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[ CAS No. 10540-45-1 ] {[proInfo.proName]}

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Chemical Structure| 10540-45-1
Chemical Structure| 10540-45-1
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Product Details of [ 10540-45-1 ]

CAS No. :10540-45-1 MDL No. :MFCD03424674
Formula : C12H10FN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 187.21 Pubchem ID :-
Synonyms :

Safety of [ 10540-45-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10540-45-1 ]

* 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 [ 10540-45-1 ]

[ 10540-45-1 ] Synthesis Path-Downstream   1~25

  • 1
  • 3-(4-Fluoro-phenyl)-cyclohex-2-enone oxime [ No CAS ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
48% In diethylene glycol dimethyl ether at 188℃; for 0.75h;
  • 2
  • [ 10540-42-8 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
(hydrolysis);
  • 5
  • [ 1765-93-1 ]
  • [ 626-01-7 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
59% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide for 19h; Inert atmosphere; Heating;
59% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 80℃; for 19h; Inert atmosphere; PREPARATION OF 4'-FLUORO-[1,1'-BIPHENYL]-3-AMINE (COMPOUND 1) To a solution of 3-iodoaniline (5.00 g, 22.83 mmol) in dry DMF (40 mL) under anhydrous conditions was added (4-fluorophenyl) boronic acid (3.83 g, 27.40 mmol), Pd(PPh3)4 (1.32 g, 1.14 mmol), and Cs2CO3 (22.31 g, 68.49 mmol). The mixture was heated to 80 °C under nitrogen and stirred for 19 h. The solvent was then removed under reduced pressure, and the residue was taken into EtOAc (100 mL). The solution was washed with water (2 × 50 mL), brine (50 mL), and dried over MgSO4. After the filtration, the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, hexanes:EtOAc = 3:1) to afford 1 (2.53 g, 59% yield) as an off-white solid.1H NMR (500 MHz, CDCl3): δ ppm 7.53-7.50 (m, 2H), 7.23 (t, J = 7.8 Hz, 1H), 7.11 (t, J = 8.8 Hz, 1H), 6.94 (d, J = 7.6 Hz, 1H), 6.86 (s, 1H), 6.69-6.67 (m, 1H), 3.74 (brs, 2H).13C NMR (125 MHz, CDCl3): δ ppm 163.51, 161.55, 146.89, 141.58, 137.63, 137.60, 129.88, 128.76, 128.70, 117.62, 115.67, 115.50, 114.18, 113.84. HRMS (ESI) Calcd. for C12H11FN (M+H)+ 188.0876, found 188.0877. (0498) b. PREPARATION OF 4'-CHLORO-2'-FLUORO-[1,1'-BIPHENYL]-3-AMINE (COMPOUND 2) [00320] (0.45 g, 42% yield) as a yellow oil.1H NMR (500 MHz, CDCl3): δ ppm 7.36 (t, J = 8.4 Hz, 1H), 7.23 (t, J = 7.8 Hz, 1H), 7.19-7.16 (m, 2H), 6.90 (d, J = 7.7 Hz, 1H), 6.83 (s, 1H), 6.71 (d, J = 8.0 Hz, 1H), 3.74 (s, 2H).13C NMR (125 MHz, CDCl3): δ ppm 160.70, 158.70, 146.75, 136.02, 133.90, 133.82, 131.61, 131.57, 129.71, 124.89, 124.86, 119.44, 119.42, 117.11, 116.89, 115.74, 115.72, 114.98. HRMS (ESI) Calcd. for C12H10ClFN
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide In tetrahydrofuran for 12h; Reflux;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Microwave irradiation;

