Ethyl 5-bromo-1H-imidazole-2-carboxylate

CAS No. 944900-49-6
Cat. No. CS-W005885
Purity≥97%
MDL No.MFCD09842485

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Ethyl 5-bromo-1H-imidazole-2-carboxylate|CS-W005885

Structure of 944900-49-6

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Description

Ethyl 5-bromo-1H-imidazole-2-carboxylate features a brominated imidazole core with enhanced electrophilicity at the C5 position, enabling efficient coupling in cross-coupling reactions. The ester functionality provides solubility in common organic solvents and facilitates downstream transformations. This bench-stable reagent integrates readily into heterocyclic synthesis workflows.

Application

Ethyl 5-bromo-1H-imidazole-2-carboxylate serves as a versatile building block for the synthesis of imidazole-based heterocycles, enabling direct functionalization at the C5 position via palladium-catalyzed cross-coupling reactions. The bromo group exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the ester functionality supports subsequent hydrolysis or reduction. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for medicinal chemistry campaigns and API intermediate development.

General Information

CAS No. 944900-49-6
Cat. No. CS-W005885
Purity ≥97%
MDL No. MFCD09842485
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₇BrN₂O₂
Molecular Weight 219.04
Synonym(s) ethyl 5-bromo-Imidazole-2-carboxylate
SMILES O=C(C1=NC=C(Br)N1)OCC

Computational Chemistry Data

TPSA 54.98
LogP 1.3489
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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Ethyl 5-bromo-1H-imidazole-2-carboxylate

CAS No. 944900-49-6

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