Methyl 6-aminonicotinate
[CAS# 36052-24-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Methyl 6-aminonicotinate
• Synonyms: 6-Aminonicotinic acid methyl ester
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• CAS Registry Number: 36052-24-1
• EC Number: 629-051-2
• SMILES: COC(=O)C1=CN=C(C=C1)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 154-156 °C (Expl.)
• Index of Refraction: 1.571, Calc.^*
• Boiling Point: 304.5±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 137.9±22.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovery and Applications

Methyl 6-aminonicotinate is an organic compound with the molecular formula C7H8N2O2. It consists of a pyridine ring with an amino group at the 6-position and a methyl ester at the 2-position. This chemical is an important derivative of nicotinic acid (vitamin B3) and is synthesized by introducing a methyl group to the carboxyl group of 6-aminonicotinic acid, typically through esterification reactions.

The discovery of methyl 6-aminonicotinate is linked to ongoing research into the chemical properties of nicotinic acid derivatives. Nicotinic acid and its derivatives have long been studied for their biological activity, especially in relation to their role in the human body and their potential therapeutic uses. Methyl 6-aminonicotinate, being a methyl ester of 6-aminonicotinic acid, retains the basic structural features of nicotinic acid but with modifications that alter its chemical reactivity and biological activity.

One of the key applications of methyl 6-aminonicotinate is in medicinal chemistry, where it serves as an intermediate for the synthesis of pharmaceutical compounds. The amino group at the 6-position of the pyridine ring makes this compound a valuable precursor for creating other bioactive molecules. It has been used as a starting material for the synthesis of various nicotinate-based drugs, especially those related to cardiovascular health and metabolic diseases.

Methyl 6-aminonicotinate has been researched for its potential pharmacological properties. Like other nicotinic acid derivatives, it may have effects on lipid metabolism, which is important for the treatment of conditions such as hyperlipidemia and atherosclerosis. The compound's structure allows for modification and functionalization, making it a useful tool in the development of more targeted treatments for metabolic disorders.

Beyond its medicinal applications, methyl 6-aminonicotinate also finds uses in the field of material science. Pyridine derivatives, including methyl 6-aminonicotinate, have shown potential as ligands in coordination chemistry. Their ability to form stable complexes with metal ions has been explored for the development of catalysts and other materials with specialized properties.

In addition, methyl 6-aminonicotinate has been used in research settings as a reagent in organic synthesis. The presence of both the amino group and the ester group makes this compound versatile in the formation of new chemical bonds and the construction of more complex molecules. It can be employed in various transformations, such as nucleophilic substitution reactions and ester hydrolysis, that are useful in both academic and industrial chemical processes.

In summary, methyl 6-aminonicotinate is a valuable chemical compound with applications in medicinal chemistry, material science, and organic synthesis. Its role as an intermediate in drug development and its potential in the synthesis of metal complexes highlight its importance in chemical research and industrial applications.

References

2023. Synthesis and biological evaluation of 2,4,6-functionalized pyrido[2,3-d]pyrimidine derivatives. Medicinal Chemistry Research, 32(11).
DOI: 10.1007/s00044-023-03148-1

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