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Chemical Structure| 57478-19-0 Chemical Structure| 57478-19-0
Chemical Structure| 57478-19-0

4-(4-(Trifluoromethyl)phenoxy)aniline

CAS No.: 57478-19-0

4.5 *For Research Use Only !

Cat. No.: A246003 Purity: 98%

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Product Details of [ 57478-19-0 ]

CAS No. :57478-19-0
Formula : C13H10F3NO
M.W : 253.22
SMILES Code : NC1=CC=C(OC2=CC=C(C(F)(F)F)C=C2)C=C1
MDL No. :MFCD00170930
Boiling Point : No data available
InChI Key :SMLYUHJGJWSUEC-UHFFFAOYSA-N
Pubchem ID :2760751

Safety of [ 57478-19-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis [ 57478-19-0 ]

* 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 [ 57478-19-0 ]

[ 57478-19-0 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 90763-46-5 ]
  • [ 57478-19-0 ]
  • 2-Methoxy-5-nitro-N-[4-(4-trifluoromethyl-phenoxy)-phenyl]-benzamide [ No CAS ]
  • 2
  • [ 16130-58-8 ]
  • [ 57478-19-0 ]
  • 2-Cyano-N-[4-(4-trifluoromethyl-phenoxy)-phenyl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iron; ammonium chloride; In tetrahydrofuran; methanol; water; at 50℃; for 18h; General procedure: Intermediate H (808 mg,3.52 mmol) was dissolved in a mixture of THF (10 ml_) and MeOH (5 ml_). Ammonium chloride (566 mg,10.6 mmol) was dissolved in water (2 ml_) and added to the reaction mixture along with iron (591 mg,10.6 mmol). The reaction mixture was heated to 50 C for 18h. After cooling to r.t.,the mixture was filtered through Dicalite,washing with EtOAc. The filtrate was washed with water,and the aqueous layer extracted with EtOAc. The combined organics were washed (brine),dried (MgS04) and concentrated in vacuo to yield the title compound as a yellow solid (609 mg,87%). NMR dH(500 MHz,DMSO-d6) 7.45 - 7.35 (m,4H),7.34 - 7.27 (m,1 H),6.75 - 6.69 (m,2H),6.53 - 6.47 (m,2H),4.94 (s,2H),4.62 (br s,2H); LCMS: (Method A) 3.32 min,(200.2,MH+).
  • 4
  • [ 907190-45-8 ]
  • [ 57478-19-0 ]
  • 4-hydroxy-3<i>H</i>-benzotriazole-5-carboxylic acid [4-(4-trifluoromethyl-phenoxy)-phenyl]-amide [ No CAS ]
  • 5
  • [ 907190-32-3 ]
  • [ 57478-19-0 ]
  • 7-hydroxy-1<i>H</i>-indazole-6-carboxylic acid [4-(4-trifluoromethyl-phenoxy)-phenyl]-amide [ No CAS ]
  • 6
  • [ 907190-67-4 ]
  • [ 57478-19-0 ]
  • 6-hydroxy-1-[2-(trimethylsilanyl)ethoxymethyl]-1H-thieno[3,2-c]pyrazole-5-carboxylic acid 4-(4-trifluoromethylphenoxy)phenylamide [ No CAS ]
  • 7
  • [ 57478-19-0 ]
  • [ 124-63-0 ]
  • [ 1008530-98-0 ]
YieldReaction ConditionsOperation in experiment
92% With pyridine; In dichloromethane; at 0℃; for 1h; To a solution of 4-(4-trifluoromethyl-phenoxy)-phenylamine (15.18 g, 60 mmol) and pyridine (7.2 mL, 90 mmol) in dried CH2Cl2 (100 mL) under N2 at 0 C. was added methanesulfonyl chloride (5.22 mL, 66 mmol) dropwise. The mixture was stirred at 0 C. for 1 h and was then poured into CH2Cl2/H2O (100 mL/100 mL). 2N HCl(aq) (30 mL) was added into additional funnel. The organic layer was then washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product can be resolidified from Et2O/hexane to give 18.2 g of the titled product (92%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) delta 7.58 (d, J=9.0 Hz, 2H), 7.30 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 4H), 6.93 (s, 1H, NH), 3.04 (s, 3H); MS (EI) 331 (M+), 330 (M+-1, 100).
