N,N-Dimethylethanolamine
[CAS# 108-01-0]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> Halogenated, sulfonated, nitrated or nitrosated derivatives of alcohols
• Name: N,N-Dimethylethanolamine
• Synonyms: 2-Dimethylaminoethanol; Deanol
• Molecular Formula: C₄H₁₁NO
• Molecular Weight: 89.14
• Protein Sequence: G
• CAS Registry Number: 108-01-0
• EC Number: 203-542-8
• SMILES: CN(C)CCO

Properties

• Density: 0.888
• Melting point: -70 °C
• Boiling point: 139 °C
• Refractive index: 1.429-1.43
• Flash point: 40 °C
• Water solubility: miscible

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H332-H312-H302-H314
• Safety Statements: P210-P233-P234-P240-P241-P242-P243-P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P362+P364-P363-P370+P378-P390-P403+P233-P403+P235-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H331
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1A	H314
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H331

• Transport Information: UN 2051

Discovery and Applications

N,N-Dimethylethanolamine, commonly referred to as DMEA, is a tertiary amine with the molecular formula C4H11NO. Its structure consists of a dimethylamino group attached to an ethanol backbone, making it a versatile compound in organic synthesis and industrial applications. DMEA was first synthesized and studied in the early 20th century as part of research into nitrogen-containing compounds and their potential uses in industry and pharmaceuticals.

DMEA is widely used as a catalyst and intermediate in various chemical processes. One of its primary applications is in the production of polyurethane foams, where it acts as a catalyst to promote the reaction between isocyanates and polyols. This type of foam is commonly used in furniture, insulation, and automotive seating. The efficiency of DMEA in this context has made it a crucial component in the polyurethane industry, where precise control of reaction kinetics is essential for producing foams with desirable properties.

Another important application of DMEA is its role in water treatment processes. It is often used in the production of ion-exchange resins, which are crucial for softening water and removing unwanted ions such as calcium and magnesium. DMEA’s ability to participate in the formation of quaternary ammonium compounds makes it valuable in resin production, where it contributes to the resin’s capacity to exchange ions effectively.

DMEA is also used as an intermediate in the synthesis of various pharmaceuticals and fine chemicals. Its basic nitrogen atom allows it to react with acidic compounds to form salts, which are often used as intermediates in the preparation of more complex molecules. Additionally, it has found applications in the production of coatings, adhesives, and surfactants due to its ability to modify the chemical properties of materials.

In organic chemistry, DMEA serves as a useful reagent for introducing amine functionalities into organic molecules. Its reactivity, combined with its relatively low toxicity compared to other amines, makes it a preferred choice in laboratory settings for synthetic routes that require mild conditions. It can be used to form quaternary ammonium salts, amides, and other nitrogen-containing compounds that are essential in drug development and material science.

Despite its wide range of applications, DMEA should be handled with care due to its potential irritant effects on the skin, eyes, and respiratory system. Proper safety precautions, such as the use of personal protective equipment and adequate ventilation, are necessary when working with DMEA, especially in industrial environments where exposure may be higher.

Overall, N,N-Dimethylethanolamine has proven to be a valuable compound in multiple industries, from polyurethane production to pharmaceuticals. Its versatility as both a catalyst and chemical intermediate continues to make it a key substance in modern chemical manufacturing and research.

References

2021. Synthesis and Properties of Cleavable Quaternary Ammonium Compounds. Journal of Oleo Science.
DOI: 10.5650/jos.ess20216

2024. Ionic Conductivity and Aggregation Behavior of N,N-Dimethylethanolammonium Carboxylate Protic Ionic Liquids in Aqueous, Ethanolic, and Acetonitrile Solutions. Russian Journal of Physical Chemistry A.
DOI: 10.1134/s0036024424701723

2012. Determination of 14 amines in air samples using midget impingers sampling followed by analysis with ion chromatography in tandem with mass spectrometry. Journal of Environmental Monitoring.
DOI: 10.1039/c2em10636a