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[ CAS No. 5728-66-5 ]

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Chemical Structure| 5728-66-5
Chemical Structure| 5728-66-5
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Product Details of [ 5728-66-5 ]

CAS No. :5728-66-5 MDL No. :MFCD03424688
Formula : C12H10FN Boiling Point : 310.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :187.21 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5728-66-5 ]

Signal Word:Warning Class:
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5728-66-5 ]

  • Downstream synthetic route of [ 5728-66-5 ]

[ 5728-66-5 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 5728-57-4 ]
  • [ 5728-66-5 ]
YieldReaction ConditionsOperation in experiment
(i) PCl5, benzene, (ii) aq. HCl, EtOH; Multistep reaction;
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water for 16h; Reflux; Inert atmosphere; General Suzuki Procedure B General procedure: To a stirred solution of the arylhalide (1 equiv.), boronic acid (1.1 equiv.) and sodium carbonate (2 equiv.) in dioxane (0.02 M) and water (0.05 M) was degassed for 10 min with nitrogen. Bis(cyclopentyldiphenylphosphane) dichloromethane palladium chloride iron (0.1 equiv.) was added to the reaction mixture and it was heated to reflux for 16 h. The reaction mixture was allowed to cool and filtered over Celite. It was diluted with water and extracted with ethyl acetate. The combined organic layers were dried with magnesium sulphate and concentrated under vacuum. The crude compound was purified by column chromatography to afford the desired product.
  • 3
  • [ 5728-66-5 ]
  • [ 56875-59-3 ]
  • [ 1360630-58-5 ]
YieldReaction ConditionsOperation in experiment
30% With pyridine 5.1.35. Methyl 4'-(naphthalene-2-sulfonamido)biphenyl-3-carboxylate (11a) General procedure: To a solution of 32a (230 mg, 1 mmol) in 3 mL pyridine was added 38 (230 mg, 1 mmol) and the reaction mixture was stirred overnight. The mixture was acidified to pH 2 and then extracted with EtOAc (2 × 75 mL), washed with water and brine, dried (Na2SO4), filtered, and concentrated to afford brown solid which was washed with methanol to provide 220 mg of 11a. White powder, Yield 53%
  • 4
  • [ 768-35-4 ]
  • [ 106-40-1 ]
  • [ 5728-66-5 ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; Biphenyl-4-ylamine (35a) General procedure: To a stirred solution of 4-bromoaniline (0.69g, 4 mmol) in 40 mL of toluene was added Pd(Ph3P)4 (0.32 g, 0.28 mmol), a solution of sodium carbonate (2.54 g, 24 mmol) in water (20 mL) and a solution of phenylboronic acid (0.98 g, 8 mmol) in EtOH (20 mL) under nitrogen atmosphere. The reaction mixture was stirred vigorously under reflux overnight and cooled, water was added and the reaction mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried and concentrated to provide brown solid which was flash chromatographed on silica gel eluting with 30% EtOAc in hexanes to provide 0.18 g (27%) of 35a
  • 5
  • [ 768-35-4 ]
  • [ 540-37-4 ]
  • [ 5728-66-5 ]
YieldReaction ConditionsOperation in experiment
94% With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In water; acetonitrile at 100℃; for 3h; Microwave irradiation;
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water Inert atmosphere; Reflux; General coupling procedure for compounds 5&6 General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6.
  • 6
  • [ 5728-66-5 ]
  • [ 90-02-8 ]
