2-Bromo-5-thiazolecarboxylic acid

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Cat Number

INT54045760

CAS Number

54045-76-0

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Product Detail Description Customer Q&A

CAS Number

54045-76-0

EINECS

626-804-7

Storage

Room temperature

Synonyms

2-Bromothiazole-5-carboxylicacid

Molecular Formula

C4H2BrNO2S

Molecular Weight

208.03

Smiles

S1C(C(O)=O)=CN=C1Br

Appearance

White to off-white solid

Melting Point

182℃

Boiling Point

350℃

Relative Density

2.06

pKa

2.52

General Description

2-Bromo-5-thiazolecarboxylic acid is a brominated thiazole intermediate featuring a carboxylic acid at the C-5 position and a bromine atom at the C-2 position of the thiazole ring. The thiazole heterocycle is a five-membered ring containing nitrogen and sulfur, which confers unique electronic and coordination properties. The bromine at C-2 is positioned for Suzuki and other cross-coupling reactions, while the carboxylic acid serves as a handle for further amide bond formation.

Mechanism of Action

2-Bromo-5-thiazolecarboxylic acid is used as a versatile heterocyclic building block in pharmaceutical synthesis. The thiazole ring's nitrogen and sulfur atoms can coordinate with metal centers in metalloenzymes, contributing to its broad spectrum of biological activities. The C-2 bromine is a functional handle for transition-metal-catalyzed cross-coupling reactions, and the carboxylic acid group enables amide bond formation with amines, alcohols, or hydrazines.

Application

2-Bromo-5-thiazolecarboxylic acid is used as an intermediate in the synthesis of thiazole-containing pharmaceuticals including the antibiotic thiostrepton, the antihelmintic drug nitazoxanide, and numerous kinase inhibitors in clinical development. The thiazole scaffold is found in drugs targeting diabetes, inflammation, bacterial infections, and hypertension. It is also used in the synthesis of chiral ligands for asymmetric catalysis.

What is the recommended storage condition for 2-Bromo-5-thiazolecarboxylic acid?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Can we obtain batch-specific analytical data for 2-Bromo-5-thiazolecarboxylic acid?

Batch-specific COA documents are standard with every shipment. Additional analytical reports, including HPLC chromatograms or spectral data, may be provided upon request.

What is the primary synthetic application of 2-Bromo-5-thiazolecarboxylic acid?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

What scale of supply is available for 2-Bromo-5-thiazolecarboxylic acid for pilot or commercial synthesis?

Supply is available from laboratory research scale through multi-kilogram pilot quantities. Commercial-scale supply can be discussed based on projected demand.

What is the minimum order quantity (MOQ) for 2-Bromo-5-thiazolecarboxylic acid?

Flexible MOQ options are available to support both early-stage research and large-scale manufacturing needs. Our team can tailor order quantities to match your specific requirements.