2025-06-13
2-Chloro-3-trifluoromethylpyridine is a valuable intermediate widely used in the pharmaceutical, agrochemical, and specialty chemical industries. Known for its halogenated aromatic structure and electron-withdrawing trifluoromethyl group, this compound plays a key role in complex molecule synthesis, especially in the production of biologically active compounds.
In this guide, we cover everything you need to know about 2-Chloro-3-trifluoromethylpyridine, including its chemical properties, synthesis, applications, safety data, and sourcing options.
IUPAC Name: 2-Chloro-3-(trifluoromethyl)pyridine
CAS Number: 39890-95-4
Molecular Formula: C6H3ClF3N
Molecular Weight: 181.54 g/mol
Chemical Structure:
This compound is a chlorinated pyridine derivative substituted with a trifluoromethyl group at the 3-position. The presence of both Cl and CF₃ groups gives it unique reactivity and stability under various reaction conditions.
Property | Value |
---|---|
Appearance | Colorless to pale yellow liquid |
Boiling Point | ~165–170°C |
Flash Point | ~63°C |
Density | ~1.43 g/cm³ |
Purity | ≥98% (common in commercial supply) |
Solubility | Soluble in organic solvents (e.g., DCM, MeOH) |
This compound is primarily used as a building block in organic synthesis. Its halogen and trifluoromethyl substitutions allow for further derivatization through reactions like:
Suzuki, Sonogashira, or Buchwald coupling (via the chloro group)
Nucleophilic aromatic substitution (SNAr)
Oxidation/reduction of the pyridine ring
Trifluoromethylation chemistry
Pharmaceuticals
Intermediate for developing anti-inflammatory, anti-infective, and anticancer agents.
Precursor for heterocyclic compounds with CNS activity.
Agrochemicals
Used in the synthesis of herbicides, insecticides, and fungicides.
Enhances biological activity and metabolic stability due to CF₃ group.
Fluorinated Specialty Chemicals
Functionalized fluoropyridines are often required in high-performance materials and advanced intermediates.
Typical Synthesis Route:
One common synthetic method involves electrophilic chlorination and selective trifluoromethylation of pyridine derivatives. Industrial production may start from 3-trifluoromethylpyridine, followed by chlorination at the 2-position using reagents like N-chlorosuccinimide (NCS) or SO₂Cl₂ in the presence of a catalyst.
Due to its reactive chloro group, it an excellent intermediate for cross-coupling reactions and other nucleophilic substitutions.
Hazard Class | Irritant, Harmful if Swallowed/Inhaled |
---|---|
GHS Labeling | ⚠️ (Exclamation mark symbol) |
Handling Advice | Use under fume hood, wear gloves/goggles |
Storage | Store in cool, dry, ventilated area; tightly sealed |
Incompatible Materials | Strong oxidizers, acids, and bases |
Always consult the latest Safety Data Sheet (SDS) for full regulatory and hazard information.
When sourcing 2-Chloro-3-trifluoromethylpyridine, it’s essential to verify supplier credibility, purity specifications, and compliance documentation (e.g., COA, SDS, REACH).
Merck / Sigma-Aldrich
TCI Chemicals
Thermo Fisher Scientific
Alfa Aesar
Biosynth Carbosynth
CDMO & CRO partners in China and India
💡 For bulk purchases or custom synthesis, contact manufacturers for sample testing and pricing tiers.
2-Bromo-3-trifluoromethylpyridine (for Suzuki coupling)
3-Trifluoromethylpyridine (precursor)
2-Amino-3-trifluoromethylpyridine (for pharmaceutical synthesis)
Halogenated pyridine derivatives with bioactive scaffolds
Q1: Is 2-Chloro-3-trifluoromethylpyridine stable under normal storage conditions?
Yes, when stored properly in a sealed container away from light and moisture, it is stable for long-term use.
Q2: Can I use this compound for Suzuki coupling?
Yes. The chloro substituent at position 2 can participate in palladium-catalyzed cross-coupling reactions.
Q3: What solvents are ideal for reactions using this compound?
Common organic solvents like THF, toluene, DMSO, and acetonitrile are suitable depending on the reaction mechanism.
2-Chloro-3-trifluoromethylpyridine is a versatile and in-demand intermediate for synthetic chemists working in pharmaceuticals, agrochemicals, and fluorinated materials. Its dual halogen-fluoro functionality offers broad reactivity and opens the door for diverse downstream modifications.
Whether you’re developing a new drug candidate or optimizing a reaction for scale-up, this compound offers consistent performance and functional reliability.