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Chemical Structure| 171364-86-6
Chemical Structure| 171364-86-6
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Product Details of [ 171364-86-6 ]

CAS No. :171364-86-6 MDL No. :MFCD11110552
Formula : C14H17BO2S Boiling Point : -
Linear Structure Formula :- InChI Key :LTSGSDOTQABJMA-UHFFFAOYSA-N
M.W : 260.16 Pubchem ID :10658979
Synonyms :

Safety of [ 171364-86-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 171364-86-6 ]

* 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 [ 171364-86-6 ]

[ 171364-86-6 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 7342-82-7 ]
  • [ 25015-63-8 ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; 1,4-dioxane at 60℃; 16 Example 16 Intermediate 16-2-(benzo[b]thiophen-3-yl0-4,4,5,5-tetramethyl-[1,2]oxaborolane To a solution of 3-bromobenzothiophene (10 g) in dioxane (30 ml) a solution of pinacoleborane (1 M, 9.0 g) in THF (70 ml) was added followed by TEA (10.7 g) and PdCl2, dpp ferrocene. The reaction was heated at 60° C. overnight. The solvent was removed under vacuum. Ether was added and the insoluble was filtered. The filtrate was evaporated and filtered through silica gel (300 ml) using 5% Ethyl acetate/Hexane to give 9.0 g of desired product.
With triethylamine In tetrahydrofuran; 1,4-dioxane at 60℃; 16 To a solution of 3-bromobenzothiophene (lOg) in dioxane (30 ml) a solution of pinacoleborane (1 M, 9.0 g) in THF (70 ml) was added followed by TEA (10.7 g) and PDCL2, dpp ferrocene. The reaction was heated at 60 C overnight. The solvent was removed under vacuum. Ether was added and the insoluble was filtered. The filtrate was evaporated and filtered through silica gel (300 ml) using 5% Ethyl acetate/Hexane to give 9.0 g of desired product.
  • 2
  • [ 171364-86-6 ]
  • [ 170011-47-9 ]
  • [ 796851-37-1 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water at 70℃; 21 Example 21 Intermediate 21-8-benzo[b]thiophen-3-yl-1,4-dioxa-spiro[4,5]dec-7-ene To a mixture of 2-(benzo[b]thiophen-3-yl0-4,4,5,5-tetramethyl-[1,2]oxaborolane (2.6 g) and trifluoro-methanesulfonic acid 1,4-dioxa-spiro[4.5]dec-7-en-8yl ester (2.9 g) in 1,2-dimethoxyethane (DME, 10 ml), Na2CO3 (2.8 g in 10 ml H2O) was added followed by LiCl (0.421 g) in water and Tetrakis(triphenylphosphine)Palladium(0) (0.100 g). The reaction was heated at 70° C. overnight. The reaction was then cooled to room temperature and the solvent removed under vacuum. The residue was taken in CH2Cl2 and washed with aqueous 2N Na2CO3. The organic phase was separated and dried over MgSO4. The solvent was then removed and the residue filtered through 200 ml of silica gel using 15% ethyl acetate/hexane to give 2.0 g of the title compound. MP: 80-83° C.; MS (ES) m/z (relative intensity): 273 (M++H, 100). Elemental analysis for C16H16O2S: Calculated: C, 70.56; H, 5.92. Found: C, 68.79; H, 5.88.
