3-Chloro-1H-pyrazol-4-amine: Properties & Lab Use FAQ

3-Chloro-1H-pyrazol-4-amine is a halogenated aminopyrazole heterocycle widely used as a versatile building block in medicinal chemistry and the synthesis of pharmaceutically relevant compounds.

Chemical Name

3-Chloro-1H-pyrazol-4-amine

SKU / Catalog Number

C189417

Molecular Formula

C3H4ClN3

Molecular Weight

117.54 g/mol

Compound Class

Halogenated aminopyrazole; heterocyclic building block

Key Functional Groups

Primary amine (–NH2), C–Cl bond, pyrazole ring (NH tautomer)

Chemical Identity and Structure

3-Chloro-1H-pyrazol-4-amine (Aladdin SKU: C189417) is a five-membered nitrogen-containing heterocycle belonging to the pyrazole family. Its molecular formula is C3H4ClN3, giving a molecular weight of approximately 117.54 g/mol. The compound features a primary amine group at the 4-position and a chlorine substituent at the 3-position of the pyrazole ring. The NH tautomer (1H form) is the predominant form in solid state and in common organic solvents. The co-existence of both an electron-withdrawing chloro group and an electron-donating amino group on the heterocyclic scaffold creates a bifunctional reactivity profile that makes this compound particularly attractive in synthetic chemistry.

Research Applications

3-Chloro-1H-pyrazol-4-amine serves primarily as a synthetic building block and intermediate in medicinal chemistry. The reactive C–Cl bond at the 3-position is amenable to a variety of transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig, and Negishi couplings), enabling rapid diversification of the pyrazole scaffold. The free primary amine at the 4-position can participate in condensations, acylations, sulfonylations, and reductive aminations, providing additional handles for library synthesis.

Aminopyrazole motifs are well-recognized pharmacophores found in kinase inhibitors, anti-inflammatory agents, and antimicrobial scaffolds. Consequently, 3-Chloro-1H-pyrazol-4-amine is frequently employed in the early-stage exploration of structure–activity relationships (SAR) during drug discovery campaigns.

Handling, Storage, and Safety

As with all fine chemical reagents containing a primary amine and an aryl chloride, standard laboratory precautions should be observed when working with 3-Chloro-1H-pyrazol-4-amine. Use appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be performed in a well-ventilated fume hood.

For storage, keep the compound in a tightly sealed container away from moisture, light, and incompatible materials such as strong oxidizers and strong acids. Storage under inert atmosphere (nitrogen or argon) at room temperature or under refrigeration (2–8 °C) is recommended to maintain long-term stability. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for detailed hazard classification, first-aid measures, and disposal guidelines before use.

Ordering and Specifications

3-Chloro-1H-pyrazol-4-amine is available from Aladdin Scientific under catalog number C189417. Customers are encouraged to confirm current available pack sizes, purity grades, and pricing through the Aladdin Scientific website or by contacting customer service. For bulk or custom quantity inquiries, please reach out to the Aladdin sales team directly. Certificate of Analysis (CoA) documents are available upon request and provide lot-specific purity data and analytical characterization.

Frequently asked questions

What is 3-Chloro-1H-pyrazol-4-amine used for in research?

3-Chloro-1H-pyrazol-4-amine is primarily used as a bifunctional building block in medicinal and synthetic chemistry. Its reactive C–Cl bond supports cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig), while the primary amine enables acylation, sulfonylation, and condensation reactions, facilitating the construction of diverse aminopyrazole-containing pharmacophores relevant to drug discovery.

How should 3-Chloro-1H-pyrazol-4-amine be stored to ensure stability?

The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon), protected from moisture and light. Refrigerated storage at 2–8 °C is recommended for long-term stability. Always consult the Aladdin Scientific SDS for specific storage and handling requirements.

What is the molecular formula and molecular weight of 3-Chloro-1H-pyrazol-4-amine?

The molecular formula of 3-Chloro-1H-pyrazol-4-amine is C3H4ClN3, with a molecular weight of approximately 117.54 g/mol. The structure contains a pyrazole ring bearing a chlorine substituent at the 3-position and a primary amine at the 4-position.

Can 3-Chloro-1H-pyrazol-4-amine undergo cross-coupling reactions?

Yes. The C–Cl bond at the 3-position of the pyrazole ring can participate in transition-metal-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Buchwald–Hartwig amination, and Negishi coupling, making it a versatile handle for scaffold elaboration. Reaction conditions should be optimized for the specific coupling partner and catalyst system employed.

How can I obtain a Certificate of Analysis (CoA) for catalog number C189417?

Certificates of Analysis for 3-Chloro-1H-pyrazol-4-amine (C189417) are available upon request from Aladdin Scientific. You may access them through the product page on the Aladdin Scientific website by entering the lot number, or by contacting Aladdin customer service directly.

References

1. Aladdin Scientific product page: 3-Chloro-1H-pyrazol-4-amine, SKU C189417.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for cross-coupling and amine reactivity.
3. Elguero, J. Pyrazoles as pharmacophores: a general review of aminopyrazole scaffolds in drug discovery. (General textbook-level knowledge; specific citation requires verification.)

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