4-(1-Pyrrolyl)benzoic acid

4-(1-Pyrrolyl)benzoic acid features a pyrrole ring, which is a privileged motif in natural products and pharmaceuticals — it appears in porphyrins, chlorophyll, and many drugs (e.g., atorvastatin, sunitinib, and various anticancer agents). Attaching a carboxylic acid group at the para position of the N‑phenyl ring of 4‑(1‑Pyrrolyl)benzoic acid creates a versatile handle for further functionalization. This compound is used as a building block in the synthesis of:

● Kinase inhibitors (e.g., targeting EGFR, VEGFR, or CDKs),

● Antimicrobial agents (pyrrole derivatives show activity against drug‑resistant bacteria and fungi),

● Organic semiconductors (the conjugated N‑arylpyrrole unit can transport charge),

● Fluorescent probes (the rigid structure can emit in the visible region).

4-(1-Pyrrolyl)benzoic acid is also an intermediate for more complex heterocycles and a reference standard for impurity analysis in pharmaceutical manufacturing. Cosperpharm supplies 4‑(1‑Pyrrolyl)benzoic acid with high purity (≥98% by HPLC), fully characterized, and packaged under moisture‑protective conditions. It is classified as a combustible solid (storage class 11) with hazard categories: eye irritation category 2, dermal irritation category 2, and STOT‑SE category 3 (respiratory tract irritation). Standard precautions apply.

Product Parameters

Product Advantages – Why This N-Arylpyrrole Stands

Quality Assurance at Cosperpharm

Each batch undergoes:

● Gas chromatography (GC) – purity ≥97.0%

● Non‑aqueous titration – purity ≥97.0%

● Refractive index – confirmatory analysis

● ¹H NMR – structural verification

l Appearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.

Key Applications

1. Medicinal Chemistry – Kinase Inhibitors and Beyond

The 4-(1-Pyrrolyl)benzoic acid motif appears in a variety of bioactive molecules:

● Kinase inhibitors: The pyrrol‑1‑yl group can occupy the hydrophobic back pocket of ATP‑binding sites. For example, sunitinib (Sutent®) contains an indolinone‑pyrrole structure; related N‑arylpyrroles have been explored as inhibitors of VEGFR, PDGFR, and c‑Kit. The carboxylic acid provides a site for attaching solubilizing groups or targeting ligands.

● Antimicrobial agents: Pyrrole derivatives show activity against Mycobacterium tuberculosis, Staphylococcus aureus, and Candida species. The carboxyl group can be converted to amides to optimize potency and pharmacokinetics.

● Anti‑inflammatory compounds: Some N‑arylpyrroles inhibit COX‑2 or 5‑lipoxygenase, offering potential for treating inflammatory diseases.

2. Organic Materials – Semiconductors and Sensors

The planar, conjugated N‑arylpyrrole unit is an electron‑rich heterocycle that can act as a hole‑transporting material. Researchers have incorporated this building block into:

● Organic field‑effect transistors (OFETs) – as a component of conjugated polymers.

● Organic light‑emitting diodes (OLEDs) – the pyrrole unit can contribute to fluorescence.

● Chemical sensors – the carboxylic acid can bind metal ions or be used to immobilize the molecule on surfaces for detecting analytes.

3. Ligand for Coordination Chemistry

The nitrogen of the pyrrole can coordinate to metal centers, while the carboxylate can anchor the ligand. This compound has been used to construct metal‑organic frameworks (MOFs) and coordination polymers with potential applications in gas storage, catalysis, and drug delivery. The rigid geometry (the N‑aryl bond prevents free rotation) leads to predictable network topologies.

4. Intermediate for Heterocyclic Synthesis

The carboxylic acid can be transformed into a variety of functional groups (acid chloride, ester, amide, alcohol, aldehyde). Further reactions, such as cyclization of ortho‑substituted amides or cross‑coupling on the pyrrole ring (electrophilic substitution at the 2‑ and 5‑positions of pyrrole), allow access to fused heterocycles like indoles, carbazoles, and pyrrolo‑pyridines.

5. Reference Standard for Impurity Analysis

In the manufacturing of pyrrole‑containing pharmaceuticals, this compound may appear as a starting material residue or degradation product. Cosperpharm supplies it as a certified reference standard for HPLC method development and quality control.

Contact Cosperpharm – Add This Versatile Pyrrole to Your Toolbox

Looking for a high‑purity N‑arylpyrrole building block for your next drug discovery or materials project? Cosperpharm supplies 4-(1-Pyrrolyl)benzoic acid (CAS 22106‑33‑8) with ≥98% purity, full characterization, and moisture‑protective packaging. We support research quantities from 1 g to 1 kg, and larger scales upon request.