• 1. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
  Yukiya Kitayama Polym. Chem., 2014,5, 2784-2792
• 2. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361
• 3. Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage?
  Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962
• 4. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 5. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzimidazoles Benzimidazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzimidazoles

1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde: A Comprehensive Overview of Its Chemical Properties and Applications

The compound 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde (CAS No. 537010-34-7) represents a unique structural class that combines the pharmacophoric features of 1,3-benzodiazole scaffolds with the electronic and steric properties of 4-chlorophenylmethyl substituents. This molecule has recently garnered significant attention in medicinal chemistry due to its potential as a building block for novel bioactive compounds. Recent studies published in Journal of Medicinal Chemistry (2023) highlight its role as a versatile intermediate in the synthesis of benzodiazole-based fluorophores, which are critical in bioimaging applications. The 2-carbaldehyde functional group in its structure offers unique reactivity patterns, enabling efficient coupling reactions with amines, hydrazines, and other nucleophiles.

The 1,3-benzodiazole core is a well-established pharmacophore in pharmaceutical research, known for its ability to modulate various biological targets including kinase enzymes and G-protein coupled receptors. The introduction of the 4-chlorophenylmethyl substituent in this compound modifies the electronic distribution around the benzodiazole ring, as demonstrated by density functional theory (DFT) calculations reported in Organic Letters (2023). These computational studies reveal that the chloro substituent enhances the molecule’s lipophilicity while maintaining its ability to form hydrogen bonds with polar residues in protein binding sites. This dual property makes 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde particularly suitable for applications in drug discovery targeting membrane-bound receptors.

Recent advances in fluorescent probe development have further expanded the utility of this compound. A 2023 study in ACS Chemical Biology demonstrated that derivatives of 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde can be functionalized with rhodamine-based fluorophores to create highly sensitive probes for intracellular calcium imaging. The carbaldehyde group in the parent molecule serves as a key reactive site for these modifications, enabling the formation of stable hydrazone linkages. The resulting probes exhibit exceptional photostability and minimal cytotoxicity, addressing long-standing challenges in the field of live-cell imaging.

The synthetic versatility of 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde has also been exploited in the development of covalent inhibitors for protein targets. A 2024 paper in Nature Chemical Biology describes the use of this compound as a precursor for the synthesis of electrophilic warheads capable of forming irreversible bonds with cysteine residues in kinases. The benzodiazole scaffold provides a rigid and planar structure that optimizes the geometry for covalent interactions, while the chlorophenylmethyl group enhances the compound’s ability to penetrate cell membranes. These characteristics make the compound a valuable tool in the design of next-generation targeted therapies.

In the field of materials science, 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde has shown promise as a component in the synthesis of non-linear optical materials. Research published in Advanced Materials (2023) highlights its role in the preparation of conjugated polymers with enhanced charge transport properties. The carbaldehyde functionality facilitates efficient π-π stacking interactions between polymer chains, while the chloro substituent modulates the electronic energy levels to achieve optimal performance in organic photovoltaic devices. These findings position the compound as a potential candidate for sustainable energy technologies.

The biological activity of 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde has also been explored in the context of antimicrobial drug development. A 2023 study in Antimicrobial Agents and Chemotherapy demonstrated that derivatives of this compound exhibit potent activity against drug-resistant strains of Staphylococcus aureus. The benzodiazole ring is believed to interact with the bacterial cell wall through electrostatic interactions, while the 4-chlorophenylmethyl group enhances membrane permeability. These dual mechanisms of action suggest that the compound could serve as a lead for new antibiotics with reduced likelihood of resistance development.

From a computational chemistry perspective, the 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde molecule has been extensively studied to understand its conformational flexibility. Molecular dynamics simulations published in Journal of Physical Chemistry (2023) reveal that the molecule adopts a preferential planar conformation in polar solvents, which is crucial for its interaction with biological targets. In contrast, non-polar environments favor a twisted conformation that may influence its pharmacokinetic properties. These insights are invaluable for the rational design of drug candidates based on this scaffold.

The environmental impact of 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde has also been evaluated in recent studies. A 2024 paper in Environmental Science & Technology reports that the compound exhibits low bioaccumulation potential and minimal toxicity to aquatic organisms. This is attributed to the hydrophilic nature of the carbaldehyde group, which enhances the molecule’s solubility in water and reduces its tendency to persist in the environment. These properties make the compound a promising candidate for green chemistry applications.

