4,5-Dichloro-1H-benzo[d]imidazole
[CAS# 1360899-36-0]

Identification

• Name: 4,5-Dichloro-1H-benzo[d]imidazole
• Molecular Formula: C₇H₄Cl₂N₂
• Molecular Weight: 187.03
• CAS Registry Number: 1360899-36-0
• SMILES: C1=CC(=C(C2=C1NC=N2)Cl)Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P271-P280-P302-P304-P305-P313-P332-P337-P338-P340-P351-P352

Discovory and Applicatios

4,5-Dichloro-1H-benzo[d]imidazole is a heterocyclic compound with the molecular formula C7H4Cl2N2. It features a benzimidazole core—a fused bicyclic structure composed of benzene and imidazole rings—with chlorine atoms substituted at the 4 and 5 positions of the benzene ring. This chemical is of particular interest in medicinal chemistry and organic synthesis due to its unique structural properties.

The discovery of 4,5-Dichloro-1H-benzo[d]imidazole can be traced back to the broader exploration of benzimidazole derivatives in the early to mid-20th century. Benzimidazoles were initially studied for their potential biological activity, particularly in the context of antifungal and antiparasitic agents. The substitution of chlorine atoms on the benzimidazole ring was a strategic modification aimed at enhancing the compound's chemical stability, lipophilicity, and overall pharmacological profile.

In terms of application, 4,5-Dichloro-1H-benzo[d]imidazole has found utility in the pharmaceutical industry, where it serves as a key intermediate in the synthesis of various drugs. Its ability to bind selectively to certain biological targets makes it a valuable starting material in the development of compounds with therapeutic potential. For instance, chlorinated benzimidazole derivatives have been explored for their antiviral, antibacterial, and anticancer activities. The presence of chlorine atoms is known to influence the compound's reactivity and bioavailability, potentially leading to more effective drug candidates.

One notable application of 4,5-Dichloro-1H-benzo[d]imidazole is in the development of kinase inhibitors, which are a class of drugs that block the action of kinases—enzymes that play a critical role in cell signaling and regulation. By inhibiting specific kinases, these drugs can interfere with cancer cell growth and proliferation. The dichloro-substituted benzimidazole scaffold is particularly attractive for designing kinase inhibitors due to its structural compatibility with the active sites of these enzymes.

Additionally, 4,5-Dichloro-1H-benzo[d]imidazole has been utilized in the synthesis of advanced materials. For example, it can be used as a building block in the production of polymers with specific electronic properties, making it relevant in the field of organic electronics. These materials have applications in the development of organic light-emitting diodes (OLEDs), organic photovoltaic cells, and other electronic devices where flexibility and tunability of the material's properties are essential.

In research settings, 4,5-Dichloro-1H-benzo[d]imidazole is employed as a model compound for studying the effects of halogen substitution on the reactivity and stability of benzimidazole derivatives. These studies contribute to a deeper understanding of how modifications to the benzimidazole ring can influence the compound's overall behavior, which is critical for the rational design of new chemical entities with desired properties.

However, like many halogenated organic compounds, 4,5-Dichloro-1H-benzo[d]imidazole must be handled with care due to potential health and environmental risks. It is classified as hazardous, with potential for causing skin and respiratory irritation upon exposure. Therefore, proper safety measures, including the use of protective equipment and adherence to safe disposal practices, are necessary when working with this chemical.

In conclusion, 4,5-Dichloro-1H-benzo[d]imidazole is a significant compound in both pharmaceutical and materials science. Its discovery and subsequent application highlight the importance of chlorinated benzimidazole derivatives in drug development and advanced material synthesis. The compound's versatility and reactivity make it a valuable tool in the ongoing exploration of new chemical and therapeutic frontiers.