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Chemical Structure| 87100-28-5 Chemical Structure| 87100-28-5
Chemical Structure| 87100-28-5

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Product Details of Benzylboronic acid pinacol ester

CAS No. :87100-28-5
Formula : C13H19BO2
M.W : 218.10
SMILES Code : CC1(C)OB(CC2=CC=CC=C2)OC1(C)C
MDL No. :MFCD05663841
InChI Key :YCNQPAVKQPLZRS-UHFFFAOYSA-N
Pubchem ID :3864964

Safety of Benzylboronic acid pinacol ester

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Benzylboronic acid pinacol ester

* 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 [ 87100-28-5 ]

[ 87100-28-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1070879-27-4 ]
  • [ 87100-28-5 ]
  • 4-benzyl-7-methoxyquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; General procedure: According to Scheme C,7-Methoxyquinolin-4-ol (1 eq) and POBr3 (10.4 eq.) Were placed in a round bottom flask,And the mixture was stirred for 3 hours. After completion of the reaction, the reaction solution was slowly added to the ice water and basified to pH 8 or more with ammonia water.The organic layer was extracted three times with ethyl acetate from the mixture of water and solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained mixture was subjected to column chromatography to give <strong>[1070879-27-4]4-bromo-7-methoxyquinoline</strong>. (1 eq.), 2-benzyl-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane (1.2 eq.), Potassium carbonate (3 eq.), Tetrakis Phosphine) palladium (0) (0.05 eq.) Was stirred at 100 C for 6 h under a solution of 1,4-dioxane and water in a ratio of 4: 1. After cooling to room temperature, the mixture was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate and filtered, and then concentrated under reduced pressure. Subsequently, a 4-benzylquinoline compound was obtained by column chromatography.
  • 2
  • [ 939-57-1 ]
  • [ 87100-28-5 ]
  • [ 83135-54-0 ]
  • 3
  • [ 16642-93-6 ]
  • [ 87100-28-5 ]
  • C16H13N [ No CAS ]
  • 4
  • [ 893566-75-1 ]
  • [ 87100-28-5 ]
  • C21H25NO2 [ No CAS ]
  • 5
  • [ 87100-28-5 ]
  • [ 791626-58-9 ]
  • 6-benzylquinolin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 80℃; for 18h; Intermediate Z (900 mg, 4.03 mmol), cesium carbonate (3.94 g, 12.1 mmol) and benzylboronic acid pinacol ester (2.69 ml_, 12.1 mmol) were taken up in dioxane (20 ml_)/water (7 ml_) and degassed for 5 minutes. [1 , T-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (659 mg, 0.807 mmol) was added and the reaction mixture was heated at 80 C for 18 h. The reaction was cooled to rt, water (10 ml_) was added and the mixture was extracted with EtOAc (3 x 15 ml_). The combined organic extracts were dried (MgSCU) and concentrated under vacuum. The residue was purified by column chromatography (SiC , 0-60 % EtOAc in PE), to give the title compound as a light yellow solid (492 mg, 52 %).1H NMR dH(400 MHz, DMSO-d6) 7.79 - 7.50 (m, 1 H), 7.42 (m, 5H), 7.22 (m, 3H), 7.10 (m,1 H), 4.50 (m, 2H) 3.57 (s, 2H); LCMS (Method B): 1.82 min, (235.1 , MH+).
 

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