4-Hydrazinyl-2-(methylthio)pyrimidine: FAQs & Lab Guide

4-Hydrazinyl-2-(methylthio)pyrimidine is a versatile bifunctional heterocyclic building block widely employed in medicinal chemistry and organic synthesis for the construction of pharmacologically relevant nitrogen-containing ring systems.

CAS Number

Consult product datasheet (review required)

SKU

H727596

Molecular Formula

C5H8N4S (review required)

Functional Groups

Hydrazinyl (-NHNH2) and methylthio (-SCH3) on a pyrimidine ring

Primary Application

Heterocyclic synthesis intermediate; precursor for triazolo-, pyrazolo-, and thio-fused pyrimidines

Recommended Storage

Cool, dry, dark conditions; specific temperature should be confirmed on the product datasheet

What Is 4-Hydrazinyl-2-(methylthio)pyrimidine and Why Is It Used?

4-Hydrazinyl-2-(methylthio)pyrimidine is a heterocyclic organic compound bearing two synthetically valuable functional groups: a nucleophilic hydrazinyl group at the 4-position and a methylthio group at the 2-position of the pyrimidine ring. This dual functionality makes it an exceptionally useful bifunctional building block in synthetic and medicinal chemistry.

The hydrazinyl moiety readily undergoes condensation reactions with carbonyl compounds (aldehydes, ketones, and β-dicarbonyls) to form hydrazones, pyrazoles, and triazoles. Meanwhile, the methylthio group serves as a leaving group or as a handle for further nucleophilic substitution, enabling the introduction of diverse heteroatom substituents. Together, these features allow chemists to access a broad chemical space of fused and substituted nitrogen-heterocyclic scaffolds from a single starting material.

Researchers in drug discovery frequently use such pyrimidine-based intermediates because the pyrimidine core is prevalent in many biologically active molecules, including kinase inhibitors, antimicrobial agents, and antiviral compounds.

How Should I Handle and Store This Compound Safely?

As with all hydrazine-containing compounds, 4-Hydrazinyl-2-(methylthio)pyrimidine should be handled with appropriate precaution. Hydrazinyl derivatives are generally considered potentially toxic and should be treated as hazardous materials. Always consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific before use.

Personal Protective Equipment (PPE): Wear appropriate laboratory gloves (nitrile recommended), a laboratory coat, and safety glasses or goggles. Work in a well-ventilated area or under a fume hood to avoid inhalation of dust or vapors.

Storage: Store the compound in a tightly sealed container in a cool, dry, and dark environment. The precise recommended storage temperature should be confirmed from the official product datasheet (H727596). Avoid exposure to moisture, light, and incompatible reagents such as strong oxidizers and strong acids.

Disposal: Dispose of waste in accordance with local institutional and governmental regulations for hazardous chemical waste.

What Are the Key Synthetic Applications of This Reagent?

4-Hydrazinyl-2-(methylthio)pyrimidine is a valuable intermediate in the synthesis of a variety of pharmacologically relevant heterocyclic compounds. Key applications include:

• Pyrazole and Triazole Formation: The hydrazinyl group condenses with 1,3-dicarbonyl compounds or α,β-unsaturated carbonyl systems to yield pyrazolo[x,y-d]pyrimidine or triazolopyrimidine frameworks, which are of significant interest as kinase inhibitors and anti-inflammatory agents.
• Hydrazone Synthesis: Reaction with aldehydes or ketones under mild acidic conditions affords hydrazones that may themselves possess biological activity or serve as intermediates for further cyclization.
• SNAr and Thio-Substitution Reactions: The methylthio group at the 2-position can be displaced by a range of nitrogen, oxygen, or sulfur nucleophiles under appropriate conditions, allowing rapid diversification of the pyrimidine scaffold.
• Scaffold Hopping in Drug Discovery: The compound serves as a key starting material for generating compound libraries targeting enzymes such as dihydrofolate reductase (DHFR), kinases, and other therapeutically relevant targets (specific biological data should be verified in primary literature).

Solubility and Formulation Guidance

Understanding the solubility profile of 4-Hydrazinyl-2-(methylthio)pyrimidine is essential for preparing stock solutions for biological assays or chemical reactions.