With sodium carbonate; lithium chloride In 1,2-dimethoxyethane; water at 70℃; 21 To a mixture of 2- (benzo [b] THIOPHEN-3-YL0-4, 4,5, 5-TETRAMETHYL- [L, 2] oxaborolane (2.6g) and trifluoro-methanesulfonic acid 1, 4-dioxa-spiro [4.5] DEC-7-EN-8YL ester (2.9g) in 1, 2-DIMETHOXYETHANE (DME, 10 ml), Na2C03 (2.8g in 10 ml H20) was added followed by LiCI (. 421G) in water and Tetrakis (triphenylphosphine) Palladium (0) (. LOOG). The reaction was heated at 70 C overnight. The reaction was then cooled to room temperature and the solvent removed under vacuum. The residue was taken in CH2C12 and washed with aqueous 2N NA2C03. The organic phase was separated and dried over MGS04. The solvent was then removed and the residue filtered through 200 ml of silica gel using 15% ethyl acetate/hexane to give 2.0 g of the title compound. MP: 80-83°C ; MS (ES) M/Z (relative intensity): 273 (M++H, 100). Elemental analysis for CI6 HIE 02 S: Calculated: C: 70.56 ; H: 5.92 ; Found: C: 68.79 ; H: 5.88.
  • 3
  • [ 7342-82-7 ]
  • [ 61676-62-8 ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 3-Bromothianaphthene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃;
20% Stage #1: 3-Bromothianaphthene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78℃; for 0.5h;
With n-butyllithium at -78℃; for 24h; Inert atmosphere; 1.1 (1) under the protection of nitrogen conditions, 3-bromobenzothiophene and organic lithium reagent - n-butyl lithium reaction to generate benzothiophene lithium salt, then add isopropanol pinacol borate ester, the reaction is completed Boronic acid pinacol ester; the reaction temperature is _78 ° C, the reaction time is 24 hours;
  • 4
  • [ 171364-86-6 ]
  • [ 1135148-66-1 ]
  • [ 1135148-67-2 ]
YieldReaction ConditionsOperation in experiment
17% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In 1,4-dioxane; water at 90℃; for 48h; Inert atmosphere;
  • 5
  • [ 171364-86-6 ]
  • [ 105361-77-1 ]
  • [ 1174298-62-4 ]
YieldReaction ConditionsOperation in experiment
20% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In 1,4-dioxane; water at 110℃; for 12h; Inert atmosphere;
  • 6
  • [ 171364-86-6 ]
  • [ 1403580-57-3 ]
  • [ 1403580-37-9 ]
YieldReaction ConditionsOperation in experiment
17% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In 1,4-dioxane; water at 110℃; for 48h; Inert atmosphere;
  • 7
  • [ 171364-86-6 ]
  • C21H25BrOSi [ No CAS ]
  • C29H30OSSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 40℃; for 2h;
  • 8
  • [ 128-08-5 ]
  • [ 171364-86-6 ]
  • C14H16BBrO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% In N,N-dimethyl-formamide at 20℃; for 14h; General procedure: General procedure: To a solution of 3-anisyl pinacol borane (50 mg, 0.21 mmol)in DMF (1 mL) was added N-bromosuccinimide (82 mg, 0.46 mmol). After stirring at room temperature for 14 h, resultant solution was treated with 10% Na2S2O3aq (10 ml) and was extracted with Et2O (10 ml3). The combined organic phase was washed with H2O (10 ml2) and brine (10 ml1) and dried over MgSO4. After removal of solvent under reduced pressure, the residue was chromatographed on silica gel with Hexane to afford 2-bromo-5-methoxyphenyl pinacol borate (57.3 mg, 87% yield) as colorless oil
  • 9
  • [ 171364-86-6 ]
  • C14H16BBrO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 14h; General procedure General procedure: To a solution of 3-anisyl pinacol borane (50mg, 0.21mmol) in DMF (1mL) was added N-bromosuccinimide (82mg, 0.46mmol). After stirring at room temperature for 14h, resultant solution was treated with 10% Na2S2O3 aq (10 ml) and was extracted with Et2O (10ml×3). The combined organic phase was washed with H2O (10ml×2) and brine (10ml×1) and dried over MgSO4. After removal of solvent under reduced pressure, the residue was chromatographed on silica gel with Hexane to afford 2-bromo-5-methoxyphenyl pinacol borate (57.3mg, 87% yield) as colorless oil
