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Chemical Structure| 318288-78-7 Chemical Structure| 318288-78-7

Structure of 318288-78-7

Chemical Structure| 318288-78-7

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Product Details of [ 318288-78-7 ]

CAS No. :318288-78-7
Formula : C11H6ClF3N2O
M.W : 274.63
SMILES Code : O=CC1=C(Cl)N(C2=CC=CC=C2)N=C1C(F)(F)F
MDL No. :MFCD00793866

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Application In Synthesis of [ 318288-78-7 ]

* 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 [ 318288-78-7 ]

[ 318288-78-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 96145-98-1 ]
  • [ 68-12-2 ]
  • [ 318288-78-7 ]
YieldReaction ConditionsOperation in experiment
95% With trichlorophosphate; at 0℃;Heating; 1-Phenyl-3-(trifluoromethyl)-1H-pyrazol-5-ol (3) (1 mmol,0.23 g), N, N-dimethylformamide (DMF, 4 mmol, 0.3 g) were added into phosphoryl trichloride (2 mL) at 0 C. After the mixture were refluxed for 5 h, excess phosphoryl trichloride was distilled off. The residue was extracted by ethyl acetate and purified through column chromatography. Compound 4 was obtained as white solid in 95% yield. 1H NMR (500 MHz, CDCl3) delta: 10.02 (s, 1H), 7.54 (m, 5H) ppm.13C NMR (125 MHz, CDCl3) delta: 181.2, 142.7 (q, 2JC-F=40 Hz, C=N),136.1, 134.0, 130.3, 129.7, 129.6, 125.5, 120.1 (q, 1JC-F =267.5 Hz, CF3),116.6 ppm. 19F NMR (470 MHz, CDCl3) delta: 62.00 (s, CF3) ppm.
90% With trichlorophosphate; at 95℃; for 4.5h; Phosphorus oxychloride (21.47 g, 140.0 mmol) was slowly added to dimethylformamide (2.56 g, 35.0 mmol) at 0 C while stirring, then <strong>[96145-98-1]1-<strong>[96145-98-1]phenyl-3-(trifluoromethyl)-1H-pyrazol-5-ol</strong></strong> (1) (8.00 g, 35.0 mmol) was added and the mixture was heated at 95 C for 4.5 h. After cooling to rt, it was slowly poured into ice-water (200 mL) under vigorous stirring, in the process an orange oil was formed. The mixture was extracted with EtOAc (3×50 mL), the combined organic phases were washed with brine, 5% aq NaHCO3 solution and brine (each 30 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was subjected to column chromatography (SiO2, EtOAc/light petroleum 1:1) to afford 8.65 g (90 %) of a colorless oil which slowly solidified while standing: mp 34-36 C. 1H NMR (500 MHz, CDCl3): delta 7.56 (m, 5H, Ph H), 10.06 (s, 1H, CHO) ppm. 13C NMR (125 MHz, CDCl3): delta 116.6 (2JC4,CHO = 28.9 Hz, C-4), 120.1 (q, 1JCF3 = 270.7 Hz, CF3), 125.5 (Ph C-2,6), 129.5 (Ph C-3,5), 130.3 (Ph C-4), 133.7 (3JC5,CHO = 3.3 Hz, C-5), 136.1 (Ph C-1), 142.9 (2JC3,CF3 = 40.0 Hz, 3JC3,CHO = 2.0 Hz, C-3), 181.1 (1J = 183.9 Hz, CHO) ppm. 19F NMR (470 MHz, CDCl3): delta -61.9 (CF3) ppm. IR (KBr): = 1700 (C=O) cm-1. EIMS, m/z (rel. int.): 276 (28), 275 (44), 274 (80) [M]+, 273 (100), 255 (4), 245 (6), 209 (5), 136 (6), 77 (51), 51 (22).
  • 2
  • [ 96145-98-1 ]
  • [ 318288-78-7 ]
YieldReaction ConditionsOperation in experiment
79.1% With trichlorophosphate; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 1h;Heating / reflux; 33.6 g (219.1 mmoles) of phosphorus oxychloride was added to 7.7 g (105.2 mmoles) of N,N-dimethylformamide with ice-cooling. Thereto was added, at room temperature, 20 g (87.7 mmoles) of <strong>[96145-98-1]1-phenyl-3-trifluoromethyl-1H-pyrazol-5-ol</strong>. The resulting mixture was refluxed for 1 hour with heating, to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water with ice-cooling, followed by extraction with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 19.1 g (yield: 79.1%) of 5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde as white crystals. 1H-NMR [CDCl3/TMS, delta (ppm)]: 10.06 (1H,s), 7.57 (5H,s)
79.1% With trichlorophosphate; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 1h;Heating / reflux; REFERENCE EXAMPLE 10 Production of 5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde; 33.6 g (219.1 mmoles) of phosphorus oxychloride was added to 7.7 g (105.2 mmoles) of N,N-dimethylformamide with ice-cooling. Thereto was added, at room temperature, 20 g (87.7 mmoles) of <strong>[96145-98-1]1-phenyl-3-trifluoromethyl-1H-pyrazol-5-ol</strong>. The resulting mixture was refluxed for 1 hour with heating, to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water with ice-cooling, followed by extraction with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 19.1 g (yield: 79.1%) of 5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde as white crystals. 1H-NMR [CDCl3/TMS, delta (ppm)]: 10.06 (1H,s), 7.57 (5H,s)
 

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