What Is 2-(4-Nitrophenyl)-1H-benzo[d]imidazole?

2-(4-Nitrophenyl)-1H-benzo[d]imidazole is an aromatic heterocyclic compound belonging to the benzimidazole family. The molecule consists of a benzimidazole bicyclic core—formed by fusion of a benzene ring and an imidazole ring—bearing a 4-nitrophenyl group at the C-2 position. The presence of the electron-withdrawing nitro group significantly modulates the electronic density of the ring system, influencing the compound's reactivity, acidity of the N-H proton, and photophysical properties.

Benzimidazole derivatives are well-recognized privileged scaffolds in medicinal chemistry owing to their ability to mimic purine bases and engage in diverse non-covalent interactions with biological macromolecules. The nitrophenyl variant offers additional handles for chemical transformation, including reduction of the nitro group to an amine and subsequent functionalization.

Physical and Chemical Properties

As an aromatic solid, 2-(4-Nitrophenyl)-1H-benzo[d]imidazole is expected to display a relatively high melting point consistent with other 2-arylbenzimidazoles, and it typically appears as a pale yellow to off-white crystalline powder. The nitro group renders the compound moderately electron-deficient, which can be observed by shifts in UV-Vis absorption relative to unsubstituted 2-phenylbenzimidazole.

The compound is sparingly soluble in water but generally soluble in polar aprotic solvents such as DMSO and DMF, and in alcohols such as methanol and ethanol. Stock solutions are most reliably prepared in DMSO. The N-H tautomerism characteristic of 1H-benzimidazoles is present, making the compound amphoteric—capable of acting as both a weak acid and a weak base.

Note: Specific melting point, molecular weight, and spectral data (NMR, MS) should be confirmed against the certificate of analysis (CoA) provided with SKU H708834.

Research and Synthetic Applications

2-(4-Nitrophenyl)-1H-benzo[d]imidazole serves several roles in research:

• Synthetic intermediate: The nitro group can be selectively reduced (e.g., catalytic hydrogenation, iron/acetic acid, or sodium dithionite) to afford 2-(4-aminophenyl)-1H-benzo[d]imidazole, a versatile amine building block for further derivatization including acylation, sulfonylation, and reductive amination.
• Medicinal chemistry scaffold: 2-Arylbenzimidazoles are extensively studied for a range of biological activities. The nitrophenyl moiety is a common pharmacophore element explored in anti-infective, anticancer, and enzyme-inhibition studies.
• Materials and photophysical studies: Benzimidazole derivatives exhibit interesting fluorescence properties exploited in organic light-emitting diode (OLED) research and as chemosensors. The push-pull electronic character introduced by the nitro group can be leveraged in dye and sensor design.
• Reference standard: The compound can be used as a purity reference or analytical standard in HPLC method development.

Safe Handling and Storage

As with all fine chemical reagents, appropriate laboratory safety precautions should be observed when handling 2-(4-Nitrophenyl)-1H-benzo[d]imidazole:

• Wear appropriate personal protective equipment (PPE): lab coat, chemical-resistant gloves, and eye protection.
• Handle in a well-ventilated area or fume hood to avoid inhalation of dust.
• Aromatic nitro compounds may be sensitizers or irritants; consult the Safety Data Sheet (SDS) for SKU H708834 for specific hazard classifications, GHS pictograms, and first-aid measures.
• Store in a cool, dry place, away from light, heat, and incompatible materials such as strong reducing agents.
• Dispose of waste in accordance with local institutional and governmental regulations for aromatic nitrogen-containing compounds.

Note: Always refer to the current SDS for authoritative safety information specific to this product.

Ordering and Quality Information

2-(4-Nitrophenyl)-1H-benzo[d]imidazole is available from Aladdin Scientific under SKU H708834. Each lot is accompanied by a certificate of analysis (CoA) specifying purity (typically assessed by HPLC or titration), appearance, and identity confirmation by spectroscopic methods.

For bulk quantities, custom packaging, or specific purity grades, please contact Aladdin Scientific's sales team or submit an inquiry through the website. Volume pricing and institutional accounts may be available depending on quantity and region.

To ensure product integrity, inspect the packaging upon receipt and store according to the label instructions. If you have questions about compatibility with your specific application, our technical support team is available to assist.