6-Fluoroquinaldine CAS 1128-61-6
6-Fluoroquinaldine Basic information
| Product Name: | 6-Fluoroquinaldine |
| Synonyms: | 6-Fluoro-2-methylquinoline, 98+%;6-Fluoro-2-methyl-1-azanaphthalene;AKOS 1002;6-FLUORO-2-METHYLQUINOLINE;6-FLUOROQUINALDINE;6-Fluoro-2-methylquinoline 97%;6-Fluoro-2-methylquinoline97%;2-METHYL-6-FLUOROQUINOLINE |
| CAS: | 1128-61-6 |
| MF: | C10H8FN |
| MW: | 161.18 |
| EINECS: | 214-439-2 |
| Product Categories: | Aromatics Compounds;Quinolines, Quinazolines and derivatives;Quinoline&Isoquinoline;Alkylquinolines;Haloquinolines;Quinolines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Heterocyclic Building Blocks |
| Mol File: | 1128-61-6.mol |
6-Fluoroquinaldine Chemical Properties
| Melting point | 49-53 °C (lit.) |
| Boiling point | 99 °C / 3mmHg |
| density | 1.1465 (estimate) |
| Fp | >230 °F |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Soluble in Chloroform. |
| pka | 5.16±0.43(Predicted) |
| form | powder to crystal |
| color | White to Almost white |
| BRN | 1281677 |
| InChI | 1S/C10H8FN/c1-7-2-3-8-6-9(11)4-5-10(8)12-7/h2-6H,1H3 |
| InChIKey | GPIARMSVZOEZCV-UHFFFAOYSA-N |
| SMILES | Cc1ccc2cc(F)ccc2n1 |
| CAS DataBase Reference | 1128-61-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 38-41-36/37/38 |
| Safety Statements | 26-37/39-36 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29334990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1 Skin Irrit. 2 |
| Chemical Properties | brown powder or granules |
| Uses | Metal-free transfer hydrogenation of 6-fluoro-2-methylquinoline by employing several chiral Br?nsted acid catalysts was carried out in combination with dihydropyridines as the hydride source in asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation. Hydrogenation product of 6-fluoro-2-methylquinoline is the key intermediate of the antibacterial agent. |
| Uses | Quinoline derivative as a highly potent thrombin receptor antagonist |
| Synthesis | 42835-89-2 1128-61-6 General procedure for the synthesis of 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline from 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline: 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (0.50 mmol), FeCl2 (1.9 mg, 1.5 × 10-2 mmol), DMSO (31.2 mg, 0.4 mmol) and p-xylene (1 mL). The reaction mixture was stirred using a balloon at 110 °C and oxygen atmosphere and the progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was cooled to room temperature and purified by fast chromatography (eluent: hexane-ethyl acetate, 10:1) to afford the target product 6-fluoro-2-methylquinoline in 70% yield. 6-fluoro-2-methylquinoline was a colorless oil.1H NMR (400 MHz, CDCl3): δ = 8.93 (m, 1H), 8.10 (m, 1H) , 7.64 (d, J=4.0 Hz, 1H), 7.54 (m, 1H), 7.43-7.35 (m, 2H), 2.82 (s, 3H).13C NMR (100 MHz, CDCl3): δ=149.2, 147.3, 137.1, 136.3, 129.6, 128.3, 126.3, 125.9. 120.8, 18.2. HRMS: m/z calculated value of [C10H9FN+H]+: 144.0813; measured value: 144.0813. |
| References | [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227 [2] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4 [3] Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 6983 - 6987 [4] Ross. Khim. Zh., 2013, vol. 125, # 27, p. 7121 - 7125,5 [5] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10652 - 10658 |
6-Fluoroquinaldine Preparation Products And Raw materials
| Raw materials | (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline-->2-AMINO-5-FLUOROBENZALDEHYDE-->6-Bromo-2-methylquinoline-->6-Fluoro-1,2,3,4-tetrahydro-2-methylquinoline-->Ethanol-->Crotonaldehyde (trans predominantly)-->4-Fluoroaniline-->Acetaldehyde-->Ethyl vinyl ether-->Diacetone Alcohol-->Acetic acid |
