Home Cart Sign in  
Chemical Structure| 269409-73-6 Chemical Structure| 269409-73-6
Chemical Structure| 269409-73-6

3-Carboxyphenylboronic acid pinacol ester

CAS No.: 269409-73-6

4.5 *For Research Use Only !

Cat. No.: A230904 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
250mg łÇʶÊÊ Inquiry Inquiry
1g łÇ˶ÊÊ Inquiry Inquiry
5g łÇÿ¶ÊÊ Inquiry Inquiry
10g łÇó¶ÊÊ Inquiry Inquiry
25g ł§Ê¶ÊÊ Inquiry Inquiry
100g łîî¶ÊÊ Inquiry Inquiry
500g ł§ÿò¶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 250mg

    łÇʶÊÊ

  • 1g

    łÇ˶ÊÊ

  • 5g

    łÇÿ¶ÊÊ

  • 10g

    łÇó¶ÊÊ

  • 25g

    ł§Ê¶ÊÊ

  • 100g

    łîî¶ÊÊ

  • 500g

    ł§ÿò¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of 3-Carboxyphenylboronic acid pinacol ester

CAS No. :269409-73-6
Formula : C13H17BO4
M.W : 248.08
SMILES Code : C1=C(C=CC=C1B2OC(C(O2)(C)C)(C)C)C(=O)O
MDL No. :MFCD03411930
InChI Key :OPWAPCOSDAFWFB-UHFFFAOYSA-N
Pubchem ID :2734653

Safety of 3-Carboxyphenylboronic acid pinacol ester

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

Application In Synthesis of 3-Carboxyphenylboronic 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 [ 269409-73-6 ]

[ 269409-73-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 269409-73-6 ]
  • [ 141-43-5 ]
  • [ 943911-66-8 ]
YieldReaction ConditionsOperation in experiment
To a solution of 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-benzoic acid (1.15 g, 4.63 mmol) and HBTU (1.52 g, 4.03 mmol) in anhydrous DMF (20 ml) was added N,N-diisopropylethylamine (1.2 ml, 6.71 mmol). The resultant solution was stirred at room temperature for 45 min. Ethanolamine (0.29 ml, 4.84 mmol) was added slowly to the solution, and the stirring was continued for another 25 h. After evaporation of solvent, the residue was subjected to flash column chromatography on silica gel (elution with CH2C12-EtOAC) to yield N-(2-hydroxyethyl)-3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-benzamide as white crystals (398 mg). ESI-MS: m/z 292 (M+l); IH NMR (600 MHz, CDC13): δ 8.11 (IH, s), 7.98 (IH, d, J= 7.2 Hz), 7.94 (IH, d, J= 7.2 Hz), 7.46 (IH, t, J= 7.2 Hz), 3.85 (2H, t, J= 4.8 Hz), 3.64 (2H, dd, J= 4.8, 10.2 Hz); 13C NMR (150.9 MHz, CDC13): δ 168.69, 138.00, 133.42, 132.39, 130.52, 128.21, 84.19, 62.47, 42.97, 24.88.
  • 2
  • [ 269409-73-6 ]
  • [ 6274-22-2 ]
  • [ 1415695-08-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 24h; A mixture of 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid (0.8 g, 3.22 mmol), <strong>[6274-22-2]4-amino-N-methylbenzamide</strong> (0.58 g, 3.86 mmol), HATU (1.47 g, 3.8 mmol) and DIEA (1 g, 7.7 mmol) in DMF (10 mL) was stirred at room temperature for 24 h. The solvent was evaporated at 70C under reduced pressure to give a crude product. It was filtered through a plug of silica gel and the filter cake washed with ethyl acetate / petroleum ether (1: 1, v/v). The combined filtrates were concentrated to give crude N-(4- (methylcarbamoyl)phenyl)-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide (0.56 g, 45.9 %) as a white solid that was used directly without further purification.LC/MS: 381.1 [M+H]+.
  • 3
  • [ 269409-73-6 ]
  • [ 49851-36-7 ]
  • methyl 2-(2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
TEA (1.685 mL, 12.09 mmol) was added to a mixture of 3-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)benzoic acid (CAS 269409-73-6) (1 g, 4.03 mmol) and HATU (1.686 g, 4.43 mmol) in DMF (4.5 mL). After 30 min, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851-36-7) (0.666 g, 4.03 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction was diluted with a 4:1 EtOAc/heptanes mixture and water. The aqueous phase was extracted with 4:1 EtOAc/heptanes. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (heptane/EtOAc with 10% MeOH, 100:0 to 0:100) to give the title compound. MS (ESI+) m/z 396.4 (M+H).
  • 4
  • [ 109-04-6 ]
  • [ 269409-73-6 ]
  • [ 4467-07-6 ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; N,N-dimethyl-formamide; at 110℃;Inert atmosphere; To a degassed souton of DMF:H20 (10:1 raUo) (0.3 M), under an atmosphere of nitrogen, was added the pnaco ester (1 mmo), 2-bromopyrdne or 2-choropyrmdne (1 .5 eq.), and Cs2CO3 (4.4 eq.). The whoe mxture was degassed once agan and then Pd(PPh3)4 (5mo%) was added. The resutng souton was heated to 110C overnght. The sovent was removed in vacuo to give a dark gummy residue, which was taken up nto EtOAc and H20, then acdfied with 2 M HC to pH 2. The organic ayer was separated and the aqueous ayer was further extracted with EtOAc (2x). The combined organic ayers were dried over MgSO4 and concentrated in vacuo to gve a back ofly residue. The residue was dry oaded ontosWca ge in vacuo then purfied by flash coumn chromatography, eutng with 10-30% EtOAc/petroeum benzne and 1% acetic acid to afford the tWe compound.The foHowng compounds were made by Suzuk CoupUng F:P1B1Off white soUd (75% yed). 1H NMR (400 MHz,DMSO) 6 8.71 8.68 (m, 1 H), 8.67 (s, 1 H), 8.29 (d,J = 7.8 Hz, 1 H), 8.01 (t, J = 8.4 Hz, 2H), 7.91 (td, J =7.8, 1.8 Hz, 1 H), 7.61 (t, J = 7.7 Hz, 1 H), 7.42 7.37(m, 1H). LCMS B rt3.17, m/z200.1 [M + H].
  • 5
  • [ 269409-73-6 ]
  • [ 95-46-5 ]
  • [ 168618-44-8 ]
YieldReaction ConditionsOperation in experiment
78% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere; General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 mol%) and further degassed (5times). The resulting mixture was stirred at 95 C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100%) to yield the desired product.
  • 6
  • [ 17321-93-6 ]
  • [ 269409-73-6 ]
  • C12H11N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere; General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.
 

Historical Records

Technical Information

Categories