| Identification | More | [Name]
Ethyl 2-bromothiazole-4-carboxylate | [CAS]
100367-77-9 | [Synonyms]
2-BROMO-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
ETHYL 2-BROMOTHIAZOLE-4-CARBOXYLATE
Ethyl 2-bromothiazole-4-carboxylate 96%
ethyl 2-bromo-1,3-thiazole-4-carboxylate | [Molecular Formula]
C6H6BrNO2S | [MDL Number]
MFCD03788564 | [Molecular Weight]
236.09 | [MOL File]
100367-77-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
67-71 °C | [Boiling point ]
154°C/13mmHg(lit.) | [density ]
1.654±0.06 g/cm3(Predicted) | [Fp ]
>110℃ | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
-1.50±0.10(Predicted) | [color ]
White to Almost white | [Sensitive ]
Moisture & Light Sensitive | [InChI]
InChI=1S/C6H6BrNO2S/c1-2-10-5(9)4-3-11-6(7)8-4/h3H,2H2,1H3 | [InChIKey]
CNHISCQPKKGDPO-UHFFFAOYSA-N | [SMILES]
S1C=C(C(OCC)=O)N=C1Br | [CAS DataBase Reference]
100367-77-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
2 | [Hazard Note ]
Irritant/Keep Cold | [HazardClass ]
IRRITANT | [HS Code ]
29341000 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
Ethyl 2-bromothiazole-4-carboxylate is an essential organic reagent that can be used as a building block for the synthesis of many organic compounds, such as 4-Thiazolecarboxylic acid, Ethyl thiazole-4-carboxylate， 2-Bromothiazole-4-carboxylic acid and so on.
| [Synthesis]
Ethyl 2-aminothiazole-4-carboxylate (100 g, 581 mmol) and copper(II) bromide (195 g, 871 mmol) were dissolved in acetonitrile (1000 ml) at 0 °C. Subsequently, tert-butyl nitrite (104 ml, 871 mmol) was added slowly and dropwise. The reaction mixture was gradually warmed to room temperature and stirred continuously for 12 hours. After completion of the reaction, the reaction mixture was diluted with a mixture of ethyl acetate (1000 ml) and water (3000 ml) and the pH was adjusted to 2 with 1 N hydrochloric acid.The organic and aqueous layers were separated, and the aqueous layer was extracted three times with ethyl acetate (500 ml). All organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by recrystallization from hexane to give pure ethyl 2-bromothiazole-4-carboxylate (115 g, 84% yield). The product was confirmed by 1H-NMR (400 MHz, DMSO-d6): δ 8.52 (s, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H). Mass spectral analysis showed m/z 235.90 [M+1]. | [References]
[1] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 2766 - 2775
[2] Zh. Obshch. Khim., 2017, vol. 87, # 12, p. 1947 - 1956,10
[3] Patent: WO2018/193387, 2018, A1. Location in patent: Page/Page column 92
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 2, p. 533 - 536
[5] Patent: US6468979, 2002, B1 |
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