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| | 4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco Basic information |
| Product Name: | 4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco | | Synonyms: | 4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco;Ethyl 2-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate;Benzeneacetic acid, 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, ethyl ester;ETHYL 2-(4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL)ACETATE（WS202804）;(4-(2-ETHOXY-2-OXOETHYL)PHENYL)BORONIC ACID PINACOL ESTER;Ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-;Ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetic acid ethyl ester | | CAS: | 859169-20-3 | | MF: | C16H23BO4 | | MW: | 290.16 | | EINECS: | | | Product Categories: | | | Mol File: | 859169-20-3.mol |  |
| | 4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco Chemical Properties |
| Boiling point | 377.7±25.0 °C(Predicted) | | density | 1.06±0.1 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | clear liquid | | color | Colorless to Light yellow to Light orange | | InChI | 1S/C16H23BO4/c1-6-19-14(18)11-12-7-9-13(10-8-12)17-20-15(2,3)16(4,5)21-17/h7-10H,6,11H2,1-5H3 | | InChIKey | RPRBNRDIESZHFL-UHFFFAOYSA-N | | SMILES | O=C(CC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)OCC |
| HS Code | 2931900090 | | Storage Class | 11 - Combustible Solids |
| | 4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco Usage And Synthesis |
| Uses | 4-Ethoxycarbonylmethylphenylboronic acid, pinacol ester | | Synthesis | GENERAL STEPS: Ethyl (4-bromophenyl)acetate (100 g, 411 mmol), bis(pinacolato)diboron (125.4 g, 493.7 mmol), and potassium acetate (125.4 g, 493.7 mmol) were added to a 2L round bottom flask. 1,4-dioxane (1 L) was added and stirred under nitrogen protection for 15 min. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (3.36 g, 4.11 mmol) was added, and the reaction mixture was heated in an oil bath at 100 °C for 2 hours. The reaction process was monitored by analytical HPLC. After completion of the reaction, 1,4-dioxane was removed by concentration under reduced pressure and the residue was dissolved in ethyl acetate. The solution was filtered through a silica gel column (6 x 4 in.) and ethyl acetate (1.5 L) was used as eluent to afford ethyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (117 g, 98% yield).1H NMR (400 MHz, DMSO) δ ppm: 7.63 (d, 2H, J=8 Hz). 7.27 (d, 2H, J=8Hz), 4.07 (q, 2H, J=7Hz), 3.68 (s, 2H), 1.28 (s, 12H), 1.16 (t, 3H, J=7Hz). | | References | [1] Patent: WO2006/86609, 2006, A2. Location in patent: Page/Page column 152-153
[2] Patent: US2014/206686, 2014, A1. Location in patent: Paragraph 0452-0454
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7920 - 7939,20
[4] Patent: WO2013/189865, 2013, A1. Location in patent: Page/Page column 30
[5] Patent: US2012/295874, 2012, A1. Location in patent: Page/Page column 230 |
| | 4-(ethoxycarbonylmethyl)phenylboronic acid, pinaco Preparation Products And Raw materials |
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