N,N-Di(hydroxyethyl)-m-toluidine
[CAS# 91-99-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: N,N-Di(hydroxyethyl)-m-toluidine
• Synonyms: 2-2'-(m-Tolylimido)diethanol; 2,2'-[(3-Methylphenyl)imino]bis-ethanol
• Protein Sequence: G
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• CAS Registry Number: 91-99-6
• EC Number: 202-114-8
• SMILES: CC1=CC(=CC=C1)N(CCO)CCO

Properties

• Solubility: 4571 mg/L (25 ºC water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.587, Calc.^*
• Melting point: 102.13 ºC
• Boiling Point: 371.9±32.0 ºC (760 mmHg), Calc.^*, 342.62 ºC
• Flash Point: 201.8±23.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Hazard Statements: H301-H302-H312-H315-H317-H318-H319-H373
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P272-P280-P301+P316-P301+P317-P302+P352-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H301

Discovory and Applicatios

N,N-Di(hydroxyethyl)-m-toluidine is an organic compound belonging to the class of aromatic amines, specifically a substituted toluidine. Characterized by the presence of two hydroxyethyl groups attached to the nitrogen atom and a methyl group on the aromatic ring, this compound exhibits unique properties that make it valuable in various industrial applications, particularly in the fields of adhesives, coatings, and polymer chemistry. The discovery and development of N,N-di(hydroxyethyl)-m-toluidine are linked to the broader exploration of amines and their derivatives, which have been extensively studied since the early 20th century.

The synthesis of N,N-di(hydroxyethyl)-m-toluidine typically involves the reaction of m-toluidine with ethylene oxide in the presence of a catalyst, resulting in the formation of hydroxyethyl substituents on the nitrogen atom. This synthetic pathway has been refined over the years to improve yield and purity, making the compound more accessible for industrial use. The discovery of this compound is part of the ongoing research into amine derivatives and their functionality, particularly in enhancing the properties of polymers and resins.

One of the primary applications of N,N-di(hydroxyethyl)-m-toluidine is as a hardener or curing agent in epoxy resins. Epoxy systems are widely used in various industries due to their excellent adhesion, chemical resistance, and mechanical properties. The inclusion of N,N-di(hydroxyethyl)-m-toluidine as a hardener facilitates the cross-linking process in epoxy formulations, enhancing the final material's durability and thermal stability. This property makes it suitable for applications in automotive, aerospace, and construction industries, where high-performance materials are essential.

In addition to its role as a hardener, N,N-di(hydroxyethyl)-m-toluidine serves as a reactive diluent in the formulation of coatings and adhesives. Its ability to lower the viscosity of resin systems without significantly compromising their mechanical properties makes it an ideal candidate for producing high-quality finishes. This characteristic is particularly beneficial in applications where ease of application and flow properties are crucial, such as in industrial coatings and sealants. The compound's reactivity allows it to participate in further polymerization processes, resulting in a robust and well-cured end product.

The compound's unique structure, featuring both amine and hydroxy groups, imparts enhanced hydrophilicity, making it useful in formulations that require improved wetting and adhesion to substrates. This attribute is advantageous in industries where strong bonds between dissimilar materials are necessary, such as in metal and plastic bonding applications.

Moreover, N,N-di(hydroxyethyl)-m-toluidine has been investigated for potential use in biomedical applications. Its biocompatibility and ability to form stable bonds with biological tissues position it as a candidate for use in drug delivery systems and tissue engineering scaffolds. Research in this area is ongoing, with scientists exploring the compound's properties and its potential to improve the performance of biomaterials.

Despite its numerous benefits, safety and environmental considerations are important when handling N,N-di(hydroxyethyl)-m-toluidine. The compound is classified as an irritant and can pose health risks, including skin and respiratory irritation. Therefore, it is crucial to follow appropriate safety protocols, including the use of personal protective equipment and adequate ventilation during its application. Regulatory agencies have established guidelines to ensure safe handling practices, emphasizing the importance of workplace safety and environmental protection.

In conclusion, N,N-Di(hydroxyethyl)-m-toluidine is a versatile compound with significant applications in epoxy resin curing, coatings, adhesives, and potential biomedical materials. Its discovery and ongoing research reflect advancements in organic chemistry and materials science, and continued exploration may uncover new applications and improved methodologies, further expanding its utility across various industries.

References

2015. Effect of hard segment architecture on shape memory properties of polycaprolactone-based polyurethane containing azobenzene. Journal of Materials Science, 51(5).
DOI: 10.1007/s10853-015-9586-8

2003. New Type of Cationic Glycerophospholipids. Russian Journal of General Chemistry, 73(10).
DOI: 10.1023/b:rugc.0000016014.90042.3b

1993. Manicure preparations. Poucher's Perfumes, Cosmetics and Soaps.
DOI: 10.1007/978-94-011-1482-0_10