3-(4-Bromophenyl)-1H-1,2,4-triazole: Properties & Lab FAQ

3-(4-Bromophenyl)-1H-1,2,4-triazole is a halogenated heteroaromatic building block widely used in medicinal chemistry, materials science, and synthetic organic chemistry for the preparation of triazole-containing bioactive compounds and functional materials.

Product SKU

B179984

Molecular Formula

C₈H₆BrN₃

Core Scaffold

1H-1,2,4-triazole with a 4-bromophenyl substituent at the 3-position

Key Functional Handle

Aryl bromide suitable for palladium-catalyzed cross-coupling reactions

Primary Application

Pharmaceutical intermediate and heterocyclic building block in drug discovery

Storage Recommendation

Store in a cool, dry, well-ventilated area away from light and moisture

What Is 3-(4-Bromophenyl)-1H-1,2,4-triazole?

3-(4-Bromophenyl)-1H-1,2,4-triazole (Aladdin SKU: B179984) is a nitrogen-rich heterocyclic compound combining a 1H-1,2,4-triazole ring with a para-bromophenyl group at the 3-position. The 1,2,4-triazole ring is a five-membered aromatic heterocycle containing three nitrogen atoms, known for its metabolic stability, hydrogen-bonding capability, and ability to coordinate metal ions. The para-bromine substituent on the phenyl ring provides a versatile handle for further chemical elaboration via cross-coupling and other transition-metal-catalyzed reactions.

This compound belongs to the broader family of aryl triazoles that are extensively explored in drug discovery programs due to the privileged status of the triazole motif in medicinal chemistry. It is supplied by Aladdin Scientific as a high-purity research reagent for use in synthetic and pharmaceutical research.

Chemical Properties and Structure

The 1H-1,2,4-triazole tautomer is the predominant form of this compound under standard conditions. The ring nitrogen atoms can act as both hydrogen-bond donors (N–H) and acceptors, making the molecule an effective pharmacophore element. Key structural features include:

• Aromaticity: The triazole ring is fully aromatic, conferring planar geometry and electronic delocalization.
• Aryl Bromide: The C–Br bond at the para position of the phenyl ring is well-suited for Suzuki–Miyaura, Buchwald–Hartwig, and other palladium- or copper-catalyzed coupling reactions, enabling library synthesis and lead optimization.
• Amphiphilic Character: The combination of a polar triazole ring and a lipophilic bromophenyl group balances aqueous solubility and membrane permeability considerations relevant to drug-like properties.

The molecular weight is approximately 224.06 g/mol (subject to confirmation against the certificate of analysis). Researchers should consult the product certificate of analysis (CoA) for the exact confirmed molecular weight, purity, and spectral data.

Handling, Solubility, and Storage

Solubility: 3-(4-Bromophenyl)-1H-1,2,4-triazole is generally soluble in polar organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and methanol. Solubility in water alone is expected to be limited due to the lipophilic bromophenyl group; co-solvent systems or pH adjustment may be required for aqueous assays. Always prepare a fresh stock solution and verify concentration by UV-Vis or analytical HPLC before use in sensitive biological assays.

Handling: Follow standard laboratory safety practices. Wear appropriate personal protective equipment (PPE) including gloves, lab coat, and eye protection. The aryl bromide moiety poses no extraordinary acute hazard under normal research use, but the compound should be handled in a fume hood. Consult the Safety Data Sheet (SDS) provided with the product for comprehensive hazard information.

Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated location away from direct light and sources of ignition. Refrigerated storage (2–8 °C) is commonly recommended for long-term stability of aryl triazoles; confirm the recommended storage conditions on the product label or CoA.

Applications in Research

3-(4-Bromophenyl)-1H-1,2,4-triazole serves as a versatile intermediate in multiple research domains:

• Medicinal Chemistry and Drug Discovery: The 1,2,4-triazole nucleus is present in numerous clinical drugs (e.g., antifungal agents such as fluconazole and related azoles). This building block allows researchers to construct novel triazole-containing analogs for biological evaluation. The aryl bromide handle enables rapid diversification via palladium-catalyzed coupling to introduce diverse aryl, heteroaryl, or amino substituents.
• Coordination Chemistry and Materials Science: Triazoles are excellent ligands for transition metals (Cu, Ag, Zn, Co, etc.), making this compound a precursor for metal–organic frameworks (MOFs), coordination polymers, and luminescent materials.
• Fragment-Based Drug Design: The compact, rigid, and pharmacophore-rich structure of this compound makes it suitable as a fragment in fragment-based lead discovery (FBLD) campaigns.
• Agrochemical Research: Triazole-based scaffolds are important in fungicide and herbicide research, and aryl-substituted triazoles serve as starting points for structure–activity relationship (SAR) studies.

