Chemical Identity and Structure

4-Bromo-1H-pyrrole-2-carbonitrile (CAS 41733-55-5) is a five-membered nitrogen-containing aromatic heterocycle bearing two key substituents: a bromine atom at the 4-position and a nitrile (cyano) group at the 2-position. The molecular formula is C₅H₃BrN₂ with a molecular weight of approximately 171.00 g/mol. The pyrrole ring retains its NH proton at the 1-position, making this compound a valuable bifunctional synthon in which the C–Br bond is amenable to palladium-catalyzed cross-coupling and the nitrile group can be transformed into amidines, tetrazoles, amines, or carboxylic acid derivatives under appropriate conditions.

Solubility, Storage, and Handling

4-Bromo-1H-pyrrole-2-carbonitrile is generally soluble in common polar aprotic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and tetrahydrofuran (THF). Solubility in dichloromethane and ethyl acetate is also reported to be moderate to good, while solubility in water is low due to the compound's relatively hydrophobic character. For stock solution preparation, DMSO is typically the preferred solvent for biological assay compatibility.

The compound should be stored in a cool, dry, well-ventilated location, tightly sealed, and protected from light and moisture. Refrigerated storage (2–8 °C) under an inert atmosphere (nitrogen or argon) is recommended for long-term preservation. When handling, standard laboratory personal protective equipment (PPE) — including nitrile gloves, safety goggles, and a laboratory coat — should be worn. Operations should be performed in a fume hood given the potential for irritation associated with both organobromine and nitrile-containing compounds.

Synthetic Applications and Reactivity

The dual electrophilic handles on 4-Bromo-1H-pyrrole-2-carbonitrile make it an exceptionally versatile intermediate in multi-step synthesis. The aryl C–Br bond undergoes efficient palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura, Negishi, Stille, and Buchwald–Hartwig amination reactions, enabling rapid diversification of the pyrrole core with aryl, vinyl, alkyl, and amino substituents.

The nitrile group at C-2 can be hydrolyzed to the corresponding carboxylic acid, reduced to the primary amine, reacted with azides to form tetrazoles, or converted to amidines — all transformations frequently exploited in medicinal chemistry lead optimization. The NH at N-1 can also be alkylated or acylated to modulate pharmacokinetic properties. Together, these features make 4-Bromo-1H-pyrrole-2-carbonitrile a privileged scaffold for the preparation of bioactive heterocyclic libraries.

Purity, Specification, and Quality

Aladdin Scientific supplies 4-Bromo-1H-pyrrole-2-carbonitrile (SKU: B480200) as a research-grade reagent. Typical purity specifications for research-grade material are ≥95% as determined by HPLC or GC analysis. Customers requiring confirmation of purity and identity for their specific application are encouraged to request a Certificate of Analysis (CoA), which includes data such as melting point, NMR, HPLC purity, and appearance. For applications with stringent purity requirements — such as biological screening or reference standard preparation — please contact Aladdin Scientific to discuss available grades and custom analytical services.

Regulatory and Safety Considerations

As with all organobromine and nitrile-containing compounds, 4-Bromo-1H-pyrrole-2-carbonitrile should be treated as a potential irritant to skin, eyes, and the respiratory tract. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use. Waste disposal must comply with applicable local, national, and institutional regulations governing halogenated organic waste. The compound is intended for research use only and is not approved for use in humans, animals, or food products. Import/export of this material may be subject to country-specific regulations; buyers are responsible for ensuring compliance.