2-[2-(2-Ethylamino-ethoxy)-ethoxy]-ethanol (97.4%)

2-[2-(2-Ethylamino-ethoxy)-ethoxy]-ethanol

Molecular Formula: C8H19NO3

CAS#: 1694210-96-2

SMILES: OCCOCCOCCNCC

MDL#: MFCD32869444

Catalog#: AMTGC561-EE20

Molecular weight: 177.14 g/mol

Appearance: Pale orange liquid

Purity: 97.4%

Storage: Room temperature

Solubility: Dichloromethane, Chloroform, Methanol

Other names:

• N-Ethyl-2-[2-(2-hydroxyethoxy)ethoxy]ethanamine
• Ethylamino-PEG2-OH
• Secondary amine PEG alcohol
• Amino-hydroxy PEG-like linker

Fields of Interest

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

Background

2-[2-(2-Ethylaminoethoxy)ethoxy]ethanol (CAS 1694210-96-2) is a compact, heterobifunctional PEG-like building block containing a secondary ethylamine and a terminal primary alcohol connected through a flexible, hydrophilic oligoethylene glycol chain. The molecule combines the polarity and flexibility of an ether-rich spacer with two chemically distinct functional groups that can be used for further molecular modification.

The secondary amine provides a nucleophilic and basic functional site suitable for reactions such as alkylation, acylation, and other amine-directed transformations, while the terminal hydroxyl group can be converted into esters, ethers, sulfonates, or other activated derivatives. This combination makes the compound a versatile intermediate for preparing more complex functionalized PEG derivatives and for applications requiring both hydrophilic spacing and additional synthetic flexibility.

Applications

2-[2-(2-Ethylaminoethoxy)ethoxy]ethanol is useful as a synthetic intermediate and functional building block in medicinal chemistry, materials science, polymer modification, and specialty chemical synthesis. Its secondary amine and terminal alcohol provide two differentiated sites for chemical modification, enabling sequential functionalization and incorporation into more complex molecular architectures.

The ether-rich chain can introduce flexibility and hydrophilic character into a target molecule, while the ethyl-substituted secondary amine provides a basic nitrogen center that can be retained in the final structure or further derivatized. The terminal alcohol also provides a convenient route for introducing additional functionality, including activated leaving groups or conjugation handles. These characteristics make the compound useful for the development of functionalized PEG-like linkers, molecular probes, polymer modifiers, and specialty intermediates.

Literature:

• Dykhuizen, E. C.; Kiessling, L. L. “Potent Ligands for Prokaryotic UDP-Galactopyranose Mutase That Exploit an Enzyme Subsite.” Organic Letters 2009, 11, 193–196. DOI: 10.1021/ol802094p.
  • Synopsis: Developed high-affinity ligands for UDP-galactopyranose mutase, using short hydrophilic linker chemistry to access an additional enzyme-binding region. The closely related amino-PEG alcohol 2-[2-(2-aminoethoxy)ethoxy]ethanol is associated with the synthetic chemistry for this work.
• Simonin, J.; Vernekar, S. K. V.; Thompson, A. J.; et al. “High-affinity fluorescent ligands for the 5-HT3 receptor.” Bioorganic & Medicinal Chemistry Letters 2012, 22, 1151–1155. DOI: 10.1016/j.bmcl.2011.11.097.
  • Synopsis: Synthesized fluorescent granisetron conjugates as high-affinity probes for the human 5-HT3 receptor, illustrating the utility of compact linker structures in connecting biologically active ligands with fluorescent reporter groups.
• Heller, K.; Ochtrop, P.; Albers, M. F.; Zauner, F. B.; Itzen, A.; Hedberg, C. “Covalent Protein Labeling by Enzymatic Phosphocholination.” Angewandte Chemie International Edition 2015, 54, 10327–10330. DOI: 10.1002/anie.201502618.
  • Synopsis: Developed an enzymatic method for site-selective protein labeling in which a small PEG-containing linker connects functional cargo to proteins, demonstrating the value of short PEG spacers in bioconjugation and protein modification.
• Lebeau, L.; Oudet, P.; Mioskowski, C. “Synthesis of New Phospholipids Linked to Steroid-Hormone Derivatives Designed for Two-Dimensional Crystallization of Proteins.” Helvetica Chimica Acta 1991, 74, 1697–1706. DOI: 10.1002/hlca.19910740810.
  • Synopsis: Described the synthesis of functionalized lipid–steroid conjugates designed for protein-interaction studies, providing an early example of functional linker chemistry used to connect molecular components for biological applications. This paper is indexed as a literature reference for the closely related amino-PEG alcohol.