2-Chloro-6-aminopyrazine
2-Chloro-6-aminopyrazine (CAS 33332-28-4) is a strategically bifunctional pyrazine scaffold engineered for heterocyclic diversification, pharmaceutical intermediate synthesis, and agrochemical development. This molecule integrates an electron-deficient pyrazine core—a six-membered aromatic diazine ring with nitrogen atoms at para positions (1,4)—with a chlorine substituent at the C2 position and an amino group at the C6 position. The C2-chloro handle is activated by the adjacent ring nitrogen, enabling efficient nucleophilic aromatic substitution (SNAr) or Pd-catalyzed cross-coupling (Suzuki, Buchwald-Hartwig), while the C6-amino group provides orthogonal reactivity for acylation, alkylation, diazotization, or heterocyclic fusion. This dual-functionality architecture enables sequential or selective functionalization, making it particularly valuable for constructing fused heterocycles (pyrazino-fused systems), kinase inhibitor cores, and nitrogen-rich ligands where the chloroamino-pyrazine motif optimizes target engagement through specific hydrogen-bonding patterns and electronic tuning. Manufactured with purity ≥98% under controlled conditions, it supports drug discovery programs requiring modular access to differentially functionalized electron-deficient heterocycles.
Property
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Product Name
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2-Chloro-6-aminopyrazine
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CAS Number
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33332-28-4
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Chinese Name
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2-氯 -6-氨基吡嗪
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Synonyms
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6-Amino-2-chloropyrazine; 2-Chloropyrazin-6-amine; Pyrazine, 2-chloro-6-amino-; C₄H₄ClN₃ heterocycle
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Chinese Synonyms
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6-氨基-2-氯吡嗪; 2-氯吡嗪-6-胺; 氯氨基吡嗪; 2-氯-6-位氨基吡嗪
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Molecular Formula
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C₄H₄ClN₃
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Molecular Weight
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129.55 g/mol
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Purity
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≥ 98% (HPLC/GC area normalization)
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Product Category
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Pharmaceutical Intermediates / Pyrazine Derivatives / Halogenated Aminoheterocycles
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Appearance
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Purple Crystalline Powder
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Melting Point
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~144 – 147 °C (decomposition, literature reference recommended)
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Storage Conditions
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Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong oxidizing agents to avoid amino group oxidation and from strong bases to avoid premature chloride displacement.
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Shelf Life
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24 months under recommended storage conditions
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Packaging
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100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
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Applications
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Kinase inhibitor synthesis, antiviral drug development, agrochemical intermediate synthesis, heterocyclic library construction (pyrazino-fused systems), sequential functionalization via orthogonal Cl/NH₂ reactivity, ligand synthesis for coordination chemistry
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Reactivity
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Suitable for nucleophilic aromatic substitution (C2-Cl displacement), amino group acylation/alkylation, diazotization, heterocyclic fusion (e.g., triazolo-pyrazine), electrophilic aromatic substitution at C3/C5, and Pd-catalyzed cross-coupling
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Special Note
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✅ Orthogonal Bifunctional Scaffold—C2-Cl for coupling/SNAr, C6-NH₂ for nucleophilic derivatization. Electron-deficient pyrazine core provides unique binding geometry vs. pyridine analogs. Part of our halogenated aminopyrazine series.
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