Ethyl 2-bromothiazole-5-carboxylate

China [CN]

Physical Properties (referencing similar derivatives)

Appearance: Mostly colorless to pale yellow liquid or crystalline solid.

Possesses typical properties of ester compounds, soluble in organic solvents such as ethyl acetate, dichloromethane, and toluene, with low solubility in water.

High boiling point; usually requires distillation under reduced pressure for purification.  Storage requires protection from light and airtight sealing to prevent photochemical substitution reactions of the bromine atom.

Main Uses: As a highly active pharmaceutical and pesticide intermediate, the bromine atom and ester group in its structure can serve as reaction sites for derivatization.  Main applications include:

Synthesis of antibacterial and antiviral drugs: The thiazole ring is the core scaffold of many anti-infective drugs. The bromine atom can be substituted by amino, thiol, and other groups to construct biologically active molecules.

Development of heterocyclic pesticides: Such as insecticides and fungicides, by modifying the ester group and thiazole ring substituents to optimize the target activity of the compound.

Synthesis and Reaction Characteristics

Common synthesis route: Using 2-aminothiazole-5-ethyl carboxylate as the starting material, a diazonium salt is formed through a diazotization reaction, followed by a Sandmeyer reaction with cuprous bromide to convert the amino group to a bromine atom.

Reaction activity: The bromine atom at the 2-position readily undergoes nucleophilic substitution reactions, allowing the introduction of various functional groups; the ester group at the 5-position can undergo hydrolysis to form a carboxylic acid, or undergo alcoholysis or aminolysis to form the corresponding ester or amide.