Description

6-Bromo-5-methylpyrazin-2-amine (CAS No. 74290-68-9) is a high-purity heterocyclic organic compound with the molecular formula C₅H₆BrN₃. This brominated pyrazine derivative is a valuable building block in pharmaceutical and agrochemical research, offering a reactive bromine substituent for cross-coupling reactions and an amino group for further functionalization. The compound is characterized by its white to off-white crystalline appearance and is supplied with ≥95% purity (HPLC). It is stable under recommended storage conditions (2-8°C, inert atmosphere) and is compatible with common organic solvents, including DMSO, methanol, and dichloromethane. Ideal for medicinal chemistry, this intermediate is particularly useful in the synthesis of kinase inhibitors and other bioactive molecules.

Properties

• CAS Number: 74290-68-9
• Complexity: 98.2
• IUPAC Name: 6-bromo-5-methyl-pyrazin-2-amine
• InChI: InChI=1S/C5H6BrN3/c1-3-5(6)9-4(7)2-8-3/h2H,1H3,(H2,7,9)
• InChI Key: LRZBSKCGVMDZHW-UHFFFAOYSA-N
• Exact Mass: 186.97451
• Molecular Formula: C5H6BrN3
• Molecular Weight: 188.03
• SMILES: CC1=NC=C(N=C1Br)N
• Topological: 51.8
• Monoisotopic Mass: 186.97451
• Synonyms: 6-bromo-5-methylpyrazin-2-amine, 74290-68-9, 2-amino-6-bromo-5-methylpyrazine, MFCD17011819, SCHEMBL15542181, DTXSID70618015, LRZBSKCGVMDZHW-UHFFFAOYSA-N, AKOS015842574, CS-W019079, DS-3869, SY104467, DB-074808, Y10498

Application

6-Bromo-5-methylpyrazin-2-amine serves as a key intermediate in the synthesis of pharmacologically active compounds, particularly in the development of kinase inhibitors for cancer research. Its reactive bromine atom enables participation in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Stille), while the amino group allows for amide formation or reductive amination. Researchers utilize this compound in fragment-based drug discovery and as a scaffold for building diverse heterocyclic libraries. The methyl substituent enhances metabolic stability in resulting drug candidates, making it valuable for medicinal chemistry optimization programs.

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