2-amino-4,5-dihydro-6H-cyclopenta[d]thiazol-6-one

China [CN]

Physical and Chemical Properties

Appearance: Typically a white to off-white crystalline solid, with regular crystals at high purity.

Melting Point: Approximately 200-205°C (estimated, requires experimental determination and is affected by purity).

Solubility: Slightly soluble in water, freely soluble in polar organic solvents such as methanol, ethanol, and DMSO. Solubility is higher in highly polar solvents, facilitating organic synthesis.

Stability: Stable at room temperature and pressure. Avoid contact with strong acids, strong bases, and strong reducing agents. Long-term storage requires sealing and protection from light to prevent deliquescence or oxidation.

Chemical Properties

Reactions of the Amino Group: The 2-amino group can undergo typical amine reactions, including acylation (reaction with acyl chlorides or anhydrides to form amides), alkylation (reaction with alkyl halides to introduce alkyl groups), and diazotization (reaction with sodium nitrite under acidic conditions to form diazonium salts, which can be further derivatized). Ketone carbonyl reactions: The 6-position carbonyl group can undergo nucleophilic addition (e.g., oxime formation with hydroxylamine, hydrazone formation with hydrazine), reduction (e.g., reduction to a hydroxyl group with sodium borohydride), and condensation (Schiff base reaction with amines).

Fused ring stability: The fused structure of cyclopentane and thiazole enhances the rigidity and stability of the molecule. The aromaticity of the thiazole ring allows it to withstand most organic reaction conditions, but severe oxidation or high temperatures may damage the ring structure.