N-(2-Hydroxyethyl)-N-methylaniline
[CAS# 93-90-3]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: N-(2-Hydroxyethyl)-N-methylaniline
• Synonyms: 2-(N-Methylanilino)ethanol
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Protein Sequence: G
• CAS Registry Number: 93-90-3
• EC Number: 202-285-9
• SMILES: CN(CCO)C1=CC=CC=C1

Properties

• Density: 1.06
• Boiling point: 229 °C
• Refractive index: 1.573
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H334-H335-H4112
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

N-(2-Hydroxyethyl)-N-methylaniline is an organic compound that belongs to the class of tertiary amines, characterized by a methylaniline backbone with a hydroxyethyl substituent. This compound has gained attention in various industrial applications due to its unique chemical properties and versatility. The discovery of N-(2-hydroxyethyl)-N-methylaniline can be traced back to the ongoing exploration of substituted anilines, which has been a significant area of research in organic chemistry since the late 19th century.

The synthesis of N-(2-hydroxyethyl)-N-methylaniline typically involves the reaction of N-methylaniline with ethylene oxide or similar hydroxyethylating agents. This method allows for the straightforward introduction of the hydroxyethyl group while maintaining high yields and purity. The resulting compound exhibits enhanced solubility in water and organic solvents, making it suitable for various applications in different fields.

One of the primary applications of N-(2-hydroxyethyl)-N-methylaniline is in the formulation of coatings and adhesives. Its hydroxyl group increases the compatibility of the compound with various resins, enhancing the performance of coatings and improving adhesion properties. These attributes make it valuable in industries such as automotive, construction, and electronics, where durable and high-performance coatings are essential.

In addition to coatings, N-(2-hydroxyethyl)-N-methylaniline is utilized as a surfactant and emulsifying agent. Its ability to lower surface tension makes it effective in stabilizing emulsions and dispersions in formulations such as paints, inks, and personal care products. The compound’s surfactant properties are particularly beneficial in enhancing the stability and performance of these products.

Furthermore, N-(2-hydroxyethyl)-N-methylaniline has potential applications in the pharmaceutical industry. It can serve as an intermediate in the synthesis of various active pharmaceutical ingredients (APIs), contributing to the development of new drugs. The compound’s structure allows it to participate in various chemical reactions, enabling the creation of complex organic molecules with potential therapeutic applications.

Safety considerations are essential when handling N-(2-hydroxyethyl)-N-methylaniline, as it may cause irritation upon contact with skin or eyes. Proper safety measures, including the use of personal protective equipment and adherence to regulatory guidelines, are necessary to minimize health risks during its use in industrial processes.

Recent research has focused on optimizing the synthesis of N-(2-hydroxyethyl)-N-methylaniline and exploring its potential in green chemistry applications. Efforts to develop more sustainable synthesis routes align with the principles of green chemistry, which aim to minimize environmental impact while maximizing efficiency in chemical processes. Innovations in this area may lead to more sustainable production methods for this compound and similar derivatives.

In conclusion, N-(2-Hydroxyethyl)-N-methylaniline is a versatile compound with significant applications in coatings, adhesives, surfactants, and pharmaceutical synthesis. Its discovery and continued development reflect advancements in organic chemistry and materials science, offering opportunities for new applications and improved methodologies across various industries.

References

2022. Large photo-actuated surface change of an electrospun nanofibrous membrane. Polymer Bulletin, 80(8).
DOI: 10.1007/s00289-022-04628-x

2021. Aza-Matteson Homologations: Selective Mono- and Double-Carbenoid Insertions into Aminoboranes. Synfacts, 17(02).
DOI: 10.1055/s-0041-1737074

2020. Boron-Catalyzed N-Methylation of Amines with Formic Acid. Studies on Green Synthetic Reactions Based on Formic Acid from Biomass.
DOI: 10.1007/978-981-15-7623-2_2