3-Ethylanilinopropiononitrile
[CAS# 148-87-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Imide
• Name: 3-Ethylanilinopropiononitrile
• Synonyms: 3-(N-Ethylanilino)propiononitrile; N-(2-Cyanoethyl)-N-ethylaniline; 3-(Ethylphenylamino)-propanenitrile
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24
• CAS Registry Number: 148-87-8
• EC Number: 205-728-4
• SMILES: CCN(CCC#N)C1=CC=CC=C1

Properties

• Solubility: 443 mg/L (25 ºC water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.551, Calc.^*
• Melting point: 61.87 ºC
• Boiling Point: 311.9±25.0 ºC (760 mmHg), Calc.^*, 296.22 ºC
• Flash Point: 132.8±12.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H312-H3157-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

3-Ethylanilinopropiononitrile is an organic compound with the molecular formula C12H14N2, belonging to the family of nitriles. This compound features an ethylaniline moiety coupled with a propiononitrile group, which contributes to its unique chemical properties. The discovery and development of 3-ethylanilinopropiononitrile are rooted in the exploration of substituted anilines and their reactivity in various synthetic applications.

The synthesis of 3-ethylanilinopropiononitrile is typically achieved through a multi-step process involving the reaction of 3-ethylaniline with propiononitrile. The reaction conditions, such as temperature and solvent choice, play a crucial role in determining the yield and purity of the final product. The exploration of substituted anilines has led to the identification of compounds with diverse functionalities, making them valuable building blocks in organic synthesis.

The applications of 3-ethylanilinopropiononitrile span several fields, particularly in pharmaceuticals and agrochemicals. In medicinal chemistry, compounds containing anilines and nitriles have been investigated for their potential biological activity. The presence of the ethylaniline group may enhance the compound's interaction with biological targets, making it a promising candidate for drug discovery. Researchers are exploring its structure-activity relationships (SAR) to identify its efficacy as a therapeutic agent in treating various diseases.

In the agrochemical sector, 3-ethylanilinopropiononitrile has potential uses as an intermediate in the synthesis of herbicides and pesticides. The incorporation of nitrile groups in agrochemical formulations can improve their biological activity and stability, offering effective solutions for crop protection. The continuous need for innovative agrochemical products to address agricultural challenges has increased the importance of compounds like 3-ethylanilinopropiononitrile in the formulation of safer and more efficient agrochemicals.

Additionally, 3-ethylanilinopropiononitrile may find applications in materials science. Its unique chemical structure can be utilized in the synthesis of polymer materials, where the aniline group can participate in various polymerization processes. By integrating this compound into polymer matrices, researchers can enhance the mechanical properties and thermal stability of the resulting materials. This versatility opens new avenues for the development of advanced materials with tailored properties for specific applications.

Safety considerations are paramount when working with 3-ethylanilinopropiononitrile, as with many organic compounds. Proper laboratory practices should be observed to minimize exposure risks, including the use of personal protective equipment and adherence to safety protocols. Understanding the toxicological properties of the compound is essential for ensuring safe handling and disposal.

In conclusion, 3-ethylanilinopropiononitrile is a versatile compound with promising applications in pharmaceuticals, agrochemicals, and materials science. Its discovery highlights the importance of substituted anilines in organic synthesis, providing valuable intermediates for the development of innovative solutions across various industries. As research progresses, the potential of 3-ethylanilinopropiononitrile in drug discovery and agrochemical formulations may pave the way for advancements that contribute to the development of effective therapeutic agents and sustainable agricultural practices.

References

1995. Neuropharmacological and neurochemical properties of N-(2-cyanoethyl)-2-phenylethylamine, a prodrug of 2-phenylethylamine. British Journal of Pharmacology.
URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1853650

2022. Discovery of small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase. Journal of Enzyme Inhibition and Medicinal Chemistry.
DOI: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9090415