456-24-6

Basic information

• Product Name: 2-Fluoro-5-nitropyridine
• Synonyms: 2-FLUORO-5-NITROPYRIDINE;6-FLUORO-3-NITROPYRIDINE
• CAS NO: 456-24-6
• Molecular Formula: C₅H₃FN₂O₂
• Molecular Weight: 142.09
• EINECS: 207-260-6
• Product Categories: Fluorin-contained pyridine series;blocks;FluoroCompounds;NitroCompounds;Pyridines;Pyridine;Pyridine series;Boronic Acid;Fluorine series
• Mol File: 456-24-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 142-144 C
• Boiling Point: 86-87℃/7mm lit.
• Flash Point: 97.5 °C
• Appearance: Colorless to pale yellow/Liquid
• Density: 4,64g/cm
• Vapor Pressure: 0.0686mmHg at 25°C
• Refractive Index: 1.5250
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -4.47±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2-Fluoro-5-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-5-nitropyridine(456-24-6)
• EPA Substance Registry System: 2-Fluoro-5-nitropyridine(456-24-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-22
• Safety Statements: 36
• RIDADR: UN 1549
• Hazardous Substances Data: 456-24-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 456-24-6 differently. You can refer to the following data:
1. It is used in the preparation of nitropyridines by nitration of pyridines with nitric acid.
2. 2-Fluoro-5-nitropyridine can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

Synthesis of 5-amino-2-fluoropyridine. A mixture of 5-nitro-2-chloropyridine (2.0 g, 12.6 mmol) and anhydrous potassium fluoride (2.2 g, 38 mmol) in a combination of sulfalone ( 6 mL) and benzene (4 mL) was stirred at RT for 20 min. The benzene was then removed by distillation. The resulting mixture was heated at 150 °C for 12h. The mixture was cooled to RT whereupon water (60 mL) was added. The desired product was separated from the solution via steam distillation. Extraction of the distillate with diethyl ether (2 × 1 0 mL) followed by drying (Na2SO4) and concentration gave the compound. 5-nitro-2-fluoropyridine, water white oil (1.3 g, 73%).

InChI:InChI=1/C5H3FN2O2/c6-5-2-1-4(3-7-5)8(9)10/h1-3H

Upstream product

• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 372-48-5 2-fluoropyridine 
• 4548-45-2 2-chloro-5-nitropyridine 
• 2127-10-8 5,5'-dinitro-2,2'-disulfanediyl-bis-pyridine 

Downstream Products

• 5446-92-4 2-methoxy-5-nitropyridine 
• 1827-27-6 2-fluoro-5-aminopyridine 
• 55758-32-2 6-fluoropyridin-3-ol 
• 20168-70-1 u202fN,N-diethyl-5-nitropyridin-2-amine 
• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 2127-10-8 5,5'-dinitro-2,2'-disulfanediyl-bis-pyridine 

Relevant articles and documents

Method for pipeline continuous fluorination with fluorine salt as fluorine source

The method comprises the following steps: dissolving a fluorine salt in an aqueous polar aprotic solvent as reaction liquid A, dissolving an aryl (heterocyclic) chloride in a polar aprotic solvent as reaction liquid B, and reacting a polar aprotic solvent in the reaction liquid A with a polar aprotic solvent of the reaction liquid B. The reaction medium consisting of the preheated reaction liquid A and the preheated reaction liquid B enters the reaction coil for a fluorination reaction, and the resulting product from the reaction coil is subjected to post-treatment to obtain the product. The method has the characteristics of no need of adding a phase transfer catalyst, continuous production, low production cost and the like.

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.

Anhydrous Tetramethylammonium Fluoride for Room-Temperature SNAr Fluorination

This paper describes the room-temperature SNAr fluorination of aryl halides and nitroarenes using anhydrous tetramethylammonium fluoride (NMe4F). This reagent effectively converts aryl-X (X = Cl, Br, I, NO2, OTf) to aryl-F under mild conditions (often room temperature). Substrates for this reaction include electron-deficient heteroaromatics (22 examples) and arenes (5 examples). The relative rates of the reactions vary with X as well as with the structure of the substrate. However, in general, substrates bearing X = NO2 or Br react fastest. In all cases examined, the yields of these reactions are comparable to or better than those obtained with CsF at elevated temperatures (i.e., more traditional halex fluorination conditions). The reactions also afford comparable yields on scales ranging from 100 mg to 10 g. A cost analysis is presented, which shows that fluorination with NMe4F is generally more cost-effective than fluorination with CsF.