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Chemical Structure| 25236-64-0 Chemical Structure| 25236-64-0
Chemical Structure| 25236-64-0

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CAS No.: 25236-64-0

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Product Details of [ 25236-64-0 ]

CAS No. :25236-64-0
Formula : C3H5F3O3S
M.W : 178.13
SMILES Code : CS(=O)(OCC(F)(F)F)=O
MDL No. :MFCD00025058
InChI Key :ICECLJDLAVVEOW-UHFFFAOYSA-N
Pubchem ID :556565

Safety of [ 25236-64-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 25236-64-0 ]

* 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.

  • Downstream synthetic route of [ 25236-64-0 ]

[ 25236-64-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 25236-64-0 ]
  • [ 617-05-0 ]
  • [ 330999-80-9 ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h; a) Potassium carbonate (62.2 g, 450 mmol) was added to a solution of <strong>[617-05-0]ethyl vanillate</strong> (58.9 g, 300 mmol) in dimethylformamide (400 ml) and the reaction heated to 120 C. 2,2,2-Trifluoroethyl methanesulphonate (63.4 g, 360 mmol) was added over 15 minutes and the reaction heated at 120 C for 15 hours. The reaction was cooled to ambient temperature, diethyl ether (400 ml) was added and the reaction was filtered. The filtrate was evaporated in vacuo and the residue was taken up in a mixture of diethyl ether (375 ml) and isohexane (375 ml). The organic layer was concentrated in vacuo to a total volume of 250 ml and the solid which crystallized out was collected by suction filtration. Drying of the solid in vacuo yielded ethyl 4-(2,2,2-trifluoroethoxy)-3-methoxybenzoate (43.0 g, 52 % yield) as a white crystalline solid: 1H-NMR (DMSO d6): 7.57 (dd, 1H, J = 2, 8 Hz), 7.49 (d, 1H, J = 2 Hz), 7.18 (d, 1H, J = 8 Hz), 5.81 (q, 2H, J = 7 Hz), 5.29 (q, 2H, J = 7 Hz), 3.82 (s, 3H), 1.30 (t, 3H, J = 7 Hz): MS (+ve ESI): 279 (M+H)+.
52% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 15.25h; a) Potassium carbonate (62.2 g, 450 mmol) was added to a solution of <strong>[617-05-0]ethyl vanillate</strong> (58.9 g, 300 mmol) in dimethylformamide (400 ml) and the reaction heated to 120 C. 2,2,2-Trifluoroethyl methanesulphonate (63.4 g, 360 mmol) was added over 15 minutes and the reaction heated at 120 C. for 15 hours. The reaction was cooled to ambient temperature, diethyl ether (400 ml) was added and the reaction was filtered. The filtrate was evaporated in vacuo and the residue was taken up in a mixture of diethyl ether (375 ml) and isohexane (375 ml). The organic layer was concentrated in vacuo to a total volume of 250 ml and the solid which crystallised out was collected by suction filtration. Drying of the solid in vacuo yielded ethyl 4-(2,2,2-trifluoroethoxy)-3-methoxybenzoate (43.0 g, 52% yield) as a white crystalline solid:1H-NMR (DMSO d6): 7.57 (dd, 1H, J=2, 8 Hz), 7.49 (d, 1H, J=2 Hz), 7.18 (d, 1H, J=8 Hz), 5.81 (q, 2H, J=7 Hz), 5.29 (q, 2H, J=7 Hz), 3.82 (s, 3H), 1.30 (t, 3H, J=7 Hz):MS (+ve ESI): 279 (M+H)+.
  • 2
  • [ 107-83-5 ]
  • [ 25236-64-0 ]
  • [ 617-05-0 ]
  • [ 330999-80-9 ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate; In N-methyl-acetamide; diethyl ether; a) Potassium carbonate (62.2 g, 450 mmol) was added to a solution of <strong>[617-05-0]ethyl vanillate</strong> (58.9 g, 300 mmol) in dimethylformamide (400 ml) and the reaction heated to 120 C. 2,2,2-Trifluoroethyl methanesulphonate (63.4 g, 360 mmol) was added over 15 minutes and the reaction heated at 120 C. for 15 hours. The reaction was cooled to ambient temperature, diethyl ether (400 ml) was added and the reaction was filtered. The filtrate was evaporated in vacuo and the residue was taken up in a mixture of diethyl ether (375 ml) and isohexane (375 ml). The organic layer was concentrated in vacuo to a total volume of 250 ml and the solid which crystallized out was collected by suction filtration. Drying of the solid in vacuo yielded ethyl 4-(2,2,2-trifluoroethoxy)-3-methoxybenzoate (43.0 g, 52% yield) as a white crystalline solid: 1H-NMR (DMSO-d6): 7.57 (dd, 1H, J=2, 8 Hz), 7.49 (d, 1H, J=2 Hz), 7.18 (d, 1H, J=8 Hz), 5.81 (q, 2H, J=7 Hz), 5.29 (q, 2H, J=7 Hz), 3.82 (s, 3H), 1.30 (t, 3H, J=7 Hz): MS (+ve ESI): 279 (M+H)+.
  • 3
  • [ 269410-08-4 ]
  • [ 25236-64-0 ]
  • [ 1049730-42-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 1h;Inert atmosphere; Microwave irradiation; Sealed tube; Step 1: 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-(2,2,2-trifluoroethyl)-lH- pyrazole [00249] A 25 mL teflon cap tube was charged with 4-pyrazoleboronic acid pinacol ester (0.94 g, 4.87 mmol), cesium carbonate (2.58 g, 7.31 mmol), 2,2,2 trifluoroethyl methanesulfonate (1.30 g, 0.86 mL, 7.31 mmol) and anhydrous DMF (8 mL). The reagents were capped under N2 and heated at 100 C under microwave irradiation for 1 h. After this time the reaction mixture was cooled to rt and partitioned with EtOAc (60 mL) and water (100 mL). Organic layers were extracted, washed with brine (2 x 65 mL), then dried and filtered (phase separator) to give a pale yellow oil. The crude product was purified by flash silica column chromatography (gradient elution /so-hexane to 33% EtOAc in i'so-hexane) to give the title compound as a colorless oil (0.37 g, 35% - mixture of target material and 2,2,2 trifluoroethyl methanesulfonate 1:2). MS (ES+) consistent with target (M+H)+.
  • 4
  • [ 25236-64-0 ]
  • [ 100859-88-9 ]
  • 3-chloro-6-(methylthio)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3,4-d]pyrimidin [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With caesium carbonate; In N,N-dimethyl-formamide; at 80.0℃; for 5.0h; 3-Chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (70 mg, 0.49 mmol) was dissolved in an N,N-dimethylformamide solvent (63 ml). Cesium carbonate (243 mg, 0.74 mmol) and 2,2,2-trifluoroethyl methane sulfonate (70.0 ml, 0.59 mmol) were added thereto, which was stirred at 80C for 5 hours. The temperature was lowered to room temperature, and it was extracted with water and ethyl acetate. The organic layer was dried over MgSO4, filtered under reduced pressure, and concentrated. It was subjected to column chromatography to obtain 48.3 mg of the target compound (yield: 48%). MS (ESI) m/z 282.8, 285.0 [M+H]+; 1H NMR (300 MHz, Acetone-d6) δ 9.09 (s, 1H), 5.27 (q, J = 8.7 Hz, 2H), 2.66 (s, 3H).
 

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