2-CHLOROQUINOLINE-3-CARBALDEHYDE CAS 73568-25-9
2-CHLOROQUINOLINE-3-CARBALDEHYDE Basic information
| Product Name: | 2-CHLOROQUINOLINE-3-CARBALDEHYDE |
| Synonyms: | TIMTEC-BB SBB000302;RARECHEM AK ML 0551;2-CHLOROQUINOLINE-3-CARBALDEHYDE;2-CHLOROQUINOLINE-3-CARBOXALDEHYDE;2-CHLORO-3-QUINOLINECARBOXALDEHYDE;ASISCHEM C51996;IFLAB-BB F0010-0600;AKOS AU36-M569 |
| CAS: | 73568-25-9 |
| MF: | C10H6ClNO |
| MW: | 191.61 |
| EINECS: | |
| Product Categories: | Halogenated Heterocycles;Heterocyclic Building Blocks;Building Blocks;Quinolines;QuinolinesHeterocyclic Building Blocks |
| Mol File: | 73568-25-9.mol |
2-CHLOROQUINOLINE-3-CARBALDEHYDE Chemical Properties
| Melting point | 148-150 °C (lit.) |
| Boiling point | 335.8±22.0 °C(Predicted) |
| density | 1.364 |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| form | Liquid |
| pka | -1.31±0.50(Predicted) |
| color | Clear colorless to yellow |
| Sensitive | Air Sensitive |
| InChI | 1S/C10H6ClNO/c11-10-8(6-13)5-7-3-1-2-4-9(7)12-10/h1-6H |
| InChIKey | SDKQWXCBSNMYBN-UHFFFAOYSA-N |
| SMILES | Clc1nc2ccccc2cc1C=O |
| CAS DataBase Reference | 73568-25-9(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-37/39 |
| WGK Germany | 3 |
| HS Code | 29334900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | Yellow to yellow-brown crystalline powder |
| Synthesis | 612-62-4 73568-25-9 Example 7 Synthesis of 2-chloro-3-quinolinecarboxaldehyde: 1.53 mL (3.30 mmol) of n-butyllithium (n-BuLi) was added slowly and dropwise to an 8 mL THF solution containing 0.46 mL (3.30 mmol) of diisopropylamine at 0 °C. After 20 minutes of reaction, the solution was cooled to -78 °C and 2-chloroquinoline (491 mg, 3.0 mmol) was added at this temperature. The mixture was stirred at -78 °C for 30 min, followed by dropwise addition of dimethylformamide (0.39 mL, 5.04 mmol) and continued stirring at the same temperature for 30 min. Upon completion of the reaction, the reaction was quenched with glacial acetic acid (1 mL) at -78 °C, then the mixture was slowly warmed to room temperature and diluted with ether (30 mL). The organic phase was washed sequentially with saturated NaHCO3 solution (10 mL) and brine (10 mL) and dried over anhydrous MgSO4. Concentration gave 2-chloro-3-quinolinecarboxaldehyde (530 mg, 92% yield) as a light yellow solid with melting point 145-149 °C, which could be used in the next reaction without further purification. By recrystallization from ethyl acetate, a pure product was obtained as pale yellow acicular crystals with a melting point of 149-150 °C (literature values 148-149 °C, see Meth-Cohn, O.; Narhe, B.; Tarnowski, B. J. Chem. Soc. Perkin Trans. I 1981, 1520).1H NMR (300 MHz, CDCl3) δ 10.57 (s, 1H), 8.77 (s, 1H), 8.08 (d, 1H, J = 9 Hz), 8.0 (d, 1H, J = 9 Hz), 7.90 (t, 1H, J = 9 Hz), 7.67 (t, 1H, J = 9 Hz); IR (nujol) 1685, 1575, 1045, 760, 745 cm-1. 745 cm-1. |
| References | [1] Patent: US5212317, 1993, A [2] Patent: US5162532, 1992, A |
2-CHLOROQUINOLINE-3-CARBALDEHYDE Preparation Products And Raw materials
| Raw materials | 2-Chloroquinoline-->(2-CHLORO-3-QUINOLINYL)METHANOL-->Acetophenone oxime-->2-CHLORO-3-QUINOLINECARBOXALDEHYDE OXIME-->DIETHYL HYDRAZODICARBOXYLATE-->Diethyl azodicarboxylate-->Aniline-->Acetanilide-->2-METHYLACETANILIDE-->Acetic anhydride-->Ethyl formate |
| Preparation Products | 2-MORPHOLIN-4-YL-QUINOLINE-3-CARBALDEHYDE-->Acridin-3-ol |
