What Is 2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile?

2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile (Aladdin SKU: H730188) is a benzimidazole-derived heterocyclic compound bearing two key functional groups: a chloromethyl group (–CH₂Cl) at the 2-position of the imidazole ring and a nitrile group (–CN) at the 6-position of the fused benzene ring. The benzimidazole scaffold is a privileged structure in medicinal chemistry, appearing in numerous bioactive molecules and approved pharmaceuticals. The chloromethyl moiety serves as an electrophilic alkylating handle, enabling nucleophilic substitution reactions with amines, thiols, and other nucleophiles. The nitrile group offers additional reactivity for further functional-group transformations, such as hydrolysis to carboxylic acids or reduction to amines, making this compound a highly versatile synthetic intermediate.

How Should This Compound Be Stored and Handled Safely?

As with all chloromethyl-bearing compounds, 2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile should be handled with appropriate precautions. Chloromethyl groups are electrophilic and potentially lachrymatory or irritating; therefore, work should be conducted in a well-ventilated fume hood with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a lab coat. The nitrile (cyano) group is also a hazard indicator requiring care in handling.

For storage, the compound should be kept in a tightly sealed container away from moisture, heat, and incompatible nucleophilic reagents. Cool, dry conditions (typically 2–8 °C or as specified on the product label) are recommended to maintain stability and prevent hydrolysis or decomposition of the chloromethyl group. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

What Are the Typical Applications in Research?

2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile is primarily used as a building block in synthetic and medicinal chemistry. Its bifunctional nature makes it particularly attractive for the preparation of more complex heterocyclic libraries. Common applications include:

• N-Alkylation reactions: The chloromethyl group readily alkylates nitrogen nucleophiles (e.g., amines, imidazoles, indoles) under mild basic conditions, facilitating the assembly of N-linked heterocyclic conjugates.
• S-Alkylation reactions: Thiol-containing compounds can be efficiently alkylated to generate thioether derivatives.
• Further nitrile elaboration: The 6-CN group can be transformed into amidines, tetrazoles, amides, or carboxylic acids, expanding the structural diversity achievable from this single starting material.
• Drug discovery and lead optimization: The benzimidazole core is associated with a wide range of biological activities; derivatives of this scaffold are explored as potential kinase inhibitors, antimicrobial agents, and antiparasitic leads.

Researchers in combinatorial chemistry and fragment-based drug discovery will find this compound useful for rapid library synthesis.

Purity, Specifications, and Quality Assurance

Aladdin Scientific supplies 2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile (H730188) as a research-grade reagent. For specific purity data, analytical certificates (CoA), HPLC traces, NMR spectra, and mass spectrometry data, please refer to the product page on the Aladdin Scientific website or contact our technical support team. Each lot is subject to quality control testing to ensure identity and purity meet the stated specifications.

Researchers requiring higher-purity material or specific analytical documentation for GMP-adjacent workflows should contact Aladdin Scientific directly to discuss available options. Specification sheets and SDS documents are available for download on the product detail page.

How to Order 2-(Chloromethyl)-1H-benzo[d]imidazole-6-carbonitrile from Aladdin Scientific

Ordering is straightforward through the Aladdin Scientific online platform. Use SKU H730188 to locate the product directly. The following options are available to customers:

• Online ordering: Add the desired quantity to your cart and check out using a purchase order, credit card, or other accepted payment methods.
• Bulk or custom quantities: Contact our sales team for volume pricing and availability of larger pack sizes.
• Institutional accounts: Lab managers and procurement officers can set up institutional accounts for streamlined purchasing, invoicing, and order tracking.
• Returns and refunds: Please refer to Aladdin Scientific's returns policy for information on eligibility and procedures.

For shipping conditions, estimated lead times, and regional availability, please consult the product page or contact customer service directly. Aladdin Scientific is committed to reliable supply and prompt delivery of research reagents worldwide.