2-Methyl-5-nitropyridine
[CAS# 21203-68-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Nitropyridine
• Name: 2-Methyl-5-nitropyridine
• Synonyms: 5-Nitro-2-picoline
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12
• CAS Registry Number: 21203-68-9
• EC Number: 677-568-7
• SMILES: CC1=NC=C(C=C1)[N+](=O)[O-]

Properties

• Melting point: 107-109 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-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
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Methyl-5-nitropyridine, a derivative of pyridine, was discovered in the mid-20th century during investigations into the reactivity and synthesis of pyridine compounds. The synthesis typically involves the nitration of 2-methylpyridine, resulting in the introduction of a nitro group at the 5-position of the pyridine ring. Its discovery marked a significant advancement in organic chemistry, providing chemists with a versatile building block.

2-Methyl-5-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 antihypertensives, antivirals, and anti-inflammatory agents. Chemical modifications of the nitro group or the pyridine ring enable the creation of drug candidates with improved efficacy, bioavailability, or selectivity.

In the agricultural sector, 2-Methyl-5-nitropyridine finds application as a precursor for the synthesis of agrochemicals and pesticides. Pyridine derivatives possess pesticidal properties, and modifications of their structure can enhance their effectiveness against pests and weeds. By incorporating 2-Methyl-5-nitropyridine into pesticide formulations, researchers aim to develop products that can protect crops from damage caused by insects, fungi, and other pathogens.

2-Methyl-5-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.



In laboratory settings, 2-Methyl-5-nitropyridine serves as a solvent or reagent in chemical reactions and synthesis processes. Its solubility properties and compatibility with a wide range of organic and inorganic compounds make it useful for dissolving or reacting with other substances to form desired products.

Beyond its established applications, ongoing research explores new uses for 2-Methyl-5-nitropyridine in fields such as material science, catalysis, and drug discovery. Scientists investigate its reactivity, properties, and potential interactions with other molecules to develop innovative materials, catalysts, and chemical processes.

References

2000. IR spectra of 2-alkylamino-and alkylnitramino-3-or 5-nitro-4-methylpyridine derivatives. Chemistry of Heterocyclic Compounds, 36(7).
DOI: 10.1007/bf02256912

2016. Nitration of Pyridines. Science of Synthesis.
URL: SD-115-00302

2012. Palladium-Catalyzed Asymmetric Addition of Alkylazaarenes to Imines and Nitroalkenes. Synfacts, 8(12).
DOI: 10.1055/s-0032-1317750