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Chemical Structure| 180516-87-4

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Product Details of 4-Carboxyphenylboronic acid pinacol ester

CAS No. :180516-87-4
Formula : C13H17BO4
M.W : 248.08
SMILES Code : C1=C(C=CC(=C1)C(=O)O)B2OC(C(O2)(C)C)(C)C
MDL No. :MFCD01863710
InChI Key :IYDKBQIEOBXLTP-UHFFFAOYSA-N
Pubchem ID :2734621

Safety of 4-Carboxyphenylboronic acid pinacol ester

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

Application In Synthesis of 4-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.

  • Upstream synthesis route of [ 180516-87-4 ]
  • Downstream synthetic route of [ 180516-87-4 ]

[ 180516-87-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 180516-87-4 ]
  • [ 179117-44-3 ]
YieldReaction ConditionsOperation in experiment
45% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3 h; Step 1
4-(4,4,5,5-Metramethyl-1,3,2-dioxaborolan-2-yl)benzamide
Procedure
To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.746 mmol), EDCI (214 mg, 1.12 mmol), HOBt (151 mg, 1.12 mmol) and Et3N (151 mg, 1.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation.
The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (90 mg, 45percent) as a yellow solid. LC-MS: 248 [M+H]+, tR=1.421 min.
References: [1] Patent: US2012/252777, 2012, A1, . Location in patent: Page/Page column 96.
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040.
 

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