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[ CAS No. 756520-47-5 ] {[proInfo.proName]}

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Chemical Structure| 756520-47-5
Chemical Structure| 756520-47-5
Structure of 756520-47-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 756520-47-5 ]

CAS No. :756520-47-5 MDL No. :MFCD20527213
Formula : C19H22BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JTURKCDVNAXKIF-UHFFFAOYSA-N
M.W : 339.19 Pubchem ID :58885831
Synonyms :

Safety of [ 756520-47-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 756520-47-5 ]

* 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 [ 756520-47-5 ]

[ 756520-47-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 109-01-3 ]
  • [ 756520-47-5 ]
  • [ 879486-90-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane 10.2 [4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid phenyl ester (500 mg, 1.3 mmol) was dissolved in anhydrous dichloromethane (0.5 mL) and trethylamine (0.187 mL, 1.3 mmol). To this stirred solution was added 1-methyl piperazine (or any other amine) (0.144 mL, 1.3 mmol). The solution turned yellow instantly, and tlc analysis showed consumption of all starting material. The reaction was washed with water (3x500 mL), saturated sodium bicarbonate (2x200 mL) and dried prior to removal of solvents in vacuo. The boronic esters were used without purification.
  • 2
  • [ 7693-46-1 ]
  • [ 214360-73-3 ]
  • [ 756520-47-5 ]
YieldReaction ConditionsOperation in experiment
91% With pyridine In dichloromethane for 13h; Heating / reflux; 10.1 4-(4,4,5,5-tetramethyl 1,3,2 dioxaboralan-2-yl) aniline (3 g, 0.013 mol) was dissolved in dichloromethane (350 mL) to which pyridine (1.02 g, 0.013 mol) and 4-nitrophenyl chloroformate was added. The reaction was stirred for 13 hr where TLC analysis showed consumption of all starting materials. The solution was washed with saturated NaHCO3 (3x50 mL), water (3x50 mL) and brine (3x50 mL). The organic layer was dried over Na2SO4 and solvent removed to yield a white crystalline solid [4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid phenyl ester, 4.45 g, 91%. 1H NMR (CDCl3 300 MHz) ? 1.4 (s, 12H), 7.1 (brs, 1H), 7.3 (d, 2H), 7.5 (d, 2H), 7.8 (d, 2H), 8.3 (d, 2H).
  • 3
  • [ 1885-14-9 ]
  • [ 214360-73-3 ]
  • [ 756520-47-5 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine In dichloromethane at -10 - 20℃; for 1h; 462.1 Step 1: Preparation of phenyl 4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)phenylcarbamate To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (25.0 g, 114 mmol) and pyridine (4 mL, 57 mmol) in dry dichloromethane (250 mL) phenyl chloroformate (12 mL, 114 mmol) was added drop wise at -10° C. The reaction mixture was stirred at -10° C. for 30 min and then at room temperature for 30 minutes. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (2×70 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to get the crude product. Then the crude product was dissolved in diethyl ether (15 mL) and sonicated for 10 min and then pentane (30 mL) was added. the resulting solid was filtered and washed with pentane to give phenyl 4-(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)phenylcarbamate (26 g, 88% yield). 1HNMR (300 MHz, CDCl3): δ 7.8 (d, 2H) 7.5 (d, 2H), 7.4 (m, 2H), 7.2 (m, 3H), 7.0 (s, 1H), 1.3 (s, 12H).
  • 5
  • [ 756520-47-5 ]
  • [ 74-89-5 ]
  • [ 874290-99-0 ]
YieldReaction ConditionsOperation in experiment
88% In tetrahydrofuran at 20℃; for 6h; 462.2 Step 2: Preparation of 1-methyl-3-(4-(4,4,5,5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)phenyl) urea A mixture of phenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (26 g, 76.6 mmol)), 2.0M Methylamine/ THF (265 mL, 530 mmol) in 150 mL of THF was stirred at room temperature for 6 hours, then excess solvent was distilled off from the reaction mixture; residue was dissolved into water, extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure. The crude product was purified by silica gel column chromatography by using 5-60% ethyl acetate in pet-ether as an eluent. to give 1-methyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea. (20 g, 88% yield) as white solid. 1HNMR (300 MHz, CDCl3): δ 7.7 (d, 2H), 7.2 (d, 2H), 6.7 (s, 1H), 5.0 (s, 1H), 2.8 (s, 3H), 1.2 (s, 12H).
  • 6
  • [ 756520-47-5 ]
  • 1-(4-(4-chloro-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-methylurea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 6 h / 20 °C 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane / 8 h / 65 °C / Inert atmosphere
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Chemical Structure| N/A

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Reason: Derivatives