4-Chloro-6-hydrazinylpyrimidine Hydrate: Properties & Applications

4-Chloro-6-hydrazinylpyrimidine hydrate is a bifunctional pyrimidine-based building block bearing both a reactive chloro substituent and a hydrazinyl group, making it a versatile intermediate for the construction of diverse nitrogen-rich heterocyclic scaffolds in medicinal and synthetic chemistry.

Product Name

4-Chloro-6-hydrazinylpyrimidine hydrate

SKU

C191195

Molecular Formula

C4H7ClN4O (monohydrate form)

Functional Groups

Chloro (C–Cl) and hydrazinyl (–NHNH2) on a pyrimidine ring

Primary Role

Bifunctional heterocyclic building block for medicinal and synthetic chemistry

Key Reactivity

Nucleophilic aromatic substitution at C-4 chloro position; condensation reactions via hydrazinyl group

Storage Recommendation

Store in a cool, dry place away from moisture and light; handle with appropriate PPE

Chemical Identity and Structure

4-Chloro-6-hydrazinylpyrimidine hydrate (Aladdin SKU: C191195) is a substituted pyrimidine featuring a chlorine atom at the 4-position and a hydrazinyl (–NHNH₂) group at the 6-position of the aromatic ring, supplied as its stable monohydrate form. The pyrimidine core is a six-membered aromatic ring containing two nitrogen atoms at positions 1 and 3, which imparts significant electron deficiency to the ring system and strongly activates the C-4 chloro substituent toward nucleophilic aromatic substitution (SNAr).

The coexistence of two orthogonal reactive handles—the electrophilic chloro group and the nucleophilic hydrazinyl group—on a single scaffold gives this compound its characteristic synthetic versatility. The hydrate form enhances handling stability under ambient laboratory conditions while preserving the full reactivity of both functional groups. Researchers should verify the exact molecular weight and purity specification from the current product Certificate of Analysis prior to use in quantitative experiments.

Synthetic Applications and Reactivity

The dual functionality of 4-Chloro-6-hydrazinylpyrimidine hydrate makes it a high-value intermediate across several classes of organic transformations:

• Nucleophilic Aromatic Substitution (SNAr): The electron-withdrawing ring nitrogens render the C-4 chloro position highly susceptible to displacement by a broad range of N-, O-, and S-nucleophiles, enabling rapid library synthesis of 4-amino-, 4-alkoxy-, and 4-thioether-substituted pyrimidines.
• Condensation and Cyclization via Hydrazinyl Group: The –NHNH₂ moiety readily undergoes condensation with aldehydes, ketones, and 1,3-dicarbonyl compounds to form hydrazones, pyrazoles, and triazoles. This reaction pathway is widely exploited in the synthesis of pyrazolo[3,4-d]pyrimidine and related fused bicyclic systems with demonstrated biological relevance.
• Sequential Functionalization: Because the two reactive sites exhibit distinct chemoselectivity under appropriate conditions, chemists can perform stepwise reactions—first modifying the chloro group, then cyclizing via the hydrazinyl handle, or vice versa—to access structurally complex polyheterocyclic products in a controlled manner.

These properties collectively position 4-Chloro-6-hydrazinylpyrimidine hydrate as a privileged building block in combinatorial and medicinal chemistry workflows.

Relevance in Medicinal Chemistry and Drug Discovery

Pyrimidine and pyrazolopyrimidine scaffolds are prominent pharmacophores found in numerous approved therapeutics, particularly kinase inhibitors, antivirals, and antimicrobials. 4-Chloro-6-hydrazinylpyrimidine hydrate serves as a gateway intermediate to these privileged scaffolds by enabling rapid access to fused ring systems that are otherwise difficult to assemble.

The hydrazinylpyrimidine motif itself has attracted attention as a potential pharmacophore in compounds investigated for antiproliferative, anti-inflammatory, and antimicrobial activities. The reactive chloro group further allows lead optimization through straightforward installation of diverse amine or heteroatom substituents, facilitating structure–activity relationship (SAR) studies without requiring lengthy de novo synthesis. Researchers engaged in target-based drug discovery and fragment-based screening may find this compound particularly useful as a central scaffold around which medicinal chemistry campaigns can be efficiently orchestrated.

Note: Specific biological activity data for this compound should be obtained from peer-reviewed primary literature; researchers are encouraged to search current databases for the latest findings.

