Ethyl 2-amino-1,3-thiazole-4-carboxylate 948182-12-5 98% off-white to light yellow crystalline powder pharmaceutical intermediate

1. Product Overview

Ethyl 2-amino-1,3-thiazole-4-carboxylate (CAS 948182-12-5) is a 2-aminothiazole derivative bearing an ethyl carboxylate group at the 4-position of the 1,3-thiazole ring. Also referred to as ethyl 2-amino-4-thiazolecarboxylate or 2-amino-4-carbethoxythiazole, it serves as a versatile building block in medicinal chemistry and heterocyclic synthesis. The electron-rich thiazole core combined with an orthogonally reactive 2-amino group (diazotization, acylation, condensation) and a hydrolyzable ethyl ester (to acid or reduction to alcohol) makes it valuable for constructing thiazole-containing active pharmaceutical ingredients (APIs), kinase inhibitors, antimicrobials, and agrochemical fungicides. The compound typically appears as an off-white to light yellow crystalline powder with good stability under dry, refrigerated conditions.

2. Key Features and Advantages

• Orthogonal reactivity: 2-amino supports diazotization, acylation, Schiff-base formation, and heterocyclic annulation; ethyl ester can be hydrolyzed to acid or reduced to alcohol without disturbing the thiazole ring.

• 2-Aminothiazole is a privileged scaffold in drug discovery (kinase inhibitors, antibacterials, antifungals) and agrochemicals, enabling rapid SAR exploration via 4- and 5-position diversification.

• High purity grade (≥98%) ensures clean multi-step conversion with minimal thiazole-related impurities.

• Stable crystalline solid facilitates accurate weighing, handling, and QC by melting point (~145–147 °C lit.), HPLC, NMR, and LC-MS.

• Compatible with standard protecting-group strategies: amino can be acetylated/Boc-protected; ester deprotected selectively under mild acid/base.

3. Main Applications

• Pharmaceutical intermediate for thiazole-based drug candidates, especially kinase inhibitors, anti-infectives, and CNS programs where 2-amino-4-substituted thiazoles are key pharmacophores.

• Building block for fused thiazolo[4,5-d]pyrimidines, thiazole-oxazoles, and purine analogs via diazotization/cyclization at C2 and ester transformation at C4.

• Intermediate in CRO/CDMO custom synthesis and academic research for thiazole library generation, Hantzsch thiazole synthesis derivatives, and peptidomimetic design.

• Precursor to 2-amino-1,3-thiazole-4-carboxylic acid (via ester hydrolysis) and 2-amino-4-(hydroxymethyl)thiazole (via reduction), relevant to agrochemical fungicide/insecticide programs.

• Used in fragment-based drug design to introduce a 2-amino-4-ethoxycarbonylthiazole handle for amide/urea formation after ester deprotection and coupling.

4. Technical Specifications

5. Storage and Handling

Store in a cool, dry place at 2–8 °C in a tightly sealed, light-protected container under desiccated conditions. For long-term storage, keep at –20 °C in a dry inert atmosphere to prevent moisture uptake and slow darkening of the amino-thiazole. The 2-amino group is moderately sensitive to oxidation under strong acid/light; avoid prolonged exposure to air and UV light. Handle in a well-ventilated area with standard PPE (lab coat, nitrile gloves, safety glasses). Reseal promptly after use. Under recommended conditions, shelf life is typically 24 months; periodic HPLC check advised if stored above 8 °C.

6. Safety Overview

Intended for research and synthetic use only; not for direct human or veterinary therapeutic administration. May cause irritation to eyes, skin, and respiratory tract upon contact or dust inhalation (typical GHS07 profile: H315/H319/H335). Aminothiazoles and esters can be mildly irritating to mucous membranes; handle as a fine organic powder with standard laboratory precautions. Prevent dust generation. In case of skin contact, wash thoroughly with soap and water; for eye contact, rinse cautiously with plenty of water for several minutes and seek medical advice if irritation persists. Dispose according to local regulations for non-halogenated heterocyclic organic laboratory chemicals. Always consult the latest SDS from the supplier before use.