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| | 2-Formylfuran-5-boronic acid Basic information |
| | 2-Formylfuran-5-boronic acid Chemical Properties |
| Melting point | 136 °C (dec.) (lit.) | | Boiling point | 379.3±52.0 °C(Predicted) | | density | 1.36±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | 1.38g/l | | form | powder | | pka | 7.11±0.53(Predicted) | | color | brown | | Water Solubility | Insoluble in water. | | Sensitive | Air Sensitive | | BRN | 1637050 | | InChI | InChI=1S/C5H5BO4/c7-3-4-1-2-5(10-4)6(8)9/h1-3,8-9H | | InChIKey | JUWYQISLQJRRNT-UHFFFAOYSA-N | | SMILES | B(C1=CC=C(C=O)O1)(O)O | | CAS DataBase Reference | 27329-70-0(CAS DataBase Reference) |
| Hazard Codes | C,Xi | | Risk Statements | 34-36/37/38 | | Safety Statements | 26-36/37/39-45-37/39-27 | | RIDADR | UN 3261 8/PG 3 | | WGK Germany | 3 | | Hazard Note | Irritant | | TSCA | No | | HazardClass | IRRITANT, KEEP COLD | | PackingGroup | Ⅲ | | HS Code | 29321900 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Skin Corr. 1B |
| | 2-Formylfuran-5-boronic acid Usage And Synthesis |
| Chemical Properties | beige to brown powder | | Uses | suzuki reaction | | Uses | As a bifunctional reagent used in the synthesis of π -extended heteroarylfuran systems. Reactant involved in Suzuki coupling for synthesis of stable dye-sensitized solar cells. Reactant involved in synthesis of biologically active molecules including, heteroarylation for the synthesis of HIF-1 inhibitors, disalicylic acid-furanyl derivatives to inhibit ephrin binding, HIV-1 integrase inhibitors, epidermal growth factor receptor inhibitors. | | Synthesis | Under nitrogen protection, 20.16 g (0.118 mol) of 2-(diethoxymethyl)furan, 33.4 g (0.177 mol) of triisopropyl borate, and 40 mL of anhydrous tetrahydrofuran (THF) were added to a dry 500 mL three-necked flask equipped with a mechanical stirrer, an internal thermometer, and a dosing funnel. The water content of the reaction mixture was determined by Karl-Fischer titration to ensure that it was less than 800 μg/mL. the reaction mixture was cooled to an internal temperature of -10 °C. The reaction mixture was then purified to a temperature of -10 °C. The water content of the reaction mixture was determined by titration. With the temperature maintained at -10 °C to 0 °C, 84 mL (25 wt%, 1.84 M THF solution containing heptane and ethylbenzene from Chemmetal, content determined by titration, 1.3 equivalents) of LDA solution was slowly added through the addition funnel over a period of 1 hour. Upon completion of addition, the reaction mixture was transferred via cannula to a pre-cooled aqueous hydrochloric acid solution (prepared by mixing 33 mL of concentrated hydrochloric acid and 55 mL of water). The reaction temperature was controlled not to exceed 30 °C. The resulting tan slurry of 5-formylfuran-2-boronic acid was cooled to 0°C and filtered. The filter cake was washed twice with 20 mL of cold water to obtain 17.6 g of wet filter cake. The wet filter cake was dried in a vacuum oven at 40 °C to give 12.41 g of an off-white product, 5-formylfuran-2-boronic acid, in a total yield of 75%. The amount of unreacted furfural in the crude product was determined to be less than 0.1% by analysis. | | References | [1] Patent: EP1403271, 2004, A1. Location in patent: Page 3, 4
[2] Organic and Biomolecular Chemistry, 2003, vol. 1, # 9, p. 1447 - 1449 |
| | 2-Formylfuran-5-boronic acid Preparation Products And Raw materials |
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