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CS-W001157 4
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Ethyl 2-bromo-1H-imidazole-5-carboxylate

  • CAS No. 74478-93-6

  • Cat. No. CS-W019080
  • Purity≥98%
  • MDL No.MFCD10697827

*For research and further manufacturing use only, not for direct human use.

Ethyl 2-bromo-1H-imidazole-5-carboxylate|CS-W019080

Structure of 74478-93-6

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General Information

  • CAS No. 74478-93-6
  • Cat. No. CS-W019080
  • Purity ≥98%
  • MDL No. MFCD10697827
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇BrN₂O₂
  • Molecular Weight 219.04
  • Synonym(s) methyl 2-bromo-1H-imidazole-5-carboxylate
  • SMILES O=C(C1=CN=C(Br)N1)OCC

Description

Ethyl 2-bromo-1H-imidazole-5-carboxylate features a brominated imidazole core with a pendant ethyl ester, enabling direct functionalization in cross-coupling and heterocycle elaboration. The electron-deficient ring facilitates nucleophilic substitution, while the ester group supports further derivatization. This bench-stable reagent integrates efficiently into synthetic sequences requiring regioselective halogen handling.

Application

Ethyl 2-bromo-1H-imidazole-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions at the C2 position. The bromine substituent exhibits high reactivity in Suzuki, Stille, and Negishi couplings, facilitating the construction of biologically relevant imidazole scaffolds. Its bench-stable nature and compatibility with diverse functional groups make it ideal for iterative synthetic sequences in medicinal chemistry and process development workflows.

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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Computational Chemistry Data

  • TPSA   54.98
  • LogP   1.3489
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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