2-Amino-3-acetylpyridine
[CAS# 65326-33-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2-Amino-3-acetylpyridine
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15
• CAS Registry Number: 65326-33-2
• EC Number: 962-528-6
• SMILES: CC(=O)C1=C(N=CC=C1)N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 283.8±20.0 °C 760 mmHg (Calc.)^*
• Flash point: 125.5±21.8 °C (Calc.)^*
• Index of refraction: 1.577 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H312-H315-H318-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

2-Amino-3-acetylpyridine is an organic compound belonging to the class of aminopyridines, characterized by the presence of an amino group at the 2-position and an acetyl group at the 3-position on a pyridine ring. It has the molecular formula C₇H₈N₂O and appears as a crystalline solid under ambient conditions. This compound has attracted attention due to its utility in synthetic organic chemistry and its role as an intermediate in pharmaceutical research.

The synthesis of 2-amino-3-acetylpyridine has been documented in literature sources focused on heterocyclic compound preparation. A common method involves the functionalization of pyridine derivatives through directed substitution or ring modification reactions, with particular emphasis on maintaining regiochemical control during the introduction of amino and acetyl groups. It may be synthesized via acetylation of 2-aminopyridine using acetylating agents such as acetic anhydride under acidic or basic conditions. Other strategies may involve cyclization of precursor compounds followed by selective functional group transformations.

This compound has found application primarily as a building block in medicinal and agrochemical research. Its molecular framework, incorporating both electron-donating (amino) and electron-withdrawing (acetyl) groups, makes it a versatile intermediate in the construction of more complex heterocyclic systems. It participates in various organic reactions, such as condensation, nucleophilic substitution, and coupling processes, which can be exploited to generate biologically active compounds.

2-Amino-3-acetylpyridine has been investigated as a precursor in the synthesis of ligands for metal complexes, particularly those involving transition metals. The nitrogen atoms present in the molecule provide coordination sites that can bind to metal centers, resulting in stable organometallic compounds. These complexes have potential uses in catalysis and material science.

In pharmaceutical research, 2-amino-3-acetylpyridine derivatives have been studied for their biological activity, although the parent compound itself may not be directly used as a therapeutic agent. Structural analogs incorporating similar functional motifs have demonstrated activity in antimicrobial, anti-inflammatory, and central nervous system (CNS) studies. As such, 2-amino-3-acetylpyridine serves as a valuable scaffold for structure–activity relationship (SAR) exploration in drug development programs.

The presence of both amino and carbonyl functional groups within the molecule also enables it to participate in Schiff base formation, a reaction commonly used in the synthesis of compounds with potential pharmacological properties. Schiff bases derived from 2-amino-3-acetylpyridine have been studied for their coordination chemistry, and in some cases, evaluated for biological activity in vitro.

Although not produced on a large industrial scale, 2-amino-3-acetylpyridine is available from commercial chemical suppliers for laboratory-scale use. It is typically handled with standard precautions applicable to aromatic amines, which may include moderate toxicity and the need for appropriate protective equipment during use. Stability under storage is generally good when the compound is kept in a cool, dry environment, away from light and strong oxidizing agents.

Overall, 2-amino-3-acetylpyridine represents a useful chemical entity in synthetic and medicinal chemistry due to its functional diversity and reactivity. Its applications, while largely confined to research and development settings, underscore the importance of small heterocyclic compounds as versatile intermediates in the discovery and design of more complex molecules with practical applications in various fields.

References

2011. Combinatorially-generated library of 6-fluoroquinolone analogs as potential novel antitubercular agents: a chemometric and molecular modeling assessment. Journal of Molecular Modeling, 18(5).
DOI: 10.1007/s00894-011-1179-0

2023. Hydrogen production and storage through adsorption and dissociation of H2O on pristine and functionalized SWCNT: a DFT approach. Journal of Molecular Modeling, 29(10).
DOI: 10.1007/s00894-023-05678-2

1928. Zur Pharmakologie von einigen Pyridylpyrrolen und einigen Abkommlingen des alpha-Aminopyridins. Naunyn-Schmiedebergs Archiv fur experimentelle Pathologie und Pharmakologie, 132.
DOI: 10.1007/bf01859845