Description

Ethyl 5-bromo-1H-imidazole-4-carboxylate (CAS No. 944906-76-7) is a high-purity brominated imidazole derivative with the molecular formula C₆H₇BrN₂O₂. This compound is a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure, featuring a reactive bromo substituent and an ester group, makes it an ideal building block for heterocyclic chemistry and medicinal chemistry applications. The product is supplied as a crystalline solid with ≥95% purity (HPLC), ensuring consistency for research and industrial use. It is packaged under inert conditions to maintain stability and is available in quantities ranging from milligrams to kilograms to meet diverse laboratory and production needs. Suitable for use in Suzuki couplings, nucleophilic substitutions, and other cross-coupling reactions.

Properties

• CAS Number: 944906-76-7
• Complexity: 154
• IUPAC Name: ethyl 5-bromo-1H-imidazole-4-carboxylate
• InChI: InChI=1S/C6H7BrN2O2/c1-2-11-6(10)4-5(7)9-3-8-4/h3H,2H2,1H3,(H,8,9)
• InChI Key: YFNDBQRGZTZNRU-UHFFFAOYSA-N
• Exact Mass: 217.96909
• Molecular Formula: C6H7BrN2O2
• Molecular Weight: 219.04
• SMILES: CCOC(=O)C1=C(NC=N1)Br
• Topological: 55
• Monoisotopic Mass: 217.96909
• Synonyms: ethyl 5-bromo-1H-imidazole-4-carboxylate, 944906-76-7, 840-825-0, Ethyl 4-bromo-1H-imidazole-5-carboxylate, MFCD10697506, 5-Imidazolic acid, 4-bromo-, ethyl ester, SCHEMBL16102526, BCP34561, UMB90676, AB59775, ethyl5-bromo-1H-imidazole-4-carboxylate, DB-108919, CS-0056203, Ethyl 4-bromo-1H-imidazole-5-carboxylate #, F30600, EN300-3175119, Ethyl 4-bromo-1H-imidazole-5-carboxylate;5-Bromo-1(3)H-imidazole-4-carboxylic acid ethyl ester

Application

Ethyl 5-bromo-1H-imidazole-4-carboxylate is widely used as a key intermediate in the synthesis of biologically active molecules, including antiviral and anticancer agents. Its reactive bromo group facilitates palladium-catalyzed cross-coupling reactions, enabling the construction of complex imidazole-based scaffolds. Researchers also employ this compound in the development of enzyme inhibitors and receptor modulators due to its imidazole core, which mimics histidine residues in proteins. Additionally, it serves as a precursor for functionalized imidazoles in material science and coordination chemistry.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• Acute Tox. 4 (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.