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| | Indole-4-boronic acid pinacol ester Basic information |
| Product Name: | Indole-4-boronic acid pinacol ester | | Synonyms: | 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole;Indole-4-boronic acid pin...;1H-Indole-4-boronic acid, pinacol ester;1H-Indole,4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;Indole-4-boronic acid pinacol ester, 97+%;4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, 2-(1H-Indol-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1H-indol-4-ylboronic acid pinacol | | CAS: | 388116-27-6 | | MF: | C14H18BNO2 | | MW: | 243.11 | | EINECS: | 210-702-0 | | Product Categories: | Boronic Acids & Esters;Pyrroles & Indoles;Boronic acid;Indole;Organoborons;Boronic Acids & Esters;Pyrroles & Indoles | | Mol File: | 388116-27-6.mol |  |
| | Indole-4-boronic acid pinacol ester Chemical Properties |
| Melting point | 120-125 °C(lit.) | | Boiling point | 396.0±15.0 °C(Predicted) | | density | 1.11±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | solid | | pka | 16.83±0.30(Predicted) | | Appearance | White to off-white Solid | | InChI | InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-6-5-7-12-10(11)8-9-16-12/h5-9,16H,1-4H3 | | InChIKey | QDCIXBBEUHMLDN-UHFFFAOYSA-N | | SMILES | N1C2=C(C(B3OC(C)(C)C(C)(C)O3)=CC=C2)C=C1 |
| Hazard Codes | Xi | | Risk Statements | 36/37/38-36 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2933299090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Indole-4-boronic acid pinacol ester Usage And Synthesis |
| Chemical Properties | White powder | | Uses | Indole-4-boronic acid, pinacol ester | | Synthesis | The general procedure for the synthesis of 4-indoleboronic acid pinacol ester from 4-bromoindole and biboronic acid pinacol ester is as follows:
(a) Preparation of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole. 4-Bromoindole (1.00 g, 5.10 mmol), bis(pinacolato)diboron (1.68 g, 6.63 mmol), potassium acetate (1.44 g, 15.3 mmol), and dichlorodi(diphenylphosphine)palladium(II) dichloride dichloromethane complex (206 mg, 0.26 mmol) were added to a 50 mL round-bottomed flask under argon gas protection. Anhydrous dimethyl sulfoxide (16 mL) was then added and the reaction mixture was heated at 90 °C with stirring for 4 hours. After completion of the reaction, it was cooled to room temperature, filtered through a short column of silica gel and the filter cake was washed with tert-butyl methyl ether (2 x 50 mL). The filtrates were combined, washed with saturated saline (3 x 50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by fast column chromatography (ethyl acetate/heptane, 1:4) to afford 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole as a white solid (1.24 g, quantitative yield). | | References | [1] Patent: US2008/280891, 2008, A1. Location in patent: Page/Page column 30
[2] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 81-82
[3] Organic Letters, 2012, vol. 14, # 2, p. 600 - 603
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2496 - 2500
[5] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276 |
| | Indole-4-boronic acid pinacol ester Preparation Products And Raw materials |
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