Polystyrene-linked-benzyl (5-hydroxy-2-nitrobenzyl)(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate

Polystyrene-linked-benzyl (5-hydroxy-2-nitrobenzyl)(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate

Polystyrene-linked-benzyl (5-hydroxy-2-nitrobenzyl)(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)carbamate is a complex polymer compound designed for advanced applications in organic synthesis and materials science. Its structure integrates a polystyrene backbone with various functional groups that enhance its reactivity and versatility.

Structural Features

• Polystyrene Backbone: Provides a stable, crosslinked framework that is insoluble in many organic solvents, making it suitable for solid-phase reactions.
• Functional Groups:
  • Benzyl carbamate: Serves as a protective group for amines, allowing for selective reactions in synthetic pathways.
  • 5-Hydroxy-2-nitrobenzyl: Contains a nitro group that enhances electrophilicity and reactivity, while the hydroxyl group allows for further modifications.
  • Hydroxyethoxyethyl chain: A hydrophilic segment that increases solubility and provides additional reactive sites for further functionalization.

Key Properties

• Molecular Formula: C₁₅H₁₉N₃O₈
• Molecular Weight: Approximately 357.32 g/mol
• Reactivity: The presence of hydroxyl and nitro groups facilitates diverse chemical transformations, including nucleophilic substitutions and coupling reactions.

Applications

• Solid-phase synthesis: Acts as a support for synthesizing peptides or small molecules, allowing for efficient purification and recovery.
• Catalyst support: Can immobilize catalysts for heterogeneous reactions due to its functionalized nature.
• Pharmaceutical synthesis: Useful in the development of drug candidates by enabling selective modifications of active pharmaceutical ingredients.

This compound exemplifies the integration of polymer chemistry with functional organic groups, providing a versatile platform for researchers in synthetic chemistry and materials science.

Citations:

1. https://onlinelibrary.wiley.com/doi/10.1002/polb.23170
2. https://testbook.com/chemistry/polystyrene
3. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5100170.htm
4. https://en.wikipedia.org/wiki/Benzyl_carbamate
5. https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-carbamate
6. https://onlinelibrary.wiley.com/doi/full/10.1002/macp.202100127
7. https://www.mdpi.com/1420-3049/28/22/7648
8. https://www.sciencedirect.com/science/article/abs/pii/S0016236107000312