structural features of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol make it a valuable intermediate in pharmaceutical research. The trifluoromethyl group enhances the metabolic stability and bioavailability of drug candidates, while the pyrazole ring is a common motif in bioactive molecules. This compound is a cornerstone for the development of new drugs with potential anti-inflammatory, anticancer, and antiviral properties.

In agrochemical development, this compound is used to synthesize herbicides, fungicides, and insecticides. It is able to improve the efficacy and stability of active ingredients, becoming an important component in protecting crops and improving agricultural productivity.

As a reagent in chemical research, 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol is used to study reaction mechanisms and develop new synthetic methods. Its functional groups allow chemists to explore a wide range of chemical transformations and create innovative molecules for a variety of applications.

This compound is useful in materials science for the development of advanced polymers and functional materials. Its trifluoromethyl group has unique properties, such as enhanced hydrophobicity and thermal stability, making it suitable for high-performance materials in coatings, electronics, and other industries.

While 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol has a wide range of applications, safety guidelines must be followed when handling and using it. As with many compounds, appropriate protection measures should be taken to prevent exposure and potential hazards in industrial and laboratory settings.

References

2009. 1-Methyl-3-trifluoromethyl-1H-pyrazol-5-ol. Acta Crystallographica. Section E, Structure Reports Online.
DOI: 10.1107/s1600536809035624

2016. A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. Journal of Biomolecular Screening.
DOI: 10.1177/1087057116635503