92% With pyridine; In dichloromethane; at 0℃; for 1h; N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide. (1b-1) To a solution of <strong>[57478-19-0]4-(4-trifluoromethylphenoxy)aniline</strong> (15.18 g, 60 mmol) and pyridine (7.2 mL, 90 mmol) in dried CH2Cl2 (100 mL) under N2 at 0 C. was added methanesulfonyl chloride (5.22 mL, 66 mmol) dropwise. The mixture was stirred at 0 C. for 1 h and was then poured into CH2Cl2/H2O (100 mL/100 mL). 2N HCl(aq) (30 mL) was added into additional funnel. The organic layer was then washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product can be resolidified from Et2O/hexane to give 18.2 g of N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (92%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) delta 7.58 (d, J=9.0 Hz, 2H), 7.30 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 4H), 6.93 (s, 1H, NH), 3.04 (s, 3H); MS (EI, m/z): 331 (M+), 330 (M+-1, 100).
  • 8
  • [ 321596-57-0 ]
  • [ 57478-19-0 ]
  • [ 321597-60-8 ]
YieldReaction ConditionsOperation in experiment
With dmap;Pd on carbon; In dichloromethane; ethyl acetate; COUPLING PROCEDURE B: PREPARATION OF 3-HYDROXY-4-METHOXY-N-(4-(4-TRIFLUOROMETHYLPHENOXY)PHENYL)-PYRIDINE-2-CARBOXAMIDE (425). To a stirred solution of 4-(4-trifluoromethylphenoxy) aniline (0.20 g, 0.8 mmol) and DMAP (0.10 g, 0.085 mmol) in CH2Cl2 (10 mL) was added all at once a solution of 3-benzyloxy-6-bromo-4-methoxypyridin-2-carbonylchloride (3) (0.29 g, 0.8 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred overnight at room temperature then poured into 2N HCl (10 mL). The organic layer was separated and the aqueous layer extracted with CH2Cl2 (2*10 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a gummy solid. This solid was taken up in EtOAc (20 mL), and triethylamine (0.80 g, 0.8 mmol) and 5% Pd on carbon (0.10 g) were added. The resulting mixture was subjected to a hydrogen atmosphere (initial pressure=50 psi) on a Parr shaker for 30 minutes. The mixture was filtered, washed with 0.1N HCl (20 mL), dried (MgSO4) and concentrated to give the title compound as an off-white solid (0.14 g), m.p.=122-129 C. COUPLING PROCEDURE C: PREPARATION OF N-(4-CYCLOHEXYLPHENYL)-3-HYDROXYPYRIDINE-2-CARBOXAMIDE.
  • 9
  • [ 75-44-5 ]
  • [ 57478-19-0 ]
  • 4-(4'-Trifluoromethylphenoxy)phenyl isocyanate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; 4-Amino-4'-trifluoromethyldiphenyl ether (15 g.) was added in small portions to a stirred solution of phosgene in toluene (180 ml, 12.5% solution) at 0. The mixture was refluxed, with stirring, for 3 hours. The solvent was removed in vacuo. Distillation gave 4-(4'-trifluoromethyl-phenoxy)phenylisocyanate as a pale yellow oil (8.1 g, boiling point 110-114, 0.5 mm).
  • 10
  • 3-(methoxycarbonyl)amino-4-methoxy-isoxazole-5-carboxylic acid [ No CAS ]
  • [ 57478-19-0 ]
  • [ 144-55-8 ]
  • [ 3945-69-5 ]
