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

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Identification
ClassificationPharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Hydroxypyridine
Name2-Hydroxy-6-trifluoromethylpyridine
Synonyms6-(trifluoromethyl)-1H-pyridin-2-one
Molecular StructureCAS # 34486-06-1, 2-Hydroxy-6-trifluoromethylpyridine
Molecular FormulaC6H4F3NO
Molecular Weight163.10
CAS Registry Number34486-06-1
EC Number803-542-3
SMILESC1=CC(=O)NC(=C1)C(F)(F)F
Properties
Melting point122-125 °C
Safety Data
Hazard Symbolssymbol   GHS0 Danger  Details
Risk StatementsH301-H319  Details
Safety StatementsP301+P310-P305+P351+P338  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H301
Eye irritationEye Irrit.2H319
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2AH319
Specific target organ toxicity - single exposureSTOT SE3H335
SDSAvailable
up Discovery and Applications
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.

References

2014. Synthesis of Fluorinated Pyridines. Fluorine in Heterocyclic Chemistry Volume 2.
DOI: 10.1007/978-3-319-04435-4_1
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