Ethyl 5-amino-2-bromothiazole-4-carboxylate

Name: Ethyl 5-amino-2-bromothiazole-4-carboxylate
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CAS No. 1228281-54-6
Cat. No. CS-0096149
Purity≥97%
MDL No.MFCD27977252

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FedEx Limited Quantities Ground	$0.00
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Ethyl 5-amino-2-bromothiazole-4-carboxylate|CS-0096149

Structure of 1228281-54-6

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General Information

CAS No. 1228281-54-6
Cat. No. CS-0096149
Purity ≥97%
MDL No. MFCD27977252
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₇BrN₂O₂S
Molecular Weight 251.10
Synonym(s) 4-Thiazolecarboxylic acid, 5-amino-2-bromo-, ethyl ester
SMILES O=C(C1=C(N)SC(Br)=N1)OCC

Description

Ethyl 5-amino-2-bromothiazole-4-carboxylate features a brominated thiazole core with complementary amino and ester functionalities, enabling direct coupling in cross-coupling reactions. This bench-stable reagent integrates readily into heterocyclic synthesis, offering regioselective access to complex thiazole architectures under standard conditions.

Application

Ethyl 5-amino-2-bromothiazole-4-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to thiazole-based scaffolds through palladium-catalyzed cross-coupling and nucleophilic substitution reactions. The amino and bromo groups offer orthogonal reactivity for sequential functionalization, while the ester moiety supports further transformations. Bench-stable and readily purified, it facilitates scalable synthesis of biologically relevant motifs in medicinal chemistry and agrochemical research.

Synthesis

Route1
- In-stock
  
  18903-18-9
- ~58%
- In-stock
  
  1228281-54-6
References
- Sawa, Masaaki; Moriyama, Hideki; Yamada, Tesshi; Shitashige, Miki; Kawase, Yusuke; Uno, Yuko Patent: US2013/317218 A1, 2013 ; Location in patent: Paragraph 0122-0124 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 65.21
LogP 1.6645
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Thiazole compounds

Key Words

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Ethyl 5-amino-2-bromothiazole-4-carboxylate

CAS No. 1228281-54-6

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