Ethyl 2-bromothiazole-4-carboxylate

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Cat Number

INT100367779

CAS Number

100367-77-9

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Product Detail Description Customer Q&A

CAS Number

100367-77-9

Storage

2-8℃

Synonyms

2-Bromo-4-(ethoxycarbonyl)-1,3-thiazole

Molecular Formula

C6H6BrNO2S

Molecular Weight

236.09

Smiles

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

Appearance

White to off-white powder

Melting Point

67-71℃

Boiling Point

154℃

Relative Density

1.65

General Description

Ethyl 2-bromothiazole-4-carboxylate is a brominated thiazole intermediate featuring an ethyl ester at the C-4 position and a bromine atom at the C-2 position of the thiazole ring. The ethyl ester provides lipophilicity and can be hydrolyzed to the free carboxylic acid or transesterified, while the C-2 bromine is a versatile handle for transition-metal-catalyzed cross-coupling reactions. The 2-bromo-4-carboxylate substitution pattern is common in pharmaceutical intermediates targeting the thiazole pharmacophore.

Mechanism of Action

Ethyl 2-bromothiazole-4-carboxylate functions as a dual-functionalized thiazole building block. The C-2 bromine undergoes oxidative addition with palladium(0) catalysts, enabling Suzuki-Miyaura, Stille, and other cross-coupling reactions to introduce diverse aryl, heteroaryl, and vinyl substituents. The ethyl ester can be hydrolyzed to the carboxylic acid, reduced to the primary alcohol (via DIBAL-H), or amidated. The thiazole nitrogen coordinates to metal centers in metalloenzyme inhibitors.

Application

Ethyl 2-bromothiazole-4-carboxylate is used as an intermediate in the synthesis of thiazole-containing pharmaceuticals including the anti-inflammatory agent rilonacept analogs, antifungal agents, and kinase inhibitors. The thiazole-4-ethyl ester scaffold is found in several clinical candidates for cancer, inflammation, and metabolic disorders. It is also used in the synthesis of agrochemicals and fluorescent probes.

What is the recommended storage condition for Ethyl 2-bromothiazole-4-carboxylate?

It should be stored at 2-8°C 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 Ethyl 2-bromothiazole-4-carboxylate?

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 functional groups in Ethyl 2-bromothiazole-4-carboxylate 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 analytical characterization data is available for Ethyl 2-bromothiazole-4-carboxylate?

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.

Is Ethyl 2-bromothiazole-4-carboxylate suitable for use in regulated pharmaceutical processes?

Yes, it is manufactured under quality standards consistent with regulated pharmaceutical applications, including in-process controls and release testing aligned with industry requirements.