  • 10
  • [ 171364-86-6 ]
  • [ 75264-92-5 ]
  • 3-((trifluoromethyl)selanyl)benzo[b]thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With [2,2]bipyridinyl; oxygen; copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 20℃; for 18h;
  • 11
  • [ 7342-82-7 ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diisopropylamine; hydrogenchloride; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II) / diethyl ether; toluene / 16 h / 0 - 110 °C / Inert atmosphere 2: 1 h / -5 - 20 °C 3: diethyl ether / 4 h / 20 °C
  • 12
  • [ 171364-86-6 ]
  • [ 13720-06-4 ]
  • 2,6-bis(benzo[b]furan-3-yl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: (2-benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2,6-dibromonaphthalene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #2: With sodium carbonate In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;
  • 13
  • [ 73183-34-3 ]
  • [ 95-15-8 ]
  • [ 171364-86-6 ]
  • [ 376584-76-8 ]
YieldReaction ConditionsOperation in experiment
With Pt(N,N′-dicyclohexylimidazol-2-ylidene)(divinyltetramethylsiloxane) In n-heptane at 100℃; for 20h; Inert atmosphere; Sealed tube; Overall yield = 44 %; Overall yield = 34 mg;
With n-butyllithium; C28H41ClNPPtSi In hexane; 1,3,5-trimethyl-benzene at 20 - 150℃; for 4h; Inert atmosphere; Overall yield = 76%; Overall yield = 79.2 mg; regioselective reaction;
With C23H38N2OPtSi2 In n-heptane for 20h; Overall yield = 44 %;
  • 14
  • [ 171364-86-6 ]
  • [ 18013-97-3 ]
  • [ 1443022-43-2 ]
  • 15
  • [ 7342-82-7 ]
  • [ 73183-34-3 ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
96% With C54H44NO2PPdS; potassium acetate In 2-methyltetrahydrofuran at 90℃; for 24h; Inert atmosphere; Sealed tube;
84% With (2’-methylamino-1,1’-biphenyl-2-yl)methanesulfonatopalladium dimer; potassium acetate; C40H29P In 2-methyltetrahydrofuran at 90℃; for 24h; Inert atmosphere; 5 In a glove box filled with nitrogen, Pd G4 dimer (2.0 mg, 0.0026 mmol),Ligand 11 (3.2 mg, 0.0059 mmol) and anhydrous 2-MeTHF (1.0 mL) were added to a 48 mL glass thick-walled pressure vessel, and the mixture was stirred in a glove box at room temperature for 15 minutes.Then add 3-bromobenzothiophene (1.065g, 5.0mmol, 1.0equiv) in turn,Pinacol diborate (1.60 g, 6.3 mmol, 1.26 equiv), anhydrous potassium acetate (980 mg, 10.0 mmol, 2.00 equiv) and anhydrous 2-MeTHF (24.0 mL) were put into the reaction flask.The reaction flask was covered with a lid and removed from the glove box, and stirred vigorously at 90°C for 24 hours.The reaction mixture was cooled to room temperature and filtered through short silica gel with the aid of ethyl acetate (100 mL).Then the solvent was removed under reduced pressure and purified by silica gel column chromatography.A white solid 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)benzothiophene (1.092 g, 84% yield) was obtained.
82% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 6h; I.1.1 (1) Synthesis of Sub 1-I-2 Round bottom flask 3-bromobenzothiophene (CAS Registry Number: 7342-82-7) (19.00 g, 89.16 mmol) Bis (pinacolato) diboron (27.17 g, 107.00 mmol), PdCl 2 (dppf) (2.18 g, 2.67 mmol), KOAc (26.25 g, 267.49 mmol), Add DMF (450 ml) and reflux at 100 ° C. for 6 hours. After the reaction is completed, the temperature of the reactant is cooled to room temperature, Extract with MC and wipe with water, The organic layer is dried over MgSO 4 and concentrated. after, The concentrate was separated using a silica gel column to give 19.02 g (yield: 82%) of product.
75% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 120℃; for 4h; 1 Preparation of Compound 1-1 To a 3 L round bottom flask (RBF) was added 60 g (281 mmol) of 3-bromo- [b] benzothiophene, 4,4,4 ', 4', 5,5,5 ' 10 g (14 mmol) of bis (triphenylphosphine) palladium (II) dichloride (PdCl2 (PPh3) 2), potassium acetate (KOAc) 694 g (704 mmol) of 1,4-dioxane and 1400 ml of 1,4-dioxane were placed," The reaction mixture was worked up with ethyl acetate (EA) / H2O, water was removed with MgSO4, and the residue was subjected to vacuum distillation. The crude product was subjected to column chromatography with methylene chloride (MC): hexane (Hx) to obtain 1-15 g (75%) of a white solid.4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-vi (1,3,2-dioxaborolane)
70.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 3h; Inert atmosphere; Reflux; 2.2.1.1. Synthesis of 2-(benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (SM-4) intermediate. To a degassed solution of 3-bromobenzo[b]thiophene (1.00 g, 4.69 mmol), bis(pinacolato)diboron(1.43 g, 5.63 mmol) and KOAc (921 mg, 9.39 mmol) in dry dioxane(15 mL), Pd(dppf)Cl2 (200 mg) was added under stirring. After 3 hrefluxing, the reaction solution was cooled and filtered through Celite.The solution was diluted with EtOAc (40 mL) and water (10 mL). Thephases were separated, and the aqueous phase was extracted withEtOAc. The combined organic phase was washed with brine andconcentrated. The residue was purified by column chromatographyon silica gel, eluted with EtOAc/hexanes (1:200, v/v) to give SM-4(0.86 mg, 70.9%) as a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm)8.36 (d, J=7.9 Hz, 1H), 8.06 (s, 1H), 7.88 (d, J=7.8 Hz, 1H),7.31-7.41 (m, 2H), 1.38 (s, 12H).
30% With sodium methylate In N,N-dimethyl acetamide at 60℃; for 6h; Inert atmosphere; Schlenk technique;

  • 16
  • [ 171364-86-6 ]
  • [ 3460-18-2 ]
  • C14H8BrNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 130℃; for 8h; 1 Preparation of Compound 1-2 3RBF in the compound L 1-155g (211mmol), 2,5- dibromo-nitrobenzene 83g (296mmol), tetrakis (triphenylphosphine) palladium (O) (Pd (PPh3) 4), 12.2g (10.5mmol) , Na2CO360.5g (570mmol), 1100ml of toluene, 285 ml of ethanol and dissolved back into the water 285 ml, was stirred for 8 hours under a 130 ° C. The reaction mixture after the water was removed by treatment with EA / H2O and, MgSO4, it was evaporated under reduced pressure. The crude product MC: Hx to the column chromatography to obtain a yellow liquid of compound 1-240g (56%).
  • 17
  • [ 171364-86-6 ]
  • C26H16N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water; ethanol / 8 h / 130 °C 2: triethyl phosphite / 1,2-dichloro-benzene / 3 h / 150 °C 3: copper(l) iodide; ethylenediamine; potassium phosphate / toluene / 1.5 h / 100 °C 4: caesium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / toluene / 3 h / 130 °C 5: palladium diacetate; potassium carbonate; Trimethylacetic acid / 25 h / 140 °C
  • 18
  • [ 171364-86-6 ]
  • C47H29N5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water; ethanol / 8 h / 130 °C 2: triethyl phosphite / 1,2-dichloro-benzene / 3 h / 150 °C 3: copper(l) iodide; ethylenediamine; potassium phosphate / toluene / 1.5 h / 100 °C 4: caesium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / toluene / 3 h / 130 °C 5: palladium diacetate; potassium carbonate; Trimethylacetic acid / 25 h / 140 °C 6: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium t-butanolate / toluene / 5 h / 120 °C