Organic Solvents: The compound is expected to dissolve in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF), which are commonly used for preparing stock solutions in biological screening. Solubility in ethanol and methanol may also be acceptable. Specific solubility values (mg/mL) should be confirmed experimentally or from the official product documentation.

Aqueous Solubility: Aqueous solubility is expected to be limited due to the hydrophobic methylthio group and the aromatic ring system. For biological applications requiring aqueous media, co-solvent systems (e.g., DMSO/buffer) are recommended; ensure the final DMSO concentration does not interfere with the assay system.

Stock Solution Preparation: Prepare stock solutions under inert atmosphere conditions if the compound shows sensitivity to air or moisture, and aliquot to avoid repeated freeze-thaw cycles, which may degrade the compound over time.

Ordering, Purity, and Quality Information

4-Hydrazinyl-2-(methylthio)pyrimidine is available from Aladdin Scientific under SKU H727596. When placing an order, researchers and procurement teams should note the following:

Purity and Specifications: The exact purity specification (e.g., ≥95%, ≥97%) and analytical data (such as HPLC purity, NMR, and elemental analysis) for this lot should be confirmed by reviewing the Certificate of Analysis (CoA) available upon request or via the Aladdin Scientific website. Researchers are encouraged to verify that the specification meets the requirements of their specific application before ordering.

Available Pack Sizes: Please consult the Aladdin Scientific product page for H727596 for current available quantities and pricing.

Quality Assurance: Aladdin Scientific applies quality-control procedures to ensure reagent integrity. If you receive material that does not meet the stated specification, please contact customer service to initiate a return or replacement in accordance with the company's returns and refunds policy.

Custom Quantities: For custom synthesis, bulk quantities, or special packaging requirements, contact the Aladdin Scientific sales team directly.

Frequently asked questions

What is the CAS number for 4-Hydrazinyl-2-(methylthio)pyrimidine (H727596)?

The CAS number should be confirmed from the official product datasheet or Certificate of Analysis available on the Aladdin Scientific website for SKU H727596, as it was not explicitly provided in the current source material. Please visit the product page or contact customer support for the most accurate information.

Is 4-Hydrazinyl-2-(methylthio)pyrimidine stable at room temperature?

Hydrazinyl-functionalized pyrimidines can be sensitive to moisture, oxygen, and light over prolonged periods. It is recommended to store H727596 in a tightly sealed container under cool, dry, and dark conditions. Always consult the product SDS and CoA for specific stability data, and avoid unnecessary exposure to ambient conditions during weighing and handling.

What solvents are recommended for dissolving 4-Hydrazinyl-2-(methylthio)pyrimidine?

DMSO and DMF are the most commonly recommended solvents for dissolving heterocyclic hydrazinyl compounds of this type, providing good solubility for stock solution preparation. Ethanol or methanol may also be used depending on the downstream application. Aqueous solubility is expected to be limited; for biological assays, dilute stock solutions in the appropriate aqueous buffer to achieve the desired working concentration while keeping the organic co-solvent content within acceptable limits.

Can the methylthio group in this compound be further functionalized?

Yes. The methylthio group at the 2-position of the pyrimidine ring is a well-known activating and leaving group in nucleophilic aromatic substitution (SNAr) chemistry. It can be displaced by a variety of primary and secondary amines, alkoxides, and thiolates under appropriate reaction conditions (often mild heating in a polar solvent), providing rapid access to 2-amino-, 2-alkoxy-, or 2-thio-substituted pyrimidine analogs bearing the hydrazinyl group at C-4.

How do I request a Certificate of Analysis (CoA) for H727596?

You can request the Certificate of Analysis for H727596 by visiting the Aladdin Scientific website and navigating to the product page for 4-Hydrazinyl-2-(methylthio)pyrimidine, or by contacting Aladdin Scientific customer service directly with your lot number. The CoA includes analytical data such as purity, NMR confirmation, and other quality metrics relevant to your research requirements.

References

1. General reference: Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell, 2010. (Textbook-level background on pyrimidine and hydrazine chemistry.)
2. Aladdin Scientific Product Page for H727596, 4-Hydrazinyl-2-(methylthio)pyrimidine. Retrieved from Aladdin Scientific official website.
3. General reference: Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press, 2012. (Background on SNAr reactions and nucleophilic substitution of heteroaromatic thioethers.)

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