65753-52-8

Basic information

• Product Name: 2-Fluoro-3-trifluoromethylpyridine
• Synonyms: 2-FLUORO-3-(TRIFLUOROMETHYL)PYRIDINE;2-FLUORO-TRIFLUOROMETHYLPYRIDINE;2-FLUORO-3-(TRIFLUOROMETHOXY)PYRIDINE;Pyridine, 2-fluoro-3-(trifluoroMethyl)-;alpha,alpha,alpha,2-Tetrafluoro-3-picoline;2-Floro-3-(trifluoroMethyl)pyridine;-Fluoro-3-(trifluoromethyl)pyridine
• CAS NO: 65753-52-8
• Molecular Formula: C₆H₃F₄N
• Molecular Weight: 165.09
• EINECS: 1312995-182-4
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines;Pyridine;Building Blocks;Fluorinated;Fluorine series
• Mol File: 65753-52-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 149.3 °C at 760 mmHg
• Flash Point: 44.1 °C
• Appearance: clear liquid
• Density: 1.371 g/cm³
• Refractive Index: 1.523
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.86±0.10(Predicted)
• CAS DataBase Reference: 2-Fluoro-3-trifluoromethylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-3-trifluoromethylpyridine(65753-52-8)
• EPA Substance Registry System: 2-Fluoro-3-trifluoromethylpyridine(65753-52-8)

Safety Data

• Hazard Codes: Xi,Xn,T
• Statements: 20/21/22-36/37/38-36-25
• Safety Statements: 26-36/37/39-36-45
• HazardClass: IRRITANT
• Hazardous Substances Data: 65753-52-8(Hazardous Substances Data)

Usage

Description

2-Fluoro-3-trifluoromethylpyridine is an organic compound characterized by its colorless liquid state. It is a significant synthetic intermediate in the pharmaceutical industry due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2-Fluoro-3-trifluoromethylpyridine is used as a synthetic intermediate for the development of antihypertensive β-adrenergic blocking agents. These agents are crucial in the treatment of high blood pressure and related cardiovascular conditions, as they help to regulate heart rate and blood vessel constriction.
Additionally, 2-Fluoro-3-trifluoromethylpyridine is utilized in the synthesis of HCV NS5B thumb pocket 2 allosteric inhibitors. These inhibitors play a vital role in the treatment of Hepatitis C, a viral infection that affects the liver and can lead to severe health complications if left untreated.

InChI:InChI=1/C6H3F3IN/c7-6(8,9)4-2-1-3-11-5(4)10/h1-3H

Upstream product

• 65753-47-1 2-chloro-3-trifluoromethyl-pyridine 
• 3796-23-4 3-(trifluoromethyl)pyridine 

Downstream Products

• 87394-63-6 1-(3-trifluoromethylpyridin-2-yl)piperazine 
• 1115639-63-8 C₁₄H₁₀F₄N₂O₃ 
• 1163691-96-0 C₁₈H₁₉F₃N₂O₄ 
• 1276040-22-2 C₂₂H₁₈F₄N₂O₃ 
• 1276035-85-8 C₂₂H₁₅F₄N₃O₂ 
• 1276040-27-7 C₁₄H₉F₃INO₃ 
• 1276039-85-0 C₂₁H₁₄F₆N₂O₃ 
• 1276039-86-1 C₂₀H₁₃F₆N₃O₂ 
• 183610-70-0 2-amino-3-trifluoromethylpyridine 

Relevant articles and documents

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

PROCESS FOR FLUORINATING COMPOUNDS

Disclosed are mild temperature (e.g., from 0 to 80°C) SNAr fluorinations of a variety of halide and sulfonate substituted aryl and heteroaryl substrates using NMe4F.

Acyl azolium fluorides for room temperature nucleophilic aromatic fluorination of chloro- and nitroarenes

The reaction of acid fluorides with N-heterocyclic carbenes (NHCs) produces anhydrous acyl azolium fluorides. With appropriate selection of acid fluoride and NHC, these salts can be used for the room temperature SNAr fluorination of a variety of aryl chlorides and nitroarenes.