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Chemical Structure| 4612-26-4

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Product Details of 1,4-Phenylenediboronic acid

CAS No. :4612-26-4
Formula : C6H8B2O4
M.W : 165.75
SMILES Code : C1=CC(=CC=C1B(O)O)B(O)O
MDL No. :MFCD00236018
InChI Key :BODYVHJTUHHINQ-UHFFFAOYSA-N
Pubchem ID :230478

Safety of 1,4-Phenylenediboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P501

Application In Synthesis of 1,4-Phenylenediboronic 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 [ 4612-26-4 ]

[ 4612-26-4 ] Synthesis Path-Downstream   1~9

  • 2
  • [ 586-76-5 ]
  • [ 4612-26-4 ]
  • [ 13653-84-4 ]
  • 3
  • [ 104-92-7 ]
  • [ 4612-26-4 ]
  • [ 104197-14-0 ]
  • 3,5-difluoro-4,4''-bis(methoxy)-1,1’:4’,1’’-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; water; for 12h;Reflux; Inert atmosphere; 1,4-Phenylene diboronic acid (1.0 g, 6.03 mmol) was dissolved in 1,2-dimethoxyethanol (100 mL) and methanol (10 mL)4-Bromoanisole (1.24 g, 6.64 mmol) and <strong>[104197-14-0]2,6-difluoro-4-bromoanisole</strong> (1.48 g, 6.64 mmol) were added dropwise to the above mixed solution,2 M aqueous potassium carbonate solution (20 mL) was added and degassed. Palladium tetrakis (triphenylphosphine) (349 mg, 0.30 mmol) was added to the mixed solution, and the mixture was refluxed under nitrogen atmosphere for 12 hours.An excessive amount of distilled water was added to the reaction solution to terminate the reaction,After extracting with dichloromethane, the solvent was concentrated under reduced pressure. The mixture obtained above was purified by column chromatography to give the desired compound (913 mg, 45%) as a white solid.
  • 4
  • [ 104-92-7 ]
  • [ 406482-22-2 ]
  • [ 4612-26-4 ]
  • 2,3-difluoro-4,4''-bis(methoxy)-1,1’:4’,1’’-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; water; for 12h;Reflux; Inert atmosphere; 1,4-phenylene diboronic acid (1.0 g, 6.03 mmol)1,2-Dimethoxyethanol (100 mL)And methanol (10 mL) was addedAfter dissolution,4-Bromoanisole (1.24 g, 6.64 mmol) and <strong>[406482-22-2]2,3-difluoro-4-bromoanisole</strong> (1.48 g, 6.64 mmol) were added dropwise to the mixed solution,2 M aqueous potassium carbonate solution (20 mL) was added and degassed.To the mixed solution, palladium tetrakis (triphenylphosphine)(349 mg, 0.30 mmol), and the mixture was refluxed under nitrogen atmosphere for 12 hours.An excessive amount of distilled water was added to the reaction solution to terminate the reaction,After extraction with dichloromethane, the solvent was concentrated under reduced pressure,The residue was purified by column chromatography to give the desired compound (827 mg, 42%) as a white solid.
  • 5
  • [ 363-52-0 ]
  • [ 4612-26-4 ]
  • C18H10B2F2O4 [ No CAS ]
  • C12H9B2FO4 [ No CAS ]
  • 6
  • [ 5469-19-2 ]
  • [ 4612-26-4 ]
  • 2,2'',4,4'',5,5''-hexamethyl-1,1':4,1''-terphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 85℃; for 24h;Inert atmosphere; Bromo-2,4,5-trimethyl-benzene (1) (2.64 g, 13.26 mmol), benezene- 1 ,4-diboronic acid (3) (1.00 g, 6.03 mmol) and a catalytic amount of tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.08 mmol) were added into a two-necked flask fitted with an Allihn condenser. The system was degassed and refilled with nitrogen three times. Then, 60 mL of distilled THF was injected, followed with an aqueous solution of potassium carbonate (0.15 g, 20 mL). After stifling at 85 C for 24 h, the mixture was extracted with DCM. The organic layer was collected and washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure, and the crude product was purified by silica gel column chromatography using hexanelDCM (5/1, v/v) as eluent. A white powder of TPh-TM was obtained in 75.3% yield (1.42 g, 4.52 mmol).
  • 7
  • [ 497-09-6 ]
  • [ 4612-26-4 ]
  • C58H92N14O13 [ No CAS ]
  • C70H106N14O17 [ No CAS ]
  • 8
  • [ 4612-26-4 ]
  • [ 39549-79-6 ]
  • 2,2'-(1,4-phenylene)bis(7-methyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one) [ No CAS ]
  • 9
  • [ 54151-74-5 ]
  • [ 4612-26-4 ]
  • C28H20N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; for 24h;Inert atmosphere; Resolution of racemate; (i) Combine 1,4-biphenylboronic acid (1.04g, 6.30mmol) and <strong>[54151-74-5]2-bromo-4-phenylpyridine</strong> (4.42g, 18.9mmol), K2CO3 (1.80g, 13.0mmol), tetrakis(triphenyl) Phosphine) Palladium (1.31g, 1.13mmol) dissolvedIn 1,4-dioxane (50.0 mL). The mixture was refluxed under N2 for 24 hours. After the reaction mixture was cooled to room temperature and all solvents were removed by rotary evaporation, it was extracted with dichloromethane, washed with water, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by silica gel column chromatography to obtain compound III as a white solid.
 

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