Description

2-Bromo-5-hydroxypyrazine (CAS No. 374063-92-0) is a high-purity heterocyclic organic compound with the molecular formula C₄H₃BrN₂O. This brominated pyrazine derivative, also known by its IUPAC name 5-bromo-1H-pyrazin-2-one, is a valuable building block in pharmaceutical and agrochemical research. The compound features a reactive bromine atom at the 2-position and a hydroxyl group at the 5-position, making it an excellent intermediate for nucleophilic substitution reactions and metal-catalyzed cross-coupling reactions. Offered with >95% purity (HPLC), this chemical is supplied as an off-white to light brown crystalline powder with excellent batch-to-batch consistency. Proper storage at 2-8°C under inert atmosphere is recommended for long-term stability. Suitable for use in medicinal chemistry, material science, and as a precursor for more complex heterocyclic systems.

Properties

• CAS Number: 374063-92-0
• Complexity: 173
• IUPAC Name: 5-bromo-1H-pyrazin-2-one
• InChI: InChI=1S/C4H3BrN2O/c5-3-1-7-4(8)2-6-3/h1-2H,(H,7,8)
• InChI Key: ITTXBHQAWOFJAI-UHFFFAOYSA-N
• Exact Mass: 173.94288
• Molecular Formula: C4H3BrN2O
• Molecular Weight: 174.98
• SMILES: C1=C(N=CC(=O)N1)Br
• Topological: 41.5
• Monoisotopic Mass: 173.94288
• Synonyms: 2-Bromo-5-hydroxypyrazine, 374063-92-0, 5-Bromo-2(1H)-pyrazinone, DTXSID50377976, DTXCID80329004, 639-374-0, 5-bromopyrazin-2-ol, 5-bromo-1H-pyrazin-2-one, 5-bromopyrazin-2(1H)-one, 5-BROMO-2-PYRAZINOL, MFCD06245330, 2-Bromo-5-hydroxy-pyrazine, 2(1H)-Pyrazinone, 5-bromo-, 5-Bromo-pyrazin-2-ol, 2-hydroxy-5-bromopyrazine, SCHEMBL387405, 5-bromanyl-1H-pyrazin-2-one, SCHEMBL5199343, ITTXBHQAWOFJAI-UHFFFAOYSA-N, 2-Bromo-5-hydroxypyrazine, 95%, BCP27479, BBL101963, SBB062713, STL555760, AKOS005137905, AC-1971, BCP9000180, CS-W003277, FS-2379, PB26179, SY009737, DB-030958, B3881, EN300-111685, A823629

Application

2-Bromo-5-hydroxypyrazine serves as a key intermediate in the synthesis of various biologically active compounds, particularly in pharmaceutical research for developing kinase inhibitors and antimicrobial agents. This compound is valuable in medicinal chemistry for structure-activity relationship (SAR) studies due to its reactive bromine and hydroxyl functional groups. Researchers utilize it in palladium-catalyzed cross-coupling reactions to create more complex heterocyclic systems with potential therapeutic applications.

Safety and Hazards

GHS Hazard Statements

• H302 (95.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H318 (93%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501

Hazard Classes and Categories

• Acute Tox. 4 (95.3%)
• Eye Dam. 1 (93%)

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