benzyl N-[2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl] carbamate (99%)

Name: benzyl N-[2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl]carbamate 

Molecular Formula: C₁₆H₂₆N₂O₅ 

CAS#: 863973-20-0 

SMILES: C1=CC=C(C=C1)COC(=O)NCCOCCOCCOCCN 

MDL#: MFCD28155474 

Catalog#: AMTGC1381-BA24 

Molecular weight:  326.39 g/mol 

Other names: 

• CbzNH-PEG3-CH₂CH₂NH₂ 

• Benzyl (2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)carbamate 

Fields of Interest: PEGylation, bioconjugation, drug delivery, materials science 

Background & Applications: 

Background
Benzyl N-[2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl]carbamate (CAS 863973-20-0) is a protected amine-functionalized PEG derivative based on a PEG4 backbone, featuring a terminal benzyl-protected (Cbz-protected) primary amine. The polyethylene glycol spacer provides hydrophilicity, flexibility, and compatibility with aqueous and biological environments, while the benzyl carbamate protecting group enables controlled, stepwise synthetic strategies and temporary masking of the amine functionality. The Cbz group can be removed under mild hydrogenolysis conditions to generate the free amine for downstream conjugation. This compound serves as a versatile intermediate within a robust portfolio of functionalized PEGs designed for precise molecular assembly. 

Applications
This Cbz-protected PEG amine is commonly used in bioconjugation, drug delivery, and materials science applications where staged functional group exposure is required. Typical uses include stepwise construction of multifunctional PEG linkers, selective PEGylation of small molecules or polymers, and preparation of intermediates for pharmaceutical and biomaterials research. Following deprotection, the resulting PEG4 primary amine is suitable for direct coupling to activated carboxylic acids, NHS esters, and isocyanates. As part of a comprehensive functionalized PEG product line, benzyl N-[2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl]carbamate supports modular design strategies for advanced chemical and biological applications. 

Appearance: Colorless liquid  

Purity: 99% 

Storage: 0-3 °C for long term storage 

Solubility: DCM, Chloroform, Ethyl Acetate, Acetonitrile 

Literature:  

Cbz-protected amino-PEG linkers are well-established intermediates in bioconjugation, drug delivery, and polymer–drug conjugate research, where controlled and orthogonal amine protection is required during multistep synthesis. These compounds combine the hydrophilicity and flexibility of a polyethylene glycol (PEG) spacer with a carboxybenzyl (Cbz)–protected amine, allowing selective deprotection by catalytic hydrogenolysis at a late synthetic stage.   

In the peer-reviewed literature, Cbz-protected PEG amines are frequently employed as enabling building blocks for the construction of PEGylated small molecules, biomaterials, and antibody–drug conjugates, providing improved solubility, reduced nonspecific interactions, and precise control over linker architecture.  

Their role in modern conjugate design is discussed in broader reviews of PEG-based linker strategies, such as the Journal of Controlled Release review on polyethylene glycol linkers in advanced drug conjugates: https://www.sciencedirect.com/science/article/pii/S0168365921003849