ETHYL 4-(1H-PYRROL-1-YL)BENZOATE

ETHYL 4-(1H-PYRROL-1-YL)BENZOATE features a pyrrole unit – a five‑membered, nitrogen‑containing heterocycle – widely recognized as a privileged scaffold in both natural products and synthetic drug molecules, with established utility across pharmaceutical, agrochemical, and materials science applications. The conjugated system of the pyrrole ring with the electron‑withdrawing ester group in ETHYL 4-(1H-PYRROL-1-YL)BENZOATE imparts unique reactivity and enhances its utility as a synthetic intermediate.

At room temperature, ETHYL 4-(1H-PYRROL-1-YL)BENZOATE is reported as either a solid (melting point 74 °C) or a colorless liquid with a characteristic aromatic odor similar to benzoic esters. The ethyl ester group provides a convenient handle for further transformation, including hydrolysis to the corresponding carboxylic acid or reduction to the alcohol.

In recent years, with the continuous expansion of heterocyclic chemistry in drug discovery and the growing demand for versatile pyrrole‑containing building blocks, ETHYL 4-(1H-PYRROL-1-YL)BENZOATE has gained significant traction in medicinal chemistry, organic synthesis, and fine chemical research worldwide.

Product Parameters

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

● 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.

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Preparation Notes

Ethyl 4‑(1H‑pyrrol‑1‑yl)benzoate can be synthesized via the Clauson‑Kaas reaction, which involves the condensation of 4‑aminobenzoic acid ethyl ester (ethyl 4‑aminobenzoate) with 2,5‑dimethoxytetrahydrofuran under acidic conditions. The reaction proceeds through the formation of a dicarbonyl intermediate, followed by Paal‑Knorr‑type cyclization to afford the N‑substituted pyrrole product. Purification is typically achieved by recrystallization or column chromatography, yielding the target compound as a white to off‑white solid (melting point 74 °C). This synthetic route is scalable and amenable to good manufacturing practices (GMP) for pharmaceutical intermediate production.

Frequently Asked Questions (FAQ)

Q1: What is the structural difference between ethyl 4‑(1H‑pyrrol‑1‑yl)benzoate and its regioisomer ethyl 2‑pyrrol‑1‑ylbenzoate?

A: The key difference lies in the position of the pyrrole substitution on the benzene ring.

● Ethyl 4‑(1H‑pyrrol‑1‑yl)benzoate (CAS 5044‑37‑1) has the pyrrole ring attached at the para position (position 4) relative to the ethyl ester group.

● Ethyl 2‑pyrrol‑1‑ylbenzoate (CAS ‑) has the pyrrole attached at the ortho position (position 2).

The para‑substituted isomer (5044‑37‑1) is more commonly used in pharmaceutical research due to its synthetic accessibility and predictable reactivity profile. The ortho isomer can exhibit different steric and electronic properties, which may affect its behavior in cross‑coupling reactions and biological assays.

Q2: What are the typical reaction pathways for further functionalizing this compound?

A: Ethyl 4‑(1H‑pyrrol‑1‑yl)benzoate offers two primary handles for further chemistry:

● Ester group: Can be hydrolyzed (e.g., with NaOH/EtOH) to yield 4‑(1H‑pyrrol‑1‑yl)benzoic acid, which can then be converted to amides, hydrazides, or acid chlorides. It can also be reduced (e.g., with LiAlH₄ or DIBAL‑H) to the corresponding primary alcohol (4‑(1H‑pyrrol‑1‑yl)benzyl alcohol). The ester can also undergo transesterification to produce other alkyl ester derivatives.

● Pyrrole ring: The pyrrole nitrogen can undergo N‑alkylation or N‑acylation under basic conditions. The pyrrole ring can also participate in electrophilic substitution reactions (e.g., Vilsmeier‑Haack formylation, bromination) due to its electron‑rich character, offering additional sites for diversification.

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