  • 19
  • [ 171364-86-6 ]
  • C14H8BrNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water; ethanol / 8 h / 130 °C 2: triethyl phosphite / 1,2-dichloro-benzene / 3 h / 150 °C
  • 20
  • [ 171364-86-6 ]
  • C20H12BrNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water; ethanol / 8 h / 130 °C 2: triethyl phosphite / 1,2-dichloro-benzene / 3 h / 150 °C 3: copper(l) iodide; ethylenediamine; potassium phosphate / toluene / 1.5 h / 100 °C
  • 21
  • [ 171364-86-6 ]
  • C26H18N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; water; ethanol / 8 h / 130 °C 2: triethyl phosphite / 1,2-dichloro-benzene / 3 h / 150 °C 3: copper(l) iodide; ethylenediamine; potassium phosphate / toluene / 1.5 h / 100 °C 4: caesium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate / toluene / 3 h / 130 °C
  • 22
  • [ 636-28-2 ]
  • [ 171364-86-6 ]
  • 1,2,4,5-tetrakis(benzothienyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 90 - 110℃; for 24h; Inert atmosphere; 3.2 (2) in the presence of a catalyst, the R substituted benzothiophene 3-boronic acid pinacol ester were mixed with 1,2,4,5-bromophenyl Suzuki reaction, the reaction is complete to give 1,2,4 , 5-tetrakis (benzothienyl) phenyl compound; the 2,4, 5-tetrabromobenzene, R substituted benzothiophene 3-boronic acid pinacol ester and the catalyst the molar ratio of 1: 4: 0.15; the catalyst is tetrakis (triphenylphosphine) palladium; the reaction temperature was 90 deg.] C, the reaction time was 24 hours; the reaction is carried out in a solvent, the solvent is tetrahydrofuran,The specific operation steps are as follows: dissolved in 1,2,4,5-bromobenzene in tetrahydrofuran (100mL tetrahydrofuran was dissolved proportion 1mmol), degassed, was added Pd (PPh3) 4, stirred under argon, benzothiophene 3-boronic acid was added, further added 2Mol / L aqueous sodium carbonate (1 mmol of 1,2,4,5-tetrabromobenzene was added 10-20 mL), warmed to reflux by Suzuki reaction was 24 hours; after cooling direct filtration, extracted with dichloromethane, washed with petroleum ether, after recrystallization from chlorobenzene to give a white solid.
  • 23
  • [ 171364-86-6 ]
  • [ 175205-81-9 ]
  • 2-(benzo[b]thiophen-3-yl)-4-(trifluoromethyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate tribasic trihydrate; In N,N-dimethyl-formamide; at 100℃; for 10h;Inert atmosphere; General procedure: Toa degassed solution of <strong>[175205-81-9]2-bromo-4-(trifluoromethyl)pyridine</strong> (500 mg,2.21 mmol) and the corresponding boric acid (1.2 equiv) or boric acidester (SM-4, 1.2 equiv) in dry DMF (10 mL) were added Pd(dppf)Cl2(50 mg) and K3PO4*3H2O (1.18 g, 4.42 mmol). After 10 h heating at100 °C, the reaction mixture was cooled to room temperature, dilutedwith EtOAc (50 mL) and filtered through a pad of Celite. The filtratewas washed with H2O and brine. After the solvent was removed, theresidue was purified by column chromatography on silica gel, elutedwith EtOAc/hexanes (1:50, v/v) to give corresponding cyclometalatedligands
  • 24
  • [ 171364-86-6 ]
  • N-(+/-)-(α-methoxycarbonylethyl)-2,4,6-triphenyl-pyridinium tetrafluoroborate [ No CAS ]
  • 4,4,5,5-tetramethyl-2-(2-(1-(methylperoxy)-12-propan-2-yl)benzo[b]thiophen-3-yl)-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With morpholine In dimethyl sulfoxide for 48h; Inert atmosphere; Sealed tube; Irradiation;
  • 25
  • [ 171364-86-6 ]
