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Chemical Structure| 150255-96-2 Chemical Structure| 150255-96-2
Chemical Structure| 150255-96-2

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Product Details of 3-Cyanophenylboronic acid

CAS No. :150255-96-2
Formula : C7H6BNO2
M.W : 146.94
SMILES Code : OB(O)C1=CC(=CC=C1)C#N
MDL No. :MFCD01318967
InChI Key :XDBHWPLGGBLUHH-UHFFFAOYSA-N
Pubchem ID :2734325

Safety of 3-Cyanophenylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3-Cyanophenylboronic acid

* 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 [ 150255-96-2 ]

[ 150255-96-2 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 53848-17-2 ]
  • [ 150255-96-2 ]
  • 2'-amino-3'-methyl-biphenyl-3-carbonitrile [ No CAS ]
  • 2
  • [ 126717-59-7 ]
  • [ 150255-96-2 ]
  • [ 867006-62-0 ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; toluene;Heating / reflux; Step 2: 3-(6-Methoxy-2-meth(at)lpyridin-3-(at))benzonitrile: To a nitrogen flushed mixture of 3- cyanophenylboronic acid (5.0 g, 34 mmol), <strong>[126717-59-7]3-bromo-6-methoxy-2-methylpyridine</strong> (4.6 g, 22.7 mmol) and palladium tetrakis (triphenylphosphine) mg, 0.68 mmol) is added toluene (150 mL), methanol (12 mL) and sodium carbonate (22.7 mmol) and the mixture is heated overnight at reflux. The cooled reaction is concentrated and the residue is purified by chromatography eluting with cyclohexane-3.2 to 9% ethyl acetate. Product containing fractions are combined and concentrated to afford 3-(6-methoxy-2-methylpyridin-3- yl) benzonitrile (3.09g, 61% yield) as a white solid. LC/MS: MS m/e = 225 (M + H) ; RT 3.58 min; ¹H NMR (CDCl3, 8 ppm) 7.65 (1H, m), 7.60 (1H, m), 7.56 (2H, m), 7.40 (1H, d), 6.63 (1H, d), 3.98 (3H, s), 2.40 (3H, s).
  • 3
  • [ 108-86-1 ]
  • [ 150255-96-2 ]
  • [ 24973-50-0 ]
YieldReaction ConditionsOperation in experiment
88% With bis(((1Z,3Z)-3-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)-1,3-diphenylprop-1-en-1-yl)oxy)palladium; potassium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 4.5h;Catalytic behavior; General procedure: A mixture of aryl halide (1mmol), olefin (1mmol), K2CO3 (1mmol), and the Pd-Schiff base complex (2.1mg, 0.2mol %) in DMF-H2O (1:1) was stirred at 80C for 3-4h. The reaction progress was monitored periodically by TLC. After completion of the reaction, it was cooled to room temperature and the product was extracted with ethyl acetate (3×10mL) from aqueous phase. The combined organic fractions were dried over Na2SO4, the solvent removed under reduced pressure to afford a crude product. The residue was purified by short column chromatography on silica gel eluted with petroleum ether/ethyl acetate afforded the desired coupled products up to 98% yield. The products were confirmed by 1H and 13C NMR.General procedure for the Suzuki-Miyaura reaction: A mixture of aryl halide (1mmol), arylboronic acid (1mmol), K2CO3 (1mmol), and the Pd- Schiff base complex (2.1mg, 0.2mol %) in DMF-H2O (1:1) was stirred at 80C for 3-5h. The progress of reaction was monitored by TLC until the complete consumption of the aryl halide. After the reaction, the mixture was cooled down to room temperature and repeatedly extracted with ethyl acetate. The combined organic layer was separated, dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding coupling products in up to 95% isolated yield. The products were confirmed by 1H and 13C NMR.
83% With potassium carbonate; In water; at 70℃; for 0.5h;Inert atmosphere; General procedure: In a typical run, h-BN(at)Fur(at)Pd(OAc)2 (0.05 mmol) was added to a mixture of arylboronic acid 1 (1.0 mmol), aryl bromide 2 (1.5 mmol) and K2CO3 (1.5 mmol) in water (1 mL). The resulting mixture was stirred at 70 C under Ar protection, and the progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added to the reaction mixture and the catalyst was separated. The organic phase was washed with water, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. Finally, the residue was isolated by chromatography on a column of silica gel to afford the corresponding product 3.
