What Is 4-(Chloromethyl)-1-methyl-1H-imidazole Hydrochloride?

4-(Chloromethyl)-1-methyl-1H-imidazole hydrochloride (Aladdin SKU: C191527) is a salt form of a chloromethyl-substituted N-methylimidazole. The compound consists of an imidazole ring bearing a methyl group on nitrogen-1 and a chloromethyl (–CH₂Cl) substituent at the 4-position, supplied as the stable hydrochloride salt to improve handling and shelf life.

The imidazole scaffold is a ubiquitous pharmacophore found in numerous marketed drugs and natural products. Introduction of the chloromethyl handle at C-4 converts the ring into a versatile electrophilic synthon capable of reacting with a wide range of nucleophiles including amines, thiols, and alkoxides, making this compound a valuable intermediate in medicinal chemistry programs.

Chemical Properties and Stability

The hydrochloride salt form enhances the compound's crystallinity and hygroscopic stability relative to the free base. The chloromethyl group is inherently reactive toward nucleophilic substitution (S_N2); consequently, the compound should be kept away from moisture, strong bases, and nucleophilic reagents during storage.

As a benzylic-type chloride on an electron-rich heterocycle, the C–Cl bond exhibits moderate to high electrophilic reactivity. Solutions in polar aprotic solvents such as DMF, DMSO, or acetonitrile are recommended for most synthetic applications. Aqueous solutions should be prepared freshly and used promptly, because hydrolysis of the chloromethyl group can occur under basic or prolonged aqueous conditions.

Note: Specific melting point, purity grade, and spectroscopic data are provided on the Certificate of Analysis (CoA) supplied with each lot of C191527. Researchers should consult the CoA for lot-specific values.

Handling, Storage, and Safety

Like other chloromethyl-containing compounds, 4-(Chloromethyl)-1-methyl-1H-imidazole hydrochloride should be treated as a potential lachrymator and irritant. Work should be performed in a well-ventilated fume hood with appropriate personal protective equipment (PPE), including chemically resistant gloves, safety glasses, and a lab coat.

Store the compound in a tightly sealed container in a cool, dry location away from light, moisture, and incompatible materials (strong oxidizers, strong bases, and nucleophiles). Refrigerated storage (2–8 °C) or as indicated on the product label is generally recommended for chloromethyl heterocycle salts to minimize decomposition.

Consult the Safety Data Sheet (SDS) for C191527 before first use for complete hazard classification, first-aid measures, and disposal guidelines in accordance with local regulations.

Research and Synthetic Applications

The primary utility of this compound lies in its role as an electrophilic building block for the synthesis of N-methylimidazole-containing target molecules. Representative application areas include:

• Medicinal chemistry: Synthesis of imidazole-bearing drug candidates and pharmacological probes, particularly in programs targeting enzymes or receptors that recognize the imidazole pharmacophore.
• Bioconjugation linkers: The chloromethyl group can be used to alkylate thiol or amine residues on biomolecules or solid supports under controlled conditions.
• Heterocyclic library synthesis: High-throughput parallel synthesis of compound libraries incorporating the 1-methylimidazol-4-yl methylene scaffold.
• Prodrug design: Introduction of a cleavable imidazolylmethyl protecting group or solubilizing moiety onto active pharmaceutical ingredients.

Reaction conditions should be optimized for each specific nucleophile; mild base (e.g., K₂CO₃, Et₃N) is typically used to neutralize the HCl salt and liberate the free base in situ prior to or during coupling.

Ordering and Quality Information

4-(Chloromethyl)-1-methyl-1H-imidazole hydrochloride is available from Aladdin Scientific under catalog number C191527. Each shipment is accompanied by a Certificate of Analysis (CoA) detailing lot-specific purity, appearance, and analytical test results.

For bulk quantities, custom pack sizes, or additional technical information, contact the Aladdin Scientific sales or technical support team. Standard ordering, payment, and return policies apply as described in the Aladdin customer service documentation.