  • C53H36N2S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 90 °C 2.1: tetrahydrofuran / 12 h / 90 °C 2.2: 12 h / 120 °C 3.1: bromine / dichloromethane / 6 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 4 h / 60 °C 5.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 8 h / 120 °C
  • 26
  • [ 171364-86-6 ]
  • C17H13ClS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 90 °C 2.1: tetrahydrofuran / 12 h / 90 °C 2.2: 12 h / 120 °C
  • 27
  • [ 171364-86-6 ]
  • C17H12BrClS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 90 °C 2.1: tetrahydrofuran / 12 h / 90 °C 2.2: 12 h / 120 °C 3.1: bromine / dichloromethane / 6 h / 20 °C
  • 28
  • [ 171364-86-6 ]
  • C35H24ClNS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 12 h / 90 °C 2.1: tetrahydrofuran / 12 h / 90 °C 2.2: 12 h / 120 °C 3.1: bromine / dichloromethane / 6 h / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate / toluene / 4 h / 60 °C
  • 29
  • [ 171364-86-6 ]
  • [ 1107627-14-4 ]
  • C16H11ClO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃; for 12h; I.1.2 (2) Synthesis of Sub 1-II-2 Sub 1-I-2 (13.00 g, 49.97 mmol) In methyl 2-bromo-3-chlorobenzoate (12.47 g, 49.47 mmol), Pd (PPh 3) 4 (1.73 g, 1.50 mmol), K 2 CO 3 (13.81 g, 99.94 mmol), THF (160ml), Add H 2 O (80 ml) and reflux at 90 ° C. for 12 hours. After the reaction is completed, the temperature of the reactant is cooled to room temperature, Extract with MC and wipe with water, The organic layer is dried over MgSO 4 and concentrated. after, The concentrate was separated using a silica gel column to give 11.95 g (79%) of product.
  • 30
  • [ 56423-63-3 ]
  • [ 171364-86-6 ]
  • 2-(benzo[b]thiophen-3-yl)pyrazine [ No CAS ]
  • 31
  • [ 1532-97-4 ]
  • [ 171364-86-6 ]
  • [ 1610790-48-1 ]
YieldReaction ConditionsOperation in experiment
75.2 mg With C54H44NO2PPdS; water; potassium carbonate In 2-methyltetrahydrofuran at 90℃; for 24h; Inert atmosphere; Sealed tube;
  • 32
  • [ 34784-04-8 ]
  • [ 171364-86-6 ]
  • 5-(benzo[b]thiophen-3-yl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.7 mg With C54H44NO2PPdS; water; potassium carbonate In 2-methyltetrahydrofuran at 90℃; for 24h; Inert atmosphere; Sealed tube;
  • 33
  • [ 171364-86-6 ]
  • [ 90-14-2 ]
  • [ 80-48-8 ]
  • [ 1402929-77-4 ]
YieldReaction ConditionsOperation in experiment
64% With 5-norbornene-2-carbonitrile; palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 80℃; for 15h; Inert atmosphere; Schlenk technique;
  • 34
  • [ 171364-86-6 ]
  • C28H16O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2: potassium hydroxide; water / ethanol / Reflux
Multi-step reaction with 2 steps 1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2: water; potassium hydroxide / ethanol / Reflux
  • 35
  • [ 171364-86-6 ]
  • C28H14Cl2O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2: potassium hydroxide; water / ethanol / Reflux 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h
Multi-step reaction with 3 steps 1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2: water; potassium hydroxide / ethanol / Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 12 h
  • 36
  • [ 171364-86-6 ]
  • C28H12O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2: potassium hydroxide; water / ethanol / Reflux 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h 4: aluminum (III) chloride / dichloromethane
Multi-step reaction with 4 steps 1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2: water; potassium hydroxide / ethanol / Reflux 3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 12 h 4: aluminum (III) chloride / dichloromethane