  • 7
  • [ 585-79-5 ]
  • [ 1765-93-1 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
74% With β-D-mannose; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 130℃; for 1h; Microwave irradiation; Green chemistry;
  • 8
  • [ 10540-45-1 ]
  • 6-(2-((tert-butoxycarbonyl)amino)ethoxy)-4'-fluoro-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • 2-((4'-fluoro-5-((4'-fluoro-[1,1'-biphenyl]-3-yl)carbamoyl)-[1,1'-biphenyl]-2-yl)oxy)ethanaminium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 20 °C 2: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 h / 20 °C 2: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 20 °C
  • 9
  • [ 10540-45-1 ]
  • 6-(2-((tert-butoxycarbonyl)amino)ethoxy)-4'-fluoro-[1,1'-biphenyl]-3-carboxylic acid [ No CAS ]
  • tert-butyl (2-((4'-fluoro-5-((4'-fluoro-[1,1'-biphenyl]-3-yl)carbamoyl)-[1,1'-biphenyl]-2-yl)oxy)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 20h;
34% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h; PREPARATION OF TERT-BUTYL (2-((4'-FLUORO-5-((4'-FLUORO-[1,1'- BIPHENYL]-3-YL) CARBAMOYL)-[1,1'-BIPHENYL]-2-YL) OXY) ETHYL) CARBAMATE (COMPOUND 44A) To a solution of 43a (0.25 g, 0.67 mmol) in CH2Cl2 (20 mL) was added 1 (0.14 g, 0.73 mmol), Et3N (0.23 mL, 1.67 mmol), EDC^HCl (0.17 g, 0.88 mmol), and DMAP (0.09 g, 0.73 mmol). The mixture was then stirred at room temperature for 20 h. The mixture was diluted with CH2Cl2 (50 mL) and washed with water (50 mL), brine (50 ml), and dried over MgSO4. After the filtration, the solvent was removed under reduced pressure. The residue was then purified by column chromatography (silica gel, hexanes:EtOAc = 1:1) to yield 44a (0.12 g, 34% yield) as a white solid.1H NMR (500 MHz, d6-Acetone): δ ppm 9.65 (s, 1H), 8.16 (d, J = 1.9 Hz, 1H), 8.06-8.04 (m, 2H), 7.87 (s, 1H), 7.69-7.65 (m, 4H), 7.43 (ddd, J = 1.8, 6.0, 7.9 Hz, 1H), 7.36 (dd, J = 1.4, 6.3 Hz, 1H), 7.30-7.16 (m, 5H), 6.08 (s, 1H), 4.19 (t, J = 5.5 Hz, 2H), 3.48- 3.45 (m, 2H), 1.41 (s, 9H).13C NMR (125 MHz, d6-Acetone): δ ppm 165.46, 164.01, 163.58, 162.07, 161.64, 158.85, 140.95, 140.73, 137.84, 137.81, 134.57, 134.54, 132.04, 131.98, 130.44, 129.79, 129.41, 129.30, 129.23, 128.31, 128.28, 122.52, 122.50, 119.59, 119.50, 119.12, 119.03, 116.17, 115.99, 115.38, 115.21, 112.87, 78.61, 67.91, 40.21, 28.30.
  • 10
  • [ 10540-45-1 ]
  • 6-((4′-fluoro-[1,1′-biphenyl]-3-yl)amino)-3-hydroxypyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: <i>N</i>,<i>N</i>-dimethyl-aniline / 0.42 h / 170 °C / Microwave irradiation 2: palladium on carbon; hydrogen / methanol / 4 h / 20 °C / 2068.65 - 2585.81 Torr
  • 11
  • [ 10540-45-1 ]
  • 3-(benzyloxy)-6-chloropyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • 3-(benzyloxy)-6-((4'-fluoro-[1,1'-biphenyl]-3-yl)amino)-1-methylpyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With <i>N</i>,<i>N</i>-dimethyl-aniline at 170℃; for 0.416667h; Microwave irradiation;
  • 12
  • [ 13331-27-6 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 16 h / Inert atmosphere; Reflux 2: hydrazine hydrate / water; ethanol / 2 h / 50 °C
  • 14
  • [ 460-00-4 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 16 h / Inert atmosphere; Reflux 2: hydrazine hydrate / water; ethanol / 2 h / 50 °C
  • 15
  • [ 10540-45-1 ]
  • [ 104-12-1 ]
  • 3‐(4‐chlorophenyl)‐1‐[3‐(4-fluorophenyl)phenyl]urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In chloroform at 20 - 60℃; for 16h;
  • 16
  • [ 1103929-71-0 ]
  • [ 10540-45-1 ]
  • [ 1190220-70-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl acetamide / 20 °C 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 50 °C
  • 17
  • [ 1103929-71-0 ]
  • [ 10540-45-1 ]
  • [ 1190221-92-1 ]
YieldReaction ConditionsOperation in experiment
82% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl acetamide at 20℃; Methyl 5-chloro-2-[({2-[(3-fluorophenyl)amino]-2-oxoethoxy}acetyl)amino]benzoate (12a) General procedure: A mixture of the carboxylic acid 6a (0.5 g, 1.66 mmol), amine (8a) (0.193 g, 1.74 mmol), WSC HCl(0.382 g, 1.99 mmol), HOBt (0.269 g, 1.99 mmol) in DMA (5 mL) was stirred at room temperature. Aftercompletion of the reaction, the reaction mixture was poured into an aqueous NaHCO3 solution. The solidwas separated by filtration, and washed with water to afford the corresponding amide (12a) as a solid(0.281g, 82%).
