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5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol manufacturers
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| | 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol Basic information |
| Product Name: | 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol | | Synonyms: | 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;4-Chloro-2-hydroxyphenylboronic acid pinacol ester;EOS-60944;Phenol, 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-Hydroxy-4-chlorobenzeneboronic acid pinacol ester;2-hydroxy-4-chlorobenzeneboronic acidolester;2-Hydroxy-4-Chlorobenzyl pinenatol ester | | CAS: | 1377503-12-2 | | MF: | C12H16BClO3 | | MW: | 254.52 | | EINECS: | | | Product Categories: | | | Mol File: | 1377503-12-2.mol |  |
| | 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol Chemical Properties |
| Boiling point | 342.9±32.0 °C(Predicted) | | density | 1.19±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 9.12±0.40(Predicted) | | form | Solid | | color | White to Off-White |
| | 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol Usage And Synthesis |
| Uses | 4-Chloro-2-hydroxyphenylboronic acid pinacol ester is a building block which has seen use in the preparation of 5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-ylacetic acid derivs. for treatment of HIV infection, and in the preparation of disubstituted pyridazine analogs useful in the treatment of SMN deficiency related diseases. | | Synthesis | 2-Bromo-5-chlorophenol (2.0 kg, 9.65 mol), pinacol ester of bisboronic acid (B2Pin2, 2.7 kg, 10.6 mol), potassium acetate (AcOK, 1.9 kg, 19.3 mol) and 1,4-dioxane (15 L) were added to a 30 L reactor. The mixture was stirred and displaced three times with nitrogen. Under nitrogen protection, dichloro-[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (PdCl2(dppf)-CH2Cl2, 100 g, 0.12 mol) was added, and the mixture was subsequently heated to 75 °C (if the reaction is exothermic and violent, the oil bath may be temporarily removed). The reaction system was warmed to 90 °C and kept for 16 h. HPLC monitoring showed complete reaction. After cooling to 35 °C, the reaction mixture was filtered through a diatomaceous earth pad and the resulting filtrate was a solution of 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.22 kg, 4.8 mol), which was used directly in the subsequent reaction. Mass spectrum (MS) m/z: 253.1 [M-H] ; 1H NMR (CDCl3, 400 MHz) δ: 9.2 (br, 1H), 7.25 (d, J = 8 Hz, 1H), 6.64 (d, J = 1.6 Hz, 1H), 6.62 (dd, J = 8 Hz, J = 1.6 Hz, 1H), 1.05 (s, 12H). | | References | [1] Patent: WO2014/28459, 2014, A1. Location in patent: Page/Page column 184 |
| | 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol Preparation Products And Raw materials |
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