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[ CAS No. 1005206-25-6 ]

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Chemical Structure| 1005206-25-6
Chemical Structure| 1005206-25-6
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Product Details of [ 1005206-25-6 ]

CAS No. :1005206-25-6 MDL No. :MFCD11042448
Formula : C13H16BF3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :304.14 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1005206-25-6 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P270-P273-P301+P312-P330 UN#:
Hazard Statements:H302-H413 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1005206-25-6 ]

  • Downstream synthetic route of [ 1005206-25-6 ]

[ 1005206-25-6 ] Synthesis Path-Downstream   1~23

  • 1
  • [ 333-47-1 ]
  • [ 73183-34-3 ]
  • [ 1005206-25-6 ]
YieldReaction ConditionsOperation in experiment
64% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 90℃; for 3.5h;Inert atmosphere; A suspension of 1-bromo-4-[(trifluoromethyl)thio]benzene (5.74 mL, 38.2 mmol), bis(pinacolate)diboron (9.70 g, 38.2 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex (0.934 g, 1.15 mmol) and potassium acetate (11.3 g, 115 mmol) in N,N-dimethylformamide (100 mL) was stirred under an argon atmosphere at 90 C. for 3.5 hr. After cooling, the reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) and recrystallized from hexane to give the title compound (7.38 g, yield 64%) as colorless crystals.melting point 118-119 C.1H NMR (CDCl3) δ 1.35 (12H, s), 7.62-7.66 (2H, m), 7.82-7.86 (2H, m).Elemental analysis (for C13H16BF3O2S)Calculated (%): C, 51.34; H, 5.30.Found (%): C, 51.42; H, 5.25.
  • 3
  • [ 1005206-25-6 ]
  • (4-((trifluoromethyl)thio)phenyl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% To a round-bottomed flask was added 4,4,5,5-tetramethyl-2-(4-trifluoromethylsulfanyl-phenyl)- [1 ,3,2]dioxaborolane (960 mg, 3.16 mmol) and sodium periodate (2.03 g, 9.48 mmol) in THF and water (4:1 , 26 ml_). The resulting suspension was stirred at rt for 30 min. HCI (1 N aq., 2.21 ml_) was added to the suspension and the reaction mixture was stirred at rt for 18 h. The resulting precipitate was removed by filtration and washed with hexanes. The filtrate was diluted with water (25 ml_) and extracted with EtOAc (25 ml_). The aqueous layer was extracted with EtOAc (10 ml_ x 2), and the combined organic layers dried (Na2SO4) and concentrated to yield the title compound (512 mg, 73%).
73% Step B. To a round-bottomed flask were added 4,4,5,5-tetramethyl-2-(4- trifluoromethylsulfanyl-phenyl)-[1 ,3,2]dioxaborolane (960 mg, 3.16 mmol) and sodium periodate (2.03 g, 9.48 mmol) in THF and water (4:1 , 26 mL). The resulting suspension was stirred at rt for 30 min. HCI (1 N aq., 2.21 mL) was added to the suspension and the reaction mixture was stirred at rt for 18 h. The resulting precipitate was removed by filtration and washed with hexanes. The filtrate was diluted with water (25 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (10 mL x 2), and the combined organic layers dried (Na2SO-J) and concentrated to yield the title compound (512 mg, 73%).
  • 4
  • [ 333-47-1 ]
  • [ 1005206-25-6 ]
  • 5
  • [ 76-09-5 ]
  • C13H8BF3O2S [ No CAS ]
  • [ 1005206-25-6 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; for 0.5h; General procedure: General procedure: The synthetic procedure for pentafluorophenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonate (a) is presented as an example (Scheme 1). 2,2'-Bis(1,3,2-benzodioxaborole) (cat2B2, 262 mg, 1.10 mmol), PdCl2(dppf) (25 mg, 0.030 mmol), AcOK (294 mg, 3.0 mmol), pentafluorophenyl 4-bromobenzenesulfonate (403 mg, 1.0 mmol), and EtOH (6.0 mL) were charged in a reaction vessel under an Ar atmosphere. The resulting mixture was stirred for 2 h at 80 C. After cooling to room temperature, pinacol (260 mg, 2.20 mmol) was added to the mixture. The mixture was further stirred for 30 min at room temperature. H2O and n-hexane were added to the mixture and the product was extracted into the organic layer. After drying the organic layer with anhydrous MgSO4, solids were removed by filtration. The filtrate was concentrated. The product was obtained as a white solid by Kugelrohr distillation.
