6-Quinolinecarbaldehyde CAS 4113-04-6
6-Quinolinecarbaldehyde Basic information
| Product Name: | 6-Quinolinecarbaldehyde |
| Synonyms: | RARECHEM AK ML 0559;QUINOLINE-6-CARBALDEHYDE;6-QUINOLINECARBALDEHYDE;6-QUINOLINECARBOXALDEHYDE;AKOS BBS-00005338;AKOS AUF01714;QUINOLINE-6-CARBOXALDEHYDE;Quinoline-6-carboxaldehyde 97% |
| CAS: | 4113-04-6 |
| MF: | C10H7NO |
| MW: | 157.17 |
| EINECS: | |
| Product Categories: | Quinolines, Isoquinolines & Quinoxalines;aldehyde;pharmacetical;Aldehydes;Quinolines, Isoquinolines & Quinoxalines;Quinoline Derivertives |
| Mol File: | 4113-04-6.mol |
6-Quinolinecarbaldehyde Chemical Properties
| Melting point | 74-75°C |
| Boiling point | 314.3±15.0 °C(Predicted) |
| density | 1.223±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| form | powder to crystal |
| pka | 4.13±0.10(Predicted) |
| color | White to Yellow to Green |
| InChI | 1S/C10H7NO/c12-7-8-3-4-10-9(6-8)2-1-5-11-10/h1-7H |
| InChIKey | VUAOIXANWIFYCU-UHFFFAOYSA-N |
| SMILES | O=Cc1ccc2ncccc2c1 |
| CAS DataBase Reference | 4113-04-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38-36/38-36 |
| Safety Statements | 26-37/39-36 |
| WGK Germany | WGK 3 |
| HazardClass | IRRITANT |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 |
| Chemical Properties | white to light yellow powde |
| Synthesis | 100516-88-9 4113-04-6 General procedure for the synthesis of quinoline-6-carbaldehyde from 6-hydroxymethylquinoline: method adapted from Meyers et al. (Meyers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362). Dess-Martin periodinane (2.57 g, 6.05 mmol) was added to a 0.28 M solution of 6-hydroxymethylquinoline (0.459 g, 2.88 mmol) in water-saturated dichloromethane (10 mL). The reaction mixture was stirred for 10 min and then dichloromethane (3 x 1 mL) was added in batches over 15 min. Subsequently, the reaction mixture was diluted with ether (10 mL) and 80% saturated aqueous sodium bicarbonate solution (10 mL) of sodium thiosulfate (7.87 g, 31.7 mmol) was added. The mixture was stirred rapidly for 45 minutes. The organic and aqueous layers were separated and the aqueous layer was extracted with ether (2 x 20 mL). The combined organic layers were washed sequentially with saturated aqueous sodium bicarbonate solution (30 mL), water (2 x 30 mL) and saturated sodium chloride solution (2 x 30 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (30-60% ethyl acetate/hexane) to give 0.383 g (85%) of quinoline-6-carbaldehyde (S4a) as a white solid with a melting point of 76.2-76.5 °C. 1H NMR (400 MHz, CDCl3): δ 7.53 (dd, 1H, J = 4.4, 8.4 Hz), 8.18-8.23 (m, 2H ), 8.33 (dd, 1H, J = 2.0, 8.4 Hz), 8.36 (s, 1H), 9.05 (dd, 1H, J = 2.0, 4.4 Hz), 10.20 (s, 1H).13C NMR (100 MHz, CDCl3): δ 122.4, 126.8, 127.8, 130.9, 133.8, 134.4 , 137.6, 151.0, 153.3, 191.6. HRMS-FAB (m/z): calculated value of 157.0528 for [MH]+ C10H7NO; measured value of 157.0521. |
| References | [1] Patent: WO2004/7491, 2004, A1. Location in patent: Page 56 [2] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6404 - 6410 [3] Patent: WO2009/75778, 2009, A2. Location in patent: Page/Page column 49; 50-51 [4] Patent: US2005/54670, 2005, A1. Location in patent: Page/Page column 27 |
6-Quinolinecarbaldehyde Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Ethyl acetate-->Methanol-->Sulfuric acid-->PETROLEUM ETHER-->Sodium sulfate-->Sodium chloride-->Benzene-->Carbon tetrachloride-->N-Bromosuccinimide-->Benzoyl peroxide-->Glycerol-->Sodium iodide-->Selenium dioxide-->p-Toluidine-->XYLENE-->6-Methylquinoline |