80% With potassium phosphate; [bis{2-(3-(2,4,6-trimethylbenzyl)imidazolin-2-yliden-1-yl)-4-methylphenyl}amido]chloronickel; In 1,4-dioxane;Inert atmosphere; Schlenk technique; Reflux; General procedure: In a typical reaction, to a 25-mL Schlenk tube equipped with amagnetic stirring bar were added nickel(II) catalyst 2a (0.005mmol, 1.0mol %), aryl halides (0.5mmol), phenylboronic acids (0.75mmol), and anhydrous K3PO4 (2.0mmol). The tube was then evacuated (3×5min) under vacuum and backfilled with N2. Dried dioxane (4.0mL) was injected via a syringe, and the reaction mixture was stirred at reflux until the aryl halides had disappeared as monitored by TLC. The reaction mixture was treated with H2O (20mL), then extracted with Et2O (3×15mL). The combined organic extracts were washed with sat. aq NaCl (10mL) and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the crude material was purified by silica gel column chromatography to give the corresponding biaryl. All the coupling products are known and their structures were identified by comparing their 1H NMR and 13C NMR spectral data with those reported in literature.
67% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; for 4h;Heating / reflux; Preparation Example 5. C-Biphenyl-3-yl-methylamine To a solution of 3-cyanophenylboronic acid (1.0g, 6.81 mmol) and bromobenzene (1.07g, 6.81mmol) in N,N-dimethylformamide (100mL) were added tetrakis(triphenylphosphine)palladium(0) (0.393g, 0.341 mmol) and cesium carbonate (2.77g, 8.51mmol) under nitrogen atmosphere, and the mixture was stirred for 4 hours under reflux. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and biphenyl-3-carbonitrile (821 mg, 67%) was obtained as a yellow solid. Next, a solution of the resulting biphenyl-3-carbonitrile (821 mg, 4.58mmol) in tetrahydrofuran (5mL) was added to a solution of lithium aluminum hydride (0.435g, 11.5mmol) in tetrahydrofuran (5mL) that had been cooled on an ice bath, and the solution was stirred for 6 hours at room temperature. The reaction solution was cooled on an ice bath, a mixture solution of methanol and water (9:1) was added thereto, an aqueous solution of saturated ammonium chloride was further added, filtration was carried out through Celite pad and insoluble matter was removed. The filtrate was partitioned, the organic layer was dried over anhydrous magnesium sulfate, and the title compound (527mg, 63%) was obtained as a brown oil. This was used in the next reaction without further purification.
67% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; for 4h;Heating / reflux; To a solution of 3-cyanophenylboronic acid (1.0g, 6.81 mmol) and bromobenzene (1.07g, 6.81mmol) in N,N-dimethylformamide (100mL) were added tetrakis(triphenylphosphine)palladium(0) (0.393g, 0.341 mmol) and cesium carbonate (2.77g, 8.51mmol) under nitrogen atmosphere, and the mixture was stirred for 4 hours under reflux. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 10 : 1), and biphenyl-3-carbonitrile (821 mg, 67%) was obtained as a yellow solid. Next, a solution of the resulting biphenyl-3-carbonitrile (821mg, 4.58mmol) in tetrahydrofuran (5mL) was added to a solution of lithium aluminum hydride (0.435g, 11.5mmol) in tetrahydrofuran (5mL) that had been cooled on an ice bath, and the solution was stirred for 6 hours at room temperature. The reaction solution was cooled on an ice bath, a mixture solution of methanol and water (9:1) was added thereto, an aqueous solution of saturated ammonium chloride was further added, filtration was carried out through Celite pad and insoluble matter was removed. The filtrate was partitioned, the organic layer was dried over anhydrous magnesium sulfate, and the title compound (527mg, 63%) was obtained as a brown oil. This was used in the next reaction without further purification.
64% With Ti0.97Pd0.03O1.97; potassium carbonate; In water; at 100℃; for 6h; General procedure: A mixture of aryl halide 1 (0.4mmol), arylboronic acid 2 (0.8mmol), Ti0.97Pd0.03O1.97 (nanoparticles; 10wt %), K2CO3 (110mg, 0.8mmol) in water (2mL) was stirred at 100C for 6h. After the completion of the reaction, diethyl ether (15ml x 3 times) was poured into the mixture, washed with water (15mL), extracted with diethyl ether (3×20mL), dried over anhydrous Na2SO4 and evaporated under vacuum; the residue was purified by column chromatography (petroleum ether or petroleum ether/ethyl acetate) to obtain the desired coupled product.

