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CAS No. : | 26944-43-4 | MDL No. : | MFCD00461894 |
Formula : | C9H7F3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SKDHRHGYJIMXRJ-UHFFFAOYSA-N |
M.W : | 204.15 | Pubchem ID : | 2759733 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | 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 |
---|---|---|
58% | Stage #1: 2-bromoanisole With iodine; magnesium In tetrahydrofuran for 2h; Heating; Stage #2: N-(trifluoroacetyl)piperidine at 0 - 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.4% | Stage #1: 4-iodoanisol With n-butyllithium In tetrahydrofuran at -78℃; for 9h; Inert atmosphere; Stage #2: N-(trifluoroacetyl)piperidine In tetrahydrofuran at -78℃; for 4h; Inert atmosphere; | |
72.4% | Stage #1: 4-iodoanisol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 9h; Inert atmosphere; Stage #2: N-(trifluoroacetyl)piperidine In tetrahydrofuran; hexane at -78℃; for 4h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With triethylamine In N,N-dimethyl-formamide at 0 - 80℃; for 3.25h; stereoselective reaction; | General procedure for the synthesis of β-CF3 enones (4a-l) General procedure: To a THF (20 mL) solution of (benzoylmethyl)triphenylphosphonium bromide (7.5 mmol) and triethylamine (7.5 mmol) was added a solution of a trifluoromethyl ketone (5 mmol) in DMF (1.6 mL) at 0 °C. The mixture was stirred for 15 min at this temperature. After warming to room temperature,the reaction mixture was heated at 80 °C for 3 h. The solution was quenched with NH4Cl saturatedaqueous solution, extracted with ethyl acetate, dried over MgSO4, and concentrated under reducedpressure. The mixture was purified by column chromatography on silica gel (petroleum ether / ethylacetate : 30/1) to give in majority the E β-CF3-enones and trace amount of the Z isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2'-methoxy-2,2,2-trifluoroacetophenone With triethylamine In dichloromethane at 20℃; for 1h; Stage #2: 3,5-dimethyl-4-nitroisoxazole In dichloromethane at 20℃; for 72h; | 2-Substituted (R)-1,1,1-Trifluoro-3-(3-methyl-4-nitroisoxazol-5-yl)propan-2-ols 3a-o; General Procedure General procedure: A 10-mL glass tube equipped with a stirring bar was charged with trifluoromethyl ketone 2 (0.6 mmol, 1.5 equiv), catalyst 4k (0.02 mmol,5 mol%), and CH2Cl2 (0.15 mL, 4.0 M). The resulting solution was stirred at r.t. for 1 h, then 3,5-dimethyl-4-nitroisoxazole 1 (0.4 mmol,1.0 equiv) was added and the mixture was stirred for 72 h. The crude was purified by flash chromatography (n-pentane/EtOAc 9:1) to provide the desired products 3 as colorless solids or viscous oils. |