4-(2-Chloro-9H-purin-6-yl)morpholine: Properties & Lab Use

4-(2-Chloro-9H-purin-6-yl)morpholine is a halogenated purine derivative bearing a morpholine substituent at the 6-position and a chloro group at the 2-position, widely used as a versatile synthetic building block in medicinal chemistry and nucleoside analogue research.

SKU

M708616

Chemical Name

4-(2-Chloro-9H-purin-6-yl)morpholine

Functional Class

Halogenated purine building block for organic synthesis

Key Reactive Site

C-2 chloro group (nucleophilic aromatic substitution); C-6 morpholine (modifiable)

Primary Applications

Medicinal chemistry, nucleoside analogue synthesis, heterocyclic scaffold elaboration

Storage Recommendation

Store in a cool, dry place away from light; follow SDS guidelines

What Is 4-(2-Chloro-9H-purin-6-yl)morpholine?

4-(2-Chloro-9H-purin-6-yl)morpholine (Aladdin SKU M708616) is a synthetic purine derivative in which the adenine scaffold has been modified by introduction of a chloro substituent at C-2 and replacement of the C-6 amino group with a morpholine ring. These dual modifications make the molecule a valuable intermediate in the preparation of pharmacologically active purine analogues, kinase inhibitor scaffolds, and nucleoside-based probes.

The compound belongs to the broad class of 2,6-disubstituted purines. The electron-withdrawing chlorine at C-2 activates the ring toward further nucleophilic aromatic substitution (SNAr), while the morpholine group at C-6 provides metabolic stability and modulates physicochemical properties such as solubility and lipophilicity relative to the free amine.

How Is This Compound Used in Research?

This building block is primarily employed in two broad research contexts:

• Medicinal chemistry: The C-2 chloro handle allows chemists to introduce diverse nucleophiles (amines, thiols, alcohols) via SNAr to generate libraries of 2,6-disubstituted purine analogues for biological screening, particularly against kinases and adenosine receptors.
• Nucleoside analogue synthesis: The compound can be coupled to sugar moieties or sugar surrogates under standard glycosylation conditions to afford nucleoside analogues for antiviral or anticancer research.

Researchers working on structure–activity relationship (SAR) studies frequently use 2-chloro-6-morpholinopurine as a versatile precursor because the morpholine group keeps the C-6 position temporarily blocked yet accessible to further elaboration under forcing conditions if needed.

Handling, Storage, and Safety Considerations

As with all halogenated heterocyclic compounds, appropriate precautions should be observed when working with 4-(2-Chloro-9H-purin-6-yl)morpholine:

• Personal protective equipment: Wear appropriate gloves, lab coat, and eye protection. Work in a well-ventilated area or under a fume hood.
• Storage: Store in a tightly sealed container in a cool, dry, dark environment. Refer to the product SDS for specific hazard classifications and storage temperature requirements.
• Stability: The C-2 chloro group may be susceptible to hydrolysis under prolonged exposure to moisture; keep the compound dry and minimize exposure to atmospheric humidity.
• Disposal: Dispose of waste in accordance with local regulations for halogenated organic compounds.

Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Ordering and Availability from Aladdin Scientific

4-(2-Chloro-9H-purin-6-yl)morpholine is available from Aladdin Scientific under SKU M708616. To place an order or request a quotation, visit the Aladdin Scientific website or contact your regional sales representative. Bulk quantities and custom packaging may be available upon request.

For purity specifications, certificate of analysis (CoA), and SDS documents, please refer to the product listing page or contact technical support. Aladdin Scientific is committed to providing research-grade reagents with rigorous quality control to support reproducible science.

Frequently asked questions

What is the CAS number of 4-(2-Chloro-9H-purin-6-yl)morpholine?

The CAS number for 4-(2-Chloro-9H-purin-6-yl)morpholine should be confirmed directly from the Aladdin Scientific product page or Certificate of Analysis for SKU M708616, as this information was not included in the source material provided.

Can 4-(2-Chloro-9H-purin-6-yl)morpholine undergo nucleophilic aromatic substitution at C-2?

Yes. The electron-deficient purine ring system, combined with the chloro leaving group at C-2, makes this position amenable to nucleophilic aromatic substitution (SNAr) with primary and secondary amines, thiols, and alkoxides, enabling straightforward derivatisation to build diverse purine analogue libraries.

What solvents are suitable for dissolving 4-(2-Chloro-9H-purin-6-yl)morpholine?

Common polar aprotic solvents such as DMSO, DMF, and acetonitrile are generally suitable for dissolving halogenated purine derivatives of this type. Water solubility is typically limited. Always verify solubility experimentally for your specific application and consult the product SDS.

How should I store SKU M708616 to maintain its stability?

Store the compound in a tightly sealed container under cool, dry, and dark conditions to minimise risk of hydrolysis of the C-2 chloro group and degradation of the purine ring. Specific storage temperature and shelf-life data should be obtained from the Aladdin Scientific SDS and Certificate of Analysis.

Is this compound suitable for use as a kinase inhibitor scaffold?

2,6-Disubstituted purines, including 2-chloro-6-morpholinopurine derivatives, are well-established scaffolds in kinase inhibitor medicinal chemistry programs. However, biological activity data specific to this compound were not provided in the source material; researchers should conduct their own assays or consult the primary literature for relevant SAR data.

References

1. Aladdin Scientific product listing for 4-(2-Chloro-9H-purin-6-yl)morpholine, SKU M708616.
2. General reference: Legraverend, M.; Grierson, D. S. The purines: potent and versatile small molecule inhibitors and modulators of key biological targets. Bioorganic & Medicinal Chemistry, 2006. [Details require verification]

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.