2-Bromo-5-thiazolecarboxylic acid
[CAS# 54045-76-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2-Bromo-5-thiazolecarboxylic acid
• Synonyms: 2-Bromothiazole-5-carboxylic acid
• Molecular Formula: C₄H₂BrNO₂S
• Molecular Weight: 208.03
• CAS Registry Number: 54045-76-0
• EC Number: 626-804-7
• SMILES: C1=C(SC(=N1)Br)C(=O)O

Properties

• Density: 2.1±0.1 g/cm³ Calc.^*
• Melting point: 182 °C (Decomposes) (Expl.)
• Boiling point: 350.0±15.0 °C 760 mmHg (Calc.)^*
• Flash point: 165.5±20.4 °C (Calc.)^*
• Index of refraction: 1.663 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Bromo-5-thiazolecarboxylic acid is an organic compound that belongs to the class of thiazole derivatives. It is characterized by a thiazole ring structure, a sulfur and nitrogen-containing five-membered heterocyclic ring, along with a carboxylic acid group at the 5-position and a bromine atom at the 2-position on the ring. This chemical structure gives 2-bromo-5-thiazolecarboxylic acid distinct chemical properties and makes it useful in various synthetic and pharmaceutical applications.

The synthesis of 2-bromo-5-thiazolecarboxylic acid typically involves the functionalization of a thiazole ring with both a bromine atom and a carboxyl group. This can be achieved through a sequence of chemical reactions, such as bromination of 5-thiazolecarboxylic acid using bromine or brominating agents like NBS (N-Bromosuccinimide), followed by appropriate purification methods to isolate the desired product. The synthetic process must be controlled to ensure selective halogenation at the 2-position of the thiazole ring, as this position is reactive toward bromination.

2-Bromo-5-thiazolecarboxylic acid has several applications in both organic synthesis and medicinal chemistry. The compound is often used as a building block in the synthesis of more complex thiazole-containing molecules, which can be important for the development of pharmaceuticals, agrochemicals, and materials. The presence of both the carboxyl group and the bromine atom makes it an attractive precursor for further functionalization, allowing the creation of a variety of derivatives with diverse biological and chemical activities.

In medicinal chemistry, thiazole derivatives, including 2-bromo-5-thiazolecarboxylic acid, have been investigated for their potential biological activities. Thiazole rings are commonly found in biologically active compounds, and their derivatives can exhibit antimicrobial, antifungal, antiviral, and anticancer properties. The presence of a bromine atom in 2-bromo-5-thiazolecarboxylic acid may also enhance its reactivity and interaction with biological targets, contributing to its potential activity as a pharmacologically relevant compound.

Additionally, the carboxyl group at the 5-position can enable the compound to form various derivatives by esterification or amidation, which may further alter its bioactivity and chemical reactivity. These derivatives can be tested for specific activities such as enzyme inhibition, receptor binding, or cellular interactions, potentially leading to the development of novel therapeutic agents.

Beyond its potential in pharmaceuticals, 2-bromo-5-thiazolecarboxylic acid is also a useful intermediate in the preparation of other chemical compounds, including those used in materials science. The thiazole ring can participate in polymerization reactions or serve as a part of more complex molecular structures that exhibit specific optical, electrical, or mechanical properties.

In summary, 2-bromo-5-thiazolecarboxylic acid is a versatile compound with applications in both synthetic chemistry and pharmaceutical research. Its thiazole ring structure, combined with the bromine and carboxyl functional groups, provides opportunities for further chemical modifications. Its potential bioactivity and reactivity make it an attractive building block for the synthesis of more complex compounds with a wide range of applications, particularly in the development of new drugs and materials.

References

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