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[ CAS No. 155820-88-5 ]

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Chemical Structure| 155820-88-5
Chemical Structure| 155820-88-5
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CAS No. :155820-88-5 MDL No. :MFCD10697865
Formula : C8H6BrF3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :239.03 g/mol Pubchem ID :-
Synonyms :

Safety of [ 155820-88-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 155820-88-5 ]

  • Downstream synthetic route of [ 155820-88-5 ]

[ 155820-88-5 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 383-62-0 ]
  • [ 873-75-6 ]
  • [ 155820-88-5 ]
  • 2
  • 4-bromobenzyl fluorosulfonyldifluoroacetate [ No CAS ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide In N,N-dimethyl-formamide at 70℃; for 8h;
  • 3
  • [ 84750-93-6 ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 70℃; for 4h;
64 %Spectr. With potassium fluoride; 18-crown-6 ether In water; N,N-dimethyl-formamide at 80 - 140℃; sealed tube;
  • 4
  • [ 680-15-9 ]
  • [ 589-15-1 ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
67% In 1-methyl-pyrrolidin-2-one at 20 - 80℃; 40A 1-Bromo-4-(2,2,2-trifluoroethyl)benzene Example 40A 1-Bromo-4-(2,2,2-trifluoroethyl)benzene A solution of 25.0 g (100 mmol) of 4-bromobenzyl bromide in 1-methyl-2-pyrrolidone (121 ml) was admixed at RT with 4.95 g (26.0 mmol) of copper(I) iodide and 37.5 g (195 mmol) of methyl 2,2-difluoro-2-(fluorosulphonyl)acetate. The mixture was heated to 80° C. and then stirred overnight. The reaction solution was added to water and extracted with diethyl ether, and the organic phase was dried over sodium sulphate. After filtering and concentrating the organic phase under reduced pressure, the residue was purified by means of column chromatography (silica gel, cyclohexane/ethyl acetate 20:1). Yield: 16.1 g (67% of theory) GC-MS (Method 1F): Rt=2.66 min; MS (ESIpos): m/z=240 [M+H]+.
67% In 1-methyl-pyrrolidin-2-one at 20 - 80℃; 51A 1-bromo-4-(2,2,2-trifluoroethyl)benzene Example 51A1-Bromo-4-(2,2,2-trifluoroethyl)benzene A solution of 25.0 g (100 mmol) of 4-bromobenzyl bromide in 1-methyl-2-pyrrolidone (121 ml) was admixed at RT with 4.95 g (26.0 mmol) of copper(I) iodide and 37.5 g (195 mmol) of methyl 2,2-difluoro-2-(fluorosulphonyl)acetate. The mixture was heated to 80° C. and then stirred overnight. The reaction solution was added to water and extracted with diethyl ether, and the organic phase was dried over sodium sulphate. After filtering and concentrating the organic phase in vacuo, the residue was purified by means of column chromatography (silica gel, cyclohexane/ethyl acetate 20:1). Yield: 16.1 g (67% of theory)GC-MS (Method 1F): Rt=2.66 min; MS (ESIpos): m/z=240 [M+H]+.
With copper(l) iodide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h;
  • 6
  • [ 873-75-6 ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / pyridine / 0.17 h / 0 - 10 °C 2: 72 percent / CuI / dimethylformamide / 8 h / 70 °C
Multi-step reaction with 2 steps 1.1: sodium hydride; 1H-imidazole / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 1.3: 20 °C / Inert atmosphere 2.1: copper / acetonitrile / 9 h / 60 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C 1.2: 1 h / 20 °C 2.1: methyl iodide / N,N-dimethyl-formamide / 1 h / 20 °C 2.2: 15 h / 80 °C
  • 7
  • [ 557-21-1 ]
  • [ 155820-88-5 ]
  • 4-(2,2,2-trifluoroethyl)-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In N,N-dimethyl-formamide at 100℃; for 18h; I-17 Example 1-17 4-f2,2,2-Trifluoroethyl)benzonitrile; Intermediate 17 To the DMF (25 mL) solution of l-bromo-4-(2,2,2-trifiuoroethyl)benzene (2.15 g, 9.00 mmol) were zinc cyanide (2.11 g, 18.0 mmol) then Pd(PPh3)4 (0.828 g, 0.720 mmol) added. The mixture was heated at 1000C for 18 hours then cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a short bed of celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using hexane : ethyl acetate = 90:10 as eluent to give the title compound as a white solid, 800 mg (48%). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.67 (d, 2 H) 7.43 (d, 2 H) 3.44 (q, 2 H). 19F NMR (400 MHz, CDCl3) δ (ppm) -65.85, -65.88 and -65.91. MS (ESI) m/z 186 [M+H].
48% With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 18h;
48% In DMF (N,N-dimethylformamide) at 100℃; for 18h; I-31 To the DMF (25 niL) solution of l-bromo-4-(2,2,2-trifluoroethyl)benzene (2.15 g, 9.00 mmol) were zinc cyanide (2.11 g, 18.0 mmol) and Pd(PPh3)4 (0.828 g, 0.720 mmol) added. The mixture was heated at 1000C for 18 hours then cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a short bed of celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using hexane : ethyl acetate = 90: 10 as eluent to give the title compound as a white solid, 800 mg (48%).1H NMR (400 MHz, CDCl3) δ (ppm) 7.67 (d, 2 H) 7.43 (d, 2 H) 3.44 (q, 2 H). 19F NMR (400 MHz, CDCl3) δ (ppm) -65.85, -65.88 and -65.91. MS (ESI) m/z 186 [M+H].
48% In DMF (N,N-dimethylformamide) at 100℃; for 18h; I-16 To the DMF (25 mL) solution of l-bromo-4-(2,2,2-trifluoroethyl)benzene (2.15 g, 9.00 mmol) were zinc cyanide (2.11 g, 18.0 mmol) then Pd(PPh3)4 (0.828 g, 0.720 mmol) added. The mixture was heated at 1000C for 18 hours then cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a short bed of celite. The filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using hexane : ethyl acetate = 90:10 as eluent to give the title compound as a white solid, 800 mg (48%). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.67 (d, 2 H) 7.43 (d, 2 H) 3.44 (q, 2 H). 19F NMR (400 MHz, CDCl3) δ (ppm) -65.85, -65.88 and -65.91. MS (ESI) m/z 186 [M+H].

