4-(1H-pyrrol-1-yl)phenol

4-(1H-Pyrrol-1-yl)phenol (CAS 23351-09-9), also known as 4-pyrrolylphenol or N-(4-hydroxyphenyl)pyrrole, is a heterocyclic aromatic building block consisting of a phenol group attached to a pyrrole ring at the para position. Its structure features a pyrrole ring that contributes to its potential biological activity, while the hydroxyl group enhances its reactivity and hydrogen-bonding capabilities.

The compound typically appears as a cream to light brown powder or colorless to pale yellow solid, with a melting point of 119–122°C and a molecular weight of 159.18 g/mol. Its bifunctional nature enables broad applicability: the electron-rich pyrrole ring undergoes electrophilic substitution and participates in π-conjugated systems, while the phenolic OH provides a handle for esterification, etherification, and hydrogen-bonding interactions.

In medicinal chemistry, 4-(1H-Pyrrol-1-yl)phenol serves as the core scaffold for generating pharmacologically active molecules. A recent study synthesized a series of new 4-(1H-pyrrol-1-yl)phenyl benzoates via reaction of 4-(1H-Pyrrol-1-yl)phenol with substituted benzoyl chlorides, and these derivatives exhibited significant antimicrobial and antitubercular activities with minimum inhibitory concentration values ranging from 0.8 to 12.5 µg/mL. Moreover, 4-(1H-Pyrrol-1-yl)phenol derivatives have been incorporated into ferrocene complexes as potential chemotherapeutic drugs, with moderate anti-proliferative activity observed against the MCF-7 breast cancer cell line.

In materials science, 4-(1H-Pyrrol-1-yl)phenol has been copolymerized with pyrrole to form a cathode material for Li-ion batteries, with the resulting P(PLPY-co-Py) demonstrating a significantly improved specific capacity of 73.9 mAh·g⁻¹ compared to 21.4 mAh·g⁻¹ for pure polypyrrole. This combination of a para-phenol and an N-linked pyrrole provides a unique balance of nucleophilicity, oxidative stability, and conjugation not found in simpler substituted phenols or pyrroles.

Product Parameters

Product Advantages

1.Bifunctional architecture – Combines an electron-rich pyrrole ring (a privileged structure in drug discovery) with a phenolic OH group, enabling dual reactivity patterns: the OH supports esterification, etherification, and hydrogen bonding, while the pyrrole participates in π-conjugated systems and electrophilic substitution.

2.Biologically privileged scaffold – Derivatives have demonstrated significant antimicrobial, antitubercular, and antifungal activities. When incorporated into ferrocene complexes, they exhibit moderate anti-proliferative activity against breast cancer cells (MCF-7).

3.Energy storage potential – Copolymers with pyrrole show specific capacity of 73.9 mAh·g⁻¹ as Li-ion battery cathode materials, significantly higher than pure polypyrrole (21.4 mAh·g⁻¹).

4.Aldose reductase inhibition – The fluorinated derivative has been identified as a submicromolar aldose reductase inhibitor (IC50 = 0.443 µM) with favorable membrane permeation (pKa 7.64).

5. High purity – ≥95% as standard; ≥98% available upon request, with single impurity ≤0.5% and total impurities ≤1.0%.

Synthetic Routes

Several methods have been documented for the synthesis of 4-(1H-Pyrrol-1-yl)phenol:

Method 1: Modified Clauson–Kaas Reaction

A reliable approach involves the reaction of 4-aminophenol with 2,5-dimethoxytetrahydrofuran under acidic conditions. The di-carbonyl equivalent cyclizes with the primary amine to form the pyrrole ring directly onto the aromatic scaffold. This one-step method is convenient for laboratory-scale synthesis and has been used to prepare a series of p-substituted N-phenylpyrroles.

Method 2: Palladium-Catalyzed Cross-Coupling

Ullmann-type coupling enables the direct N-arylation of pyrrole with 4-bromophenol or 4-iodophenol in the presence of a palladium or copper catalyst. The reaction typically occurs under mild conditions and may require a solvent such as ethanol or methanol.

Method 3: Copper-Catalyzed Synthesis

Alternatively, the reaction of 4-chlorophenol with pyrrole in the presence of a copper catalyst provides another synthetic pathway. The efficiency and yield of each method vary depending on the reaction conditions and the purity of starting materials.

Frequently Asked Questions (FAQ)

Q1: What are the primary applications of 4-(1H-Pyrrol-1-yl)phenol?

A: This compound is a versatile building block used in several fields: medicinal chemistry (antimicrobial, antitubercular, anticancer research), materials science (conductive polymers, Li-ion battery cathodes), and organic synthesis (ligands for metal complexes, precursors for functional materials).

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

A: Derivatives have demonstrated significant antimicrobial and antitubercular activities with MIC values ranging from 0.8 to 12.5 µg/mL. Derivatives have also shown antifungal activity against Candida species and moderate anti-proliferative activity against the MCF-7 breast cancer cell line when incorporated into ferrocene complexes. The fluorinated derivative (2-fluoro-4-(1H-pyrrol-1-yl)phenol) is a potent aldose reductase inhibitor (IC50 = 0.443 µM).

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