Production Method 1

66422-84-2

86902-27-4

Reaction Conditions

1.1 Reagents: m-Chloroperbenzoic acid Solvents: Dichloromethane ;  5 d, rt
1.2 Reagents: Sodium methoxide Solvents: Methanol ;  1 h, rt

Reference

Design, Synthesis, and Evaluation of Orally Active Benzimidazoles and Benzoxazoles as Vascular Endothelial Growth Factor-2 Receptor Tyrosine Kinase Inhibitors

Potashman, Michele H.; et al, Journal of Medicinal Chemistry, 2007, 50(18), 4351-4373

4-(Benzyloxy)-3-chlorophenol Raw materials

• 4-(benzyloxy)-3-chlorobenzaldehyde

4-(Benzyloxy)-3-chlorophenol Preparation Products

• 4-(Benzyloxy)-3-chlorophenol (86902-27-4)

• 1. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 2. Evolution of hierarchical porous structures in supramolecular guest–host hydrogels?
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• 3. Distinct impact of glycation towards the aggregation and toxicity of murine and human amyloid-β?
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• 4. Evolutionary approaches in protein engineering towards biomaterial construction
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• 5. Evolution of important glucosinolates in three common Brassica vegetables during their processing into vegetable powder and in vitro gastric digestion
  Nan Fu,Naphaporn Chiewchan,Xiao Dong Chen Food Funct., 2020,11, 211-220

• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols 4-alkoxyphenols

Introduction to 4-(Benzyloxy)-3-chlorophenol (CAS No. 86902-27-4)

4-(Benzyloxy)-3-chlorophenol, identified by its Chemical Abstracts Service (CAS) number 86902-27-4, is a significant compound in the realm of pharmaceutical and chemical research. This aromatic heterocyclic compound features a benzyloxy group attached to a chlorophenol backbone, making it a versatile intermediate in organic synthesis and a potential candidate for various biochemical applications.

The molecular structure of 4-(Benzyloxy)-3-chlorophenol consists of a benzene ring substituted with a hydroxyl group at the 3-position and a benzyloxy group at the 4-position, with the presence of a chlorine atom further enhancing its reactivity. This unique arrangement allows for diverse chemical modifications, making it valuable in the development of novel therapeutic agents and agrochemicals.

In recent years, there has been growing interest in 4-(Benzyloxy)-3-chlorophenol due to its potential applications in medicinal chemistry. Researchers have been exploring its role as a precursor in synthesizing bioactive molecules, particularly those targeting inflammatory and infectious diseases. The compound's ability to interact with biological targets through both hydrophobic and hydrophilic interactions makes it an attractive scaffold for drug design.

One of the most compelling aspects of 4-(Benzyloxy)-3-chlorophenol is its utility in the synthesis of phenolic derivatives known for their antimicrobial and antioxidant properties. Studies have demonstrated that modifications of the chlorophenol core can lead to compounds with enhanced efficacy against resistant bacterial strains. For instance, derivatives of this compound have shown promising results in preliminary screenings as inhibitors of bacterial biofilm formation, a critical factor in antibiotic resistance.

The benzyloxy group in 4-(Benzyloxy)-3-chlorophenol also contributes to its pharmacological potential by influencing solubility and metabolic stability. This feature is particularly important in drug development, where pharmacokinetic properties often determine a drug's clinical success. Researchers have leveraged this property to design prodrugs that release active pharmaceutical ingredients under specific physiological conditions, thereby improving therapeutic outcomes.

Recent advancements in computational chemistry have further enhanced the understanding of 4-(Benzyloxy)-3-chlorophenol's interactions with biological systems. Molecular docking studies have identified potential binding sites on enzymes and receptors relevant to neurological disorders, suggesting its role as a lead compound for neuroprotective agents. These findings align with broader trends in drug discovery, where natural product-inspired scaffolds are being repurposed for modern therapeutic needs.

The agrochemical sector has also recognized the significance of 4-(Benzyloxy)-3-chlorophenol as a building block for developing novel pesticides. Its structural features allow for the creation of compounds that disrupt essential metabolic pathways in pests while maintaining low toxicity to non-target organisms. Such developments are crucial in addressing the growing challenge of pest resistance to conventional pesticides.

In conclusion, 4-(Benzyloxy)-3-chlorophenol (CAS No. 86902-27-4) represents a multifaceted compound with substantial potential across pharmaceuticals and agrochemicals. Its unique structural attributes, coupled with recent advancements in synthetic methodologies and computational biology, position it as a key player in ongoing research efforts aimed at addressing global health and agricultural challenges.

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