  • 4
  • [ 150255-96-2 ]
  • [ 197007-87-7 ]
  • 3-(3-hydroxymethyl-pyridin-4-yl)-benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux; To a flask charged with (4-bromo-pyridin-3~yl)-methanol (90 mg, 0.48 mmol), 3-cyanophenylboronic acid (84.4 mg, 0.57 mmol) and tetrakis(triphenylphousphine)-palladium(0) (28 mg) was added 2 M Na2CO3 (2 mL) and toluene (3 ml_). The reaction mixture was refluxed overnight and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and purified by column chromatography to yield 3-(3-Hydroxymethyl-pyridin-4- yl)-benzonitrile as a white solid.1HNMR (CDCI3, 300 MHz) delta (ppm) 8.74 (s, 1 H), 8.60 (d, J = 4.8 Hz, 1 H), 7.9-7.2 (m, 7H), 4.62 (s, 2H), 3.34 (bs, 1 H); LCMS: 2.815 min, m/z: 211 (M + 1)
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux; To a flask charged with <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (90 mg, 0.48 mmol), 3-cyanophenylboronic acid (84.4 mg, 0.57 mmol) and tetrakis(triphenylphousphine)-palladium(0) (28 mg) was added 2 M Na2COe (2 ml_) and toluene (3 ml_). The reaction mixture was refluxed overnight and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and purified by column chromatography to yield 3-(3-Hydroxymethyl-pyridin-4- yl)-benzonitrile as a white solid.1HNMR (CDCI3, 300 MHz) delta (ppm) 8.74 (s, 1 H), 8.60 (d, J= 4.8 Hz, 1 H), 7.9-7.2 (m, 7H), 4.62 (s, 2H), 3.34 (bs, 1 H); LCMS: 2.815 min, m/z: 211 (M + 1).
  • 6
  • [ 51376-06-8 ]
  • [ 150255-96-2 ]
  • [ 1395071-74-5 ]
  • 7
  • [ 62-53-3 ]
  • [ 150255-96-2 ]
  • [ 24973-50-0 ]
  • 8
  • [ 74137-36-3 ]
  • [ 150255-96-2 ]
  • 3,3″-diamidino-5′-methoxy-m-terphenyl dihydrochloride [ No CAS ]
  • 9
  • [ 74137-36-3 ]
  • [ 150255-96-2 ]
  • [ 1445904-42-6 ]
  • 10
  • [ 1333240-17-7 ]
  • [ 150255-96-2 ]
  • [ 1581767-54-5 ]
YieldReaction ConditionsOperation in experiment
100% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; for 5.0h;Reflux; Inert atmosphere; a. Preparation of Compound 3-(4,5-Dimethoxypyrimidin-2-yl)benzonitrile 2-Chloro-4,5-dimethoxypyrimidine (100 mg, 0.57 mmol), (3-cyanophenyl)boronic acid (126 mg, 0.86 mmol), Pd(PPh3)4 (66 mg, 0.06 mmol) and Na2C03(182 mg, 1.72 mmol) were dissolved in a mixture of dioxane (9 mL) and water (3 mL). The air was evacuated and replaced with N2. Then, the reaction mixture was refluxed for 5 hours. After the reaction was completed, it was cooled to room temperature and it was diluted with EtOAc and washed with sat. NH4CI followed by brine. The organic layer was dried over Na2S04 and concentrated in vacuo and the resulting residue was flash chromatographed on silica gel eluting with 0 to 20% EtOAc/Hexane. This afforded 3-(4,5-dimethoxypyrimidin-2-yl)benzonitrile as a white solid (138 mg, 100%); m.p.134-136 C; H NMR (400 MHz, CDC13) delta 8.61 (s, 1H), 8.54 (d, J= 8 Hz, 1H), 8.09 (s, 1H), 7.65 (d, J= 8 Hz, 1H), 7.51 (t, J= 8 Hz, 1H), 4.13 (s, 3H), 3.95 (s, 3H); 13C NMR (100 MHz, CDC13) 6 159.8, 153.6, 141.7, 138.5, 137.0, 132.8, 131.6, 131.3, 129.2, 1 18.9, 1 12.6, 56.4, 54.2
  • 11
  • [ 150255-96-2 ]
  • [ 504-63-2 ]
  • [ 684648-40-6 ]
  • 12
  • [ 591-50-4 ]
  • [ 150255-96-2 ]
  • [ 24973-50-0 ]
  • 13
  • [ 150255-96-2 ]
  • [ 151899-62-6 ]
  • 3-(1-trityl-1H-1,2,4-triazol-3-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