  • 18
  • [ 10540-45-1 ]
  • [ 530-62-1 ]
  • [ 108-93-0 ]
  • cyclohexyl (4'-fluoro-[1,1'-biphenyl]-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 3‐(4‐fluorophenyl)aniline; 1,1'-carbonyldiimidazole With dmap In acetonitrile at 100℃; for 15h; Inert atmosphere; Stage #2: cyclohexanol In acetonitrile at 100℃; for 8h; Inert atmosphere; 12 4.1.5. General procedure for the preparation of compounds 1-2a-c,3a-b General procedure: A stirred solution of the previously obtained amine (1 mmol),CDI (4 mmol, 0.648 g), and DMAP (0.2 mmol, 0.024 g) in CH3CN(8 mL) was heated at 100 C for 15 h under N2 atmosphere. Thena solution of the suitable alcohol (1.2 mmol) in CH3CN (1 mL)was added. The mixture was stirred at 100 C for 8 h and concentrated.
Stage #1: 3‐(4‐fluorophenyl)aniline; 1,1'-carbonyldiimidazole With dmap In acetonitrile Reflux; Stage #2: cyclohexanol In acetonitrile Reflux;
  • 19
  • [ 10540-45-1 ]
  • [ 530-62-1 ]
  • [ 100-51-6 ]
  • benzyl (4'-fluoro-[1,1'-biphenyl]-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 3‐(4‐fluorophenyl)aniline; 1,1'-carbonyldiimidazole With dmap In acetonitrile at 100℃; for 15h; Inert atmosphere; Stage #2: benzyl alcohol In acetonitrile at 100℃; for 8h; Inert atmosphere; 13 4.1.5. General procedure for the preparation of compounds 1-2a-c,3a-b General procedure: A stirred solution of the previously obtained amine (1 mmol),CDI (4 mmol, 0.648 g), and DMAP (0.2 mmol, 0.024 g) in CH3CN(8 mL) was heated at 100 C for 15 h under N2 atmosphere. Thena solution of the suitable alcohol (1.2 mmol) in CH3CN (1 mL)was added. The mixture was stirred at 100 C for 8 h and concentrated.
Stage #1: 3‐(4‐fluorophenyl)aniline; 1,1'-carbonyldiimidazole With dmap In acetonitrile Reflux; Stage #2: benzyl alcohol In acetonitrile Reflux;
  • 20
  • [ 1765-93-1 ]
  • [ 591-19-5 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
75.1% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux;
68% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol for 12h; Reflux; 4 4.1.1. General procedure for the Suzuki coupling reaction to obtaincompounds 4a-c General procedure: To a solution of phenylboronic acid (4.0 mmol) in 10 mL ofMeOH, Na2CO3 (8.0 mmol) and 3-bromoaniline (4.0 mmol) wereadded sequentially. To this suspension, Pd tetrakis (0.14 mmol)was added and the reaction was heated to reflux for 12 h; the suspensionwas cooled at room temperature, diluted with MeOH andthe black precipitate was removed by filtration. The filtrate was diluted with water and extracted with CH2Cl2 (3 10 mL). Theorganic phase was dried on Na2SO4 and concentrated underreduced pressure.
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol for 12h; Reflux;
YieldReaction ConditionsOperation in experiment
80% Stage #1: With hydrazine hydrate In ethanol at 50℃; for 0.25h; Stage #2: In ethanol; water General procedure B General procedure: To a solution of nitrobenzene derivative (1 eq) in ethanol (0.1 M) was added hydrazine hydrate (15 eq). The reaction was stirred at 50 °C for 15 min and an excess of Raney nickel slurry in water (1.2 eq) was added slowly. After 1 h, the bubbling ceased, the mixture was cooled to room temperature and filtered through Celite. The filtrate was condensed under reduced pressured andthe residue was either used for the next step without purification or purified by column chromatography (SiO2, ethyl acetate/hexanes) to afford the desired product.
  • 22
  • [ 1268335-33-6 ]
  • [ 10540-45-1 ]
  • 3-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-7-yl)-N-(4'-fluoro-1,1'-biphenyl-3-yl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.2% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
  • 23
  • [ 349-88-2 ]
  • [ 10540-45-1 ]
  • C18H13F2NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0 - 20℃;
  • 24
  • [ 645-00-1 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene / 100 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol / Reflux
  • 25
  • [ 1765-93-1 ]
  • [ 10540-45-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene / 100 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol / Reflux
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