2-Bromo-4-thiazolecarboxylic acid

Inquiry

Cat Number

INT5198889

CAS Number

5198-88-9

If you have any other questions, please contact our experts.

Product Detail Description Customer Q&A

CAS Number

5198-88-9

Storage

Room temperature

Synonyms

2-Bromo-4-carboxy-1,3-thiazole;2-Bromothiazole-4-carboxylic Acid

Molecular Formula

C4H2BrNO2S

Molecular Weight

208.03

Smiles

S1C=C(C(O)=O)N=C1Br

Appearance

White to off-white powder

Melting Point

212-214℃

Boiling Point

350℃

Relative Density

2.06

pKa

3.13

General Description

2-Bromo-4-thiazolecarboxylic acid is a brominated thiazole intermediate bearing a carboxylic acid at the C-4 position and a bromine atom at the C-2 position of the thiazole ring. The thiazole heterocycle is a five-membered aromatic ring containing nitrogen and sulfur, conferring unique electronic and coordination properties. The C-2 bromine and C-4 carboxylic acid are positioned in a 1,3-relationship around the thiazole ring, providing both cross-coupling and amide-coupling handles.

Mechanism of Action

2-Bromo-4-thiazolecarboxylic acid is used as a versatile heterocyclic building block in pharmaceutical synthesis. The thiazole ring's nitrogen and sulfur atoms can coordinate to metal centers in metalloenzymes. The C-2 bromine is a functional handle for transition-metal-catalyzed cross-coupling reactions (Suzuki, Heck, Buchwald-Hartwig) and for nucleophilic substitution. The carboxylic acid group enables amide bond formation with amines, alcohols, or hydrazines.

Application

2-Bromo-4-thiazolecarboxylic acid is used as an intermediate in the synthesis of thiazole-containing pharmaceuticals including the antibiotic thiostrepton, antimicrobial agents, and numerous kinase inhibitors. The thiazole-4-carboxylic acid scaffold is found in drugs targeting inflammatory disorders, diabetes, and bacterial infections. It is also used in the synthesis of chiral ligands and organocatalysts.

What is the recommended storage condition for 2-Bromo-4-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.

Is a Certificate of Analysis (COA) available for 2-Bromo-4-thiazolecarboxylic acid?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

What analytical characterization data is available for 2-Bromo-4-thiazolecarboxylic acid?

Standard analytical data including HPLC purity profile, NMR confirmation, and physical specifications are included in the COA. Additional characterization data can be arranged upon request.

What functional groups in 2-Bromo-4-thiazolecarboxylic acid are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

What quantities of 2-Bromo-4-thiazolecarboxylic acid are available for order?

We accommodate orders of varying scale, from small research quantities through bulk commercial supply. Contact our sales team to discuss pack sizes and volume pricing.