| Identification | Back Directory | [Name]
Indole-6-boronic acid pinacol ester | [CAS]
642494-36-8 | [Synonyms]
INDOLE-6-BORONIC ACID PINACOLATE
INDOLE-6-BORONIC ACID PINACOL ESTER
Indole-6-yl-boronic acid pinacol ester
1H-Indol-6-ylboronic acid, pinacol ester
Indole-6-boronic acid, pinacol ester 95+%
6-(tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
1H-Indole, 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-
3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 1H-indol-6-ylboronate | [Molecular Formula]
C14H18BNO2 | [MDL Number]
MFCD07368852 | [MOL File]
642494-36-8.mol | [Molecular Weight]
243.11 |
| Chemical Properties | Back Directory | [Melting point ]
167-172 °C | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [Appearance]
Light brown to brown Solid | [InChI]
InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-6-5-10-7-8-16-12(10)9-11/h5-9,16H,1-4H3 | [InChIKey]
VNDFXJNIKZCQRY-UHFFFAOYSA-N | [SMILES]
B1(C2C=CC3C=CNC=3C=2)OC(C)(C)C(C)(C)O1 |
| Hazard Information | Back Directory | [Uses]
Indole-6-boronic acid, pinacol ester | [Synthesis]
Under nitrogen protection, 6-bromo-1H-indole (25 g, 0.128 mol), pinacol ester of bisboronic acid (48.58 g, 0.191 mol), Pd(dppf)Cl2 (5.2 g, 5 mol%) and KOAc (37.55 g, 0.383 mol) were dissolved in DMF (500 ml). The reaction mixture was stirred at 120°C for several hours. After completion of the reaction, extraction was carried out with ethyl acetate and the organic phase was dried with magnesium sulfate. Purification by column chromatography (eluent: hexane/ethyl acetate=10:1, v/v) afforded 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (20.15 g, 65% yield). | [References]
[1] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[2] Synlett, 2003, # 8, p. 1204 - 1206
[3] Patent: JP2015/531758, 2015, A. Location in patent: Paragraph 0045-0046
[4] Patent: US2007/112005, 2007, A1. Location in patent: Page/Page column 82
[5] Patent: US2007/280928, 2007, A1. Location in patent: Page/Page column 80 |
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| Company Name: |
Energy Chemical
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021-021-58432009 400-005-6266 |
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http://www.energy-chemical.com |
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