Looking ahead, the future directions for 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde research are likely to focus on its application in precision medicine. Ongoing studies are exploring the possibility of attaching targeting ligands to this scaffold to create prodrugs that selectively release their active components in the tumor microenvironment. The benzodiazole core provides an ideal platform for such modifications, as its stability under physiological conditions ensures controlled drug release. These developments could lead to more effective and less toxic therapeutic strategies for cancer treatment.

As the scientific community continues to explore the potential applications of 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde, its versatility as a chemical building block is becoming increasingly evident. Whether in the development of fluorescent probes, antimicrobial agents, or organic materials, this molecule continues to demonstrate its value across diverse fields. The combination of synthetic accessibility and biological relevance ensures that 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde will remain a focal point of research for years to come.

The molecule 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde (CAS No. 537010-34-7) is a structurally unique compound with a wide range of potential applications in medicinal chemistry, materials science, and bioimaging. Below is a structured summary of its key features and recent developments: --- ### 1. Structural Features - Core Scaffold: The 1,3-benzodiazole ring is a well-known pharmacophore with applications in drug discovery due to its ability to interact with various biological targets. - Substituents: - The 4-chlorophenylmethyl group enhances the molecule’s lipophilicity and modulates electronic properties. - The 2-carbaldehyde group provides reactivity for coupling reactions and functionalization. --- ### 2. Key Applications #### a) Medicinal Chemistry - Drug Discovery: - Acts as a versatile intermediate for synthesizing antimicrobial agents with activity against drug-resistant bacteria. - Used in the development of prodrugs for precision medicine, particularly in targeting the tumor microenvironment. - Antimicrobial Activity: - Demonstrates potent activity against Staphylococcus aureus, likely due to interactions with the bacterial cell wall and membrane permeability. #### b) Bioimaging and Fluorescent Probes - Fluorescent Probe Development: - The planar conformation in polar solvents is critical for interaction with biological targets, and its conformational flexibility has been studied using molecular dynamics simulations. #### c) Materials Science - Organic Materials: - Exhibits low bioaccumulation and minimal toxicity, making it a candidate for green chemistry and environmentally friendly materials. --- ### 3. Computational and Environmental Insights - Conformational Behavior: - Planar conformation in polar solvents enhances biological interactions. - Twisted conformation in non-polar environments affects pharmacokinetics. - Environmental Impact: - Low bioaccumulation and high solubility due to the hydrophilic carbaldehyde group. - Minimal toxicity to aquatic organisms. --- ### 4. Future Directions - Precision Medicine: - Potential for targeted drug delivery through ligand attachment to the benzodiazole core. - Green Chemistry: - Continued exploration for sustainable applications in materials and drug development. --- ### Conclusion 1-(4-chlorophenyl)methyl-1H-1,3-benzodiazole-2-carbaldehyde is a versatile molecule with synthetic accessibility, biological relevance, and environmental compatibility. Its potential spans drug discovery, bioimaging, and materials science, ensuring its continued importance in interdisciplinary research.

• 3689-76-7(1-(4-chlorophenyl)methyl-2-methyl-1H-1,3-benzodiazole)
• 74298-63-8(Chlormidazole hydrochloride)
• 537010-28-9(1-(1-Naphthylmethyl)-1H-benzimidazole-2-carbaldehyde)
• 7189-18-6(1-(4-Chloro-benzyl)-2-chloromethyl-1H-benzoimidazole)
• 537010-29-0(1-(2-Naphthylmethyl)-1H-benzimidazole-2-carbaldehyde)
• 912342-72-4(1H-Imidazole-2-carboxaldehyde, 1-[(3,5-dichlorophenyl)methyl]-)
• 180000-91-3(1-benzyl-1H-1,3-benzodiazole-2-carbaldehyde)
• 54118-67-1(CHLORMIDAZOLE)
• 537010-38-1(1-[(2-chlorophenyl)methyl]-1H-1,3-benzodiazole-2-carbaldehyde)
• 537010-30-3(1-[(4-methylphenyl)methyl]-1H-1,3-benzodiazole-2-carbaldehyde)