Name: N-(2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethyl)-2,2,2-trifluoroacetamide
Molecular Formula: C10H17F3N4O4
CAS#: 898543-37-8
SMILES: O=C(C(F)(F)F)NCCOCCOCCOCCN=[N+]=[N-]
MDL#:
Catalog#: AMTGC993-AT22
Molecular weight: 314.26 g/mol
Other names:
- Azido-PEG4 trifluoroacetamide
- PEG4 azide TFA-protected amine
- Protected azido PEG amine (TFA)
Fields of Interest: bioconjugation, drug delivery, and materials science
Background & Applications:
Background
N-(2-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)ethyl)-2,2,2-trifluoroacetamide (CAS 898543-37-8) is a protected azide-functionalized PEG derivative based on a PEG4 backbone, featuring a terminal azide group and a trifluoroacetamide-protected amine. The polyethylene glycol spacer provides hydrophilicity, flexibility, and compatibility with aqueous and biological environments, while the trifluoroacetamide group serves as a compact, electron-withdrawing protecting group that modulates amine reactivity and can be removed under appropriate conditions to regenerate the free amine. The azide functionality enables efficient bioorthogonal click chemistry, including CuAAC and strain-promoted azide–alkyne cycloaddition. This compound serves as a versatile intermediate within a comprehensive portfolio of functionalized PEGs designed for orthogonal and controlled molecular assembly.
Applications
This trifluoroacetamide-protected azido PEG linker is commonly used in bioconjugation, drug delivery, and materials science applications where orthogonal reactivity and staged functional group control are required. Typical uses include click-based attachment of the PEG linker to alkynyl-functionalized molecules, followed by deprotection to generate a primary amine for subsequent coupling to activated carboxylic acids, NHS esters, or isocyanates. It is also useful in the preparation of multifunctional PEG intermediates and PEGylated biomolecules or materials. As part of a robust functionalized PEG product line, this compound supports modular design strategies in pharmaceutical research, diagnostics, and specialty chemical synthesis.
Appearance: Pale-yellow liquid
Purity: 97%
Storage: -20 °C
Solubility: Dichloromethane, Chloroform, Methanol
Literature:
- Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4585 – 4589