Ordering and Quality Information

3-(4-Bromophenyl)-1H-1,2,4-triazole is available from Aladdin Scientific under SKU B179984. When placing an order, consider the following:

• Purity: Aladdin Scientific provides a certificate of analysis (CoA) with each lot. Researchers requiring ultra-high purity for sensitive assays should request the CoA and confirm purity by independent analytical methods if necessary.
• Pack Sizes: Multiple pack sizes may be available to suit small-scale discovery work through to larger preparative needs. Contact Aladdin Scientific customer service or visit the product page for current availability.
• Regulatory Compliance: This compound is intended for research use only and is not approved for human therapeutic use. Ensure compliance with all applicable local regulations regarding receipt, storage, and use of chemical reagents.
• Returns and Quality Issues: If you receive a product that does not meet the stated specifications, contact Aladdin Scientific customer service promptly with your order number and lot number to initiate a return or replacement inquiry.

Frequently asked questions

What is the molecular formula and molecular weight of 3-(4-Bromophenyl)-1H-1,2,4-triazole?

The molecular formula of 3-(4-Bromophenyl)-1H-1,2,4-triazole is C₈H₆BrN₃, corresponding to a molecular weight of approximately 224.06 g/mol. Researchers should always confirm the exact molecular weight and purity against the certificate of analysis (CoA) provided with each lot from Aladdin Scientific (SKU: B179984).

In which solvents is 3-(4-Bromophenyl)-1H-1,2,4-triazole soluble?

This compound is generally soluble in polar organic solvents including DMSO, DMF, and methanol. Aqueous solubility is expected to be low due to the lipophilic bromophenyl moiety; for biological assays requiring aqueous media, prepare a concentrated DMSO stock solution and dilute into the aqueous buffer immediately before use, keeping the final DMSO concentration within assay-compatible limits.

What cross-coupling reactions can be performed using the aryl bromide of this compound?

The para-aryl bromide in 3-(4-Bromophenyl)-1H-1,2,4-triazole is compatible with a range of palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura coupling (with aryl or alkenyl boronic acids/esters), Buchwald–Hartwig amination (to introduce amine groups), Negishi coupling, and Sonogashira coupling (with terminal alkynes). Copper-mediated Ullmann-type reactions are also feasible. These reactions enable efficient diversification of the scaffold for medicinal chemistry and materials chemistry applications.

How should 3-(4-Bromophenyl)-1H-1,2,4-triazole be stored to maintain stability?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, protected from light and moisture. Refrigerated storage at 2–8 °C is commonly recommended for aryl triazole building blocks to maximize shelf life. Always confirm the storage conditions specified on the Aladdin Scientific product label or CoA for this specific lot.

What is the intended use of 3-(4-Bromophenyl)-1H-1,2,4-triazole from Aladdin Scientific?

This product (SKU: B179984) is supplied strictly for research purposes and is not intended for diagnostic, therapeutic, or food/feed applications. It is used as a synthetic building block and pharmaceutical intermediate in medicinal chemistry, coordination chemistry, and materials science research.

How can I request a certificate of analysis (CoA) or safety data sheet (SDS) for this product?

Certificates of analysis and safety data sheets for 3-(4-Bromophenyl)-1H-1,2,4-triazole (SKU: B179984) can be obtained through the Aladdin Scientific website product page or by contacting Aladdin Scientific customer service directly with your lot number. Always reference the lot number printed on the product label when requesting batch-specific documentation.

References

1. Küçükgüzel, Ş. G.; Senkardes, S. Recent advances in bioactive 1,2,4-triazoles. Eur. J. Med. Chem. 2015, 97, 786–815.
2. Gomtsyan, A. Heterocycles in drugs and drug discovery. Chem. Heterocycl. Compd. 2012, 48, 7–10.
3. Aladdin Scientific. Product Page: 3-(4-Bromophenyl)-1H-1,2,4-triazole, SKU B179984. Aladdin Scientific Corp.

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