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2,6-Dichloropurine
2,6-Dichloropurine (CAS 5451-40-1) is a highly reactive dual-halogenated purine scaffold engineered for sequential functionalization in nucleoside analog synthesis and kinase inhibitor development. Distinct from mono-chlorinated or amino-substituted purines, this molecule features chlorine substituents at both the C2 and C6 positions of the purine core, enabling two-stage diversification strategies. The C6-chlorine typically exhibits higher reactivity towards nucleophilic displacement, allowing selective mono-substitution followed by secondary modification at C2 under optimized conditions. This orthogonal reactivity profile makes it a privileged building block for constructing complex purine libraries, antiviral prodrugs, and ATP-competitive kinase inhibitors where precise control over substitution patterns is critical. The electron-deficient purine ring, enhanced by dual electron-withdrawing chloro groups, facilitates efficient coupling while maintaining metabolic stability in the final API. Manufactured with purity ≥98% under controlled conditions, it supports medicinal chemistry programs requiring modular access to multi-substituted purine architectures.
Property
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Product Name
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2,6-Dichloropurine
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CAS Number
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5451-40-1
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Chinese Name
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2,6-二氯嘌呤
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Synonyms
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Purine, 2,6-dichloro-; 2,6-Dichloro-9H-purine; C₅H₂Cl₂N₄ heterocycle; DCP
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Chinese Synonyms
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2,6-二氯 -9H-嘌呤; 二氯嘌呤; 2,6-二氯嘌呤碱; 嘌呤-2,6-二氯
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Molecular Formula
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C₅H₂Cl₂N₄
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Molecular Weight
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189.01 g/mol (calculated: C5×12.01 + H2×1.008 + Cl2×35.45 + N4×14.01)
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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 / Purine Derivatives / Dihalo heterocycles
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Appearance
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White to Off-white Crystalline Powder
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Melting Point
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178-180°C
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Storage Conditions
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Store at 2-8°C under inert atmosphere, protected from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong bases and nucleophiles to avoid premature substitution or hydrolysis.
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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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Sequential nucleophilic substitution, nucleoside analog synthesis (antiviral/anticancer), kinase inhibitor library construction, purine receptor modulator research, heterocyclic scaffold diversification
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Reactivity
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Suitable for stepwise nucleophilic aromatic substitution (C6 then C2), N9-glycosylation, cross-coupling reactions, and selective amination/alkoxylation/thiolation
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Special Note
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Dual-Reactivity Scaffold—enables sequential substitution at C2 and C6. More electrophilic than 2-amino-6-chloropurine (CAS 10310-21-1). Ideal for constructing asymmetrically substituted purines. Part of our purine building block series.
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