  • 37
  • [ 171364-86-6 ]
  • C46H36O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2.1: potassium hydroxide; water / ethanol / Reflux 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2.1: water; potassium hydroxide / ethanol / Reflux 3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere
  • 38
  • [ 171364-86-6 ]
  • C46H34S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2.1: potassium hydroxide; water / ethanol / Reflux 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere 6.1: tin(ll) chloride; trifluoroacetic acid / toluene / 3 h
Multi-step reaction with 6 steps 1.1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2.1: water; potassium hydroxide / ethanol / Reflux 3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere 6.1: tin(ll) chloride; trifluoroacetic acid / toluene / 3 h
  • 39
  • [ 171364-86-6 ]
  • C52H48O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2.1: potassium hydroxide; water / ethanol / Reflux 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2.1: water; potassium hydroxide / ethanol / Reflux 3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 5.2: -78 - 20 °C
  • 40
  • [ 171364-86-6 ]
  • C52H46S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: palladium diacetate; potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / Inert atmosphere; Reflux 2.1: potassium hydroxide; water / ethanol / Reflux 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 5.2: -78 - 20 °C / Inert atmosphere 6.1: tin(ll) chloride; trifluoroacetic acid / toluene / 4 h
Multi-step reaction with 6 steps 1.1: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / water; toluene / 1.5 h / Inert atmosphere 2.1: water; potassium hydroxide / ethanol / Reflux 3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 12 h 4.1: aluminum (III) chloride / dichloromethane 5.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 5.2: -78 - 20 °C 6.1: tin(ll) chloride; trifluoroacetic acid / toluene / 4 h / -78 °C
  • 41
  • [ 171364-86-6 ]
  • 3,7-bis(((trifluoromethyl)sulfonyl)oxy)naphthalene-2,6-dicarboxylic acid dimethyl ester [ No CAS ]
  • C30H20O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; toluene Inert atmosphere; Reflux;
87% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; toluene for 1.5h; Inert atmosphere; 8 Example 8 (0171) Synthesis of Diester 402- A two-neck round-bottom flask fitted with a condenser was charged with bistriflate 300 (0.500 g, 0.925 mmol, 1 equivalent), benzothiophene 3-pinacolate ester (0.601 g, 2.31 mmol, 2.5 equivalentz), K3PO4 (0.589 g, 2.78 mmol, 3 equivalents), Pd(OAc)2 (8.3 mg, 0.037 mmol, 0.04 equivalents), and SPhos (30.4 mg, 0.074 mmol, 0.08 equivalents). These solids were then placed under N2 atmosphere and dissolved in 40:1 toluene/H2O (41 mL) that had been sparged with N2 for 1.5 hr. After refluxing overnight and cooling to room temperature, the reaction was quenched with H2O and poured over filter paper. The precipitate was washed with H2O and MeOH to yield diester 402 as a yellow solid (409 mg, 87%); 1H NMR (500 MHz, CDCl3, 25° C.) δ 8.54 (s, 2H), 8.09 (s, 2H), 7.94 (d, J=8.0 Hz, 2H), 7.51 (d, J=7.8 Hz, 2H), 7.46 (s, 2H), 7.39 (t, J=7.3 Hz, 2H), 7.35 (t, J=7.4 Hz, 2H), 3.53 (s, 6H); 13C NMR (151 MHz, CDCl3, 25° C.) δ (ppm) 168.02, 139.82, 139.21, 136.80, 133.61, 133.24, 132.05, 131.58, 131.07, 124.58, 123.93, 123.02, 122.32, 52.50; high-resolution mass spectroscopy (HRMS) (ES+) (m/z), calculated for C30H20O4NaS2 (M+Na)+ 531.0701, found 531.0654.
