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2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride
1. Basic Information
Name: 2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride
Alias: 2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridinium chloride
CAS No.: 86604-75-3
Molecular Formula: C9H13Cl2NO
Molecular Weight: 222.11
Category: Pyridine heterocyclic pharmaceutical intermediate, proton pump inhibitor raw material, active benzyl chloride building block
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to off-white crystalline powder
- Odor: Slight pungent alkyl chloride irritating odor
- Solubility: Freely soluble in water, methanol, ethanol; soluble in DMF; slightly soluble in acetone; insoluble in toluene, hexane, ethyl acetate
- Melting Point: 136–142 ℃ (decomposes)
- Density (predicted): 1.24 g/cm3
- Hygroscopy: Strongly hygroscopic, absorbs moisture and agglomerates under high humidity
- Aqueous property: Aqueous solution strongly acidic pH 2.0–4.0; chloromethyl group prone to hydrolysis in hot water
Chemical Properties
- Molecular structure: Pyridine ring with 3,5-dimethyl, 4-methoxy, 2-chloromethyl substitution, hydrochloride salt form; highly reactive benzyl chloromethyl functional group
- SN2 nucleophilic substitution: The chloromethyl (-CH2Cl) is highly active, reacts with thiols, amines, alcohols to form sulfide, amine, ether derivatives; core intermediate for omeprazole series PPI drugs
- Hydrolysis risk: Hot water / alkaline environment hydrolyzes chloromethyl into hydroxymethyl impurity, reduces product activity
- Salt dissociation: Dissolves in polar solvents to release pyridinium cation and chloride ion
- Thermal stability: Stable below 60 ℃; above 100 ℃ decomposes to release hydrogen chloride gas
- Photostability: Light-sensitive; UV irradiation accelerates decomposition, powder turns yellow
- Compatibility: Compatible with anhydrous low-polar aprotic solvents; incompatible with strong alkali, amines, oxidants, water at high temperature
3. Main Application Fields
1. Proton Pump Inhibitor API Intermediate (Core Application)
Key raw material for synthesis of omeprazole, esomeprazole; undergoes thioether condensation with mercaptobenzimidazole to prepare gastric acid inhibiting drugs
2. Other Pyridine-Series Heterocyclic Drug Building Block
Used for synthesis of anti-ulcer, digestive system small-molecule pharmaceuticals
3. Organic Synthesis Nucleophilic Substrate
Active alkylating reagent for lab heterocyclic synthesis research
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 86604-75-3 |
| Molecular Formula | C9H13Cl2NO |
| Appearance | Uniform white crystal without yellow discoloration |
| HPLC Purity | Pharma Intermediate Grade ≥98.5% |
| Melting Point | 136–142 ℃ |
| Water Content (KF) | ≤1.00% |
| Residue on Ignition | ≤0.10% |
| Hydrolysis Impurity (Hydroxymethyl pyridine) | ≤0.20% |
| Single Maximum Related Impurity | ≤0.15% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-filled amber light-proof aluminum foil vacuum bag; bulk 25kg PE lined light-proof fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse 2–25 ℃, full light shielding, isolate humid air, alkaline materials and amines |
| Transportation Requirement | Strongly hygroscopic light-sensitive alkyl chloride pyridine salt, fully sealed moisture-proof light-blocking packaging, separate from alkaline chemicals and food |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
Safety Warning
Highly irritating chlorinated pyridinium salt powder. Dust severely irritates eyes, nasal cavity, throat and respiratory tract; skin contact causes burning redness and allergic dermatitis; hydrolysis releases irritating HCl vapor. All operations in fully ventilated fume hood with gas dust respirator, UV-blocking splash goggles and thick chemical-resistant nitrile gloves. Strictly avoid moisture, light, high temperature and contact with alkaline substances. Waste liquid neutralized with sodium carbonate solution before discharge; solid waste classified as halogen-containing pharmaceutical hazardous waste for professional incineration disposal.
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