2-(N-Ethyl-m-toluidino)ethanol
[CAS# 91-88-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: 2-(N-Ethyl-m-toluidino)ethanol
• Synonyms: N-Ethyl-N-(2-hydroxyethyl)-m-toluidine
• Protein Sequence: G
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26
• CAS Registry Number: 91-88-3
• EC Number: 202-105-9
• SMILES: CCN(CCO)C1=CC=CC(=C1)C

Properties

• Density: 1.019
• Melting point: -19 ºC
• Boiling point: 240 ºC
• Refractive index: 1.5535-1.5555
• Flash point: 124 ºC
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H302-H311-H318-H331-H412
• Precautionary Statements: P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P354+P338-P316-P317-P321-P330-P361+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

2-(N-Ethyl-m-toluidino)ethanol is an organic compound classified as a substituted ethanolamine. Its structure features an ethyl group and a methyl group in the meta position of the aromatic ring, attached to a hydroxyl group through an ethylene chain. This compound has garnered attention in various fields, particularly in the synthesis of dyes and pharmaceuticals, due to its unique chemical properties and versatility. The discovery of 2-(N-ethyl-m-toluidino)ethanol is linked to the broader exploration of substituted amines and their derivatives in organic chemistry.

The synthesis of 2-(N-ethyl-m-toluidino)ethanol can be traced back to advancements in organic synthesis techniques in the early to mid-20th century. It is typically produced through the reaction of m-toluidine with ethylene oxide in the presence of a suitable base, facilitating the alkylation process. This reaction allows for the incorporation of the ethylene glycol moiety, resulting in the formation of the desired compound. Over the years, various synthetic pathways have been developed to improve yields and optimize the reaction conditions, showcasing the evolution of synthetic organic chemistry.

2-(N-Ethyl-m-toluidino)ethanol is primarily utilized as an intermediate in the production of dyes and pigments. Its ability to undergo further chemical reactions, such as diazotization and coupling, makes it valuable in synthesizing azo dyes. Azo dyes are widely used in the textile industry due to their vibrant colors, durability, and wide range of applications. The meta position of the methyl group enhances the reactivity of the compound, allowing it to participate effectively in dye synthesis processes.

In addition to its role in dye manufacturing, 2-(N-ethyl-m-toluidino)ethanol finds applications in the pharmaceutical industry. The compound can be employed in the synthesis of various bioactive molecules, acting as a building block for more complex compounds. Its structural features may contribute to the development of pharmaceuticals with specific therapeutic properties. Furthermore, its derivatives may exhibit pharmacological activities, making it a compound of interest for medicinal chemistry research.

The compound also has potential applications in agrochemicals and surfactants. Its chemical structure allows for interactions with various substrates, making it useful in formulating products designed to enhance agricultural practices. Additionally, its surfactant properties can aid in improving the solubility and dispersion of other compounds in formulations, thereby enhancing their effectiveness.

Despite its utility, safety and environmental considerations are crucial when handling 2-(N-ethyl-m-toluidino)ethanol. The compound is classified as harmful, with potential risks including skin and eye irritation, respiratory issues, and other health concerns. Regulatory agencies have implemented guidelines for its safe use and handling, urging manufacturers and researchers to adhere to safety protocols. Additionally, there is a growing emphasis on exploring greener and safer alternatives in the synthesis and application of chemical compounds to mitigate environmental impact.

Research into 2-(N-ethyl-m-toluidino)ethanol continues to evolve, with ongoing studies focusing on its applications in various industries and its potential for new uses. The principles of green chemistry are increasingly being applied to develop sustainable methods for its synthesis and application, aiming to reduce waste and enhance safety.

In summary, 2-(N-Ethyl-m-toluidino)ethanol is a versatile compound with significant applications in dye manufacturing, pharmaceuticals, agrochemicals, and surfactants. Its discovery and subsequent utilization highlight the advancements in organic chemistry and materials science. As research progresses, the compound may find new applications and methodologies that enhance its utility while prioritizing safety and environmental sustainability.

References

2007. Of Tertiary Arylamines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-031-01519

2006. Enzymatic Catalysis in the Synthesis of Polyanilines and Derivatives of Polyanilines. Enzyme-Catalyzed Synthesis of Polymers.
DOI: 10.1007/12_036