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2-Bromothiazole-4-carboxamide
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CAS No. 848501-94-0
- Cat. No. CS-0054970
- Purity≥97%
- MDL No.None
*For research and further manufacturing use only, not for direct human use.
Structure of 848501-94-0
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General Information
- CAS No. 848501-94-0
- Cat. No. CS-0054970
- Purity ≥97%
- MDL No. None
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₄H₃BrN₂OS
- Molecular Weight 207.05
- Synonym(s) 2-BROMO-THIAZOLE-4-CARBOXAMIDE
- SMILES O=C(C1=CSC(Br)=N1)N
Description
2-Bromothiazole-4-carboxamide features a brominated thiazole core paired with a carboxamide handle, enabling direct integration into diverse synthetic scaffolds. This bench-stable compound serves as a key intermediate for bioactive heterocycles, particularly in medicinal chemistry and agrochemical development. The electron-deficient thiazole ring facilitates nucleophilic substitution, while the amide functionality supports conjugation and hydrogen bonding in target interactions.
Application
2-Bromothiazole-4-carboxamide serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the thiazole ring via palladium-catalyzed cross-coupling reactions. Its bromo group facilitates Suzuki, Stille, and Negishi couplings, while the carboxamide functionality offers hydrogen-bonding capacity and metabolic stability. The molecule exhibits excellent bench stability and compatibility with common protecting groups, making it ideal for constructing heterocyclic scaffolds in API development.
Synthesis
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Route1
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In-stock
170235-26-4 - ~99%
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In-stock
848501-94-0
References
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Billedeau, Roland Joseph; Kondru, Rama K.; Lopez-Tapia, Francisco Javier; Lou, Yan; Owens, Timothy D.; Qian, Yimin; So, Sung-Sau; Thakkar, Kshitij C.; Wanner, Jutta Patent: US2012/295885 A1, 2012 ; Location in patent: Page/Page column 33 ;
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Route2
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In-stock
100367-77-9 - ~%
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In-stock
848501-94-0
References
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WO2008/57336 A2, ; Page/Page column 35-36 ;
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Route3
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1336-21-6 -
In-stock
5198-88-9 - ~%
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In-stock
848501-94-0
References
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US2010/113512 A1, ; US 20100113512 A1
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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 55.98
- LogP 1.0045
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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