4-Bromo-1-(2-methoxyethyl)-1H-pyrazole: Properties & Uses

4-Bromo-1-(2-methoxyethyl)-1H-pyrazole is a halogenated pyrazole building block featuring a 2-methoxyethyl N-substituent and a C-4 bromine handle, making it a versatile intermediate for cross-coupling reactions and the synthesis of pharmacologically active heterocyclic compounds.

Product Name

4-Bromo-1-(2-methoxyethyl)-1H-pyrazole

SKU / Catalog Number

B590310

Core Scaffold

1H-Pyrazole with N1-(2-methoxyethyl) and C4-bromo substituents

Primary Application

Synthetic building block for cross-coupling and medicinal chemistry

Key Reactive Site

C-4 C–Br bond, suitable for Suzuki, Negishi, and Buchwald–Hartwig couplings

Supplier

Aladdin Scientific

What Is 4-Bromo-1-(2-methoxyethyl)-1H-pyrazole?

4-Bromo-1-(2-methoxyethyl)-1H-pyrazole (Aladdin SKU: B590310) is a substituted pyrazole in which the nitrogen at position 1 bears a 2-methoxyethyl group and carbon 4 carries a bromine atom. The pyrazole ring is a five-membered aromatic heterocycle containing two adjacent nitrogen atoms, widely exploited in drug discovery due to its favorable pharmacokinetic properties and capacity for hydrogen-bond interactions.

The 2-methoxyethyl substituent on N1 introduces a polar, ether-containing side chain that can enhance aqueous solubility relative to simple alkyl analogues, while also providing an additional handle for further functionalization or for modulating physicochemical properties of the final target molecule.

Key Chemical Properties and Handling

The C–Br bond at the 4-position of the pyrazole ring is the primary site of reactivity. This aryl/heteroaryl bromide is well-suited for palladium- and nickel-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Stille, and Buchwald–Hartwig amination reactions, enabling the introduction of diverse aryl, vinyl, alkyl, or amino substituents at C-4.

As with most organobromine reagents, appropriate laboratory precautions should be followed: work in a well-ventilated fume hood, wear appropriate personal protective equipment (gloves, lab coat, eye protection), and consult the Safety Data Sheet (SDS) before use. Store the compound according to the conditions specified on the product label—typically in a cool, dry location away from moisture and incompatible materials.

Researchers should verify specific physical constants (melting point, boiling point, density) and purity specifications from the Certificate of Analysis (CoA) supplied with each lot, as these values are lot-dependent.

Applications in Synthesis and Drug Discovery

Pyrazole scaffolds are prominent in medicinal chemistry; numerous approved drugs and clinical candidates contain a pyrazole core. 4-Bromo-1-(2-methoxyethyl)-1H-pyrazole serves as a versatile starting material or intermediate for:

• Fragment-based drug discovery (FBDD): The compact, functionalized pyrazole fragment can be elaborated via coupling reactions to explore structure–activity relationships (SAR).
• Kinase inhibitor synthesis: Pyrazoles are frequently incorporated into kinase inhibitor scaffolds; the bromo handle allows rapid diversification of the C-4 aryl substituent.
• Agrochemical research: Bromopyrazole intermediates appear in the synthesis of crop-protection agents.
• Materials science: Pyrazole-containing ligands find use in coordination chemistry and luminescent materials.

The 2-methoxyethyl group on N1 differentiates this compound from N-methyl or N-unsubstituted analogues and can be selected deliberately to tune logP, solubility, or metabolic stability of the target compound.

Ordering, Storage, and Quality

4-Bromo-1-(2-methoxyethyl)-1H-pyrazole is available from Aladdin Scientific under catalog number B590310. To place an order, visit the Aladdin Scientific website, search by SKU or product name, and add the required quantity to your cart. For bulk inquiries or custom pack sizes, contact the Aladdin Scientific sales team directly.

Each shipment is accompanied by a Certificate of Analysis (CoA) confirming identity and purity. Researchers are encouraged to download the CoA from the product page for lot-specific data prior to use. Storage conditions and shelf-life information are stated on the CoA and product label; always refer to these documents for authoritative guidance.

For questions regarding invoicing, returns, or delivery timelines, refer to the Help and Customer Service section of the Aladdin Scientific website or contact customer support.

Frequently asked questions

What reactions can I perform with 4-Bromo-1-(2-methoxyethyl)-1H-pyrazole?

The C-4 bromine atom is the primary reactive handle, enabling palladium- or nickel-catalyzed cross-coupling reactions such as Suzuki–Miyaura (with boronic acids/esters), Negishi (with organozinc reagents), Stille (with organostannanes), and Buchwald–Hartwig amination. These transformations allow introduction of aryl, heteroaryl, vinyl, alkyl, or amino groups at C-4 to generate diverse pyrazole-containing products.

Why choose the 2-methoxyethyl group on N1 instead of a simpler substituent such as methyl or ethyl?

The 2-methoxyethyl group introduces an ether oxygen that increases the polarity and potential aqueous solubility of the molecule compared with purely alkyl N-substituents. In a drug-discovery context, this can improve pharmacokinetic properties such as solubility and may influence metabolic stability. Selecting this substituent at the building-block stage means that the polarity benefit is carried through all downstream synthetic steps without requiring additional transformations.

How should I store 4-Bromo-1-(2-methoxyethyl)-1H-pyrazole to maintain its integrity?

Store the compound according to the conditions specified on the product label and Certificate of Analysis provided with your lot. In general, halogenated heterocyclic building blocks should be kept in a cool, dry, well-sealed container away from moisture, light, and incompatible reagents. Always consult the Safety Data Sheet (SDS) for authoritative storage and handling guidance specific to this compound.

What catalog number should I use when ordering from Aladdin Scientific?

Order 4-Bromo-1-(2-methoxyethyl)-1H-pyrazole using catalog number B590310 on the Aladdin Scientific website. You can search by SKU or full product name. For bulk quantities or special packaging needs, contact the Aladdin Scientific sales team for a custom quotation.

Is a Certificate of Analysis (CoA) available for each lot of B590310?

Yes. Aladdin Scientific provides a Certificate of Analysis with each shipment of B590310, confirming the identity and purity of the specific lot. You can typically download the lot-specific CoA directly from the product page on the Aladdin Scientific website by entering the lot number, or it is included with the physical shipment.

References

1. Elguero, J. Pyrazoles. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984. (General reference on pyrazole chemistry.)
2. Aladdin Scientific. Product page: 4-Bromo-1-(2-methoxyethyl)-1H-pyrazole, SKU B590310. Aladdin Scientific (accessed 2024).

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