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CAS No. : | 128562-95-8 | MDL No. : | MFCD09954766 |
Formula : | C9H6F3N | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | YTVBZSLUNRYKID-UHFFFAOYSA-N |
M.W : | 185.15 | Pubchem ID : | 19803703 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
89% | [0118] Step 3. l-Benzenesulfonyl-4-trifluoromethyl-lH-indole[0119] To a slurry of 60 % sodium hydride (2.4 g, 61 mmol) in dimethylformamide (125 mL) at 00C was added 4-trifluoromethyl-lH-indole (4.5 g, 24 mmol). The reaction was stirred at 00C for thirty minutes and then benzenesulfonyl chloride (3.8 mL, 30 mmol) was added drop wise to the reaction. The reaction was stirred for three hours allowing it to warm to room temperature and then poured onto ice/water and extracted with ethyl acetate. Washed the organic layer with sodium bicarbonate, ammonium chloride, and sodium chloride. Dried the organic layer with magnesium sulfate and concentrated onto silica gel. Purified using automated flash chromatography with a gradient mobile phase consisting of ethyl acetate and hexane resulting in the isolation of l-benzenesulfonyl-4-trifluoromethyl-lH-indole (7.0 g, 89 %). | |
1.08 g | Step 3d: 1-Benzenesulfonyl-<strong>[128562-95-8]4-trifluoromethyl-1H-indole</strong> 370 mg of NaH at 60% in oil are added to a solution of 0.85 g of <strong>[128562-95-8]4-trifluoromethyl-1H-indole</strong> in 15 ml of tetrahydrofuran, under an inert atmosphere. The reaction mixture is stirred at ambient temperature for one hour and then 0.88 ml of benzenesulfonyl chloride is added dropwise and the stirring is continued for 16 hours. The reaction mixture is then poured into a 10% ammonium chloride solution, extracted with ethyl acetate and dried over magnesium sulfate. After filtration and concentration under reduced pressure, the residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and diisopropyl ether (98/2, then 95/5: v/v), so as to give 1.08 g of 1-benzenesulfonyl-<strong>[128562-95-8]4-trifluoromethyl-1H-indole</strong> in the form of a pale yellow oil which is used as it is in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With iron; acetic acid;Heating / reflux; | [0116] Step 2. 4-Trifluoromethyl-lH-indole[0117] To a solution of dimethyl-[2-(2-nitro-6-trifluoromethyl-phenyl)-vinyl]-amine (6.3 g, 24 mmol) in acetic acid (150 mL) was added iron powder (4.3 g, 77 mmol). The reaction was heated to reflux overnight under nitrogen. Upon cooling, the reaction mixture was diluted with 2.0 M HCl and the aqueous phase was extracted with ethyl acetate. The organic layer was neutralized with a saturated solution of potassium carbonate and extracted. Washed <n="37"/>organic layer with sodium bicarbonate followed by sodium chloride. Dried with magnesium sulfate and concentrated to give 4-trifluoromethyl-lH-indole (4.5 g, 100%). |
959 mg | With iron; acetic acid; for 16h;Reflux; | Step 2d: 4-Trifluoromethyl-1H-indole 850 mg of powdered iron are added to a solution of 1.2 g of dimethyl[(E)-2-(2-nitro-6-trifluoromethylphenyl)vinyl]amine in 30 ml of acetic acid. The reaction mixture is refluxed for 16 hours and then poured into a solution of hydrochloric acid (HCl, 2N), and extracted with ethyl acetate. The organic phases are washed with a 10% sodium carbonate solution and then with a saturated NaCl solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure so as to give 959 mg of 4-trifluoromethyl-1H-indole which is used in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In ethanol; water; at 0 - 20℃; | (1150) A solution of aqueous formaldehyde (37%, 0.465 ml, 6.24 mmol) and dimethylamine (40%, 0.79 ml, 6.25 mmol) in 10 ml EtOH was cooled to 0 C. <strong>[128562-95-8]4-trifluoromethylindole</strong> (0.77 g, 4.16 mmol) (compound 128) was dissolved in a HOAc:EtOH mixture (1:1, 10 ml) and added dropwise to the reaction mixture. After stirring at this temperature for 2 hrs, the mixture was allowed to warm to room temperature and stirred overnight. (1151) The mixture was cautiously added to a sat'd solution of NaHCO3. 1N NaOH was added until the pH was between 9-10. The resulting mixture was extracted with CH2Cl2 (3×). The organic extracts were combined and washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 1.0 g of N,N-dimethyl-1-(4-(trifluoromethyl)-1H-indol-3-yl)methanamine (compound 129). This was used as-is without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | A. 1 -(2-Methoxy-ethyl)-4-trifluoromethyl-1 H-indole A mixture of 4-trifluoromethyl-1 H-indole (105 mg, 0.57 mmol), powder KOH (159 mg, 2.83 mmol) in DMSO (6 mL) is stirred at r.t. for 5 min. 2-Methoxyethyl bromide (80 muIota_, 0.85 mmol) is added. After the reaction mixture is stirred at r.t. overnight, it is partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer is extracted with Et2O (3x). The combined organic extracts are washed with H2O and brine, dried over MgSO , filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 70/30) as eluent to yield the product (100 mg, 72%) as a clear colorless liquid.1 H NMR (300 MHz, CDCI3) delta 7.53 (d, J = 8.2 Hz, 1 H), 7.40 (d, J = 7.3 Hz, 1 H), 7.35- 7.20 (m, 2H), 6.69 (s, 1 H), 4.32 (t, J = 5.4 Hz, 2H), 3.71 (t, J = 5.4 Hz, 2H), 3.31 (s, 3H);19F NMR (300 MHz, CDCI3) delta -60.99 (s, 3F);LC Rt: 3.21 min; MS 244 (M+H, 100%). |
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