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[ CAS No. 72534-45-3 ] {[proInfo.proName]}

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Chemical Structure| 72534-45-3
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Product Details of [ 72534-45-3 ]

CAS No. :72534-45-3 MDL No. :MFCD08532490
Formula : C7H6F3NO Boiling Point : -
Linear Structure Formula :- InChI Key :XOXAZFFGKMIJKE-UHFFFAOYSA-N
M.W : 177.12 Pubchem ID :22272746
Synonyms :

Safety of [ 72534-45-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 72534-45-3 ]

* 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 [ 72534-45-3 ]

[ 72534-45-3 ] Synthesis Path-Downstream   1~19

  • 2
  • [ 1548-62-5 ]
  • [ 7772-99-8 ]
  • [ 72534-45-3 ]
YieldReaction ConditionsOperation in experiment
94% In ethanol; a) Preparation of 3-trifluoromethyl-2-hydroxyaniline To the solution of <strong>[1548-62-5]2-trifluoromethyl-6-nitrophenol</strong> (4.2 g, 20.3 mmol) in ethanol (20 ml, Tin (II) chloride (22.9 g, 101 mmol) was added. The reaction mixture was stirred at reflux for about 4 hours, tThen it was cooled to room temperature. The NaHCO3 (aq) was added until pH=7 was obtained and then the mixture was extracted with ethyl acetate (3*). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (3.4 g, 94%). EI-MS m/z 178 (M+).
88% In ethanol; b) Preparation of 2-amino-6-trifluoromethylphenol A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80 C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(1.35 g, 88%). 1 H NMR (CD3 OD): delta 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).
88% In ethanol; b)Preparation of 2-amino-6-trifluoromethylphenol A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80 C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2 Cl2) gave the desired product(1.35 g, 88%). 1 H NMR (CD3 OD): d 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).
  • 3
  • [ 72534-45-3 ]
  • [ 182498-97-1 ]
YieldReaction ConditionsOperation in experiment
In hexane; c) Preparation of N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl] urea N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl] urea was prepared from 2-amino-6-trifluoromethylphenol (280 mg, 1.60 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/hexane(1/20) and filtering. (390 mg, 65%). 1 H NMR (CD3 OD): δ 7.99 (d, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.34 (t, 1H), 7.30 (d, 1H), 7.00 (t, 1H), 6.96 (d, 1H).
In hexane; c)Preparation of N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea was prepared from 2-amino-6-trifluoromethylphenol (280 mg, 1.60 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/ hexane(1/20) and filtering. (390 mg, 65%). 1 H NMR (CD3 OD): d 7.99 (d, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.34 (t, 1H), 7.30 (d, 1H), 7.00 (t, 1H), 6.96 (d, 1H).
In hexane; c) Preparation of N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea was prepared from 2-amino-6-trifluoromethylphenol (280 mg, 1.60 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/hexane (1/20) and filtering. (390 mg, 65%). 1H NMR (CD3OD): d 7.99 (d, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.34 (t, 1H), 7.30 (d, 1H), 7.00 (t, 1H), 6.96 (d, 1H).
  • 4
  • [ 72534-45-3 ]
  • [ 3173-56-6 ]
  • N-(2-Hydroxy-3-trifluoromethylphenyl)-N'-benzylurea [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide; b) Preparation of N-(2-Hydroxy-3-trifluoromethylphenyl)-N'-benzylurea To a solution of benzylisocyanate (74.56 mg, 0.56 mmol) in DMF (1.0 ml), 2-hydroxy-3-trifluoromethylaniline (100 mg, 0.56 mmol) was added. The reaction mixture was stirred at 80 C. for 16 hours. Chromatography of the resulting liquid on silica gel gave desired product (140 mg, 80%). EI-MS m/z 311.1 (M+).
  • 5
  • [ 72534-45-3 ]
  • [ 132741-19-6 ]
  • 2-(4-bromophenyl)-8-(trifluoromethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 3.0h;Cooling with ice; Step B: 2-(4-bromophenyl)-8-(trifluoromethyl)-2H-benzo[b][l,4]oxazin-3(4H)-one To a solution of 2-amino-6-(trifluoromethyl) phenol (5.13 g, 29 mmol) in DMF (100 mL) was added K2CO3 (16 g, 116 mmol). The mixture was cooled by ice-water bath, to which 2- bromo-2-(4-bromophenyl)acetyl chloride (10.8 g, 35 mmol) was added dropwisely. Then the reaction was stirred at room temperature for 3 h. TLC (petroleum ether: EtOAc= 5: 1) showed that the reaction was complete. The resulting mixture was quenched and diluted by H20 (400 mL), extracted with DCM (300 mL*3). The combined organic layers were washed by brine (300 mL*3), dried over a2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography (EtOAc in petroleum ether: 0-20%) to give 2-(4-bromophenyl)-8- (trifluoromethyl)-2H-benzo[b][l,4]oxazin-3(4H)-one as a solid, which was used for next step without any purification. XH NMR (CDC13, 400 MHz): δ 8.41 (br.s, 1 H), 7.48 (d, J= 8.4 Hz, 2H), 7.33 (d, J= 8.4 Hz, 2H), 7.26(d, J= 7.6 Hz, 1H), 7.04 (t, J= 8.0 Hz, 1H), 6.97 (d, J= 7.6 Hz, 1H), 5.78 (s, 1H).
