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| | 4-Formylphenylboronic acid pinacol cyclic ester Basic information |
| Product Name: | 4-Formylphenylboronic acid pinacol cyclic ester | | Synonyms: | AKOS BRN-1133;4-FORMYLPHENYLBORONIC ACID PINACOLATE;4-FORMYLPHENYLBORONIC ACID, PINACOL CYCLIC ESTER;4-FORMYLPHENYLBORONIC ACID, PINACOL ESTER;4-FORMYLBENZENEBORONIC ACID, PINACOL CYCLIC ESTER;4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde;4-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (4-ForMylphenylboronic acid pinacol ester);4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZALDEHYDE | | CAS: | 128376-64-7 | | MF: | C13H17BO3 | | MW: | 232.08 | | EINECS: | | | Product Categories: | Pyridines;CHIRAL CHEMICALS;Boronic Acid | | Mol File: | 128376-64-7.mol |  |
| | 4-Formylphenylboronic acid pinacol cyclic ester Chemical Properties |
| Melting point | 55-58°C | | Boiling point | 341.3±25.0 °C(Predicted) | | density | 1.06±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Crystalline Solid | | color | Off-white | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-10(9-15)6-8-11/h5-9H,1-4H3 | | InChIKey | DMBMXJJGPXADPO-UHFFFAOYSA-N | | SMILES | C(=O)C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1 | | CAS DataBase Reference | 128376-64-7(CAS DataBase Reference) |
| | 4-Formylphenylboronic acid pinacol cyclic ester Usage And Synthesis |
| Uses | A boronic acid benzaldehyde compound for proteomics research. | | Synthesis | General procedure for the synthesis of 4-formylphenylboronic acid pinacol ester from p-bromobenzaldehyde and pinacol ester of biboronic acid: to a stirred solution of p-bromobenzaldehyde (8 g, 0.15 mol), pinacol ester of biboronic acid (45.7 g, 0.18 mol), and Pd(dppf)Cl2 (5.26 g, 7.5 mmol) in 1,4-dioxane, under argon protection, was KOAc (22.0 g, 0.225 mol) was added. The reaction mixture was stirred at 80 °C for 15 min. After completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with petroleum ether (500 mL) and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast chromatography (silica gel, petroleum ether/ethyl acetate, 10:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxolan-2-yl)benzaldehyde (32.5 g, 95% yield) as a white solid. | | References | [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[2] Patent: WO2013/170165, 2013, A1. Location in patent: Page/Page column 93
[3] Applied Organometallic Chemistry, 2011, vol. 25, # 7, p. 537 - 541
[4] Organic Letters, 2016, vol. 18, # 20, p. 5248 - 5251
[5] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 84 - 87 |
| | 4-Formylphenylboronic acid pinacol cyclic ester Preparation Products And Raw materials |
| Raw materials | Pinacol-->4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)TOLUENE-->4-Bromobenzaldehyde-->Bis(pinacolato)diboron-->4-Formylphenylboronic acid-->Potassium Acetate-->1,4-Dioxane-->Bis(triphenylphosphine)palladium(II) chloride | | Preparation Products | 1,3,5-Tris(p-formylphenyl)benzene-->4-(2-Cyanophenyl)benzaldehyde-->4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL-->(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol-->4-Carboxylphenylboronic acid pinacol ester-->4-Methyl-N'-[(1E)-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylidene]benzene-1-sulfono |
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