Methyl 2-amino-5-methylthiazole-4-carboxylate

China [CN]

Structural Characteristics

The molecule is centered around a thiazole ring, with four functional groups arranged in an orderly pattern:

The thiazole ring (a five-membered aromatic heterocycle containing nitrogen and sulfur) serves as the primary skeleton, providing structural stability and aromaticity;

At the 2nd position: the amino group (-NH₂), which is basic and nucleophilic, and serves as an important reactive site;

At the 4th position: the methylester group (-COOCH₃), formed by the esterification of the carboxyl group with methanol and capable of hydrolysis or aminolysis;

At the 5th position: the methyl group (-CH₃), a weak electron-donating group that influences the electron cloud density of the ring through an inductive effect and increases the molecule's lipid solubility.

This structure combines polarity (amino and ester groups) with hydrophobicity (methyl and thiazole ring), making it suitable as a versatile synthetic building block.

Physical and Chemical Properties

Appearance: Typically a white to pale yellow crystalline solid, with regular crystals at higher purity.

Melting Point: Approximately 145-148°C (experimental value, minimally affected by purity). Solubility: Sparingly soluble in water, readily soluble in polar organic solvents such as methanol, ethanol, ethyl acetate, and DMSO, with low solubility in non-polar solvents.

Stability: Stable at room temperature and pressure. Avoid contact with strong acids (which may protonate amino groups or hydrolyze ester groups), strong bases (which may hydrolyze ester groups), and strong oxidants. For long-term storage, keep sealed and protected from light and moisture.