|
|
| | N-Acetic acid-indole-3-carboxaldehyde Basic information |
| | N-Acetic acid-indole-3-carboxaldehyde Chemical Properties |
| Melting point | 197-200 °C(lit.) | | Boiling point | 458.5±25.0 °C(Predicted) | | density | 1.30±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | form | solid | | pka | 4.15±0.10(Predicted) | | Appearance | Light yellow to yellow Solid | | Sensitive | Air Sensitive | | BRN | 5431204 | | InChI | InChI=1S/C11H9NO3/c13-7-8-5-12(6-11(14)15)10-4-2-1-3-9(8)10/h1-5,7H,6H2,(H,14,15) | | InChIKey | ZUUGBTJTGRTIFK-UHFFFAOYSA-N | | SMILES | N1(CC(O)=O)C2=C(C=CC=C2)C(C=O)=C1 | | CAS DataBase Reference | 138423-98-0(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | F | 8-10-23 | | HazardClass | IRRITANT | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids |
| | N-Acetic acid-indole-3-carboxaldehyde Usage And Synthesis |
| Chemical Properties | Solid | | Uses | Handle to synthesize an indolecarboxaldehyde resin by coupling to an amino-resin. Amines and derivatives can be immobilized by reductive amination of this aldehyde resin. Mild cleavage with 50% TFA | | reaction suitability | reagent type: cross-linking reagent | | Synthesis | Ethyl (3-formyl-1H-indol-1-yl)acetate (15.9 g, 69 mmol) was dissolved in 1,4-dioxane (100 mL), 1 N sodium hydroxide solution (10 mL) was added, and the resulting mixture was stirred at 0 °C. The reaction mixture was then stirred at room temperature for 4 days. After completion of the reaction, water (500 mL) was added and the mixture was washed with ether (150 mL). The aqueous phase was acidified with 5 N hydrochloric acid to pH < 2 and subsequently extracted with ethyl acetate (250 mL + 150 mL) in two fractions. The organic phases were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (3-formylindol-1-yl)acetic acid (10.3 g, 73% yield) as a white solid. The product was characterized by 1H-NMR (DMSO-d6): δH=5.20 (2H, s), 7.3 (2H, m), 7.55 (1H, d), 8.12 (1H, d), 8.30 (1H, s), 9.95 (1H, s), 13.3 (1H, br s). | | References | [1] Patent: WO2006/82245, 2006, A1. Location in patent: Page/Page column 230
[2] Patent: US2005/65066, 2005, A1. Location in patent: Page/Page column 120
[3] Patent: WO2004/80480, 2004, A1. Location in patent: Page/Page column 226
[4] Patent: WO2006/5683, 2006, A1. Location in patent: Page/Page column 225
[5] Patent: US2003/229120, 2003, A1. Location in patent: Page 75 |
| | N-Acetic acid-indole-3-carboxaldehyde Preparation Products And Raw materials |
|