Identification | Back Directory | [Name]
ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE | [CAS]
22900-83-0 | [Synonyms]
2-bromo-4-methylthiazole-5-carboxylate ETHYL 2-BROMO-4-METHYLTHIAZOLE-5-CARBOX& ETHYL 2-BROMO-4-METHYLTHIAZOLE-5-CARBOXYLATE Ethyl 2-Bromo-4-methyl-5-thiazolecarboxylate Ethyl 2-Bromo-4-methylthiazole-5-carboxylate > Ethyl 2-broMo-4-Methylthiazole-5-carboxylate 97% ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE Ethyl 2-bromop4-methyl-1,3-thiazole-5-carboxylate 2-Bromo-4-methyl-5-thiazolecarboxylic acid ethyl ester 2-bromo-4-methyl-thiazole-5-carboxylic acid ethyl ester 5-Thiazolecarboxylic acid, 2-bromo-4-methyl-, ethyl ester JR-8414, Ethyl 2-bromo-4-methylthiazole-5-carboxylate, 97% Ethyl 2-broMo-4-Methylthiazole-5-carboxylate | [Molecular Formula]
C7H8BrNO2S | [MDL Number]
MFCD03791227 | [MOL File]
22900-83-0.mol | [Molecular Weight]
250.11 |
Chemical Properties | Back Directory | [Melting point ]
65-69 °C(lit.)
| [Boiling point ]
287.1±20.0 °C(Predicted) | [density ]
1.573±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
-0.10±0.10(Predicted) | [color ]
Light yellow to Brown | [Water Solubility ]
Insoluble in water. | [InChI]
InChI=1S/C7H8BrNO2S/c1-3-11-6(10)5-4(2)9-7(8)12-5/h3H2,1-2H3 | [InChIKey]
CFBIOWPDDZPIDP-UHFFFAOYSA-N | [SMILES]
S1C(C(OCC)=O)=C(C)N=C1Br |
Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
It finds its application in the preparation of thiazole-4- and -5-carboxylates, and an infrared study of their rotational isomers and in the discovery of thiazolylpyridinone SCD1 inhibitors with preferential liver distribution and reduced mechanism-based adverse effects. | [Synthesis]
General procedure for the synthesis of ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate from ethyl 2-amino-4-methylthiazole-5-carboxylate: first, 2-methyl-1-nitro-propyl-propene (28.2 mL, 2.1 eq.) was dissolved in acetonitrile (700 mL) and the solution was cooled to 0 °C. Subsequently, bromo-trimethyl-silane (32 mL , 2.1 eq.). The reaction mixture was maintained at 0°C. Next, ethyl 2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 0.1 mol) was added to an acetonitrile/ethyl acetate (75/25) solution. After the dropwise addition was completed, the reaction mixture continued to be kept at 0°C. The mixture was warmed to room temperature and stirred for 24 hours. After completion of the reaction, the solvent was removed by evaporation and water was added. The product was extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated. Finally, purification by fast chromatography using dichloromethane as eluent gave ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate as a yellow solid (21.74 g, 87 mmol, 87% yield); GC/MS analysis: [M+] C7H8BrNO2S 250. | [References]
[1] Patent: WO2004/6923, 2004, A1. Location in patent: Page/Page column 38 [2] Patent: WO2004/6924, 2004, A1. Location in patent: Page/Page column 31-32 [3] Patent: WO2004/7493, 2004, A1. Location in patent: Page 24-25 [4] Patent: EP2518054, 2012, A1. Location in patent: Page/Page column 53 [5] Patent: WO2008/47109, 2008, A1. Location in patent: Page/Page column 38 |
|
|