3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine
[CAS# 72537-17-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine
• Molecular Formula: C₆H₂ClF₄N
• Molecular Weight: 199.53
• CAS Registry Number: 72537-17-8
• EC Number: 625-955-6
• SMILES: C1=C(C=NC(=C1Cl)F)C(F)(F)F

Properties

• Density: 1.524
• Melting point: 16-20 °C
• Boiling point: 50-55 °C (11 mmHg)
• Refractive index: 1.433
• Flash point: 52 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Warning
• Risk Statements: H226-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1993

Discovery and Applications

3-Chloro-2-fluoro-5-(trifluoromethyl)pyridine is a valuable compound with a variety of uses in organic synthesis, pharmaceuticals, and agrochemicals. Its unique molecular structure, characterized by a chlorine atom, a fluorine atom, and a trifluoromethyl group attached to the pyridine ring, gives it unique chemical properties that enhance its usefulness in various fields.

The discovery of 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine marked a major advance in the synthesis of complex organic molecules. The trifluoromethyl group is known for its strong electron-withdrawing effect, which significantly changes the reactivity of the pyridine ring, making it a versatile intermediate in chemical reactions.

In the pharmaceutical industry, this compound is used to synthesize a range of bioactive molecules. Its structure facilitates the formation of compounds with enhanced biological activity and selectivity. Researchers use its reactivity to develop new drugs with the aim of improving treatment outcomes and developing targeted treatments for various diseases.

In agrochemicals, 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine plays a vital role in the development of advanced herbicides and pesticides. The presence of the trifluoromethyl group enhances the stability and potency of these agrochemicals, resulting in more effective pest control solutions and better crop protection.

In addition, this compound is used in materials science to synthesize specialty materials with unique properties. Its chemical structure can be used to create advanced materials for electronics and coatings. Incorporating 3-chloro-2-fluoro-5-(trifluoromethyl)pyridine into polymers and other materials can improve their performance and durability.

The synthesis of this compound is relatively simple and involves standard chemical reactions, making it amenable to large-scale production. Its stability and reactivity make it widely used in research and industrial applications.

References

1999. Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements. Chemistry of Heterocyclic Compounds, 35(4).
DOI: 10.1007/bf02319329