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Chemical Structure| 153624-46-5 Chemical Structure| 153624-46-5
Chemical Structure| 153624-46-5

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CAS No.: 153624-46-5

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Product Details of 4-Isopropoxyphenylboronic acid

CAS No. :153624-46-5
Formula : C9H13BO3
M.W : 180.01
SMILES Code : C1=C(OC(C)C)C=CC(=C1)B(O)O
MDL No. :MFCD03427051
InChI Key :CJUHQADBFQRIMC-UHFFFAOYSA-N
Pubchem ID :3698726

Safety of 4-Isopropoxyphenylboronic acid

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

Application In Synthesis of 4-Isopropoxyphenylboronic 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 [ 153624-46-5 ]

[ 153624-46-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13771-68-1 ]
  • [ 153624-46-5 ]
  • [ 907945-53-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.166667h;Microwaves; A mixture of the ethyl 5-bromo-1-benzothiophene-2-carboxylate obtained in Reference Example 7 (1.00 g), 4-isopropoxyphenyl boronic acid (2.26 g), tetrakis(triphenylphosphine)palladium (0) (402 mg), 2 M sodium carbonate aqueous solution (3.5 mL) and 1,2-dimethoxyethane (16.5 mL) was exposed to microwaves for 10 minutes at 150C. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by basic silica gel column chromatography and recrystallized from ethyl acetate-hexane to obtain ethyl 5-(4-isopropoxyphenyl)-1-benzothiophene-2-carboxylate (0.76 g) as colorless crystals. 1H-NMR (300MHz, CDCl3); δ 1.38 (6H, d, J=6.0Hz), 1.43 (3H, t, J=7.2Hz), 4.42 (2H, q, J=7.2Hz), 4.61 (1H, m), 6.99 (2H, d, J=8.7Hz), 7.56 (2H, d, J=8.7Hz), 7.66 (1H, dd, J=1.5, 8.7Hz), 7.88 (1H, d, J=8.7Hz), 8.00 (1H, d, J=1.5Hz), 8.08 (1H, s)
  • 2
  • [ 474706-74-6 ]
  • [ 153624-46-5 ]
  • 3,6-bis[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h;Inert atmosphere; To a solution of 6-bromo-3-iodoimidazo[1 ,2-a]pyridine (0.3 g, 0.93 mmol) in dioxane (9 mL) and water (3 mL) was added (4-isopropoxyphenyl)boronic acid (0.334 g, 1 .86 mmol) and sodium carbonate (0.6g, 5.6 mmol). The reaction mixture was purged with nitrogen, then Pd(dppt)C12 (0.05 g, 0.06 mmol) was added. The resulting reaction mixture was heated to 90C for 12h, brought to room temperature and was extracted with ethyl acetate. Dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by SiC2 column chromatography (hexanes I EtOAc from 4:1 to 1:2) to give 0.24g (62%) of the title compound as a beige solid.1H NMR (300 MHz, CDCI3) O 8.37 (5, 1H), 7.70 (d, 1H),7.64 (5, 1 H), 7.49 (d, 2H), 7.44 (d, 2H), 7.41 (d, 1 H), 7.05 (d, 2H), 6.97 (d, 2H), 4.56 - 4.67 (m, 2H),1.40 (d, 6H), 1.37 (d, 6H).,LCIMS m/z: 387.28 (M+H).
  • 3
  • [ 474706-74-6 ]
  • [ 153624-46-5 ]
  • 6-bromo-3-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 5h;Inert atmosphere; To a solution of 6-bromo-3-iodoimidazo[1 ,2-a]pyridine (0.3 g, 0.93 mmol) in dioxane (9 mL) wereadded (4-isopropoxyphenyl)boronic acid (O.167g, 0.93mmol), tetrakis(triphenylphosphine)palladium(0) (0.075g, 0.065 mmol), sodium carbonate (0.3 g, 2.8 mmol) and water (3 mL). The resulting reaction mixture was degassed with nitrogen for 10 mm, then heated to 90C for 5 h. Then the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2504, filtered, and concentrated in vacuo. The residue was purified by SiC2 columnchromatography (hexanes I EtOAc from 4:1 to 1:2) to give 0.26g (84%) of the product as a white solid.1H NMR (500 MHz, CDCI3) O 8.36 (5, 1H), 7.62 (5, 1H), 7.57 (d, 1H), 7.42 (d, 2H), 7.23 (d, 1H), 7.03 (d, 2H), 4.62 (sep, 1H), 1.39 (d, 6H). LCIMS m/z: 331.07 (79Br, M+H), 333.14 (81Br, M+H).
  • 4
  • [ 474706-74-6 ]
  • [ 153624-46-5 ]
  • 2-(4-{3-[4-(propan-2-yloxy)phenyl]imidazo[1,2-a]pyridin-6-yl}phenyl)propan-2-ol [ No CAS ]
 

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