Name: tert-butyl 14-azido-3,6,9,12-tetraoxatetradecanoate
Molecular Formula: C14H27N3O6
CAS#: 864681-04-9
SMILES: O=C(OC(C)(C)C)COCCOCCOCCOCCN=[N+]=[N-]
MDL#: MFCD20134125
Catalog#: AMTGC720-TA20
Molecular weight: 333.38 g/mol
Other names:
- Azido-PEG4 tert-butyl ester
- PEG4 azide tBu ester
- Protected azido PEG acid linker
Fields of Interest: bioconjugation, drug delivery, and materials science
Background & Applications:
Background
tert-Butyl 14-azido-3,6,9,12-tetraoxatetradecanoate (also known as Azido-PEG4 tert-butyl ester) is a protected azide-functionalized PEG derivative based on a PEG4 backbone, featuring a terminal azide group and a tert-butyl ester-protected carboxylic acid. The polyethylene glycol spacer provides hydrophilicity, flexibility, and compatibility with aqueous and biological environments, while offering defined linker length for spatial control. The tert-butyl ester serves as an acid-labile protecting group that can be readily removed under mild acidic conditions to reveal the free carboxylic acid for downstream coupling. 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 stepwise molecular assembly.
Applications
This tert-butyl ester-protected azido PEG linker is commonly used in bioconjugation, drug delivery, and materials science applications where orthogonal reactivity and staged functional group exposure are required. Typical uses include click-based attachment of the PEG linker to alkynyl-functionalized molecules, followed by deprotection to generate a reactive carboxylic acid for amide bond formation with amines. It is also used in the preparation of multifunctional PEG intermediates, PEGylated small molecules, and biomaterials. As part of a robust functionalized PEG product line, tert-Butyl 14-azido-3,6,9,12-tetraoxatetradecanoate supports modular design strategies in pharmaceutical research, diagnostics, and specialty chemical synthesis.
Appearance: colorless liquid
Purity: 98%
Storage: -20 °C
Solubility: Dichloromethane, Chloroform, Methanol
Literature:
- Journal of Fluorine Chemistry, 2013, vol. 152, p. 173 – 181