Handling, Storage, and Safety Considerations

As with all hydrazine-containing compounds, 4-Chloro-6-hydrazinylpyrimidine hydrate should be handled with appropriate caution. Hydrazine derivatives are generally classified as potentially toxic and should be treated as hazardous materials pending review of the specific Safety Data Sheet (SDS) available from Aladdin Scientific for SKU C191195.

Recommended precautions include:

• Work in a well-ventilated fume hood to minimize inhalation exposure.
• Wear appropriate personal protective equipment (PPE): nitrile gloves, safety glasses, and a laboratory coat.
• Avoid contact with strong oxidizing agents, which may react vigorously with the hydrazinyl group.
• Store the compound in a tightly sealed container in a cool, dry environment, protected from moisture and light, to maintain stability of the hydrate form.
• Dispose of waste material in accordance with local institutional and regulatory guidelines for hazardous chemical waste.

Always consult the current SDS for authoritative hazard classification, first-aid measures, and disposal instructions before working with this reagent.

Ordering and Quality Information

4-Chloro-6-hydrazinylpyrimidine hydrate is available from Aladdin Scientific under SKU C191195. Researchers and procurement teams should request the current Certificate of Analysis (CoA) to confirm lot-specific purity, appearance, and analytical data (e.g., HPLC, NMR, or MS confirmation) before use in critical experiments.

For bulk quantities, custom packaging, or additional technical support, contact the Aladdin Scientific technical sales team. Ensure that the reagent meets the purity and specification requirements applicable to your specific application—whether that is exploratory synthesis, high-throughput screening, or reference standard preparation.

All orders are subject to Aladdin Scientific's standard terms and conditions regarding shipping, handling of hazardous materials, and returns. Consult the website or your regional representative for current pricing, availability, and lead times.

Frequently asked questions

What makes 4-Chloro-6-hydrazinylpyrimidine hydrate a useful building block in organic synthesis?

This compound carries two orthogonally reactive functional groups on a single pyrimidine scaffold: a chloro group susceptible to nucleophilic aromatic substitution and a hydrazinyl group capable of condensation and cyclization reactions. This dual reactivity allows chemists to access a wide variety of nitrogen-rich heterocyclic targets, including pyrazoles, triazoles, and fused pyrazolopyrimidine systems, in a convergent and efficient manner.

How should 4-Chloro-6-hydrazinylpyrimidine hydrate be stored to maintain its stability?

The compound should be stored in a tightly sealed container in a cool, dry location, away from moisture and direct light. Moisture control is especially important because excessive humidity can alter the hydration state or promote decomposition. Always reseal the container promptly after use and consult the product SDS for specific storage temperature recommendations.

Is 4-Chloro-6-hydrazinylpyrimidine hydrate hazardous, and what precautions should be taken?

As a hydrazine-containing compound, it should be treated as potentially hazardous. Work should be conducted in a well-ventilated fume hood with appropriate PPE including nitrile gloves, safety glasses, and a lab coat. Contact with strong oxidizers should be avoided. Researchers must consult the full Safety Data Sheet (SDS) available from Aladdin Scientific for comprehensive hazard, first-aid, and disposal information.

Can this compound be used for the synthesis of pyrazolopyrimidine-type kinase inhibitor scaffolds?

Yes, 4-Chloro-6-hydrazinylpyrimidine hydrate is well-suited as a precursor for pyrazolo[3,4-d]pyrimidine and related fused bicyclic frameworks that appear in kinase inhibitor chemotypes. The hydrazinyl group can be engaged in cyclocondensation with appropriate carbonyl partners to form the pyrazole ring, while the chloro substituent provides a handle for further diversification. Researchers should consult primary literature for specific reaction conditions and yields.

Where can I obtain the Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for SKU C191195?

The Certificate of Analysis and Safety Data Sheet for 4-Chloro-6-hydrazinylpyrimidine hydrate (SKU C191195) are available directly from the Aladdin Scientific website or by contacting Aladdin Scientific customer service. Always request the CoA specific to your lot number to ensure the data reflects the exact material you have received.

References

1. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (General reference for pyrimidine reactivity and SNAr reactions.)
2. Aladdin Scientific. Product Page and Certificate of Analysis for 4-Chloro-6-hydrazinylpyrimidine hydrate, SKU C191195. Retrieved from Aladdin Scientific official website.
3. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. The Tautomerism of Heterocycles; Academic Press, 1976. (Background on pyrazole and pyrimidine heterocyclic tautomerism relevant to hydrazinylpyrimidine chemistry.)

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