  • 8
  • [5-(methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride [ No CAS ]
  • [ 155820-88-5 ]
  • [ 1256841-40-3 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: [5-(methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride; 1-bromo-4-(2,2,2-trifluoroethyl)benzene With potassium fluoride; potassium carbonate In ethanol; water; toluene at 20℃; for 8h; Inert atmosphere; Reflux; Stage #2: for 8h; Reflux; 52A methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate Example 52AMethyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate A solution of 8.00 g (33.5 mmol) of the compound from Example 51A in toluene (304 ml) was admixed under argon at RT with 10.9 g (50.2 mmol) of the compound from Example 29A in ethanol (100 ml) and 5.10 g (36.8 mmol) of potassium carbonate. After stirring for 10 min, 3.87 g (3.35 mmol) of tetrakis(triphenylphosphine)palladium and then 5.83 g (100 mmol) of potassium fluoride in water (64 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 100:1→80:1). Yield: 9.20 g (69% of theory, purity 75%)LC-MS (Method 6B): Rt=1.06 min; MS (ESIpos): m/z=296 [M+H]+.
  • 9
  • [5-(methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride [ No CAS ]
  • [ 155820-88-5 ]
  • [ 1256841-40-3 ]
YieldReaction ConditionsOperation in experiment
69% With potassium fluoride; potassium carbonate In ethanol; water; toluene at 20℃; for 8h; Reflux; 41A Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate Example 41A Methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]nicotinate A solution of 8.00 g (33.5 mmol) of the compound from Example 40A in toluene (304 ml) was admixed under argon at RT with 10.9 g (50.2 mmol) of the compound from Example 33A in ethanol (100 ml) and 5.10 g (36.8 mmol) of potassium carbonate. After stirring for 10 min, 3.87 g (3.35 mmol) of tetrakis(triphenylphosphine)palladium and then 5.83 g (100 mmol) of potassium fluoride in water (64 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane/methanol 100:1→80:1). Yield: 9.20 g (69% of theory, purity 75%) LC-MS (Method 5B): Rt=1.06 min; MS (ESIpos): m/z=296 [M+H]+.
  • 10
  • [ 155820-88-5 ]
  • (cis)-methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate [ No CAS ]
  • (trans)-methyl 5-[4-(2,2,2-trifluoroethyl)phenyl]piperidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate; potassium fluoride / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 8 h / 20 °C / Inert atmosphere; Reflux 1.2: 8 h / Reflux 2.1: hydrogen / palladium 10% on activated carbon; platinum(IV) oxide / concentrated acetic acid / 6 h / 760.05 Torr
  • 11
  • [ 155820-88-5 ]
  • [ 73183-34-3 ]
  • [ 1310949-87-1 ]
YieldReaction ConditionsOperation in experiment
12% With triethylamine In 1,4-dioxane; water at 80℃; for 7.5h; Inert atmosphere; 5.27 Reference Example 5-27 4,4,5,5-Tetramethyl-2-[4-(2,2,2-trifluoroethyl)phenyl]-1,3,2-dioxaborolane A solution of 1-bromo-4-(2,2,2-trifluoroethyl)benzene (510 mg), bis(pinacolato)diborane (1.08 g), a 1,1'-bis(diphenylphosphino)ferrocenepalladium chloride-dichloromethane complex (70 mg) and triethylamine (1.2 mL) in 1,4-dioxane (10 mL) was stirred at 80° C. for 7.5 hours in a nitrogen atmosphere. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→10:1) to give the title compound as a colorless solid (68 mg, 12%). 1H NMR (300 MHz, CDCl3) δ ppm 1.34 (s, 12H), 3.37 (q, J=10.9 Hz, 2H), 7.29 (d, J=7.2 Hz, 2H), 7.80 (d, J=8.1 Hz, 2H).
  • 12
  • [ 155820-88-5 ]
  • [ 1198117-96-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / 16 h / -15 - 20 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / DMF (N,N-dimethylformamide) / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / -20 - 25 °C
  • 13
  • [ 155820-88-5 ]
  • [ 1198117-94-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / DMF (N,N-dimethylformamide) / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux
  • 14
  • [ 155820-88-5 ]
