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| | N-Boc-indole-2-boronic acid Basic information |
| | N-Boc-indole-2-boronic acid Chemical Properties |
| Melting point | 84-94 °C
85-90 °C (lit.) | | Boiling point | 443.5±55.0 °C(Predicted) | | density | 1.17±0.1 g/cm3(Predicted) | | storage temp. | -20°C | | form | powder to crystal | | pka | 8.12±0.30(Predicted) | | color | White to Orange to Green | | BRN | 8148683 | | InChI | 1S/C13H16BNO4/c1-13(2,3)19-12(16)15-10-7-5-4-6-9(10)8-11(15)14(17)18/h4-8,17-18H,1-3H3 | | InChIKey | SVIBPSNFXYUOFT-UHFFFAOYSA-N | | SMILES | CC(C)(C)OC(=O)n1c(cc2ccccc12)B(O)O | | CAS DataBase Reference | 213318-44-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-24/25-37/39-26 | | WGK Germany | 3 | | Hazard Note | IrritantKeep Cold | | HazardClass | IRRITANT | | HS Code | 2933998090 | | Storage Class | 4.1B - Flammable solid hazardous materials | | Hazard Classifications | Flam. Sol. 2 |
| Provider | Language |
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ALFA
| English |
| | N-Boc-indole-2-boronic acid Usage And Synthesis |
| Chemical Properties | White to light yellow crystal powde | | Uses | Reactant involved in:
- Suzuki-Miyaura cross-coupling reactions
- Copper-catalyzed trifluoromethylation
- Palladium-catalyzed benzylation
- Homocoupling reactions
| | General Description | May contain varying amounts of anhydride | | Synthesis | Step 2: Synthesis of 1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid
Lithium diisopropylammonium (140 mL, 2.0 M in hexane) was slowly added dropwise to a solution of ethoxyethane (500 mL) containing tert-butyl 1H-indole-1-carboxylate (26 g, 119.67 mmol) and triisopropylboronate (30 g, 159.57 mmol) at -70 °C. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio ethyl acetate/petroleum ether = 1:5) during the reaction. Upon completion of the reaction, the reaction was quenched with 200 g of ice-water mixture, followed by adjusting the pH with 10% hydrochloric acid solution to 7. The reaction mixture was extracted with ethyl ether (100 mL x 1), and the organic layers were combined and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 13 g (67% yield) of the target compound 1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid as a white solid. | | References | [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 8, p. 1218 - 1227
[2] Patent: US2008/139558, 2008, A1. Location in patent: Page/Page column 67
[3] Patent: EP2687530, 2014, A1. Location in patent: Paragraph 0096 |
| | N-Boc-indole-2-boronic acid Preparation Products And Raw materials |
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