2-Chloro-4-nitropyridine
[CAS# 23056-36-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
• Name: 2-Chloro-4-nitropyridine
• Molecular Formula: C₅H₃ClN₂O₂
• Molecular Weight: 158.54
• CAS Registry Number: 23056-36-2
• EC Number: 627-980-8
• SMILES: C1=CN=C(C=C1[N+](=O)[O-])Cl

Properties

• Melting point: 52-56 °C
• Flash point: 223 °F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Chloro-4-nitropyridine, a member of the pyridine family, was discovered through organic chemistry research focused on synthesizing heterocyclic compounds with diverse properties. The compound was first synthesized through the nitration of 2-chloropyridine, resulting in the introduction of a nitro group at the 4-position of the pyridine ring. Its discovery represented a significant advancement in synthetic chemistry, providing chemists with a versatile building block for creating molecules with applications in pharmaceuticals, agrochemicals, materials science, and other fields.

2-Chloro-4-nitropyridine serves as a valuable intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a versatile building block for the production of various drugs, including antivirals, antifungals, and anti-inflammatory agents. Chemical modifications of the chloro and nitro groups enable the creation of drug candidates with improved pharmacological properties, such as increased potency, selectivity, and metabolic stability. 2-Chloro-4-nitropyridine is utilized in the synthesis of active pharmaceutical ingredients (APIs) and drug intermediates, contributing to the development of new therapeutic treatments for various medical conditions.

In the agricultural sector, 2-Chloro-4-nitropyridine finds application as a precursor for the synthesis of agrochemicals and pesticides. Pyridine derivatives exhibit pesticidal properties and can be modified to enhance their effectiveness against pests, weeds, and fungal pathogens. By incorporating 2-Chloro-4-nitropyridine into pesticide formulations, researchers aim to develop products that can protect crops from damage caused by insects, fungi, and other pests, thereby improving agricultural yields and food security. Additionally, 2-Chloro-4-nitropyridine derivatives may offer advantages such as reduced environmental persistence and lower toxicity to non-target organisms.

2-Chloro-4-nitropyridine is valuable as an intermediate in organic synthesis, facilitating the production of various chemical compounds with diverse applications. Its incorporation into multistep synthesis pathways enables the creation of complex molecules used in pharmaceuticals, agrochemicals, and materials science. Chemists exploit its reactivity and versatility to design efficient synthetic routes for producing target molecules, thereby advancing the development of new materials and chemical processes.

In materials science, 2-Chloro-4-nitropyridine derivatives are utilized for the synthesis of functional materials with tailored properties. Chemical modifications of the pyridine ring enable the incorporation of 2-Chloro-4-nitropyridine into polymers, coatings, and nanoparticles, imparting specific characteristics such as adhesion, conductivity, and optical properties. These materials find applications in diverse areas such as electronics, aerospace, and biotechnology, where precise control over material properties is essential for desired performance outcomes.

Beyond its established applications, ongoing research explores new uses for 2-Chloro-4-nitropyridine in fields such as medicinal chemistry, catalysis, and drug discovery. Scientists investigate its reactivity, properties, and potential interactions with biological targets to develop innovative therapies for treating diseases and disorders. Additionally, advancements in synthetic methodologies and chemical synthesis techniques continue to expand the utility of this compound in diverse scientific and industrial applications.

References

2024. Unveiling the interaction, cytotoxicity and antibacterial potential of pyridine derivatives: an experimental and theoretical approach with bovine serum albumin. *Naunyn-Schmiedeberg's Archives of Pharmacology*, 397(11).
DOI: 10.1007/s00210-024-03541-6

2021. Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions. *Synthesis*, 53(20).
DOI: 10.1055/a-1579-2190

2015. Investigation of structure, vibrational, electronic, NBO and NMR analyses of 2-chloro-4-nitropyridine (CNP), 2-chloro-4-methyl-5-nitropyridine (CMNP) and 3-amino-2-chloro-4-methylpyridine (ACMP) by experimental and theoretical approach. *Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy*, 137.
DOI: 10.1016/j.saa.2014.08.075