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Ethyl 2-chlorooxazole-4-carboxylate
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CAS No. 460081-18-9
- Cat. No. CS-W004930
- Purity≥97%
- MDL No.MFCD06660120
*For research and further manufacturing use only, not for direct human use.
Structure of 460081-18-9
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General Information
- CAS No. 460081-18-9
- Cat. No. CS-W004930
- Purity ≥97%
- MDL No. MFCD06660120
- Storage -20°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₆H₆ClNO₃
- Molecular Weight 175.57
- Synonym(s) 2-Chloro-oxazole-4-carboxylic acid ethyl ester
- SMILES C1=C(N=C(O1)Cl)C(=O)OCC
Description
Ethyl 2-chlorooxazole-4-carboxylate features a chlorinated oxazole core enabling direct functionalization at the 2-position. This bench-stable, moisture-tolerant heterocycle integrates readily into synthetic sequences requiring electrophilic substitution or transition-metal-catalyzed coupling. The ethyl ester group provides compatibility with standard reduction and amidation protocols.
Application
Ethyl 2-chlorooxazole-4-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to oxazole-based scaffolds through nucleophilic substitution and transition-metal-catalyzed coupling reactions. Its chlorine at the C2 position exhibits high reactivity toward amines, thiols, and organometallic reagents, facilitating rapid diversification. The ester group allows for selective transformations under mild conditions, enhancing functional group tolerance and simplifying purification. This compound demonstrates excellent bench stability and compatibility with standard synthetic workflows, making it ideal for medicinal chemistry and process development applications.
Synthesis
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Route1
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In-stock
177760-52-0 - ~83%
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In-stock
460081-18-9
References
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Hodgetts, Kevin J.; Kershaw, Mark T. Organic Letters, 2002 , vol. 4, # 17 p. 2905 - 2907
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Route2
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70-23-5 - ~%
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In-stock
460081-18-9
References
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Ehmke, Veronika; Quinsaat, Jose Enrico Q.; Rivera-Fuentes, Pablo; Heindl, Cornelia; Freymond, Celine; Rottmann, Matthias; Brun, Reto; Schirmeister, Tanja; Diederich, Francois Organic and Biomolecular Chemistry, 2012 , vol. 10, # 30 p. 5764 - 5768
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Route3
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540-80-7
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In-stock
177760-52-0
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7447-39-4
- ~%
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In-stock
460081-18-9
References
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ORION CORPORATION; Törmakängas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja Patent: US2014/94474 A1, 2014 ; Location in patent: Page/Page column ;
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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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 : H302-H315-H319-H335
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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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Quality Control
Computational Chemistry Data
- TPSA 52.33
- LogP 1.5047
- H_Acceptors 4
- H_Donors 0
- Rotatable_Bonds 2
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Key Words
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