4-(1H-PYRROL-1-YL)BENZOIC ACID

4-(1H-Pyrrol-1-yl)benzoic acid (CAS 22106-33-8) is a multifunctional building block widely employed in drug discovery, organic synthesis, and functional materials. Its dual nature — featuring both an electron-rich pyrrole heterocycle and a carboxylic acid handle — allows for versatile derivatization.

In drug development, 4-(1H-Pyrrol-1-yl)benzoic acid serves as a privileged scaffold. Research has demonstrated that derivatives of this compound exhibit potent inhibition of the bacterial enzyme fatty acid synthetase, with demonstrated antibacterial activity against Staphylococcus aureus and other bacterial strains. Furthermore, pyrrole-1-yl benzoic acid derivatives have been identified as useful Myc inhibitors (e.g., c-Myc), offering therapeutic potential for Myc-mediated disorders such as cancer and other proliferative diseases.

The structure of 4-(1H-Pyrrol-1-yl)benzoic acid also enables its use as a functional material. The conjugated system facilitates electron transfer, and the compound can serve as a ligand in metal-organic frameworks (MOFs) or as a precursor for covalent organic frameworks (COFs). Additionally, 4-(1H-Pyrrol-1-yl)benzoic acid is utilized in organic electronics, particularly in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices.

Product Parameters

Frequently Asked Questions (FAQ)

Q1: What is the primary use of 4-(1H-Pyrrol-1-yl)benzoic acid?

A: It is primarily used as a building block in medicinal chemistry and organic synthesis. The compound serves as a precursor for generating drug-like molecules, especially those targeting bacterial infections (antibacterial and antitubercular agents), cancer (Myc inhibitors), and inflammatory diseases. It is also used in materials science, particularly in MOFs and OLEDs.

Q2: Is 4-(1H-Pyrrol-1-yl)benzoic acid soluble in common organic solvents?

A: The compound has limited solubility in non-polar organic solvents due to its polar carboxylic acid group. It is typically soluble in polar aprotic solvents such as DMSO and DMF, and in basic aqueous solutions (e.g., NaOH or KOH) due to deprotonation of the carboxylic acid.

Q3: What is the stability of this compound under ambient conditions?

A: The compound is moisture-sensitive and should be stored sealed in a dry environment at room temperature. When stored properly, it remains stable for extended periods.

Applications

1.Antibacterial Drug Discovery

A research team is screening novel scaffolds for activity against drug-resistant Staphylococcus aureus. 4-(1H-Pyrrol-1-yl)benzoic acid serves as a starting point for generating hydrazide analogs, which can be further cyclized to oxadiazole or triazole ring systems — classes known for enhanced antibacterial and antitubercular activities.

2.Cancer Research (Myc Inhibition)

Derivatives of 4-(1H-Pyrrol-1-yl)benzoic acid have been identified as potent inhibitors of the c-Myc oncogene. A pharmaceutical company developing targeted cancer therapies uses this scaffold to generate small-molecule candidates for Myc-mediated malignancies.

3.Materials Science (MOF and COF Synthesis)

The bifunctional structure (pyrrole and carboxylic acid) makes 4-(1H-Pyrrol-1-yl)benzoic acid an excellent ligand for constructing metal-organic frameworks. A materials science research group employs this compound to synthesize porous coordination polymers with gas adsorption or catalytic properties.

4.Organic Electronics (OLED Development)

The conjugated D–π–A system of 4-(1H-Pyrrol-1-yl)benzoic acid enables electron transport properties suitable for organic light-emitting diodes. Researchers incorporate this scaffold into hole-transporting or electron-transporting layers in next-generation OLED devices.

5.Antitubercular Research

Pyrrole-based compounds have shown significant activity against Mycobacterium tuberculosis. 4-(1H-Pyrrol-1-yl)benzoic acid is used as a core scaffold for generating inhibitors targeting enoyl ACP reductase (InhA) and dihydrofolate reductase (DHFR) — two critical enzymes for tuberculosis treatment.

Safety & Handling – What You Need to Know

This compound carries multiple hazard classifications:

Required Protective Measures:

● Eyes: Safety goggles (mandatory).

● Skin: Chemical-resistant gloves (nitrile). If you have a history of skin allergies, take extra precautions due to skin sensitizer classification.

● Respiratory: Use in a fume hood. Avoid breathing dust.

● First aid:

1. Eye contact – rinse with water for 15 min (S26).

2. Skin contact – wash with soap and water. If rash or irritation develops, seek medical advice (skin sensitizer).

3. Inhalation – move to fresh air.

● Storage: Keep container tightly sealed in a dry place at room temperature. Store away from ignition sources (combustible solid). Avoid contact with strong mineral acids (releases irritating free monoester).

● Disposal: Collect as chemical waste. WGK 1 indicates low water hazard, but best practice is not to flush down drains.

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