1-[2-(2-Chloro-ethoxy)-ethoxy]-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethane (97.7%)

1-[2-(2-Chloro-ethoxy)-ethoxy]-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethane

Molecular Formula: C11H23ClO5

CAS#: 120259-67-8

SMILES: ClCCOCCOCCOCCOCCOC

MDL#: MFCD26318778

Catalog#: AMTGC562-CE20

Molecular weight: 270.75 g/mol

Appearance: Pale orange liquid

Purity: 97.7%

Storage: Room temperature

Solubility: Dichloromethane, Chloroform, Methanol

Other names:

• m-PEG5-Cl
• Methoxy-PEG5-chloride
• Chloro-PEG5-methyl ether
• 1-[2-(2-Chloroethoxy)ethoxy]-2-[2-(2-methoxyethoxy)ethoxy]ethane

Fields of Interest

Functionalized PEGs, organic synthesis, medicinal chemistry, linker synthesis, PEGylation, polymer chemistry, materials science, surface modification, molecular probe development, specialty chemical synthesis

Background

16-Chloro-2,5,8,11,14-pentaoxahexadecane (CAS 120259-67-8) is a monofunctional, chloro-terminated oligoethylene glycol derivative commonly known as m-PEG5-Cl. The molecule combines a terminal alkyl chloride with a methoxy-capped, ether-rich PEG chain, providing a compact and flexible building block for further chemical modification.

The terminal chloride provides a site for nucleophilic substitution, while the methoxy terminus is comparatively nonreactive under many common synthetic conditions. The oligoethylene glycol portion introduces flexibility and hydrophilic character without providing a second reactive terminus. This combination makes the compound useful as a synthetic intermediate for preparing functionalized PEG derivatives and for introducing a defined oligoethylene glycol segment into more complex molecular structures.

Applications

16-Chloro-2,5,8,11,14-pentaoxahexadecane is useful in organic synthesis, functionalized PEG synthesis, medicinal chemistry, materials science, polymer modification, and specialty chemical synthesis. The terminal alkyl chloride can serve as a precursor for substitution with suitable nucleophiles, enabling preparation of derivatives containing azide, amine, thiol, or other functionality.

Because the opposite end is methoxy-capped, modification can be directed primarily through the chloro terminus. This makes m-PEG5-Cl useful for monofunctional PEGylation strategies, linker development, molecular modification, and preparation of more specialized PEG building blocks where a defined hydrophilic spacer and a single functionalization site are desired.

Literature:

• “Novel GLP-1 receptor agonist peptides,” GB2551945A. Patent.
  Synopsis: Provides a direct synthesis of 16-chloro-2,5,8,11,14-pentaoxahexadecane, prepared from the corresponding PEG alcohol in 84% yield. The compound was then used to introduce its methoxy-terminated PEG chain into a larger biologically relevant molecule through nucleophilic substitution. This is excellent direct support for positioning CAS 120259-67-8 as a PEGylating synthetic intermediate/linker building block.
• Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U. S. “Poly(ethylene glycol) in Drug Delivery: Pros and Cons as Well as Potential Alternatives.” Angewandte Chemie International Edition 2010, 49, 6288–6308. DOI: 10.1002/anie.200902672.
  Synopsis: A widely cited review of PEG in pharmaceutical and biomedical applications, including how PEG chains can modify solubility, stability, circulation behavior, and other physicochemical properties of conjugated molecules. This is a useful class-level citation supporting the rationale for incorporating PEG segments into molecular designs.