1-(4-CHLOROPHENYL)-1H-PYRROLE

1-(4-Chlorophenyl)-1H-pyrrole (CAS 5044-38-2) is a heterocyclic aromatic compound belonging to the pyrrole family — a five-membered ring structure containing one nitrogen atom — with a 4-chlorophenyl substituent directly attached to the pyrrole nitrogen. The molecular formula is C₁₀H₈ClN, with a molecular weight of 177.63 g/mol, and the compound is supplied at purities ranging from 95% to 98%.

In medicinal chemistry, 1-(4-chlorophenyl)-1H-pyrrole is a highly versatile building block. As a fragment molecule, 1-(4-chlorophenyl)-1H-pyrrole provides a structural foundation for molecular linking, expansion, and modification in drug discovery programs, serving as a key intermediate for the synthesis of biologically active molecules, including antimicrobial, anticancer, and anti-inflammatory agents. Studies have demonstrated that 1-(4-chlorophenyl)-1H-pyrrole exhibits significant antiproliferative effects against various cancer cell lines, including liver cancer (HepG-2, IC₅₀ = 5.0 μM) and breast cancer (MCF-7, IC₅₀ = 3.0 μM). Its derivatives have also shown antimicrobial activity and have been explored for their anti-inflammatory properties.

In materials science, 1-(4-chlorophenyl)-1H-pyrrole has been investigated for use in organic electronics, including organic light-emitting diodes (OLEDs) and solar cells, leveraging its conjugated π-system for charge transport properties. The 4-chlorophenyl moiety can be further functionalized, allowing the introduction of additional substituents or modifications to tailor the compound’s properties for specific applications.

1-(4-Chlorophenyl)-1H-pyrrole is also a valuable research chemical in chemical synthesis, and it is listed in the National Cancer Institute (NCI) database under NSC 116796.

Product Parameters

Frequently Asked Questions (FAQ)

Q1:What is the significance of the LogP value?

A: The calculated LogP of 3.13 indicates moderate to high lipophilicity, suggesting good membrane permeability and potential oral bioavailability for drug-like applications. Compared to unsubstituted 1-phenylpyrrole (LogP = 2.53), the chlorine substitution increases the compound’s lipophilicity, which may enhance its ability to cross cell membranes and reach biological targets.

Q2: Has 1-(4-Chlorophenyl)-1H-pyrrole demonstrated anticancer activity?

A: Yes. Studies have shown that this compound exhibits significant antiproliferative effects against various cancer cell lines, including liver cancer (HepG-2, IC₅₀ = 5.0 μM) and breast cancer (MCF-7, IC₅₀ = 3.0 μM). These findings suggest its potential as a lead scaffold for anticancer drug development.

Precautionary Statements:

● Avoid breathing dust/fume/gas/mist/vapours/spray

● Use only outdoors or in a well-ventilated area

● Wear protective gloves/protective clothing/eye protection/face protection

● Wash thoroughly after handling

● IF ON SKIN: Wash with plenty of water

● IF INHALED: Remove person to fresh air and keep comfortable for breathing

● IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing

● Call a POISON CENTER/doctor if you feel unwell

● Take off contaminated clothing and wash it before reuse

● Store in a well-ventilated place. Keep container tightly closed

● Store locked up

● Dispose of contents/container in accordance with local regulations

First aid measures:

● If inhaled: Move person into fresh air. If not breathing, give artificial respiration. Consult a physician.

● In case of skin contact: Wash off with soap and plenty of water. Consult a physician if skin irritation persists.

● In case of eye contact: Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. Continue rinsing during transport to hospital.

● If swallowed: Rinse mouth with water. Never give anything by mouth to an unconscious person. Consult a physician.

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