875781-15-0 | 5-Bromo-2-fluoropyridine-3-carboxaldehyde

CAS:875781-15-0 | 5-Bromo-2-fluoropyridine-3-carboxaldehyde,Description

5-Bromo-2-fluoropyridine-3-carboxaldehyde is a chemical compound with the molecular formula C6H3BrFNO and a molecular weight of 204. It is used in research and development.

Molecular Structure Analysis

The InChI code for 5-Bromo-2-fluoropyridine-3-carboxaldehyde is 1S/C6H3BrFNO/c7-5-1-4(3-10)6(8)9-2-5/h1-3H. The InChI key is MUYVOGAJRCBWCY-UHFFFAOYSA-N.

Physical And Chemical Properties Analysis

5-Bromo-2-fluoropyridine-3-carboxaldehyde has a predicted boiling point of 258.2±35.0 °C and a predicted density of 1.778±0.06 g/cm3. It is a solid substance that is off-white to pale yellow in color. It should be stored under inert gas (nitrogen or Argon) at 2-8°C.

Scientific Research Applications

• Synthesis of Fluorinated Pyridines

  • Field : Organic Chemistry
  • Application : 5-Bromo-2-fluoropyridine is used in the synthesis of fluorinated pyridines. Fluoropyridines have reduced basicity and are usually less reactive than their chlorinated and brominated analogues.
  • Method : The methods of synthesis of 2-, 3-, 4-fluoropyridines, di-, tri-, polyfluoropyridines, perfluoroalkylpyridines and also fluoropyridines fused with carbo-, heterocycles are presented.
  • Results : The synthesis results in fluoropyridines with interesting and unusual physical, chemical and biological properties owing to the presence of the strong electron-withdrawing substituent(s) in the aromatic ring.

• Metal-free Site-selective C–N Bond-forming Reaction

  • Field : Organic Chemistry
  • Application : 5-Bromo-2-fluoropyridine is used in a metal-free method for highly site-selective C–N bond-forming reaction of polyhalogenated pyridines and pyrimidines.
  • Method : The preferred coupling site can be tuned from the fluorine group bearing the N-heterocyclic ring to the chlorine group when changing from the pyridine ring to the pyrimidine ring.
  • Results : A wide array of halogenated pyridines preferentially reacted with amines at the fluorine group of the pyridine ring to generate monosubstituted halogenated pyridines with high selectivities.

• Synthesis of Heteroaromatic and Aniline Derivatives of Piperidines

  • Field : Medicinal Chemistry
  • Application : 5-Bromo-2-fluoropyridine is used in the synthesis of heteroaromatic and aniline derivatives of piperidines.
  • Method : The specific methods of synthesis are not detailed in the source.
  • Results : The synthesis results in potent ligands used for vesicular acetylcholine transport.

• Active Pharmaceutical Ingredients (APIs) Synthesis

  • Field : Pharmaceutical Chemistry 
  • Application : 5-Bromo-2-fluoropyridine is used as a molecular scaffold for many Active Pharmaceutical Ingredients (APIs) such as Neuropeptide Y Receptor Y5 Inhibitors, SARS-CoV-2 Major Protease Inhibitors, and Indoleamine-2,3-Dioxygenase-1 Inhibitors in cancer immunotherapy.
  • Method : The specific methods of synthesis are not detailed in the source.
  • Results : The synthesis results in potent inhibitors used for various therapeutic applications.

• Semiconductor Synthesis

  • Field : Material Science
  • Application : 5-Bromo-2-fluoropyridine is an ideal building block for semiconductors, due to its aromaticity and electron deficiency.
  • Method : The specific methods of synthesis are not detailed in the source.
  • Results : The synthesis results in semiconductors with unique properties.

• Synthesis of Herbicides and Insecticides

  • Field : Agricultural Chemistry
  • Application : 5-Bromo-2-fluoropyridine has been used as a starting material for the synthesis of some herbicides and insecticides.
  • Method : The specific methods of synthesis are not detailed in the source.
  • Results : The synthesis results in potent herbicides and insecticides.

• Metal-free Site-selective C–N Bond-forming Reaction

  • Field : Organic Chemistry
  • Application : 5-Bromo-2-fluoropyridine is used in a metal-free method for highly site-selective C–N bond-forming reaction of polyhalogenated pyridines and pyrimidines.
  • Method : The preferred coupling site can be tuned from the fluorine group bearing the N-heterocyclic ring to the chlorine group when changing from the pyridine ring to the pyrimidine ring.
  • Results : A wide array of halogenated pyridines preferentially reacted with amines at the fluorine group of the pyridine ring to generate monosubstituted halogenated pyridines with high selectivities.

Safety And Hazards

5-Bromo-2-fluoropyridine-3-carboxaldehyde is classified as a hazardous substance. It may cause skin irritation, serious eye irritation, and respiratory irritation. Precautionary measures include avoiding dust formation, breathing mist, gas or vapours, and contact with skin and eyes. It is recommended to use personal protective equipment, wear chemical impermeable gloves, ensure adequate ventilation, remove all sources of ignition, and evacuate personnel to safe areas.

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