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

Description

2-Fluoro-5-nitropyridine is a chemical compound that belongs to the family of nitropyridines. It is characterized by the presence of a fluorine atom at the 2nd position and a nitro group at the 5th position on the pyridine ring. 2-Fluoro-5-nitropyridine is known for its versatile reactivity and potential applications in various fields.

Uses

Used in Organic Synthesis:
2-Fluoro-5-nitropyridine is used as an organic synthesis intermediate for the preparation of various nitropyridine derivatives. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
2-Fluoro-5-nitropyridine can be used as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and therapeutic agents. Its presence in the molecular structure can impart specific biological activities and properties, contributing to the effectiveness of the final drug product.
Used in Laboratory Research and Development:
2-Fluoro-5-nitropyridine is utilized in laboratory research and development processes, where it serves as a key component in the synthesis and study of novel compounds. Its reactivity and structural features make it an attractive candidate for exploring new chemical reactions and mechanisms.
Used in Chemical Production Process:
In the chemical production process, 2-Fluoro-5-nitropyridine is employed as a key intermediate for the large-scale synthesis of various chemical products. Its versatility and reactivity enable the efficient production of a wide range of compounds, contributing to the advancement of the chemical industry.

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 
• 4548-45-2 2-chloro-5-nitropyridine 
• 372-48-5 2-fluoropyridine 
• 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 
• 36977-08-9 N-(5-nitro-[2]pyridyl)-phenylalanine 
• 438226-87-0 {(5,5-bis-dodecyloxymethyl-[1,3]dithian-2-yl)-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methyl}-(5-nitro-pyridin-2-yl)-amine 
• 171178-41-9 (6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester 
• 171178-42-0 5-[N-(tert-Butoxycarbonyl)-amino]-2-fluoropyridine-4-carboxylic acid 
• 305371-18-0 4-chloro-6-fluoro-[1,7]naphthyridine-3-carbonitrile 
• 305371-17-9 6-fluoro-4-hydroxy-[1.7]naphthyridine-3-carbonitrile 
• 305371-15-7 5-tert-butoxycarbonylamino-2-fluoro-isonicotinic acid, methyl ester 
• 305371-16-8 [6-fluoro-4-(3-nitrilo-propionyl)-pyridin-3-yl]-carbamic acid, tert-butyl ester 
• 305371-21-5 6-amino-4-(3-bromo-phenylamino)-[1.7]naphthyridine-3-carbonitrile 
• 305371-19-1 4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile 
• 305371-33-9 4-(3-chloro-4-fluorophenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile 
• 305371-20-4 4-(3-bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1.7]naphthyridine-3-carbonitrile 

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.

Synthesis and characterization of 2-pyridylsulfur pentafluorides

Current approaches to prepare SF5-substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5-functionalized aryl or alkyne reagents or SF5Cl as a source of the SF5 functional group. Herein we report that excess oxidative fluorination of 2,2' -dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5-pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.