  • 3-[(Methoxycarbonyl)amino]-N-para-[4-(trifluoromethyl)phenoxy]phenyl-isoxazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With hydrogenchloride; In ethanol; water; ethyl acetate; 3-[(Methoxycarbonyl)amino]-N-para-[4-(trifluoromethyl)phenoxy]phenyl-isoxazole-5-carboxamide (44) A mixture of 0.162g (0.75mmol) of 3-(methoxycarbonyl)amino-4-methoxy-isoxazole-5-carboxylic acid, 0.172g (0.68mmol) of 4-[4-(trifluoromethyl) phenoxy]aniline and 0.212g (0.75mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride in 5ml of ethanol is heated at 70C for 6 hours, and then stirred at room temperature for 16 hours. After evaporation of the ethanol, the residue is taken up in ethyl acetate and the resulting solution is washed successively with a saturated solution of sodium hydrogenocarbonate, water, 2% solution of hydrochloric acid, and water. After drying and concentrating, the residue is chromatographed (ethyl acetate/heptane, 2:8) to give 0,122g (37% yield) of a cream solid (M+1 = 452).
  • 11
  • 2-azidocarbonyl-3-methoxy-isoxazole-4-carboxylic acid [ No CAS ]
  • [ 57478-19-0 ]
  • 2-methoxycarbonyl-3-methoxy-N-para-[4-(trifluoromethyl)phenoxy]phenyl isoxazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% In tetrahydrofuran; water; ethyl acetate; 2-methoxycarbonyl-3-methoxy-N-para-[4-(trifluoromethyl)phenoxy]phenyl isoxazole-4-carboxamide (52) To a suspension of 1g (4.4 mmol) of 2-azidocarbonyl-3-methoxy-isoxazole-4-carboxylic acid (prepared according to the method described in W. Kloetzer, J. Schantz, Monatsh. Chem.,1965, 102-115) in 10ml of water cooled at 0C, is added drop-wise a solution of 3.36g (13.2 mmol) of <strong>[57478-19-0]4-[4-(trifluoromethyl)phenoxy]aniline</strong> in 15ml of tetrahydrofuran. The resulting mixture is stirred at 0C for 5 hours and leftto stand at room temperature for 16 hours. After concentration, the residue is taken up in ethyl acetate and the organic phase is washed successively with a 1% hydrochloric acid solution, and with brine. Drying and concentration give a solid which is purified on silica to give 0.72g (38% yield) of a white solid (M+1 = 436).
  • 12
  • [ 57478-19-0 ]
  • [ 36778-15-1 ]
  • [ 481687-38-1 ]
YieldReaction ConditionsOperation in experiment
1.2g (63%yield) With thionyl chloride; triethylamine; In diethyl ether; dichloromethane; 5-Nitro-N-para-[4-(trifluoromethyl)phenoxy]phenyl-isothiazole-3-carboxamide (58) To 0.8g (4.6mmol) of 5-nitro-isothiazole-3-carboxylic acid (prepared according to the method described in R. J. A. Walsh, K. R. H. Woolbridge, J. Chem. Soc. Perkin Trans 1, 1972,1247-1249) is added 14 ml of thionyl chloride under nitrogen, and the resulting mixture is stirred at reflux for 3 hours. After cooling, the solvent is evaporated to give a solid. This solid is suspended in a mixture of 20ml of diethyl ether and 20ml of dichloromethane. The suspension is added to a mixture of 2.74g (10.8mmol) of 4-[4-(trifluoromethyl) phenoxy] aniline and 2.5ml (18.3mmol) of triethylamine in 40ml of diethyl ether. The resulting mixture is stirred at room temperature for 4 hours and left to stand at room temperature overnight. The resulting suspension is filtered, the filtrate is washed with a saturated sodium chloride solution, then dried and concentrated to give a brown solid which is chromatographed (ethyl acetate/heptane) to give 1.2g (63%yield) of an orange solid (M+1 =410).
  • 13
  • [ 402-43-7 ]
  • [ 57478-19-0 ]
