2-Amino-4-methyl-5-acetylthiazole

China [CN]

Physical and Chemical Properties

Appearance: Typically a pale yellow to light brown crystalline powder. It exhibits a certain degree of stability and is not easily decomposed at room temperature.

Melting Point: Approximately 145-148°C (the specific value may fluctuate slightly depending on purity).

Solubility: Slightly soluble in water, freely soluble in polar organic solvents such as methanol, ethanol, and acetone. Solubility in DMSO (dimethyl sulfoxide) is high, making it convenient for use in organic reactions.

Structural Features: The molecule is centered around a thiazole ring, with an amino group (-NH₂) attached to the 2-position, a methyl group (-CH₃) at the 4-position, and an acetyl group (-COCH₃) at the 5-position. The presence of the amino group imparts a certain degree of alkalinity, while the acetyl group enhances the molecule's lipophilicity and reactivity.

Chemical Properties

Reactions of the amino group: The 2-position amino group exhibits typical amine chemical properties, capable of undergoing acylation, alkylation, and diazotization. For example, it can react with acyl chlorides to form amide derivatives, or undergo diazotization with sodium nitrite under acidic conditions to form diazonium salts (which can be further used in coupling reactions).

Reactions of the acetyl group: The 5-position acetyl group can undergo nucleophilic addition (such as with hydroxylamine to form oximes), condensation reactions (such as Schiff base reactions with amines), and hydrolysis under alkaline conditions to form the corresponding carboxylic acid derivatives.

Stability of the thiazole ring: The thiazole ring is an aromatic heterocycle containing nitrogen and sulfur. It has good chemical stability, is not easily oxidized or reduced, and can withstand a variety of reaction conditions.