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| | 3-Carboxyphenylboronic acid pinacol ester Basic information |
| Product Name: | 3-Carboxyphenylboronic acid pinacol ester | | Synonyms: | 3-CARBOXYPHENYLBORONIC ACID, PINACOL ESTER;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoicacid,min.97%;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID, MIN. 97%;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid,97%;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid3-Carboxyphenylboronic acid pinacol ester;2-dioxaborolan-2-yl)benzoic acid;3-Carboxybenzeneboronic acid, pinacol ester;3-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)benzoic acid, 97% 5GR | | CAS: | 269409-73-6 | | MF: | C13H17BO4 | | MW: | 248.08 | | EINECS: | | | Product Categories: | organic or inorganic borate;Acids and Derivatives;Boron, Nitrile, Thio,& TM-Cpds;Boronic acids;CHIRAL CHEMICALS | | Mol File: | 269409-73-6.mol |  |
| | 3-Carboxyphenylboronic acid pinacol ester Chemical Properties |
| Melting point | 206-211 °C | | Boiling point | 395.1±25.0 °C(Predicted) | | density | 1.15±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | pka | 4.20±0.10(Predicted) | | form | Powder | | color | White | | Water Solubility | Insoluble | | InChI | InChI=1S/C13H17BO4/c1-12(2)13(3,4)18-14(17-12)10-7-5-6-9(8-10)11(15)16/h5-8H,1-4H3,(H,15,16) | | InChIKey | OPWAPCOSDAFWFB-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1 | | CAS DataBase Reference | 269409-73-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 37/39-26 | | WGK Germany | 3 | | TSCA | No | | HS Code | 29310099 | | Storage Class | 11 - Combustible Solids |
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ACROS
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| | 3-Carboxyphenylboronic acid pinacol ester Usage And Synthesis |
| Chemical Properties | almost white to light beige crystalline powder | | Uses | 3-Carboxyphenylboronic Acid Pinacol Ester is a biochemical reagent that can be used as a biological material or organic compound for life science related research. | | Synthesis | After degassing into 1,4-dioxane (0.1 M) under nitrogen atmosphere, m-bromobenzoic acid (1 eq.), pinacol ester of bisboronic acid (1.5 eq.) and potassium acetate (4.4 eq.) were added. The mixture was degassed again followed by the addition of PdCl2 (dppf) (5%). The resulting solution was heated to 110°C for overnight reaction. Upon completion of the reaction, the solvent was removed under vacuum to give a dark colloidal residue. This residue was dissolved in ethyl acetate and water to separate the organic layer. The aqueous phase was further extracted with ethyl acetate (2×). The combined organic layers were washed with 2M HCl, dried over MgSO4 and concentrated in vacuum to give a dark brown product. To purify the product, column chromatography (petroleum ether/ethyl acetate elution) was used. The 3-carboxyphenylboronic acid pinacol ester prepared by Suzuki coupling reaction was a light brown solid in 89% yield.1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.19 (ddd, J = 21.9, 1.18, 10.1 Hz, 1H), 8.09-7.98 (m, 1H), 7.57-7.38 (m, 1H), 1.37 (m, 1H), 7.57-7.38 (m, 1H). 1H), 1.37 (s, 12H).13C NMR (101 MHz, CDCl3) δ 171.66, 139.98, 136.60, 132.84, 128.71, 127.93, 84.21, 24.89.LCMS (ESI) m/z 249.2 [M + H]+. | | References | [1] Patent: WO2016/198507, 2016, A1. Location in patent: Page/Page column 39; 49 |
| | 3-Carboxyphenylboronic acid pinacol ester Preparation Products And Raw materials |
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