  • 2-(((3'-fluoro-[1,1'-biphenyl]-4-yl)amino)methyl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine; salicylaldehyde In methanol at 20℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 0.166667h; Inert atmosphere; Reductive amination procedure General procedure: Under an atmosphere of N2, 0.175 g (1 mmol) compd. 2 was dissolved in methanol, 0.11 mL (1.05 mmol) salicylaldehyde was added and stirred overnight at room temperature. When compd. 2 disappeared, NaBH4 (61 mg, 1.6 mmol) was added. After stirring for 10 min, the reaction was quenched by sat. NH4Cl solution, then extracted with CH2Cl2 (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE:EtOAc = 15:1) to afford 0.230 g (82%) E6 as white solid.
  • 7
  • [ 74124-79-1 ]
  • [ 5728-66-5 ]
  • N‐methyl‐1‐(methylsulphonyl)piperidin‐2,2,6,6‐[13C2,2H4]‐4‐amine [ No CAS ]
  • 3‐(3′‐fluoro‐[1,1′‐biphenyl]‐4‐yl)‐1‐methyl‐1‐(1‐(methylsulphonyl)piperidin‐4‐yl)‐2,2,6,6‐[13C2,2H4]-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: di(succinimido) carbonate; 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine With pyridine In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: N‐methyl‐1‐(methylsulphonyl)piperidin‐2,2,6,6‐[13C2,2H4]‐4‐amine In tetrahydrofuran for 0.5h; Inert atmosphere;
  • 8
  • [ 51-90-1 ]
  • [ 5728-66-5 ]
  • C12(14)CH8FNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: [14C]carbon dioxide; 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine With triethylamine In dichloromethane at -20℃; for 0.5h; Inert atmosphere; Stage #2: With trichlorophosphate In dichloromethane at -78 - 20℃; for 1.5h; Inert atmosphere;
  • 9
  • 1-ethyl-4-(3-fluorophenyl)benzene [ No CAS ]
  • [ 5728-66-5 ]
YieldReaction ConditionsOperation in experiment
66% With sodium azide; oxygen; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 4h; Sealed tube; The general procedure for the C-C amination of alkylarenes is as follows. General procedure: A 20 ml vial equipped with a magnetic stirring bar was charged with alkylarenes (0.3 mmol, 1 equiv.), NaN3 (0.75 mmol, 2.5 equiv.), DDQ (0.45 mmol, 1.5 equiv.) and trifluoroacetic acid (TFA) (1.0 ml, 0.3 M). The vial was sealed and stirred under air at 40 °C for 4 h. On completion, the reaction mixture was quenched by 2 M NaOH (5 ml), extracted by ethyl acetate (5 × 2 ml) and the combined organic phase was washed with brine and dried over Na2SO4. Then the mixture was concentrated and purified by flash chromatography on a short silica gel column.
66% With sodium azide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone at 40℃; for 24h; 31 Take a reaction tube and add sodium azide 49mg, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone 100mg,60% of 3'-fluoro-[4-(1,1'-biphenylyl)]ethylbenzene and 1.0 ml of trifluoroacetic acid were stirred at 40 ° C for 24 hours.After the reaction was completed, 10 mL of a sodium hydroxide solution was added to quench the reaction, and the mixture was extracted three times with ethyl acetate.Separation by column chromatography3'-Fluoro-[4-(1,1'-biphenylyl)aniline 37.1 mg, 66% yield.
  • 10
  • [ 5728-66-5 ]
  • 1-{3’-fluoro-[1,1′-biphenyl]-4-yl}-1H,4H,9H-naphtho[2,3-d][1,2,3]triazole-4,9-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / tetrahydrofuran / 0.5 h / -15 °C 1.2: 1 h / -15 °C 1.3: 75 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 80 °C
  • 11
  • [ 5728-66-5 ]
  • 4-azido-3'- fluoro[1,1'-biphenyl] [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 3′-fluoro‐[1,1′‐biphenyl]‐4‐amine With boron trifluoride diethyl etherate In tetrahydrofuran at -15℃; for 0.5h; Stage #2: With tert.-butylnitrite In tetrahydrofuran at -15℃; for 1h; Stage #3: With sodium azide In water; acetonitrile at 75℃;
  • 12
  • [ 106-40-1 ]
  • [ 5728-66-5 ]
YieldReaction ConditionsOperation in experiment
56% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;
  • 13
  • [ 5728-66-5 ]
  • [ 98-58-8 ]
  • C18H13BrFNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0 - 20℃;
  • 14
  • [ 349-88-2 ]
  • [ 5728-66-5 ]
  • C18H13F2NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0 - 20℃;
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