Description

5-Bromo-2-iodo-3-methoxypyrazine (CAS No. 476622-89-6) is a high-purity halogenated pyrazine derivative with the molecular formula C₅H₄BrIN₂O. This heterocyclic compound features a bromo-substitution at the 5-position and an iodo-substitution at the 2-position, along with a methoxy group at the 3-position, making it a versatile intermediate for pharmaceutical and agrochemical synthesis. Its unique structure enables selective cross-coupling reactions (e.g., Suzuki, Stille) for constructing complex nitrogen-containing scaffolds. Provided as a crystalline solid with ≥95% purity (HPLC), it is rigorously tested for consistency via ¹H/¹³C NMR, LC-MS, and elemental analysis. Packaged under inert gas in amber glass vials to ensure stability, this compound is ideal for medicinal chemistry, material science, and catalysis research. Handle with appropriate PPE due to potential halogen reactivity.

Properties

• CAS Number: 476622-89-6
• Complexity: 116
• IUPAC Name: 5-bromo-2-iodo-3-methoxy-pyrazine
• InChI: InChI=1S/C5H4BrIN2O/c1-10-5-4(7)8-2-3(6)9-5/h2H,1H3
• InChI Key: NUOPFUYHRPYSNY-UHFFFAOYSA-N
• Exact Mass: 313.85517
• Molecular Formula: C5H4BrIN2O
• Molecular Weight: 314.91
• SMILES: COC1=NC(=CN=C1I)Br
• Topological: 35
• Monoisotopic Mass: 313.85517
• Synonyms: 5-BROMO-2-IODO-3-METHOXYPYRAZINE, 476622-89-6, DTXSID20457072, DTXCID80407891, 821-242-0, MFCD09909688, C5H4BrIN2O, SCHEMBL1672934, NUOPFUYHRPYSNY-UHFFFAOYSA-N, AKOS015899938, CS-W000776, DS-0550, SY058998, DB-070840, EN300-7097393

Application

5-Bromo-2-iodo-3-methoxypyrazine serves as a key building block in palladium-catalyzed cross-coupling reactions to synthesize pyrazine-based drug candidates, particularly kinase inhibitors and antiviral agents. Its halogen diversity enables sequential functionalization for structure-activity relationship (SAR) studies in medicinal chemistry. The methoxy group enhances solubility for intermediate purification while directing subsequent electrophilic substitutions. Researchers also utilize it to develop luminescent materials and ligands for transition-metal catalysts.

Safety and Hazards

GHS Hazard Statements

• H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (33.3%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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