2,2'-[(4-Methylphenyl)imino]bisethanol
[CAS# 3077-12-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Cycloalkylamines, aromatic monoamines, aromatic polyamines and derivatives and salts
• Name: 2,2'-[(4-Methylphenyl)imino]bisethanol
• Synonyms: N,N-Dihydroxyethyl-p-toluidine
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• Protein Sequence: G
• CAS Registry Number: 3077-12-1
• EC Number: 221-359-1
• SMILES: CC1=CC=C(C=C1)N(CCO)CCO

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 49-53 °C
• Index of Refraction: 1.587, Calc.^*
• Boiling Point: 339.0±0.0 °C (760 mmHg), Calc.^*, 338-340 °C
• Flash Point: 208.9±23.8 °C, Calc.^*, 113 °C

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H317-H318-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1B	H317

Discovery and Applications

2,2'-[(4-Methylphenyl)imino]bisethanol, commonly referred to as a bis(phenyl) imine derivative, is an organic compound characterized by the presence of an imine functional group connecting two ethanol units to a 4-methylphenyl moiety. The discovery of this compound is rooted in the ongoing exploration of imines and their derivatives, which have gained prominence in organic chemistry for their reactivity and potential applications in various fields, including catalysis, materials science, and pharmaceuticals.

The synthesis of 2,2'-[(4-Methylphenyl)imino]bisethanol typically involves the condensation reaction between 4-methylphenyl amine and an appropriate aldehyde, such as ethyl aldehyde, in the presence of an acid catalyst. This reaction leads to the formation of the imine linkage and the subsequent addition of ethanol units, resulting in the desired compound. The structural attributes of 2,2'-[(4-Methylphenyl)imino]bisethanol contribute to its unique chemical behavior, making it an important subject of study.

One of the notable applications of 2,2'-[(4-Methylphenyl)imino]bisethanol lies in the field of catalysis. Compounds featuring imine linkages have demonstrated significant potential as ligands in coordination chemistry, often enhancing the activity of metal complexes. In this context, 2,2'-[(4-Methylphenyl)imino]bisethanol can act as a bidentate ligand, coordinating with transition metals to form stable complexes. These metal-ligand complexes have been utilized in various catalytic processes, including oxidation reactions, polymerization, and cross-coupling reactions, thereby playing a crucial role in the development of sustainable chemical processes.

In addition to its catalytic applications, 2,2'-[(4-Methylphenyl)imino]bisethanol is also of interest in materials science. The compound's ability to form hydrogen bonds and its structural rigidity make it suitable for incorporation into polymer matrices, contributing to the development of high-performance materials with enhanced mechanical properties. Research has shown that the addition of imine-based compounds can improve thermal stability and reduce brittleness in polymer systems, making them more suitable for demanding applications in electronics and aerospace.

Furthermore, 2,2'-[(4-Methylphenyl)imino]bisethanol has potential applications in the pharmaceutical industry. The imine functional group is a common motif in drug design, as it can influence the pharmacological properties of compounds. Studies have indicated that imine derivatives can exhibit a range of biological activities, including antimicrobial and anticancer properties. As such, 2,2'-[(4-Methylphenyl)imino]bisethanol may serve as a valuable building block for the synthesis of novel therapeutic agents.

Despite its promising applications, the use of 2,2'-[(4-Methylphenyl)imino]bisethanol necessitates careful consideration of safety and regulatory aspects. As with many organic compounds, proper handling and adherence to safety guidelines are essential to minimize potential health risks. Regulatory agencies evaluate the safety profiles of chemical substances to ensure that they are used responsibly and in accordance with established guidelines.

In conclusion, 2,2'-[(4-Methylphenyl)imino]bisethanol is a versatile organic compound with diverse applications in catalysis, materials science, and pharmaceuticals. Its unique chemical structure enables it to participate in various chemical processes, enhancing the performance of materials and contributing to the development of new therapeutic agents. As research continues to explore the potential of imine derivatives, 2,2'-[(4-Methylphenyl)imino]bisethanol is expected to play an increasingly significant role in advancing multiple scientific fields.

References

2019. Room-Temperature, Base-Mediated Selective Synthesis of 2-(Arylamino)ethanols and 2-Aryloxyethanols. SynOpen, 3(3).
DOI: 10.1055/s-0039-1690334

2016. Effects of water-aging on self-healing dental composite containing microcapsules. Journal of Dentistry, 47.
DOI: 10.1016/j.jdent.2016.01.008

2020. Photoreactivity study of photoinitiated free radical polymerization using Type II photoinitiator containing thioxanthone initiator as a hydrogen acceptor and various amine-type co-initiators as hydrogen donors. Journal of Coatings Technology and Research, 18(2).
DOI: 10.1007/s11998-020-00401-9