CAS Number: 5470-66-6
Chemical Name: 4-Nitro-2-picoline N-oxide
IUPAC Name: 4-Nitro-2-methylpyridine 1-oxide
Synonyms:
4-Nitro-2-methylpyridine N-oxide;
2-Methyl-4-nitropyridine N-oxide;
4-Nitro-2-picoline 1-oxide
Molecular Formula: C₆H₆N₂O₃
Molecular Weight: ~154.12 g/mol
Appearance: Pale yellow to light yellow crystalline powder
Physical State: Solid
Melting Point: Typically reported in the range of 150–160 °C (may vary depending on purity)
Boiling Point: Not well-defined; may decompose upon strong heating
Solubility:
Soluble in polar organic solvents such as methanol, ethanol, acetone, and DMSO; moderately soluble in water
Stability:
Stable under normal laboratory conditions; may be sensitive to strong reducing agents and excessive heat
Nitro group (–NO₂)
Pyridine N-oxide functionality (N→O)
Aromatic heterocyclic ring
Methyl substituent (–CH₃)
Nitro-substituted pyridine derivative / Heterocyclic N-oxide compound
SMILES (representative):
CC1=NC(=CC=C1N+[O-])[O-]
InChI Key (representative):
(Varies by database; available from chemical registries)
5470-66-6 is widely used as an intermediate in heterocyclic organic synthesis. The presence of both a nitro group and a pyridine N-oxide moiety makes it highly reactive and versatile for chemical transformations, including:
Nucleophilic substitution reactions
Electrophilic aromatic substitution
Reduction to amino derivatives
Functional group interconversions
The N-oxide functionality enhances ring reactivity and regioselectivity in many synthetic pathways.
Used in the preparation of:
Advanced pharmaceutical intermediates
Bioactive heterocyclic compounds
Agrochemical building blocks
Specialty fine chemicals
Nitro-pyridine derivatives are frequently incorporated into biologically active molecules due to their electronic and structural properties.
Commonly employed in:
Academic research laboratories
Medicinal chemistry programs
Development of nitrogen-containing heterocycles
Structure–activity relationship (SAR) investigations
Oxidation–reduction mechanism studies
Its unique structural combination allows selective modifications for multi-step synthesis projects.
Harmful if swallowed
Causes skin and eye irritation
May cause respiratory irritation
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust
P280: Wear protective gloves and eye protection
P305 + P351 + P338: IF IN EYES, rinse cautiously with water and remove contact lenses
P301 + P312: IF SWALLOWED, call a doctor if you feel unwell
Handle in a well-ventilated laboratory using appropriate personal protective equipment (PPE).
Typical Purity: 97–99% (Research and Industrial Grade)
Storage Conditions:
Store in a tightly sealed container
Keep in a cool, dry, and well-ventilated area
Protect from direct sunlight and moisture
Keep away from strong reducing or oxidizing agents
Commercial Use:
Available from specialty chemical suppliers for research, pharmaceutical intermediate synthesis, and industrial organic chemistry applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.
5470-66-6 (4-NITRO-2-PICOLINE N-OXIDE) is an important nitro-substituted heterocyclic compound widely utilized as a synthetic intermediate in pharmaceutical, agrochemical, and fine chemical manufacturing. Its combination of a pyridine N-oxide structure and nitro functionality provides enhanced reactivity and versatility in organic synthesis, making it valuable for advanced research and industrial applications.
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