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| | 6-Azaindole-3-carboxaldehyde Basic information |
| Product Name: | 6-Azaindole-3-carboxaldehyde | | Synonyms: | 6-Azazindole-3-carboxyaldehyde.;6-Azaindole-3-carbaldehyde;1-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde (7CI);1H-Pyrrolo[2,3-c]pyridine-3-carboxaldehyde;3-c]pyridine-3-carbaldehyde;6-Azaindole-3-aldehyde;H-pyrrolo[2,3-c]pyridine-3-carbaldehyde | | CAS: | 25957-65-7 | | MF: | C8H6N2O | | MW: | 146.15 | | EINECS: | 247-364-9 | | Product Categories: | | | Mol File: | 25957-65-7.mol |  |
| | 6-Azaindole-3-carboxaldehyde Chemical Properties |
| Boiling point | 383.2±22.0 °C(Predicted) | | density | 1.368 | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 13.16±0.40(Predicted) | | Appearance | Off-white to gray Solid | | InChI | InChI=1S/C8H6N2O/c11-5-6-3-10-8-4-9-2-1-7(6)8/h1-5,10H | | InChIKey | IAMJYHYPXUQXGI-UHFFFAOYSA-N | | SMILES | C1=NC=CC2C(C=O)=CNC1=2 | | CAS DataBase Reference | 25957-65-7 |
| | 6-Azaindole-3-carboxaldehyde Usage And Synthesis |
| Uses | 1H-Pyrrolo[2,3-c]pyridine-3-carbaldehyde is used in preparation of α,β-unsaturated ketone derivatives as microtubule inhibitors for treatment of tumor. | | Synthesis | GENERAL STEPS: To a solution of 6-azaindole (0.400 g; 3.386 mmol) in a solvent mixture of 1,2-dichloroethane (10 mL) and nitromethane (10 mL), cooled to 0°C. A mixture of 1,1-dichlorodimethyl ether (1.544 mL; 16.92 mmol) and aluminum trichloride (1.500 g; 11.25 mmol) was slowly added dropwise under argon protection for a controlled time of 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water and saturated sodium bicarbonate solution. The reaction mixture was extracted with a solvent mixture of dichloromethane and ethanol (9:1 v/v, 6 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude product 1H-pyrrolo[2,3-c]pyridine-3-carboxaldehyde (0.295 g, 60% yield), which could be used in the subsequent reaction without further purification. Product characterization data: ESI/APCI(+) m/z: 147 ([M + H]+); ESI/APCI(-) m/z: 145 ([M - H]-). 1H NMR (DMSO-d6) δ: 10.01 (1H, s), 8.88 (1H, s), 8.50 (1H, s), 8.33 (1H, d), 8.00 (1H, d). d). | | References | [1] Patent: WO2013/45516, 2013, A1. Location in patent: Page/Page column 200 |
| | 6-Azaindole-3-carboxaldehyde Preparation Products And Raw materials |
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