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

CAS No. 149520-94-5
Cat. No. CS-W003670
Purity≥95%
MDL No.MFCD09864446

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Ethyl 2-amino-1H-imidazole-5-carboxylate|CS-W003670

Structure of 149520-94-5

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Description

Ethyl 2-amino-1H-imidazole-5-carboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring a nucleophilic amino group and an electrophilic ester handle. This imidazole scaffold integrates readily into medicinal chemistry campaigns, enabling direct coupling or derivatization under mild conditions. The ethyl ester facilitates downstream transformations such as hydrolysis or amidation, while the electron-rich imidazole ring supports metal coordination and hydrogen bonding in catalytic systems.

Application

Ethyl 2-amino-1H-imidazole-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to imidazole-based scaffolds. Its amino and ester functionalities provide orthogonal reactivity for derivatization, including amidation, alkylation, and transition-metal-catalyzed coupling reactions. The compound exhibits good bench stability and facilitates purification via standard chromatographic or crystallization methods, making it well-suited for medicinal chemistry campaigns and API intermediate development.

General Information

CAS No. 149520-94-5
Cat. No. CS-W003670
Purity ≥95%
MDL No. MFCD09864446
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₉N₃O₂
Molecular Weight None
Synonym(s) Ethyl 2-AMinoiMidazole-5-carboxylate
SMILES O=C(C1=CN=C(N)N1)OCC

Computational Chemistry Data

TPSA 81
LogP 0.1686
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 2

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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 2-amino-1H-imidazole-5-carboxylate

CAS No. 149520-94-5

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