52208-50-1 | 2,6-Dichloro-3-fluoropyridine

CAS:52208-50-1 | 2,6-Dichloro-3-fluoropyridine,Description

2,6-Dichloro-3-fluoropyridine is a pyridine derivative. It is a fluorinated heterocyclic building block used in chemical synthesis. The molecular formula is C5H2Cl2FN.

Synthesis Analysis

The synthesis of 2,6-Dichloro-3-fluoropyridine involves a multi-step reaction. The Balz and Schiemann reaction, a powerful methodology for preparing aryl fluorides, has been applied to the synthesis of fluoropyridines. Thus, 2,6-dichloro-3-fluoropyridine is readily prepared from 3-amino-2,6-dichloropyridine.

Molecular Structure Analysis

The molecular structure of 2,6-Dichloro-3-fluoropyridine consists of a pyridine ring with two chlorine atoms and one fluorine atom attached to it. The molecular weight is 165.980 Da.

Chemical Reactions Analysis

The Balz and Schiemann reaction is used in the synthesis of 2,6-Dichloro-3-fluoropyridine. This reaction is a powerful methodology for preparing aryl fluorides.

Physical And Chemical Properties Analysis

2,6-Dichloro-3-fluoropyridine has a melting point of 44-46°C and a predicted boiling point of 196.0±35.0 °C. The predicted density is 1.498±0.06 g/cm3. It should be stored under inert gas (nitrogen or Argon) at 2-8°C.

Scientific Research Applications

1. Synthesis of Fluorinated Pyridines

• Application Summary: 2,6-Dichloro-3-fluoropyridine is used in the synthesis of fluorinated pyridines, which are compounds with interesting and unusual physical, chemical, and biological properties. They have reduced basicity and are usually less reactive than their chlorinated and brominated analogues.
• Methods of Application: The synthesis involves fluorination of pyridine by complex AlF3 and CuF2 at 450–500°C, forming a mixture of 2-fluoropyridine and 2,6-difluoropyridine.
• Results or Outcomes: The synthesis results in fluoropyridines that have potential imaging agents for various biological applications.

2. Preparation of Self Assembled Monolayer (SAMs) Compounds

• Application Summary: 2,6-Dichloro-5-fluoropyridine-3-carboxylic acid, a derivative of 2,6-Dichloro-3-fluoropyridine, is used in the preparation of self-assembled monolayer (SAMs) compounds.
• Methods of Application: The specific methods of application or experimental procedures for this usage are not provided in the source.
• Results or Outcomes: The outcome of this application is the creation of SAMs compounds, although the source does not provide specific results or quantitative data.

3. Synthesis of Fluoroquinolone Derivatives

• Application Summary: 2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile, another derivative of 2,6-Dichloro-3-fluoropyridine, is used as a molecular scaffold for the synthesis of fluoroquinolone derivatives.
• Methods of Application: The specific methods of application or experimental procedures for this usage are not provided in the source.
• Results or Outcomes: The synthesis of fluoroquinolone derivatives can lead to the development of new pharmaceuticals with reduced side effects and expanded medical applications.

4. Synthesis of Gemifloxacin

• Application Summary: 2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile, a derivative of 2,6-Dichloro-3-fluoropyridine, is used in the synthesis of Gemifloxacin, an oral broad-spectrum antibiotic.
• Methods of Application: The specific methods of application or experimental procedures for this usage are not provided in the source.
• Results or Outcomes: The synthesis of Gemifloxacin can lead to the development of new pharmaceuticals with reduced side effects and expanded medical applications.

5. Synthesis of 1,8-Naphthyridine Derivatives

• Application Summary: 2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile is also a molecular scaffold for 1,8-naphthyridine derivatives including Enoxacin, Trovafloxacin and Tosufloxacin.
• Methods of Application: The specific methods of application or experimental procedures for this usage are not provided in the source.
• Results or Outcomes: The synthesis of 1,8-naphthyridine derivatives can lead to the development of new pharmaceuticals with reduced side effects and expanded medical applications.

6. Synthesis of Herbicides and Insecticides

• Application Summary: 2,6-Dichloro-3-fluoropyridine is used in the synthesis of some herbicides and insecticides.
• Methods of Application: The specific methods of application or experimental procedures for this usage are not provided in the source.
• Results or Outcomes: The synthesis of herbicides and insecticides can lead to the development of new agricultural products having improved physical, biological, and environmental properties.

Safety And Hazards

2,6-Dichloro-3-fluoropyridine is classified as dangerous according to the Global Harmonized System (GHS). It has hazard statements H301-H315-H318-H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye damage, and may cause respiratory irritation. Personal protective equipment/face protection should be worn and adequate ventilation should be ensured.

Future Directions

There is a growing interest in fluoropyridines due to their interesting and unusual physical, chemical, and biological properties. Fluoropyridines have reduced basicity and are usually less reactive than their chlorinated and brominated analogues. The development of new high energy density materials is an interesting and challenging problem. The synthesis and development of new energetic materials continue to focus on new heterocyclic compounds with high densities, high heats of formation, and good detonation properties.

More Information

Physical Form Synthesis