Ethyl 6-aminonicotinate
[CAS# 39658-41-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Ethyl 6-aminonicotinate
• Synonyms: 6-Amino-3-pyridinecarboxylic acid ethyl ester
• Molecular Formula: C₈H₁₀N₂O₂
• Molecular Weight: 166.18
• CAS Registry Number: 39658-41-8
• EC Number: 640-766-9
• SMILES: CCOC(=O)C1=CN=C(C=C1)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 145-147 °C (Expl.)
• Index of Refraction: 1.559, Calc.^*
• Boiling Point: 314.7±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 144.1±22.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H319
• Safety Statements: P264+P265-P280-P305+P351+P338-P337+P317

Hazard Classification

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

Discovery and Applications

Ethyl 6-aminonicotinate is a chemical compound with the molecular formula C7H8N2O2, consisting of an ethyl ester group attached to the carboxyl moiety of nicotinic acid, and a primary amine group at the 6-position of the pyridine ring. As a derivative of nicotinic acid, this compound is a key member of the aminonicotinate family, which has garnered attention for its diverse applications in medicinal chemistry, organic synthesis, and other areas of research.

The discovery of ethyl 6-aminonicotinate is rooted in the broader field of pyridine chemistry, specifically the modification of nicotinic acid derivatives. Nicotinic acid, also known as niacin, is well-known for its role in biochemistry and its applications in pharmacology. Over time, researchers have sought to expand the utility of nicotinic acid and its derivatives by altering its structure, leading to the synthesis of compounds like ethyl 6-aminonicotinate. The modification of the nicotinic acid structure provides a means to tune the chemical and biological properties of the resulting compounds.

Ethyl 6-aminonicotinate has several notable applications, particularly in organic synthesis and medicinal chemistry. The presence of both an amine and an ester group in the molecule enhances its reactivity, making it a useful intermediate in the preparation of other organic compounds. The amine group, in particular, introduces a point of reactivity that can facilitate the formation of new chemical bonds, which is essential in the synthesis of more complex molecules. This reactivity is key in developing new pharmacologically active agents and other bioactive compounds.

One of the key applications of ethyl 6-aminonicotinate lies in its role as an intermediate in the synthesis of biologically active compounds. For example, researchers have explored its potential in the development of drugs targeting specific enzymes or receptors. The presence of both a nitrogen-containing group (the amine) and an ester functional group allows the molecule to engage in a variety of chemical reactions, leading to the creation of derivatives with enhanced bioactivity. The versatility of ethyl 6-aminonicotinate in organic synthesis makes it an attractive building block for pharmaceutical research.

Additionally, ethyl 6-aminonicotinate has been studied for its potential antimicrobial and anti-inflammatory properties. The ability of nicotinic acid derivatives to interact with biological targets, including enzymes and receptors, makes them valuable in the development of therapeutic agents. The amine group in ethyl 6-aminonicotinate offers further opportunities for derivatization, which could improve the efficacy and selectivity of the compound for specific targets in biological systems.

In the realm of organic synthesis, ethyl 6-aminonicotinate serves as a versatile intermediate for the synthesis of more complex structures. The ester functional group provides a site for further modification, allowing chemists to alter the molecule’s properties for specific applications. This versatility has led to its use in the synthesis of a range of derivatives with varying functional groups that may possess desirable biological, chemical, or physical properties.

The compound’s ability to undergo substitution reactions has also been exploited in the creation of novel chemical entities. For instance, the amine group at the 6-position can be modified or reacted with other functional groups to yield a diverse array of derivatives. This has led to the development of compounds that exhibit enhanced pharmacological properties, including potential applications in the treatment of a variety of diseases and conditions.

Ethyl 6-aminonicotinate has also been explored in the context of agricultural chemistry, where it may be useful in the development of new agrochemicals. The compound’s structural features, including the ester and amine groups, offer the potential for interactions with various biological systems, making it a candidate for further research in the area of crop protection and pest management.

In conclusion, ethyl 6-aminonicotinate is an important compound in organic chemistry with a wide range of applications in drug discovery, organic synthesis, and agricultural chemistry. Its versatility as a building block in the synthesis of more complex molecules, coupled with its potential bioactivity, makes it a valuable tool in the development of new pharmaceuticals and agrochemicals. The compound’s reactivity, particularly due to the amine and ester functional groups, enables it to serve as an intermediate for the synthesis of a variety of bioactive derivatives, which are important in the ongoing search for new therapeutic agents and industrial applications. As research continues, further applications of ethyl 6-aminonicotinate may emerge, adding to its value as a chemical substance in diverse fields.

References

2015. Microwave-Assisted Synthesis of 2,2'-Azopyridine-Labeled Amines, Amino Acids, and Peptides. Synthesis, 47(24).
DOI: 10.1055/s-0035-1560523

2014. Synthesis and pharmacological evaluation of 6-aminonicotinic acid analogues as novel GABA(A) receptor agonists. European Journal of Medicinal Chemistry, 84.
DOI: 10.1016/j.ejmech.2014.07.039