  • [ 1198117-95-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / DMF (N,N-dimethylformamide) / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux
  • 15
  • [ 155820-88-5 ]
  • [ 1198117-44-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 100 °C 2.1: borane-THF / tetrahydrofuran / 18 h / 60 °C 2.2: 2 h / Reflux 3.1: 18 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate / dichloromethane / 16 h / -15 - 20 °C / Inert atmosphere 5.1: methanol / 20 °C
  • 16
  • [ 129946-88-9 ]
  • O-4-bromophenylmethyl S-methyl dithiocarbonate [ No CAS ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
60 %Spectr. With copper In acetonitrile at 60℃; for 9h; Inert atmosphere;
  • 17
  • [ 371-67-5 ]
  • [ 5467-74-3 ]
  • [ 84750-93-6 ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
75% With ammonium chloride; lithium hydroxide at 100℃; for 24h; Schlenk technique;
  • 18
  • [ 5467-74-3 ]
  • [ 373-88-6 ]
  • [ 155820-88-5 ]
  • 19
  • [ 680-15-9 ]
  • 4-bromobenzyl diphenylphosphinite [ No CAS ]
  • [ 155820-88-5 ]
YieldReaction ConditionsOperation in experiment
203 mg Stage #1: 4-bromobenzyl diphenylphosphinite With methyl iodide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2,2-difluoro-2-(fluorosulfonyl)acetate With copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 15h; 3 4.3. General procedure for the preparation of compound 3 General procedure: To a stirred solution of benzyl or allyl alcohol (1, 1.5 mmol) in THF (10 mL) was added n-BuLi (1.6 M in hexane, 0.95 mL) at 0 °C. The mixture was warmed to room temperature. After stirring for 1 h, a solution of Ph2PCl (1.5 mmol) in THF (5 mL) was added at 0 °C, and the resulted mixture was continuously stirred at room temperature for 1 h and quenched with water after completion ofthe reaction (detected by TLC). The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate. Compound 2 was obtained after filtration and evaporation. To a solution of 2 in DMF (10 mL) was added CH3I (4.5 mmol) at room temperature. After stirring for 1 h, methyl fluorosulfonyldifluoroacetate (4.5 mmol) and CuI (0.30 mmol) were added. The mixture was heated and stirred at 80 °C for 15 h. Then the reaction was quenched with water and the resulting mixture was extracted with diethyl ether. The extract was dried over sodium sulfate. After removal of solvent, the crude product was purified by chromatography on silica gel to give 3 (eluent: n-hexane).
  • 20
  • [ 22246-12-4 ]
  • [ 155820-88-5 ]
  • 6-methoxy-2-(4-(2,2,2-trifluoroethyl)phenyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere;
  • 21
  • [ 155820-88-5 ]
  • (E)-methyl 3-(4-(6-hydroxy-1-methyl-2-(4-(2,2,2-trifluoroethyl)phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 6.1: aluminum (III) chloride; ethanethiol / dichloromethane / 4 h / 0 - 20 °C
  • 22
  • [ 155820-88-5 ]
  • (E)-3-(4-(6-hydroxy-1-methyl-2-(4-(2,2,2-trifluoroethyl)phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 6.1: aluminum (III) chloride; ethanethiol / dichloromethane / 4 h / 0 - 20 °C 7.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C
  • 23
  • [ 155820-88-5 ]
  • 1-(4-bromophenyl)-6-methoxy-1-methyl-2-(4-(2,2,2-trifluoroethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C
  • 24
  • [ 155820-88-5 ]
  • C24H20BrF3NO(1+)*ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C
  • 25
  • [ 155820-88-5 ]
  • C24H21BrF3NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C
  • 26
  • [ 155820-88-5 ]
  • (E)-methyl 3-(4-(6-methoxy-1-methyl-2-(4-(2,2,2-trifluoroethyl)phenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C / Inert atmosphere 2.1: n-butyllithium / pentane; n-heptane / 1 h / 20 °C 2.2: 1 h / -78 °C 3.1: perchloric acid / tetrahydrofuran; pentane; n-heptane; water; ethyl acetate / 0.5 h / 20 °C 4.1: tetrahydrofuran / 1 h / 0 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation
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