Name: 20-Azido-3,6,9,12,15,18-hexaoxaeicosan-1-amine
Molecular Formula: C14H30N4O6
CAS#: 957486-82-7
SMILES: NCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]
MDL#: MFCD03453240
Catalog#: AMTGC1602-AH26
Molecular weight: 350.41 g/mol
Other names:
- Azido-PEG6-amine
- PEG6 azide amine
- N₃-PEG6-NH₂
- H₂N-PEG6-N₃
Fields of Interest: bioconjugation, drug delivery, chemical biology, and materials science
Background
20-Azido-3,6,9,12,15,18-hexaoxaeicosan-1-amine is a heterobifunctional azide-functionalized PEG derivative based on a PEG6 backbone, featuring a terminal azide group and a primary amine at opposite ends of the molecule. The polyethylene glycol spacer provides hydrophilicity, flexibility, and compatibility with aqueous and biological environments while offering extended linker length for increased spatial separation and reduced steric hindrance. The azide functionality enables highly efficient bioorthogonal click chemistry, including copper-catalyzed azide–alkyne cycloaddition (CuAAC) and strain-promoted azide–alkyne cycloaddition, while the primary amine readily reacts with activated carboxylic acids, NHS esters, aldehydes, and isocyanates. This dual-functional PEG linker serves as a versatile building block within a comprehensive portfolio of functionalized PEGs designed for orthogonal and modular molecular assembly. The compound is widely recognized as Azido-PEG6-amine, a commonly used heterobifunctional click chemistry linker.
Applications
20-Azido-3,6,9,12,15,18-hexaoxaeicosan-1-amine is commonly used in bioconjugation, drug delivery, chemical biology, and materials science applications where orthogonal reactivity and extended PEG spacing are required. Typical uses include click-based attachment of the PEG linker to alkynyl-functionalized molecules followed by amide bond formation through the terminal amine, enabling the preparation of multifunctional conjugates, PEGylated biomolecules, fluorescent probes, nanoparticles, and advanced materials. The longer PEG6 spacer provides enhanced flexibility, improved aqueous solubility, and reduced steric hindrance compared with shorter PEG linkers, making it particularly valuable in applications requiring greater molecular reach. The compound has also been utilized as a building block in linker design and biofunctionalized materials prepared through click chemistry.
Appearance: Colorless liquid
Purity: 96%
Storage: Long-term storage in a freezer at -20°C
Solubility: Dichloromethane, Chloroform, Methanol
Literature:
- European Journal of Medicinal Chemistry, 2021, vol. 226, art. no. 113889
- European Journal of Medicinal Chemistry, 2026, vol. 307, art. no. 118645