227 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 100℃; for 4h; 3-iodo-1-trityl -1H-1,2,4- triazole (300 mg),3-cyanophenyl boronic acid (101 mg), tetrakis triphenylphosphine palladium (79 mg), ethanol 2M aqueous sodium carbonate (1.5 mL) (1.0 mL) - toluene (1.5 mL) mixed solution of the mixture was stirred for 4 hours at 100 C. After cooling to room temperature, and separated the two layers.The aqueous layer was extracted with ethyl acetate, it was concentrated under reduced pressure and the organic layers were washed with. The residue was purified by column chromatography (silica gel cartridge, hexane: ethyl acetate = 88: 12-50: 50) to give the title compound (227 mg) as a colorless solid.
  • 14
  • [ 150255-96-2 ]
  • [ 1000016-93-2 ]
  • 15
  • [ 1005-38-5 ]
  • [ 150255-96-2 ]
  • 3-(6-amino-2-(methylthio)pyrimidin-4-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); caesium carbonate; In water; toluene; at 115℃; for 16h; Bis(di-/er/-butyl(4-dimethylamiiiophenyl)phosphine)dichloropalladium(II) (1.0 g, 5 mol%) ws added to a mixture of 6-chloro-2-(methylthio)pyrimidin-4-amine (Combi-Blocks, cat ST-1384) (5.0 g, 29 mmol), (3-cyanophenyl)boronic acid (8.4 g, 57 mmol) and cesium carbonate (37 g, 114 mmol) in toluene (100 mL) and water (10 mL) The mixture was purged with nitrogen, and then stirred at 115 C for 16 h. The reaction mixture was cooled to room temperature, filtered through a Celite plug with DCM and concentrated under reduced pressure. Water (200 mL) was added to the residue and the resulting solid was collected by filtration, and then dried to give the desired product (6.5 g, 94 %), which was used in the next step without further purification. LC-MS calculated for CnHi N+S (M+H)+: m/z = 243.1; found 243.2.
  • 16
  • 1-(benzoyl)piperidine-2,6-dione [ No CAS ]
  • [ 150255-96-2 ]
  • [ 24973-50-0 ]
  • 17
  • [ 640-60-8 ]
  • [ 150255-96-2 ]
  • [ 24973-50-0 ]
  • 18
  • [ 98-88-4 ]
  • [ 150255-96-2 ]
  • [ 24973-50-0 ]
  • 19
  • [ 6627-22-1 ]
  • [ 150255-96-2 ]
  • 6-(3-cyanophenyl)pyrimidine-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 90℃; for 5h;Inert atmosphere; To a stirred solution of <strong>[6627-22-1]methyl 6-chloropyrimidine-4-carboxylate</strong> (CAS 6627-22-1, from CombiBlocks, 0.70 g, 4.06 mmol, 1.0 eq) and (3-cyanophenyl)boronic acid (CAS 150255-96-2, from CombiBlocks, 1.19 g, 8.11 mmol, 2 eq) in 1,4-dioxane (5 mL) and water (2.5 mL) was added Cs2CO3 (2.63 g, 8.11 mmol, 2.0 eq). The reaction mixture was purged with N2 for 10 min, then tetrakis(triphenylphosphine)palladium (CAS 14221-01-3, from CombiBlocks, 0.234 g, 0.20 mmol, 0.05 eq) was added, and the mixture was heated at 90 C for 5 h. The mixture was poured into ice-cold water (30 mL) and extracted with EtOAc (2 x 30 mL). The aqueous layer was acidified with dilute HCl and extracted with EtOAc (3 x 30 mL). The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure to yield 6-(3-cyanophenyl)pyrimidine-4-carboxylic acid (0.52 g, 2.31 mmol, 56% yield). LCMS: Method C, 1.36 min, MS: ES+226.5; 1H NMR (400 MHz, DMSO-d6) d ppm: 14.11 (s, 1H), 9.48 (s, 1H), 8.79 (s, 1H), 8.68 (s, 1H), 8.63 - 8.65 (d, J = 8.0 Hz, 1H), 8.08 - 8.10 (d, J = 7.6 Hz, 1H), 7.81 (t, J = 8.0 Hz, 1H).
 

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