2-Hydroxy-6-trifluoromethylpyridine
[CAS# 34486-06-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Hydroxypyridine
• Name: 2-Hydroxy-6-trifluoromethylpyridine
• Synonyms: 6-(trifluoromethyl)-1H-pyridin-2-one
• Molecular Formula: C₆H₄F₃NO
• Molecular Weight: 163.10
• CAS Registry Number: 34486-06-1
• EC Number: 803-542-3
• SMILES: C1=CC(=O)NC(=C1)C(F)(F)F

Properties

• Melting point: 122-125 ºC

Safety Data

• Hazard Symbols: GHS0 Danger
• Hazard Statements: H301-H319
• Precautionary Statements: P301+P310-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2-Hydroxy-6-trifluoromethylpyridine is a versatile compound known for its wide range of applications in pharmaceuticals and agrochemicals. The substance has the chemical formula C6H4F3NO and features a hydroxyl group at the second position and a trifluoromethyl group at the sixth position on the pyridine ring. The unique combination of these functional groups gives it unique chemical properties that make it valuable in various industries.

The discovery of 2-hydroxy-6-trifluoromethylpyridine dates back to the mid-20th century, when chemists were exploring the potential uses of fluorinated compounds in medicine and agriculture. It is well known that fluorine atoms can significantly alter the biological activity of organic molecules, often enhancing their stability, bioavailability, and efficacy. The introduction of the trifluoromethyl group into the pyridine ring is intended to take advantage of these benefits.

One of the main applications of 2-hydroxy-6-trifluoromethylpyridine is in the pharmaceutical industry. The compound can serve as an intermediate in the synthesis of various drugs, especially those targeting the central nervous system. Its structure allows it to interact well with biological targets, allowing the development of molecules with potent therapeutic effects. For example, this compound is a key component in the synthesis of certain antipsychotics and antidepressants, and its fluorinated nature enhances the stability and absorption of the drug in the human body.

In agrochemistry, 2-hydroxy-6-trifluoromethylpyridine is used to develop herbicides and fungicides. The compound's ability to interfere with specific biochemical pathways in plants and fungi makes it an effective agent for protecting crops. In these applications, it helps to increase agricultural productivity by controlling weeds and fungal infections, ensuring healthier, more abundant harvests.

The unique properties of 2-hydroxy-6-trifluoromethylpyridine also make it a valuable tool in organic synthesis. The hydroxyl and trifluoromethyl groups provide reactive sites for a variety of chemical transformations, enabling the creation of complex molecules with high precision. This versatility is particularly beneficial in research and development, where chemists are constantly seeking to design and synthesize new compounds with desirable properties.

In addition to its direct applications, 2-hydroxy-6-trifluoromethylpyridine has also facilitated advances in chemical methodology. Researchers have studied its reactivity and interactions with other chemicals, allowing the development of new synthetic routes and techniques. These advances have broad implications that extend beyond the immediate applications of the compounds themselves, impacting the wider field of synthetic chemistry.

Handling and storage of 2-hydroxy-6-trifluoromethylpyridine requires standard laboratory precautions. The compound should be stored in a cool, dry place away from light and moisture to maintain its stability. When working with this chemical, appropriate safety precautions such as wearing gloves, goggles, and adequate ventilation should be taken to prevent contact and ensure safe handling.