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| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde Basic information |
| Product Name: | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde | | Synonyms: | 3-FormylPhen;3-FORMYLPHENYLBORONIC ACID, PINACOL ESTER;3-Formylbenzeneboronic acid, pinacol ester;Benzaldehyde, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;2-dioxaborolan-2-yl)-benzaldehyde;3-FormylPhenylboronic acid neopentyl ester pinacol ester;3-Formylbenzeneboronic acid, pinacol ester 95+%;2-(3-Formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | | CAS: | 380151-86-0 | | MF: | C13H17BO3 | | MW: | 232.08 | | EINECS: | | | Product Categories: | | | Mol File: | 380151-86-0.mol |  |
| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde Chemical Properties |
| Melting point | 50-54°C | | Boiling point | 345.1±25.0 °C(Predicted) | | density | 1.06±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | form | powder to crystal | | color | White to Light yellow | | InChI | 1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-7-5-6-10(8-11)9-15/h5-9H,1-4H3 | | InChIKey | IFYMOLFMYIDYEN-UHFFFAOYSA-N | | SMILES | B2(OC(C(O2)(C)C)(C)C)c1cc(ccc1)C=O |
| Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39 | | WGK Germany | 3 | | HS Code | 2931900090 | | Storage Class | 11 - Combustible Solids |
| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde Usage And Synthesis |
| Synthesis | To a 500 mL sealed tube was added m-bromobenzaldehyde (9.25 g, 50.0 mmol), potassium acetate (9.8 g, 100 mmol), bis(pinacolato)diborane (15.3 g, 60.3 mmol) and 1,4-dioxane (50 mL). The reaction system was degassed with nitrogen for 15 min. Subsequently, Pd(dppf)Cl2 (0.82 g, 1.0 mmol) was added and the reaction mixture was stirred at 90°C overnight. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was separated by extraction with water and ethyl acetate. The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (11.5 g, 99% yield) as a colorless liquid.LCMS (M + H)+: 233.2; 1H NMR (DMSO-d6, 300 MHz) δ: 10.06 (s, 1H), 8.21 (s, 1H), 8.01-8.04 (d, 1H), 7.96-7.99 (d, 1H), 7.61-7.66 (t, 1H), 1.33 (s, 12H). | | References | [1] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 80; 81
[2] Patent: WO2014/202528, 2014, A1. Location in patent: Page/Page column 67
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[4] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 364, p. 6 - 15
[5] Journal of the American Chemical Society, 2016, vol. 138, # 1, p. 84 - 87 |
| | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehyde Preparation Products And Raw materials |
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