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Ethyl 2-amino-1H-imidazole-5-carboxylate
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CAS No. 149520-94-5
- Cat. No. CS-W003670
- Purity≥95%
- MDL No.MFCD09864446
*For research and further manufacturing use only, not for direct human use.
Structure of 149520-94-5
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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
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.
Synthesis
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Route1
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In-stock
![Ethyl imidazo[1,2-a]pyrimidine-3-carboxylate|CS-0094357](https://file.chemscene.com/productPIC/CS-0094357.gif)
64951-07-1 - ~99%
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In-stock
149520-94-5
References
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BRISTOL-MYERS SQUIBB COMPANY Patent: WO2006/71752 A1, 2006 ; Location in patent: Page/Page column 84 ; WO 2006/071752 A1
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Route2
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In-stock
![Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate|CS-W002930](https://file.chemscene.com/productPIC/CS-W002930.gif)
64951-06-0 - ~99%
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In-stock
149520-94-5
References
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BRISTOL-MYERS SQUIBB COMPANY Patent: WO2006/71752 A1, 2006 ; Location in patent: Page/Page column 84 ; WO 2006/071752 A1
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Route3
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In-stock
109-12-6 -
70-23-5 - ~99%
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In-stock
149520-94-5
References
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Meng, Wei; Brigance, Robert P.; Chao, Hannguang J.; Fura, Aberra; Harrity, Thomas; Marcinkeviciene, Jovita; O'connor, Stephen P.; Tamura, James K.; Xie, Dianlin; Zhang, Yaqun; Klei, Herbert E.; Kish, Kevin; Weigelt, Carolyn A.; Turdi, Huji; Wang, Aiying; Zahler, Robert; Kirby, Mark S.; Hamann, Lawrence G. Journal of Medicinal Chemistry, 2010 , vol. 53, # 15 p. 5620 - 5628
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Safety Information
Download SDS|
GHS Pictogram :
N/A
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GHS No : N/A
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Signal Word : N/A
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : N/A
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Precautionary Statements : N/A
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Quality Control
Computational Chemistry Data
- TPSA 81
- LogP 0.1686
- H_Acceptors 4
- H_Donors 2
- Rotatable_Bonds 2
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