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Ethyl 3-bromo-1h-pyrazole-5-carboxylate

Ethyl 3-bromo-1H-pyrazole-5-carboxylate (CAS 1886994-07-5) is a high-purity, regiochemically defined heterocyclic building block widely used in pharmaceutical intermediates and medicinal chemistry . This strategically brominated pyrazole ester features two orthogonal reactive handles: a C3-bromine atom for diverse palladium-catalyzed cross-coupling reactions, and a C5-ethyl ester for hydrolysis or amide coupling . The unique 3,5-substitution pattern creates a distinct electronic distribution across the pyrazole ring, making this regioisomeric scaffold particularly valuable for constructing kinase inhibitors, ERK inhibitors for regulating cell proliferation and apoptosis, and agrochemical active ingredients where precise positional control dictates binding orientation in target pockets . Manufactured under controlled conditions with purity ≥95-98% , this intermediate supports drug discovery programs requiring modular diversification of nitrogen-rich heterocyclic architectures with precise regiochemical control.

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Product Name
Ethyl 3-bromo-1H-pyrazole-5-carboxylate
CAS Number
1886994-07-5
Chinese Name
3-溴-1H-吡唑 -5-羧酸乙酯
Synonyms
Ethyl 3-bromopyrazole-5-carboxylate; 1H-Pyrazole-5-carboxylic acid, 3-bromo-, ethyl ester; 3-Bromo-5-ethoxycarbonylpyrazole; C₆H₇BrN₂O₂ heterocycle; ethyl 5-bromo-1H-pyrazole-3-carboxylate
Chinese Synonyms
3-溴吡唑 -5-羧酸乙酯; 3-溴-5-乙氧羰基吡唑; 溴代吡唑羧酸乙酯; 3-溴-1H-吡唑 -5-甲酸乙酯
Molecular Formula
C₆H₇BrN₂O₂
Molecular Weight
219.04 g/mol
Purity
≥ 98% (GC/HPLC area normalization)
Product Category
Pharmaceutical Intermediates / Pyrazole Derivatives / Brominated Heterocyclic Esters
Appearance
White to pale yellow solid
Melting Point
~150-155°C (estimated, literature reference recommended)
Storage Conditions
Store in a cool, dry, well-ventilated area away from light and moisture. Keep container tightly closed under inert atmosphere (nitrogen). Protect from strong bases to avoid ester hydrolysis or debromination side reactions.
Shelf Life
24 months under recommended storage conditions
Packaging
100mg/vial, 500mg/vial, 1g/bottle, 5g/bottle, or customized according to customer requirements
Applications
Kinase inhibitor synthesis via C3 cross-coupling, fused heterocycle construction (regioselective cyclization), agrochemical active ingredient precursors, SAR exploration via bromine displacement, prodrug design via ester modification
Reactivity
Suitable for Suzuki coupling, Buchwald-Hartwig amination, Sonogashira coupling (C3-Br displacement), ester hydrolysis to acid, amide coupling, electrophilic aromatic substitution at C4, and pyrazole N1-derivatization
Special Note
3-Bromo-5-Carboxylate Regioisomer—distinct electronic profile vs. 5-bromo-3-carboxylate analogs (CAS 1328893-17-9). The C3-Br position offers unique coupling kinetics. Ethyl ester provides enhanced lipophilicity vs. methyl analogs. Part of our brominated heterocyclic building block series.