Description
Ethyl 5-(bromomethyl)thiazole-2-carboxylate (CAS No. 960235-24-9) is a high-purity brominated thiazole derivative with the molecular formula C7H8BrNO2S. This compound is a versatile intermediate in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and functional materials. Its structure features a reactive bromomethyl group at the 5-position of the thiazole ring, enabling efficient further functionalization via nucleophilic substitution or cross-coupling reactions. The ethyl carboxylate moiety enhances solubility in organic solvents, facilitating downstream reactions. Supplied as a crystalline solid or powder, it is rigorously tested for identity, purity, and stability to ensure optimal performance in demanding applications. Store under inert conditions at 2-8°C to maintain integrity.
Properties
- CAS Number: 960235-24-9
- Complexity: 167
- IUPAC Name: ethyl 5-(bromomethyl)thiazole-2-carboxylate
- InChI: InChI=1S/C7H8BrNO2S/c1-2-11-7(10)6-9-4-5(3-8)12-6/h4H,2-3H2,1H3
- InChI Key: UFBFCSKCPCZCLE-UHFFFAOYSA-N
- Exact Mass: 248.94591
- Molecular Formula: C7H8BrNO2S
- Molecular Weight: 250.12
- SMILES: CCOC(=O)C1=NC=C(S1)CBr
- Topological: 67.4
- Monoisotopic Mass: 248.94591
- Synonyms: ETHYL 5-(BROMOMETHYL)THIAZOLE-2-CARBOXYLATE, 816-516-1, 960235-24-9, ETHYL 5-(BROMOMETHYL)-1,3-THIAZOLE-2-CARBOXYLATE, ethyl5-(bromomethyl)thiazole-2-carboxylate, MFCD11976764, SCHEMBL1806521, DTXSID80677794, UFBFCSKCPCZCLE-UHFFFAOYSA-N, AKOS015836234, DB-080397, CS-0078655, C90581, EN300-343335
Application
Ethyl 5-(bromomethyl)thiazole-2-carboxylate serves as a key building block in medicinal chemistry for the synthesis of thiazole-containing drug candidates, particularly kinase inhibitors and antimicrobial agents. It is employed in Suzuki-Miyaura and Buchwald-Hartwig couplings to introduce thiazole motifs into complex molecules. Researchers also utilize it in the development of fluorescent probes and coordination polymers due to its metal-chelating potential. The bromomethyl group allows straightforward conjugation to biomolecules or polymers for material science applications.
Safety and Hazards
GHS Hazard Statements
- H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
- H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
Precautionary Statements
- P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501
Hazard Classes and Categories
- Acute Tox. 4 (100%)
- Skin Corr. 1B (100%)
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