In the realm of chemical synthesis, particularly in the advanced fields of medicinal chemistry and material science, the precise design and utility of building blocks are paramount. Polyethylene glycol (PEG) linkers have become indispensable tools, offering a unique combination of flexibility, hydrophilicity, and biocompatibility. This article provides an in-depth look at Boc-1-amino-3,6-dioxa-8-octanediamine (CAS: 153086-78-3), a crucial bifunctional PEG linker, exploring its chemical characteristics, common applications, and synthesis considerations. For professionals seeking to buy high-quality reagents, understanding these aspects is key.

Chemical Profile and Properties

Boc-1-amino-3,6-dioxa-8-octanediamine is a molecule characterized by a short PEG chain (specifically, three ethylene glycol units) capped at one end with a Boc-protected amine and at the other with a free primary amine. Its molecular formula is C11H24N2O4, with a molecular weight of approximately 248.32 g/mol. Key properties include:

  • Appearance: Typically described as a colorless to light yellow viscous liquid.
  • Purity: High purity, often exceeding 97% (verified by HNMR), is crucial for demanding synthesis applications.
  • Solubility: Its PEG backbone renders it soluble in water and many common organic solvents, which simplifies reaction conditions and purification.
  • Reactivity: The free primary amine group is reactive towards carboxylic acids (via activating agents like EDC/NHS), activated esters, isocyanates, and aldehydes/ketones (via reductive amination). The Boc group, a common amine protecting group, can be cleaved under mild acidic conditions (e.g., trifluoroacetic acid or HCl in dioxane), liberating the second primary amine for subsequent reactions.
  • CAS Number: 153086-78-3.

Synthesis and Manufacturing Considerations

The synthesis of Boc-1-amino-3,6-dioxa-8-octanediamine typically involves selective protection of one amine group in a diamine precursor. A common route involves the reaction of 1,8-diamino-3,6-dioxaoctane with di-tert-butyl dicarbonate (Boc anhydride) under controlled conditions to achieve mono-protection. As a manufacturer, maintaining high selectivity and purity during this process is essential to minimize the formation of di-protected or unreacted starting materials. Strict quality control measures, including NMR spectroscopy and chromatography, are employed to ensure the final product meets the required specifications.

Applications in Chemical Synthesis

This bifunctional PEG linker finds extensive use in various synthetic strategies:

  • PROTAC Linkers: It is a common building block for constructing Proteolysis Targeting Chimeras (PROTACs), where it bridges target-binding ligands and E3 ligase recruiters. Its length and flexibility are well-suited for these complex molecules. Researchers looking to buy such linkers for their PROTAC programs will find this a vital component.
  • Drug Conjugates: It can be employed to create antibody-drug conjugates (ADCs), peptide-drug conjugates (PDCs), or small molecule-drug conjugates, enhancing solubility and pharmacokinetic profiles.
  • Biomaterial Functionalization: For modifying surfaces, hydrogels, or nanoparticles, this linker can introduce PEG chains and provide reactive handles for attaching biomolecules or other functional groups.
  • Combinatorial Chemistry: Its well-defined reactivity makes it suitable for library synthesis and peptide modification.

Procurement and Quality Assurance

When you need to buy Boc-1-amino-3,6-dioxa-8-octanediamine, it is vital to source it from a reliable manufacturer that guarantees purity and consistency. NINGBO INNO PHARMCHEM CO.,LTD. specializes in producing high-quality chemical intermediates for research and development. We offer this Boc-protected PEG diamine with assured purity and support for bulk orders. Our commitment to quality ensures that your synthesis projects benefit from reliable and well-characterized building blocks. Explore our offerings for your next demanding synthetic challenge.