  • 6
  • [ 72534-45-3 ]
  • 2-(4-bromophenyl)-8-(trifluoromethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]
  • 7
  • [ 72534-45-3 ]
  • ethyl 2-(4-bromophenyl)-7-hydroxy-5-oxo-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate [ No CAS ]
  • 8
  • [ 72534-45-3 ]
  • tert-butyl 2-(2-(4-bromophenyl)-7-hydroxy-5-oxo-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamido)acetate [ No CAS ]
  • 9
  • [ 72534-45-3 ]
  • tert-butyl 2-(7-hydroxy-2-(4-(methylsulfonyl)phenyl)-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamido)acetate [ No CAS ]
  • 10
  • [ 72534-45-3 ]
  • 2-(7-hydroxy-2-(4-(methylsulfonyl)phenyl)-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamido)acetic acid [ No CAS ]
  • 11
  • [ 72534-45-3 ]
  • tert-butyl 2-(2-(4-cyanophenyl)-7-hydroxy-5-oxo-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamido)acetate [ No CAS ]
  • tert-butyl 2-(2-(4-cyanophenyl)-7-hydroxy-5-oxo-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamido)acetate [ No CAS ]
  • 12
  • [ 72534-45-3 ]
  • 2-(2-(4-cyanophenyl)-7-hydroxy-5-oxo-10-(trifluoromethyl)-3,5-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamido)acetic acid [ No CAS ]
  • 13
  • [ 1548-62-5 ]
  • [ 72534-45-3 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In methanol; water; at 20.0℃; under 1551.49 Torr; for 3.0h; Step A: 2-amino-6-(trifluoromethyl) phenol A 30 ml hydrogen bottle was charged with <strong>[1548-62-5]2-nitro-6-(trifluoromethyl)phenol</strong> (1.3 g, 6.3 mmol) in MeOH, and wet Pd/C(130 mg , purity: 10%) was added under 2 protection. The reaction mixture was degassed and charged by H2 (30 psi), then the reaction mixture was stirred at room temperature for 3 h. TLC (petroleum ether: EtOAc= 2: 1) showed that the starting material was consumed. The solvent was evaporated to give the desired product, which was directly used in the next step. 1HNMR (CDC13, 400 MHz): delta 6.91 (d, J=8.4 Hz, 2 H), 6.83 (t, J=8.0 Hz, 1 H).
  • 14
  • [ 444-30-4 ]
  • [ 72534-45-3 ]
  • 15
  • [ 72534-45-3 ]
  • 2-chloro-7-(trifluoromethyl)benzo[d]oxazole [ No CAS ]
  • 16
  • [ 72534-45-3 ]
  • [ 140-89-6 ]
  • 7-(trifluoromethyl)benzo[d]oxazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In ethanol; for 16.0h;Reflux; General procedure: Step-c: Synthesis of 6-(trifluoromethyl)benzo[d]oxazole-2-thiol To a solution of 2-amino-5-(trifluoromethyl)phenol (850 mg, 4.8 mmol) in ethanol (10 mL) at RT was added potassium ethyl-xanthate (1.69 g, 10.56 mmol) and the reaction mixture was refluxed for 16 h. The reaction mixture was concentrated under vacuum and diluted with cold water (50 mL), acidified with 1 N HCl. The solid obtained was filtered and dried under vacuum to afford the title compound (1.0 g, 95%); 1H NMR (400 MHz, DMSO-d6): δ 14.2 (bs, 1H), 7.98 (s, 1H), 7.66 (d, J=8.4 Hz, 1H), 7.41 (d, J=7.8 Hz, 1H); LC-MS: m/z 217.9 (M-1)-.
  • 17
  • [ 72534-45-3 ]
  • 8-(trifluoromethyl)-3,4-dihydro-2H-benzo[b][1,4]oxaazine [ No CAS ]
  • 18
  • [ 72534-45-3 ]
  • N-(3-iodo-4-methylphenyl)-8-(trifluoromethyl)-2,3-dihydro-4H-benzo[b][1,4]oxaazine-4-carboxamide [ No CAS ]
  • 19
  • [ 72534-45-3 ]
  • [ 79-04-9 ]
  • 8-(trifluoromethyl)-2H-benzo[b][1,4]oxaazine-3(4H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.02% In dichloromethane; for 2.0h; At 0C, to compound Int-K27d (2g, 11.29mmol)Methylene chloride (20mL)Add 2-chloroacetyl chloride (1.28 g, 11.29 mmol) to the solution and stir for 2 hours.LCMS showed that the reaction was complete.The mixture was concentrated and re-dissolved in N,N-dimethylformamide (5mL), potassium carbonate (1.15g, 11.29mmol) was added,The mixture was stirred at room temperature overnight.Dilute with ethyl acetate (25mL), wash with saturated sodium chloride solution (50mL), dry and concentrate the organic phase,A crude product of the title compound Int-K27e (1.3 g, 5.99 mmol, yield: 53.02%) was obtained.
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