779345-37-8 | 5-Fluoro-2-nitropyridine

CAS:779345-37-8 | 5-Fluoro-2-nitropyridine,Description

5-Fluoro-2-nitropyridine is a unique chemical compound with the empirical formula C5H3FN2O2. It has a molecular weight of 142.09. It is typically provided in a solid form.

Synthesis Analysis

The synthesis of 5-Fluoro-2-nitropyridine involves the nitration of pyridines with nitric acid. The reaction mechanism is not an electrophilic aromatic substitution, but one in which the nitro group migrates from the 1-position to the 3-position by a [1,5] sigmatropic shift. From 3-nitropyridine, 5-nitropyridine-2-sulfonic acid is formed in a two-step reaction. From this, a series of 2-substituted-5-nitro-pyridines has been synthesized.

Molecular Structure Analysis

The molecular structure of 5-Fluoro-2-nitropyridine is represented by the SMILES string O=N+C1=CC=C(F)C=N1. The InChI code for the compound is 1S/C5H3FN2O2/c6-4-1-2-5(7-3-4)8(9)10/h1-3H.

Physical And Chemical Properties Analysis

5-Fluoro-2-nitropyridine is a solid at ambient temperature. It has a molecular weight of 142.09. The compound is typically stored at ambient temperature.

Scientific Research Applications

• Synthesis of Acyl Fluorides : 5-Fluoro-2-nitropyridine derivatives have been used in the synthesis of acyl fluorides, which are important intermediates in organic synthesis. For example, 2-(difluoromethoxy)-5-nitropyridine has been utilized in the palladium-catalyzed fluoro-carbonylation of aryl, vinyl, and heteroaryl iodides. This process is significant as it provides an alternative to the use of toxic gaseous formyl fluoride under fluoride catalysis conditions (Liang, Zhao, & Shibata, 2020).
• Determination of N-terminal Amino Acids in Proteins : Fluoro-nitropyridines, including derivatives of 5-Fluoro-2-nitropyridine, have been used in the determination of N-terminal groups in peptides and proteins. This methodology is valuable for protein sequencing and analysis (Signor, Biondi, Tamburro, & Bordignon, 1969).
• Nucleoside Analog Synthesis : Derivatives of 5-Fluoro-2-nitropyridine have been involved in the synthesis of nucleoside analogs related to 5-fluorouracil and 5-fluorocytosine. These compounds have potential applications in medicinal chemistry and drug development (Nesnow & Heidelberger, 1973; 1975).
• Synthesis of Fluoropyridines : The synthesis of fluoropyridines, which are valuable in various chemical applications, has been achieved through the use of nitropyridines, including 5-Fluoro-2-nitropyridine derivatives. These methods typically involve mild conditions and result in efficient production of fluoropyridines (Kuduk, Dipardo, & Bock, 2005).
• Metabolism Studies in Plants : 5-Fluoro-2-nitropyridine derivatives have been used in studies examining the metabolism of xenobiotics in plants. Such research is crucial for understanding how plants metabolize and interact with foreign compounds (Bailey et al., 2000).
• Peptide Chemistry : Compounds like 2,2′-dithiobis(5-nitropyridine) have been employed for the activation of the thiol function of cysteine in peptides and for asymmetric disulfide formation, demonstrating the utility of 5-Fluoro-2-nitropyridine derivatives in peptide chemistry (Rabanal, DeGrado, & Dutton, 1996) .
• Fluorine-18 Labelling : 5-Fluoro-2-nitropyridine derivatives have been utilized in the development of novel fluoropyridine-based structures for fluorine-18 labeling of macromolecules using click chemistry, which is significant in the field of nuclear medicine (Kuhnast, Hinnen, Tavitian, & Dollé, 2008).

Safety And Hazards

5-Fluoro-2-nitropyridine is classified as hazardous under the Hazardous Products Regulations. It is harmful if swallowed, causes skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray, and to use only outdoors or in a well-ventilated area.

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