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5-Bromopyrimidine
5-Bromopyrimidine (CAS 4595-59-9) is a strategically functionalized halogenated pyrimidine scaffold engineered for pharmaceutical intermediate synthesis, agrochemical development, and materials science applications. This molecule integrates a pyrimidine core—a six-membered aromatic diazine ring with nitrogen atoms at meta positions (1,3)—with a bromine substituent at the C5 position. Compared to its pyrazine isomer (1,4-diazine), the pyrimidine architecture exhibits distinct electronic distribution and reactivity patterns, particularly in nucleophilic aromatic substitution and metal-catalyzed cross-coupling. The C5-bromo handle enables efficient Pd-catalyzed cross-coupling (Suzuki, Stille, Negishi, Sonogashira), while the ring nitrogens provide hydrogen-bonding acceptor capability and coordination sites. This intermediate is particularly valuable for constructing kinase inhibitor cores, antiviral agents, agrochemical actives, and functional materials where the bromopyrimidine motif optimizes target engagement through specific electronic tuning. Manufactured with purity ≥98% under controlled conditions, it supports drug discovery programs requiring modular access to electron-deficient halogenated heterocycles.
Property
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Product Name
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5-Bromopyrimidine
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CAS Number
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4595-59-9
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Chinese Name
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5-溴嘧啶
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Synonyms
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Pyrimidine, 5-bromo-; 5-Bromodiaza benzene; C₄H₃BrN₂ halogenated heterocycle
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Chinese Synonyms
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5-溴代嘧啶; 溴嘧啶; 5-位溴嘧啶; 嘧啶溴化物
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Molecular Formula
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C₄H₃BrN₂
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Molecular Weight
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158.99 g/mol
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Purity
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≥ 98% (GC/HPLC area normalization)
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Product Category
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Pharmaceutical Intermediates / Pyrimidine Derivatives / Halogenated Heterocycles
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Appearance
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White to Off-white Crystalline Powder or Solid
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Melting Point
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~60-65°C
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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 and strong bases.
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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, Pd-catalyzed cross-coupling (C5-Br), heterocyclic library construction, ligand synthesis
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Reactivity
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Suitable for Pd-catalyzed cross-coupling (C5-Br displacement), nucleophilic aromatic substitution (at C2/C4/C6), electrophilic aromatic substitution, and heterocyclic fusion
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Special Note
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✅ Electron-Deficient Heterocycle—pyrimidine core (1,3-diazine) differs from pyrazine (1,4-diazine). C5-Br enables cross-coupling diversification. Distinct from pyrazine series by nitrogen positioning. Part of our halogenated heterocycle building block series.
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