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CAS No. : | 210490-49-6 | MDL No. : | N/A |
Formula : | C10H8BrNS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 254.15 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: 5-bromo-2-phenyl-1,3-thiazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide at -78 - 20℃; for 18h; | |
65% | Stage #1: 5-bromo-2-phenyl-1,3-thiazole With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 5.5h; Inert atmosphere; | |
Stage #1: 5-bromo-2-phenyl-1,3-thiazole With lithium diisopropyl amide In tetrahydrofuran at 0℃; Stage #2: methyl iodide In tetrahydrofuran at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | 4-Bromo-5-methyl-2-phenylthiazole6 (1.2 g, 4.7 mmol) was dissolved in anhydrous THF (20 mL) under argon atmosphere. 1.6 M n-BuLi hexane solution (3.0 mL, 4.8 mmol) was slowly added dropwise to the solution at -78 C, and the mixture was stirred for 1.5 h. Tri-n-butyl borate (1.3 mL, 4.8 mmol) was slowly added to the solution at the temperature, and the mixture was stirred for 2.5 h. An adequate amount of distilled water was added to the mixture to quench the reaction. 1,2-Dibromotetrafluorobenzene (640 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (160 mg, 0.14 mmol), and 20 wt% Na2CO3 aqueous solution (7.5 mL) were added to THF (30 mL), and the mixture was refluxed for 6 h. The reaction mixture was neutralized by HCl aqueous solution, extracted with ether, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane as the eluent to give 160 mg of 2a in 15% yield based on <strong>[827-08-7]1,2-<strong>[827-08-7]dibromotetrafluorobenzene</strong></strong>. The 1H and 13C NMR spectra of 2a are shown in Figure S1. 2a: 1H NMR (300 MHz, CDCl3, TMS) delta = 2.29 (s, 6H, CH3), 7.27-7.37 (m, 6H, Aromatic H), 7.67-7.73 (m, 4H, Aromatic H). 13C NMR (75 MHz, CDCl3) delta = 12.1, 126.3, 128.9, 129.9, 133.4, 133.5, 142.7, 164.5. HR-MS (MALDI) m/z = 497.0762 (MH+). Calcd for C26H17F4N2S2+ = 497.0764. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 18h; Microwave irradiation; Sealed tube; Inert atmosphere; Heating; |