2-[2-(2-Aminoethoxy)ethoxy]ethanol
[CAS# 6338-55-2]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: 2-[2-(2-Aminoethoxy)ethoxy]ethanol
• Synonyms: 2-[2-(2-Hydroxyethoxy)ethoxy]ethylamine; 3,6,9-Trioxadecylamine; 8-Amino-3,6-dioxa-1-octanol; 8-Amino-3,6-dioxaoctanol; MA 10; NSC 40760; T3EGMA; Triethylene glycol monoamine; Triglycolamine
• Molecular Formula: C₆H₁₅NO₃
• Molecular Weight: 149.19
• CAS Registry Number: 6338-55-2
• EC Number: 804-174-6
• SMILES: C(COCCOCCO)N

Properties

• Solubility: Very soluble (1000 g/L) (25 °C), Calc.^*
• Density: 1.054±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 120-130 °C (4 Torr)^**
• Refractive index: 1.4645 (589.3 nm 20 °C)^***
• Flash point: 107.3±21.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Dickey, Joseph B.

^*** Lange, R.

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

2-[2-(2-Aminoethoxy)ethoxy]ethanol, commonly referred to as triethanolamine ether or TEE, is an organic compound characterized by its unique structure, which includes multiple ethylene glycol units and an amino group. Its chemical formula is C6H15N3O3, and it appears as a colorless to pale yellow liquid that is hygroscopic in nature, making it highly soluble in water and polar solvents.

The discovery of 2-[2-(2-aminoethoxy)ethoxy]ethanol can be traced back to advancements in the field of amine chemistry and polyether synthesis during the mid-20th century. The compound is typically synthesized through the reaction of triethanolamine with ethylene oxide, resulting in the formation of this triethanolamine ether. The ability to manipulate amine and ether functionalities has made this compound of significant interest for both industrial and research applications.

2-[2-(2-Aminoethoxy)ethoxy]ethanol finds diverse applications, particularly in the fields of biochemistry and pharmaceuticals. One of its primary uses is as a reagent and solvent in various chemical reactions. The amino group present in the compound allows it to function as a nucleophile, participating in nucleophilic substitutions and other organic transformations. This versatility makes it valuable in the synthesis of complex organic molecules, particularly in drug development and medicinal chemistry.

Additionally, 2-[2-(2-aminoethoxy)ethoxy]ethanol is utilized as a surfactant and emulsifying agent in various formulations. Its amphiphilic nature allows it to stabilize emulsions and improve the solubility of poorly water-soluble compounds. This property has significant implications in the formulation of personal care products, pharmaceuticals, and agrochemicals, where effective emulsification and solubilization are crucial for product performance.

In the pharmaceutical industry, the compound has been explored for its potential use as a drug delivery agent. Its ability to enhance the solubility of active pharmaceutical ingredients (APIs) can improve the bioavailability of certain medications. Researchers have investigated its use in formulations that require enhanced permeability and absorption, particularly in oral and transdermal drug delivery systems.

Moreover, 2-[2-(2-aminoethoxy)ethoxy]ethanol has garnered attention for its potential biocompatibility and low toxicity, making it a candidate for various biomedical applications. Studies have suggested that the compound may be suitable for use in tissue engineering and regenerative medicine, where its properties can facilitate cell adhesion and growth.

Despite its numerous applications, safety considerations are essential when handling 2-[2-(2-aminoethoxy)ethoxy]ethanol. As with many organic compounds, it can pose health risks, including skin and eye irritation. Therefore, appropriate safety measures, such as using personal protective equipment and following proper handling procedures, are crucial to minimize exposure.

In summary, 2-[2-(2-aminoethoxy)ethoxy]ethanol is a significant chemical compound with a rich history of discovery and a wide range of applications in organic synthesis, pharmaceuticals, and industrial formulations. Its unique structural characteristics and versatility continue to make it a subject of interest in contemporary chemistry, underscoring its relevance across various scientific and industrial fields.

References

2013. Versatile synthesis of probes for high-throughput enzyme activity screening. Analytical and Bioanalytical Chemistry, 405(11).
DOI: 10.1007/s00216-013-6888-z

2016. Glycopolymers Prepared by Ring-Opening Metathesis Polymerization Followed by Glycoconjugation Using a Triazole-Forming “Click” Reaction. Methods in molecular biology (Clifton, N.J.), 1367.
DOI: 10.1007/978-1-4939-3130-9_3

2021. Molecular docking studies, in-silico ADMET predictions and synthesis of novel PEGA-nucleosides as antimicrobial agents targeting class B1 metallo-β-lactamases. In Silico Pharmacology, 9(1).
DOI: 10.1007/s40203-021-00092-z