YieldReaction ConditionsOperation in experiment
27% With potassium carbonate; In dimethyl sulfoxide; 4-(4-Trifluormethylphenoxy)aniline: To a stirred solution of 4-trifluormethylbromobenzene (11.2 g, 50 mmol) in dimethylsulphoxide (50 mL) is added powdered potassium carbonate (3.4g, 60 mmol) and 4-aAminophenol (6.6 g, 55 mmol). The suspension is heated at 90C for 4.5 h, then poured into water, extracted with di-isopropylether, filtered, decanted, the organic phase washed with water, dried (magnesium sulphate) and evaporated to give 9.6 g of a brown oil. To this triturated with pentane, the resulting precipitate filtered, washed with pentane and dried to give 3.3 g of the title compound (27%, mp. 72 C).
  • 14
  • [ 34859-78-4 ]
  • [ 57478-19-0 ]
YieldReaction ConditionsOperation in experiment
81% With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 15h; To 1-nitro-4-(4-(trifluoromethyl)phenoxy)benzene (865 mg, 3.06 mmol), dissolved in MeOH(15 mL), was added Pd/C (100 mg). After the reaction mixture was stirred at ambienttemperature for 15 h, under hydrogen atmosphere (hydrogen gas in a balloon), it was filteredthrough a pad of Celite to remove Pd/C residue. The volatiles were removed in vacuo and theresulting solid triturated with DCM (1 mL) and hexanes (15 mL). 4-(4-(trifluoromethyl)phenoxy)aniline was isolated as a solid (720 mg, 81%). M.P: 70-71 C (lit.73-74 C4); 1H NMR (CDCl3, 500 MHz): 7.53 (d, J = 8.0 Hz, 2H), 6.98 (d, J = 8.0 Hz, 2H),6.89 (d, J = 8.0 Hz, 2H), 6.72 (d, J = 8.0 Hz, 2H).
With hydrogen;5% Pd(II)/C(eggshell); In methanol; under 760.051 - 1520.1 Torr;Inert atmosphere; In a hydrogenation bottle, crude (3) was dissolved in MeOH; solution was purged with N2 prior to the addition of 50- 100 mg of 5 wt % Pd on activated carbon. The reaction mixture was placed in a hydrogenator and shaken with 1-2 atm H2 for 1-2 hr. Upon completion of the reaction, the catalyst was filtered through the fritted funnel and was rinsed with MeOH. MeOH was evaporated using the rotary evaporator to give the final crude product (4). (Approx. 80 % yield).
  • 15
  • [ 57478-19-0 ]
  • [ 185099-67-6 ]
  • C25H29F3N2O3 [ No CAS ]
  • 16
  • [ 108-31-6 ]
  • [ 57478-19-0 ]
  • [ 189875-68-1 ]
  • 17
  • [ 123-30-8 ]
  • [ 98-56-6 ]
  • [ 57478-19-0 ]
  • 18
  • [ 7461-50-9 ]
  • [ 57478-19-0 ]
  • [ 1366234-42-5 ]
  • 19
  • [ 57478-19-0 ]
  • [ 33332-28-4 ]
  • [ 1366234-49-2 ]
  • 20
  • 4,7-dichloro-N-ethylquinolinium triflate [ No CAS ]
  • [ 57478-19-0 ]
  • (E)-N-(7-chloro-1-ethylquinolin-4(1H)-ylidene)-4-(4-(trifluoromethyl)phenoxy)aniline trifluoromethanesulfonate [ No CAS ]
  • 21
  • 4,7-dichloro-N-ethylquinolinium triflate [ No CAS ]
  • [ 57478-19-0 ]
  • (E)-N-(7-chloro-1-methylquinolin-4(1H)-ylidene)-4-(4-(trifluoromethyl)phenoxy)aniline trifluoromethanesulfonate [ No CAS ]
  • 22
  • [ 57478-19-0 ]
  • 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxylic acid [ No CAS ]
  • [ 1300031-15-5 ]
  • 24
  • [ 4160-80-9 ]
  • [ 57478-19-0 ]
  • 5-oxo-3-phenyl-5-((4-(4-(trifluoromethyl)phenoxy)phenyl)amino)pentanoic acid [ No CAS ]
  • 26
  • [ 57478-19-0 ]
  • [ 99-33-2 ]
  • C20H12F3N3O6 [ No CAS ]
 

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