6-Chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine: FAQs & Uses
6-Chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine: FAQs & Uses
6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine is a bifunctionally halogenated bicyclic heterocyclic building block widely used in medicinal chemistry for the synthesis of kinase-targeted small molecules via selective cross-coupling and nucleophilic aromatic substitution reactions.
- Product Name
- 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine
- SKU
- C637615
- Molecular Formula
- C5H2ClIN4
- Molecular Weight
- 280.46 g/mol
- Key Functional Groups
- C-3 iodo (for metal-catalyzed cross-coupling), C-6 chloro (for SNAr with nucleophiles)
- Scaffold Class
- Pyrazolo[3,4-d]pyrimidine (bicyclic N-heterocycle)
What Is 6-Chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine?
6-Chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (SKU: C637615) is a halogen-substituted bicyclic heterocycle belonging to the pyrazolo[3,4-d]pyrimidine family. The scaffold fuses a pyrazole ring with a pyrimidine ring, creating a purine-like nitrogen-rich framework that is highly amenable to diversification. The compound bears two distinct reactive halogens: an iodine atom at the C-3 position of the pyrazole ring and a chlorine atom at the C-6 position of the pyrimidine ring. This dual-halogen pattern enables orthogonal chemical elaboration, making it a highly versatile intermediate in drug discovery programs.
Chemical Properties and Reactivity
The two halogens in this compound exhibit markedly different reactivity profiles, which underpins its utility as a bifunctional building block. The C-3 iodo group is ideally suited for palladium- or copper-catalyzed cross-coupling reactions such as Suzuki–Miyaura, Sonogashira, and Negishi couplings, enabling introduction of aryl, heteroaryl, alkynyl, or alkyl groups at C-3. In contrast, the C-6 chloro substituent on the electron-deficient pyrimidine ring undergoes facile nucleophilic aromatic substitution (SNAr) with amines, alcohols, and thiols, providing access to C-6 amino, alkoxy, or thioether derivatives. This orthogonal reactivity allows sequential, chemoselective functionalization of both positions in a single synthetic route, significantly streamlining library synthesis.
Applications in Drug Discovery and Research
Pyrazolo[3,4-d]pyrimidine derivatives are well-established scaffolds in medicinal chemistry, particularly for the design of protein kinase inhibitors. The purine-mimicking geometry of the bicyclic core allows these compounds to interact with the ATP-binding pocket of kinases, and the halogen substituents at C-3 and C-6 provide handles for rapid analog synthesis. 6-Chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (C637615) is therefore commonly employed as a key synthetic intermediate in programs targeting kinases relevant to oncology, inflammation, and other therapeutic areas. Beyond kinase programs, the compound serves as a general-purpose heterocyclic building block for fragment-based drug discovery and structure–activity relationship (SAR) studies.
Handling, Storage, and Safety
As with most organoiodine and organochlorine heterocyclic reagents, 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine should be handled with appropriate personal protective equipment including gloves, eye protection, and a laboratory coat. Work should be conducted in a well-ventilated fume hood. The compound should be stored in a cool, dry, well-ventilated location away from incompatible materials such as strong bases and reducing agents. Users are advised to consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Proper waste disposal must comply with local institutional and regulatory requirements for halogenated organic compounds.
Ordering and Availability from Aladdin Scientific
6-Chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine is available from Aladdin Scientific under SKU C637615. Customers can place orders directly through the Aladdin Scientific website or by contacting the sales team. For bulk quantities, custom packaging, or questions about current stock levels and lead times, please reach out to customer service. Researchers requiring a certificate of analysis (CoA), SDS, or NMR spectra should request these documents at the time of ordering or via the product page. Aladdin Scientific is committed to providing high-quality research reagents with full documentation to support your experimental workflows.
Frequently asked questions
What makes 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine useful as a building block?
The compound contains two orthogonally reactive halogens: the C-3 iodine is well-suited for palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Sonogashira), while the C-6 chlorine undergoes nucleophilic aromatic substitution with nitrogen, oxygen, or sulfur nucleophiles. This allows sequential, chemoselective functionalization at both positions in a single synthetic sequence, enabling efficient library synthesis around the pyrazolo[3,4-d]pyrimidine scaffold.
How should I store 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine (SKU C637615)?
Store the compound in a cool, dry, well-ventilated area, away from strong oxidizers, strong bases, and reducing agents. Keep the container tightly sealed when not in use to prevent moisture uptake. Always consult the Aladdin Scientific Safety Data Sheet (SDS) for the most current and product-specific storage recommendations.
What types of reactions can be performed at the C-3 iodo position of this compound?
The C-3 iodo group is highly activated toward transition-metal-catalyzed cross-coupling reactions. Typical transformations include Suzuki–Miyaura coupling (with arylboronic acids), Sonogashira coupling (with terminal alkynes), Negishi coupling (with organozinc reagents), and Buchwald–Hartwig amination. These reactions proceed selectively at C-3 in preference to the less reactive C-6 chloro group under standard cross-coupling conditions.
Is 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine relevant to kinase inhibitor research?
Yes. The pyrazolo[3,4-d]pyrimidine core is a well-recognized purine bioisostere, and compounds bearing this scaffold have been extensively explored as ATP-competitive kinase inhibitors. The halogen substituents at C-3 and C-6 serve as handles to introduce pharmacophore elements that interact with the kinase hinge region or solvent-exposed areas, making this compound a valuable starting material in kinase-focused medicinal chemistry programs.
How do I obtain a Certificate of Analysis (CoA) or SDS for SKU C637615?
A Certificate of Analysis and Safety Data Sheet for C637615 can be requested through the Aladdin Scientific product page or by contacting customer service directly. Lot-specific CoA documents are typically available upon request and may also be downloadable from the product listing on the Aladdin Scientific website.
References
- General reference for pyrazolo[3,4-d]pyrimidine chemistry and kinase inhibitor applications — no specific citation available from source material; textbook-level knowledge.
- Aladdin Scientific product listing for 6-chloro-3-iodo-1H-pyrazolo[3,4-d]pyrimidine, SKU C637615.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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