2-Amino-3-methylpyrazine
[CAS# 19838-08-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: 2-Amino-3-methylpyrazine
• Synonyms: 3-methylpyrazin-2-amine
• Molecular Formula: C₅H₇N₃
• Molecular Weight: 109.13
• CAS Registry Number: 19838-08-5
• SMILES: CC1=NC=CN=C1N

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Melting point: 173 - 176 °C (Expl.)
• Boiling point: 242.6±35.0 °C 760 mmHg (Calc.)^*
• Flash point: 123.7±13.1 °C (Calc.)^*
• Index of refraction: 1.582 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

2‑Amino‑3‑methylpyrazine is an organic compound in the pyrazine family, with molecular formula C₅H₇N₃ and CAS number 19838‑08‑5. Its structure features a pyrazine ring substituted at the 2‑position by an amino group (–NH₂) and at the 3‑position by a methyl group, which gives it both nucleophilic (via the amine) and aromatic character. The molecule is commercially available, typically as a solid with purity ≥ 98%, and is used primarily as a synthetic building block.

Because of its aminopyrazine core, 2‑Amino-3-methylpyrazine is useful in heterocyclic chemistry, particularly for synthesizing more complex nitrogen-containing frameworks. The amino group allows for derivatization by acylation, reductive amination, or coupling reactions, while the methyl group can influence the electronic properties of the ring without introducing too much steric hindrance. The pyrazine ring itself is planar and aromatic, which can support conjugated systems or serve as a ligand scaffold in coordination chemistry.

In synthetic routes, 2‑Amino-3-methylpyrazine may be prepared by condensation reactions or via modified pyrazine formation strategies, though specific published synthetic procedures for this exact compound are limited. Its role as a building block means it can be used in medicinal chemistry to generate libraries of substituted pyrazine derivatives, some of which may have biological activity such as enzyme inhibition or receptor modulation. In drug discovery contexts, aminopyrazines are valuable for exploring chemical space due to their small size, polarity, and potential to make hydrogen bonds.

In materials science, the electron-rich pyrazine core can be leveraged in the design of organic semiconductors or other functional materials because heterocyclic amines can impact electronic properties, charge transport, and molecular packing. Additionally, the amino group can be used to link pyrazine units to polymers, dyes, or other heterocycles, enabling creation of advanced functional molecules.

Because the compound is primarily an intermediate rather than a final active agent, its direct biological or pharmacological use is not well documented in peer-reviewed literature. Major sources of information about 2‑Amino-3-methylpyrazine come from chemical catalogues and safety datasheets. According to supplier safety documentation, the compound is not classified as hazardous under common regulatory schemes when pure and handled in dry form.

In practical terms, handling this compound requires standard organic chemistry precautions: use of dry solvents, storage in sealed containers, and protection from moisture (since the amino group may absorb water). Given its versatility and reactive functional groups, 2‑Amino-3-methylpyrazine remains a useful small-molecule intermediate in both academic and industrial research settings.