2-[2-(Dimethylamino)ethoxy]ethanol
[CAS# 1704-62-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 2-[2-(Dimethylamino)ethoxy]ethanol
• Molecular Formula: C₆H₁₅NO₂
• Molecular Weight: 133.19
• CAS Registry Number: 1704-62-7
• EC Number: 216-940-1
• SMILES: CN(C)CCOCCO

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*, 0.954 g/cm³
• Index of Refraction: 1.444, Calc.^*, 1.442
• Boiling Point: 194.8±15.0 °C (760 mmHg), Calc.^*, 95 °C (15 mmHg)
• Flash Point: 71.6±20.4 °C, Calc.^*, 93 °C

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H312-H314--H318
• Safety Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

2-[2-(Dimethylamino)ethoxy]ethanol, commonly known as DMAEE, is an organic compound characterized by the presence of a dimethylamino group and an ethoxyethanol chain. This chemical has garnered attention in various fields due to its unique properties, making it valuable in both industrial applications and scientific research. The compound is primarily recognized for its role as a solvent, surfactant, and intermediate in the synthesis of other chemical compounds.

The discovery of DMAEE can be traced back to research in the mid-20th century focused on finding effective solvents and surfactants for various applications. The development of this compound emerged from the need for materials that could enhance solubility and stability in formulations, particularly in the fields of cosmetics, pharmaceuticals, and industrial products. Researchers recognized the potential of compounds containing dimethylamino groups for their ability to interact favorably with both polar and nonpolar substances, facilitating improved formulation characteristics.

One of the primary applications of 2-[2-(dimethylamino)ethoxy]ethanol is in the cosmetics and personal care industry. Due to its surfactant properties, DMAEE is often included in formulations such as shampoos, conditioners, and skin care products. It acts as an emulsifier, helping to blend oil and water-based ingredients, thereby improving the texture and stability of the product. Additionally, its ability to enhance the penetration of active ingredients into the skin has made it a popular choice in formulations aimed at improving skin hydration and overall efficacy.

In the pharmaceutical industry, DMAEE serves as a solvent for various active pharmaceutical ingredients (APIs). Its unique structure allows it to dissolve a wide range of compounds, making it an effective medium for drug formulation. This property is particularly beneficial in the development of liquid dosage forms, where solubility is crucial for bioavailability. Furthermore, DMAEE has been explored as a potential drug delivery agent due to its ability to facilitate the transport of therapeutic compounds across biological membranes.

Moreover, 2-[2-(dimethylamino)ethoxy]ethanol has found applications in the production of agricultural chemicals, specifically in the formulation of pesticides and herbicides. Its surfactant properties enhance the distribution and effectiveness of active ingredients, ensuring that they adhere to target surfaces and penetrate effectively. This capability is vital in maximizing the efficacy of agricultural products, contributing to improved crop yields and pest control.

Despite its numerous applications, the use of DMAEE has raised some safety and environmental concerns. Studies have shown that certain amines can pose risks to human health, particularly with prolonged exposure. As a result, regulatory agencies have begun to evaluate the safety of compounds containing dimethylamino groups, prompting manufacturers to adhere to stringent guidelines regarding their use and handling.

Research continues into the potential of 2-[2-(dimethylamino)ethoxy]ethanol to serve as a versatile building block in organic synthesis. Its ability to participate in various chemical reactions makes it a valuable intermediate for producing complex molecules in pharmaceuticals and fine chemicals. Ongoing studies aim to explore new applications and derivatives of DMAEE that could further enhance its utility in both industrial and research settings.

The discovery and application of 2-[2-(dimethylamino)ethoxy]ethanol highlight the compound's significance as a multifunctional agent in various industries. Its roles in cosmetics, pharmaceuticals, and agriculture illustrate the importance of chemical innovation in addressing contemporary needs while ensuring safety and efficacy.

References

2002. Toxicity and pharmacokinetics of 2-(2-dimethylaminoethoxy)ethanol following cutaneous dosing. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 40(7).
DOI: 10.1016/s0278-6915(02)00010-8

2021. High-density polyethylene/recycled HDPE/nanoclay composites using an amine-alcohol modified polyethylene as a compatibilizer. Iranian Polymer Journal, 30(1).
DOI: 10.1007/s13726-020-00889-3

2013. Synthesis of aminoalkylsilanes with oligo(ethylene oxide) unit as multifunctional electrolyte additives for lithium-ion batteries. Science China Chemistry, 56(7).
DOI: 10.1007/s11426-013-4861-5