Methyl 2-aminopyridine-4-carboxylate
[CAS# 6937-03-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Methyl 2-aminopyridine-4-carboxylate
• Synonyms: Methyl 2-aminoisonicotinate
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• CAS Registry Number: 6937-03-7
• EC Number: 627-546-8
• SMILES: COC(=O)C1=CC(=NC=C1)N

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 145-149 ºC (Expl.)
• Index of Refraction: 1.571, Calc.^*
• Boiling Point: 296.1±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 132.9±21.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H315-H318-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

Methyl 2-aminopyridine-4-carboxylate is an organic chemical compound that contains both an amino group and a carboxylate ester group attached to a pyridine ring. This compound is of interest due to its structural properties and its applications in organic synthesis, particularly in the preparation of various biologically active compounds.

The discovery of methyl 2-aminopyridine-4-carboxylate can be traced to studies on pyridine derivatives, which have long been known for their diverse chemical reactivity and biological activities. Pyridine itself is a six-membered aromatic heterocyclic compound containing nitrogen, and modifications to the pyridine ring have resulted in a wide range of compounds with various applications. Methyl 2-aminopyridine-4-carboxylate is one of the many derivatives that has been synthesized to explore its utility in medicinal chemistry and other synthetic applications.

The main application of methyl 2-aminopyridine-4-carboxylate is in the synthesis of pharmaceutical intermediates. The compound serves as a building block for the preparation of a variety of biologically active molecules, including antimicrobial agents, anti-inflammatory drugs, and other compounds with therapeutic potential. The presence of both an amino group and a carboxylate ester in the structure of methyl 2-aminopyridine-4-carboxylate allows for its use in a range of chemical reactions, including nucleophilic substitution, coupling reactions, and condensation processes.

In particular, methyl 2-aminopyridine-4-carboxylate has been used in the synthesis of derivatives with potential activity against various diseases, including cancer and infectious diseases. Its ability to undergo functionalization reactions, where different chemical groups are introduced into the pyridine ring, makes it a valuable intermediate in the design of novel pharmaceuticals.

The compound also plays a role in the synthesis of agrochemicals, where its chemical structure and reactivity are utilized to create new pesticides, herbicides, and fungicides. These agricultural applications take advantage of the compound’s ability to interact with biological systems, particularly through the modification of its amino and carboxylate functional groups.

Research into the properties of methyl 2-aminopyridine-4-carboxylate continues, with a focus on its reactivity and potential applications in various synthetic routes. Its utility as a versatile intermediate in organic chemistry makes it an important compound in both academic research and industrial applications, particularly in the fields of medicinal chemistry, agriculture, and materials science.

In summary, methyl 2-aminopyridine-4-carboxylate is a useful organic compound with significant applications in organic synthesis, particularly in the development of biologically active molecules. It serves as a key intermediate in the production of pharmaceuticals and agrochemicals, benefiting from its ability to undergo a variety of chemical reactions. The compound’s properties and reactivity continue to be explored for potential new applications in drug discovery and chemical synthesis.

References

2023. Solvent-dependence of KI Mediated Electrosynthesis of Imidazo[1,2-a]pyridines. Chemical Research in Chinese Universities, 39(2).
DOI: 10.1007/s40242-023-2323-y

2015. New method for preparation of (2-aminopyridin-4-yl)methanol. Russian Journal of Organic Chemistry, 51(5).
DOI: 10.1134/s1070428015050280

2013. An Efficient Method for the Protection of Aromatic Amines with Benzostabase and Its Utility in Anionic Aromatic Transformations. Synlett, 24(17).
DOI: 10.1055/s-0033-1339794