N-Ethyl-N-cyanoethyl-m-toluidine
[CAS# 148-69-6]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: N-Ethyl-N-cyanoethyl-m-toluidine
• Synonyms: 3-(N-Ethyl-meta-toluidino)-propionitrile
• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.27
• CAS Registry Number: 148-69-6
• EC Number: 205-721-6
• SMILES: CCN(CCC#N)C1=CC=CC(=C1)C

Properties

• Solubility: 129 mg/L (25 °C water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.547, Calc.^*
• Melting point: 77.99 °C
• Boiling Point: 337.8±25.0 °C (760 mmHg), Calc.^*, 310.67 °C
• Flash Point: 145.1±12.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301
• Safety Statements: P264-P270-P301+P316-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

N-Ethyl-N-cyanoethyl-m-toluidine is an organic compound with the chemical formula C12H14N2. It belongs to the class of substituted anilines and is characterized by the presence of an ethyl and a cyanoethyl group attached to the nitrogen atom of an m-toluidine moiety. This compound has garnered attention due to its potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

The discovery of N-ethyl-N-cyanoethyl-m-toluidine can be traced back to studies focused on the synthesis and reactivity of substituted anilines. m-Toluidine, which is a derivative of aniline with a methyl group in the meta position, serves as a critical precursor in the synthesis of N-ethyl-N-cyanoethyl-m-toluidine. The introduction of the ethyl and cyanoethyl groups is typically achieved through a two-step process involving the reaction of m-toluidine with appropriate reagents under controlled conditions. This process highlights the versatility of amines in organic synthesis and the importance of functional group modifications in expanding the chemical space of aniline derivatives.

One of the primary applications of N-ethyl-N-cyanoethyl-m-toluidine lies in the pharmaceutical industry, where it is explored as a potential intermediate in the synthesis of biologically active compounds. The presence of both ethyl and cyanoethyl groups may enhance the compound's ability to interact with biological targets, making it a valuable building block in drug discovery and development. Researchers are investigating its structure-activity relationship (SAR) to assess its efficacy and selectivity in modulating specific biological pathways.

In addition to its pharmaceutical potential, N-ethyl-N-cyanoethyl-m-toluidine has applications in the agrochemical sector. The compound may be used as a precursor in the synthesis of agrochemicals, such as herbicides and pesticides. The introduction of cyanoethyl groups can influence the chemical stability and bioactivity of the resulting formulations, providing opportunities for developing effective crop protection agents. The agrochemical industry continues to seek innovative solutions to address the challenges of food production, and compounds like N-ethyl-N-cyanoethyl-m-toluidine play a role in this endeavor.

Another area of application for N-ethyl-N-cyanoethyl-m-toluidine is in materials science. The compound may be used in the synthesis of polymers or as a curing agent for epoxy resins, where its reactive groups can facilitate cross-linking and improve the mechanical properties of the final material. The incorporation of this compound into polymer matrices can enhance the thermal stability and chemical resistance of the materials, making them suitable for a range of industrial applications.

While the applications of N-ethyl-N-cyanoethyl-m-toluidine are promising, it is essential to consider safety and environmental aspects. The handling of this compound should follow established safety protocols to minimize exposure risks, as with many organic chemicals. Proper laboratory practices, including the use of personal protective equipment and appropriate waste disposal methods, are crucial in ensuring safe handling during research and industrial processes.

In summary, N-ethyl-N-cyanoethyl-m-toluidine is a versatile organic compound with potential applications in pharmaceuticals, agrochemicals, and materials science. Its discovery and development highlight the significance of substituted anilines in synthetic organic chemistry. As research continues to explore its properties and applications, N-ethyl-N-cyanoethyl-m-toluidine may contribute to advancements in various industries, offering innovative solutions to meet the demands of modern technology and agriculture.

References

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