  • 6
  • [ 456-56-4 ]
  • [ 73183-34-3 ]
  • [ 1005206-25-6 ]
  • (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(trifluoromethylsulfane)benzene [ No CAS ]
  • C19H27B2F3O4S [ No CAS ]
  • 7
  • [ 456-56-4 ]
  • [ 25015-63-8 ]
  • [ 1005206-25-6 ]
  • (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(trifluoromethylsulfane)benzene [ No CAS ]
  • 8
  • [ 1005206-25-6 ]
  • [ 95889-09-1 ]
  • 1-(4-(4-((trifluoromethyl)thio)benzyl)phenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With potassium phosphate; bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); In dichloromethane; at 100℃; for 12h;Inert atmosphere; The intermediate A1 was passed through a 100 ml round bottom flask,Add 198 mg of Pd (dppf) to 2.DCM,2 g of potassium phosphate and 1.2 gP-trifluoromethylthiophenylboronic acid pinacol ester, 10 ml of toluene was added,Argon under the protection,100 C reaction 12h, spin dry solvent,100 ml of water was added, extracted twice with 20 ml of dichloromethane,Using petroleum ether: ethyl acetate = 30: 1 silica gel column,To obtain 1 g of intermediate A3 (colorless liquid)The yield was 64%
  • 9
  • [ 1005206-25-6 ]
  • [ 51359-78-5 ]
  • 4-(4-((trifluoromethyl)thio)benzyl)benzaldehyde [ No CAS ]
  • 10
  • [ 1124382-72-4 ]
  • [ 1005206-25-6 ]
  • 8-(4-(trifluoromethylthio)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; a) 8-(4-(Trifluoromethylthio)phenyl)-ri,2,41triazolori,5-alpyridin-2-amine In a 150 ml round-bottomed flask, 8-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-amine (1.40 g, 6.58 mmol), 4,4,5,5-tetramethyl-2-(4-(trifluoromethylthio)phenyl)-l,3,2-dioxaborolane (2.00 g, 6.58 mmol) and cesium carbonate (4.29 g, 13.2 mmol) were combined with dioxane (80 ml) and water (8.00 ml) to give a white suspension. l,l'-Bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (481 mg, 658 mupiiotaomicron) was added. The reaction mixture was heated to 100C and stirred overnight. Chromatography (silica gel, 70 g, ethyl acetate/heptane = 30:70 to 100:0) yielded the title compound as a light brown solid (1.77 g, 87%). MS: m/z = 311.0 [M+H]+.
  • 11
  • [ 1005206-25-6 ]
  • 2-bromo-8-(4-((trifluoromethyl)thio)phenyl)-[1,2,4]triazolo[1,5-a]pyridine [ No CAS ]
  • 12
  • [ 1005206-25-6 ]
  • N-(3-(3-methylisothiazol-5-yl)-3-azabicyclo[3.2.1]octan-8-yl)-8-(4-((trifluoromethyl)thio)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
  • 13
  • [ 1005206-25-6 ]
  • N-(3-(3-methylisothiazol-5-yl)-3-azabicyclo[3.2.1]octan-8-yl)-8-(4-(trifluoromethylsulfanyl)phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
  • 14
  • [ 1005206-25-6 ]
  • N-(3-(3-methylisothiazol-5-yl)-3-azabicyclo[3.2.1]octan-8-yl)-8-(4-(trifluoromethylsulfanyl)phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
  • N-(3-(3-methylisothiazol-5-yl)-3-azabicyclo[3.2.1]octan-8-yl)-8-(4-(trifluoromethylsulfanyl)phenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine [ No CAS ]
  • 15
  • 1,3-dioxoisoindolin-2-yl 4-((trifluoromethyl)thio)benzoate [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1005206-25-6 ]
  • 16
  • [ 330-17-6 ]
  • [ 1005206-25-6 ]
  • 17
  • [ 1005206-25-6 ]
  • 5-fluoro-3-methyl-2-(4-(4-((trifluoromethyl)thio)benzyl)phenyl)quinolin-4(1H)-one [ No CAS ]
  • 18
  • [ 1005206-25-6 ]
  • C29H24F4N2O3S [ No CAS ]
  • 19
  • [ 1005206-25-6 ]
  • C23H15F4NOS [ No CAS ]
  • 20
  • [ 10342-83-3 ]
  • [ 1005206-25-6 ]
  • 1-(4'-((trifluoromethyl)thio)-[1,1'-biphenyl]-4-yl)propan-1-one [ No CAS ]
  • 21
  • [ 456-56-4 ]
  • [ 73183-34-3 ]
  • [ 1005206-25-6 ]
  • (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(trifluoromethylsulfane)benzene [ No CAS ]
  • 22
  • [ 811-68-7 ]
  • [ 73852-88-7 ]
  • [ 1005206-25-6 ]
  • 23
  • [ 330-17-6 ]
  • [ 73183-34-3 ]
  • [ 1005206-25-6 ]
YieldReaction ConditionsOperation in experiment
70% With copper(I) tetrakis(acetonitrile)tetrafluoroborate; lithium perchlorate; sodium flouride; N-fluorobis(benzenesulfon)imide In acetonitrile for 6h; Irradiation; Inert atmosphere; Sealed tube;
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