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4-Nitro-2,3-lutidine-N-oxide
1. Basic Information
Name: 4-Nitro-2,3-lutidine-N-oxide
Alias: 2,3-Dimethyl-4-nitropyridine N-oxide
CAS No.: 37699-43-7
Molecular Formula: C7H8N2O3
Molecular Weight: 168.15
Category: Pyridine N-oxide heterocyclic intermediate, pharmaceutical synthetic building block, pesticide raw material, aromatic substitution reaction substrate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Pale yellow crystalline powder
- Odor: Faint mild heterocyclic odor
- Solubility: Soluble in DCM, chloroform, DMF, DMSO, hot ethanol; slightly soluble in cold methanol; insoluble in water, hexane, petroleum ether
- Melting Point: 92–96 ℃
- Density (predicted): 1.29 g/cm3
- Hygroscopy: Non-hygroscopic under normal ambient humidity
- Aqueous property: Neutral solid, stable in neutral water at room temperature; no hydrolysis under normal conditions
Chemical Properties
- Molecular structure: Pyridine ring with 2,3-dimethyl, 4-nitro substitution, pyridine nitrogen oxidized to N-oxide; N-oxide group activates ortho/para positions for nucleophilic substitution
- Regioselective halogenation/reduction: N-oxide directing group enables selective reduction of nitro group or deoxygenation of N-oxide to construct substituted pyridine APIs
- Nitro group derivatization: Nitro can be reduced to amino, diazotized, acylated to introduce multiple functional fragments
- N-oxide deoxygenation: React with phosphorus trichloride, iron powder to remove oxygen atom and get 4-nitro-2,3-lutidine
- Thermal stability: Stable below 85 ℃; long-term heating above melting point has risk of slight decomposition
- Photostability: Slightly light-sensitive; long-term UV irradiation turns deep yellow
- Compatibility: Compatible with anhydrous polar aprotic solvents; incompatible with strong reducing agents, concentrated strong alkali, concentrated acid at high temperature
3. Main Application Fields
1. Pharmaceutical Pyridine Intermediate (Core Application)
Precursor for synthesizing substituted aminopyridine series drugs; used to prepare digestive system, anti-inflammatory and antibacterial small-molecule APIs
2. Agricultural Chemical Intermediate
Raw material for pyridine-based fungicides, insecticides and plant growth regulators
3. Organic Synthesis Research Reagent
Classic pyridine N-oxide substrate for studying aromatic nucleophilic substitution, nitro reduction and deoxygenation reactions
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 37699-43-7 |
| Molecular Formula | C7H8N2O3 |
| Appearance | Uniform pale yellow crystal without brown impurities |
| HPLC Purity | Synthetic Intermediate Grade ≥98.0% |
| Melting Point | 92–96 ℃ |
| Water Content (KF) | ≤0.20% |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.15% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | 100g/1kg amber light-proof aluminum foil vacuum bag, 25kg PE lined fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 ℃, light shielding, isolate strong reducing agents and alkaline raw materials |
| Transportation Requirement | Slightly light-sensitive nitro pyridine crystal, conventional moisture-proof sealed packaging |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
Safety Warning
Irritant nitro heterocyclic crystalline powder. Dust irritates eyes, nasal and respiratory mucosa; long-term skin contact may cause mild allergic itching. Avoid mixing with strong reducing agents to prevent exothermic reaction. All operations in ventilated fume hood with dust mask, splash-proof goggles and chemical-resistant nitrile gloves. Waste liquid diluted and treated before discharge; solid waste classified as nitro-containing organic hazardous waste for professional disposal.
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