1-(4-BROMO-PHENYL)-1H-PYRROLE

1-(4-BROMO-PHENYL)-1H-PYRROLE (CAS 5044-39-3) is a key heterocyclic building block used in the fields of medicinal chemistry, materials science and organic synthesis. It consists of a pyrrole ring and a para-substituted bromophenyl ring attached to the pyrrole nitrogen. Owing to the bromine atom at the para position of the phenyl ring and the versatile pyrrole moiety, 1-(4-Bromophenyl)-1H-pyrrole is an important starting material for further functionalization. The compound has been used in the synthesis of more complex organic molecules for pharmaceutical and agrochemical applications, and is also applied in the development of new polymeric materials, metal-organic frameworks (MOFs), sensors and organic semiconductors. 1-(4-Bromophenyl)-1H-pyrrole is also a subject of research for its diverse biological activities, including antimicrobial, antioxidant, anti-inflammatory and anticancer properties, and its derivatives have shown potential as inhibitors in cancer therapy and as building blocks for drug discovery.

1-(4-BROMO-PHENYL)-1H-PYRROLE is also used as a precursor for the synthesis of coumarin derivatives with promising fluorescence and electrochemical properties for biological imaging applications, and for the development of novel materials with unique electronic or optical properties. In the pharmaceutical sector, 1-(4-Bromophenyl)-1H-pyrrole is widely used in the synthesis of antiviral drugs and other active pharmaceutical ingredients (APIs), and in the polymer and semiconductor industries, it serves as a valuable precursor for high-performance materials and can be used as a dopant.

Product Parameters

Synthetic Routes

This compound can be prepared from commercially available 4-bromoaniline using a recyclable L-(+)-tartaric acid/choline chloride-based deep eutectic solvent (DES) as a green and sustainable reaction medium at 90°C .

General procedure:

1.Add 4-bromoaniline (1 mmol), 2,5-dimethoxytetrahydrofuran (1.1 mmol) and L-(+)-tartaric acid/choline chloride-based DES (1.5 g) to a 50 mL round-bottom flask .

2.Stir the reaction mixture at 90 °C. Monitor the progress of the reaction by thin-layer chromatography (TLC).

3.After completion, cool the mixture to room temperature and extract the target product 1-(4-Bromophenyl)-1H-pyrrole with ethyl acetate.

4.After evaporation of the solvent, purify the residue by silica gel column chromatography to afford the pure product.

5. The DES can be dried under vacuum and reused in subsequent cycles.

Frequently Asked Questions (FAQ)

Q1:What are the key chemical reactions this compound can undergo?

A: It can participate in (1) cross-coupling reactions at the bromine position (Suzuki, Heck, Sonogashira), (2) N-alkylation or acylation at the pyrrole nitrogen, and (3) electrophilic substitution on the pyrrole ring, enabling the construction of complex molecular architectures .

Q2: What biological activities have been reported for this compound?

A: Research indicates it has antimicrobial activity against various pathogens. Compounds with a similar structure have also shown significant antibacterial effects against Gram-positive (S. aureus) and Gram-negative (E. coli) bacteria, as well as potential for use in cancer therapy, where its derivatives have been studied as inhibitors for cancer-related targets .

Storage Conditions

● Temperature: Sealed in dry, room temperature (15–25 °C); do not freeze. For long-term storage, store in a cool, dry place .

● Container: Airtight, tightly sealed container

● Protection: Store away from moisture, light, and strong oxidizing agents

● Desiccation: Keep in a dry environment; the compound is stable under anhydrous conditions

● Stability: Stable under recommended storage conditions for up to 24 months

● Incompatibilities: Strong oxidizing agents, strong bases, strong acids

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