  • 42
  • (E)-1-(benzo[b]thiophen-3-yl)butan-1-one O-perfluorobenzoyl oxime [ No CAS ]
  • [ 73183-34-3 ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
54% With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; palladium dichloride In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Sealed tube;
  • 43
  • C12H13NOS [ No CAS ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube 2: palladium dichloride; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube
  • 44
  • [ 58981-23-0 ]
  • [ 171364-86-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol / Inert atmosphere; Sealed tube 2: pyridine / dichloromethane / 0 °C / Inert atmosphere; Sealed tube 3: palladium dichloride; 2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine; tris<3,5-bis(trifluoromethyl)phenyl>phosphane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; potassium carbonate; 2,6-di-tert-butyl-4-methyl-phenol / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube
  • 45
  • [ 25015-63-8 ]
  • [ 95-15-8 ]
  • [ 171364-86-6 ]
  • [ 376584-76-8 ]
YieldReaction ConditionsOperation in experiment
With benzoic acid In hexane at 180℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube; Overall yield = 19 percentSpectr.; regioselective reaction;
  • 46
  • [ 171364-86-6 ]
  • 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole [ No CAS ]
  • C33H30N2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 18h; Reflux; 4 Synthesis of compound 4-4 Add 6.32g (14.59mmol) of 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole),3.80g (14.59mmol) of 2-(benzo[b]thiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane,0.42g (0.36mmol) of Pd(PPh3)4 and 10.08g (72.95mmol) of K2CO3 were mixed with 80mL of 1,4-dioxane and 40mL of distilled water.Then, the mixture was stirred under reflux for 18 hours. Once the temperature was lowered to room temperature, the organic layer was extracted using MC, and anhydrous magnesium sulfate (MgSO4) was added thereto to dry the organic layer.The resultant was filtered, and the solvent in the resultant filtrate was removed under reduced pressure. The residue was purified by column chromatography using EA and hexane in a ratio of 1:3 to obtain 5.33 g of compound 4-4 (75%).
  • 47
  • [ 171364-86-6 ]
  • C14H13BrClN [ No CAS ]
  • C22H18ClNS [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In water monomer; toluene at 120℃; for 8h; 5 Under an argon atmosphere, 3-3 (40.0 g, 128.8 mmol), 5-2 (40.2 g, 154.5 mmol), Tetrakis(triphenylphosphine)palladium (12.2g, 10.3mmol), potassium carbonate (71.2g, 515.1mmol), 50mL water,50mg Aliquant-336 and 100mL toluene were stirred at 120°C for 8 hours, then cooled to room temperature, 100mL ethyl acetate was added to the reaction solution,The organic phase was washed three times with deionized water (100 mL×3), and then dried with anhydrous magnesium sulfate.The concentrated solution obtained after removing the solvent from the organic phase was separated by silica gel column chromatography to obtain the product 5-3 (28.2 g, yield: 60%).
  • 48
  • [ 171364-86-6 ]
  • [ 60007-39-8 ]
  • [ 1322085-80-2 ]
YieldReaction ConditionsOperation in experiment
83% With pyridine; silver(I) fluoride In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere; Schlenk technique;
  • 49
  • [ 171364-86-6 ]
  • 1-benzyl-3-(methoxycarbonyl)pyridin-1-ium triflate [ No CAS ]
  • methyl 6-(1-benzothiophen-3-yl)-1-benzyl-1,6-dihydropyridine-3-carboxylate [ No CAS ]
  • methyl 6-(1-benzothiophen-3-yl)-1-benzyl-1,6-dihydropyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82 % ee With bis(cycloocta-1,5-diene)rhodium (I) tetrafluoroborate; anhydrous sodium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In 1,4-dioxane; lithium hydroxide monohydrate at 60℃; for 2h; Sealed tube; Inert atmosphere; Overall yield = 92 percent; Overall yield = 33.4 mg; enantioselective reaction;
  • 50
  • [ 171364-86-6 ]
  • 1-benzyl-3-(methoxycarbonyl)pyridin-1-ium triflate [ No CAS ]
  • methyl 6-(1-benzothiophen-3-yl)-1-benzyl-1,6-dihydropyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(cycloocta-1,5-diene)rhodium (I) tetrafluoroborate; anhydrous sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane; lithium hydroxide monohydrate at 60℃; for 2h; Sealed tube; Inert atmosphere;
Same Skeleton Products
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