Ethyl isonicotinate N-oxide
[CAS# 14906-37-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Ethyl isonicotinate N-oxide
• Synonyms: 4-Pyridinecarboxylic acid ethyl ester 1-oxide
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• CAS Registry Number: 14906-37-7
• SMILES: CCOC(=O)C1=CC=[N+](C=C1)[O-]

Properties

• Solubility: 1.745e+004 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.520, Calc.^*
• Melting point: 67.76 ºC
• Boiling Point: 345.8±15.0 ºC (760 mmHg), Calc.^*, 275.25 ºC
• Flash Point: 162.9±20.4 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P312-P330-P501

Discovory and Applicatios

Ethyl isonicotinate N-oxide is a chemical compound with the molecular formula C8H8N2O2. It is an N-oxide derivative of ethyl isonicotinate, which is itself a derivative of isonicotinic acid. The synthesis of ethyl isonicotinate N-oxide involves the oxidation of ethyl isonicotinate, a process that has been explored since the mid-20th century when researchers began to investigate the chemical properties and potential applications of isonicotinic acid derivatives.

The discovery of ethyl isonicotinate N-oxide is part of a broader effort to understand the chemistry of N-oxides, which are known for their reactivity and utility in organic synthesis. The synthesis typically involves the use of oxidizing agents such as hydrogen peroxide or m-chloroperbenzoic acid, leading to the formation of the N-oxide. The process allows for the introduction of oxygen functionality into the nitrogen atom of the isonicotinate structure, altering its chemical behavior and enhancing its potential applications.

Ethyl isonicotinate N-oxide has garnered attention for its potential applications in medicinal chemistry. Compounds containing the isonicotinate moiety have been investigated for their biological activities, including antimicrobial, antiviral, and anticancer properties. The introduction of the N-oxide functionality may enhance these activities, making ethyl isonicotinate N-oxide a candidate for further pharmacological studies. Research is ongoing to explore the compound’s interactions with biological targets and its efficacy in treating various diseases.

In addition to its pharmaceutical potential, ethyl isonicotinate N-oxide is being explored in the field of agrochemicals. Its structural features may allow it to act as a herbicide or pesticide, providing a means to develop effective crop protection agents. The reactivity of the N-oxide functional group may enhance the compound's ability to interact with biological systems in plants and pests, contributing to its effectiveness in agricultural applications. The ongoing demand for sustainable agricultural practices has led to increased interest in new agrochemical formulations that can address current challenges while minimizing environmental impact.

Furthermore, ethyl isonicotinate N-oxide may have applications in materials science. The presence of the N-oxide functionality can influence the chemical properties of polymers, potentially leading to materials with improved thermal stability and mechanical properties. The compound may be utilized in the synthesis of polymeric materials or as an additive to enhance the performance of existing materials, paving the way for innovations in various industrial applications.

While the potential of ethyl isonicotinate N-oxide is promising, it is essential to consider safety and environmental aspects in its handling and application. Proper laboratory protocols must be observed to mitigate any risks associated with the use of this compound, including ensuring adequate ventilation and the use of personal protective equipment. Understanding its toxicological properties is crucial for ensuring safe handling and compliance with regulatory standards.

In summary, ethyl isonicotinate N-oxide represents a versatile compound with significant potential in medicinal chemistry, agrochemicals, and materials science. Its discovery highlights the importance of N-oxide derivatives in organic synthesis and their role in developing innovative solutions across multiple industries. As research continues, ethyl isonicotinate N-oxide may contribute to advancements in drug discovery and agricultural practices, offering new avenues for addressing contemporary challenges.