5-IODOISATIN CAS 20780-76-1
5-IODOISATIN Basic information
| Product Name: | 5-IODOISATIN |
| Synonyms: | 5-IODOINDOLINE-2,3-DIONE;5-IODOISATIN;5-IODO-2,3-INDOLINEDIONE;1H-Indole-2,3-dione,5-iodo-;5-Iodo-1H-indole-2,3-dione;5-Iodo-2,3-dioxoin-doline;5-Iodoisatin 98%;5-Iodoisatine |
| CAS: | 20780-76-1 |
| MF: | C8H4INO2 |
| MW: | 273.03 |
| EINECS: | 244-035-1 |
| Product Categories: | Simple Indoles;Halogenated Heterocycles;Indane/Indanone and Derivatives;Indoles;Heterocyclic Building Blocks;IndolesBuilding Blocks |
| Mol File: | 20780-76-1.mol |
5-IODOISATIN Chemical Properties
| Melting point | 276-280 °C(lit.) |
| density | 2.106±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| form | powder to crystal |
| pka | 8.87±0.20(Predicted) |
| color | Orange to Brown to Dark red |
| Water Solubility | Soluble acetone, acetic acid, ethanol. Insoluble in water. |
| Sensitive | Light Sensitive |
| BRN | 131248 |
| InChI | 1S/C8H4INO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12) |
| InChIKey | OEUGDMOJQQLVAZ-UHFFFAOYSA-N |
| SMILES | Ic1ccc2NC(=O)C(=O)c2c1 |
| CAS DataBase Reference | 20780-76-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-36/37/38-43 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HazardClass | LIGHT SENSITIVE |
| HS Code | 29337900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 STOT SE 3 |
| Uses | 5-Iodoisatin undergoes condensation reaction with phenol yields 5-iodophenolisatin, malonic acid yields 6-iodo-2-quinolone-4-carboxylic acid. |
| Definition | ChEBI: 5-Iodoisatin is a member of indoles. It has a role as an anticoronaviral agent. |
| General Description | 5-Iodoisatin undergoes condensation reaction with:
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| Synthesis | 60313-92-0 20780-76-1 1. Preheat concentrated sulfuric acid (275 mL) at 60 °C. After stopping the heating, add p-iodoacetoacetanilide (22.0 g, 75.9 mmol) in batches with stirring, controlling the temperature to no more than 65 °C.2. The reaction mixture was heated at 80 °C for 15 min.3. After cooling to room temperature, it was further cooled to 0 °C and then the reaction mixture was slowly poured into crushed ice (550 g) and stirred at 0 °C for 1 hour.4. The orange colored precipitate formed was collected by filtration and washed with water (110 mL).5. Dissolve the precipitate in preheated 10% aqueous sodium hydroxide solution (55 mL, 60 °C).6. Acetic acid (16.5mL) was added and heated at 60°C for 30 minutes.7. After cooling to room temperature, further cooled to 0 °C, the precipitate was collected by filtration, washed with water (11 mL) and dried under vacuum to give 5-iodoindigo (17.1 g, 62.7 mmol) as an orange solid.8. Yield 83%; melting point 272-274 °C (literature value: 272-274 °C); IR (KBr) ν 1198, 1458, 1606, 1731-1751, 3241 cm-1; 1H NMR (200 MHz, DMSO-d6) δ 6.75 (d, 1H, J=8.2 Hz, H-7), 7.76 (d, 1H. J=1.8Hz, H-4), 7.88 (dd, 1H, J=1.8,8.2Hz, H-6), 11.11 (s, 1H, NH); 13C NMR (50MHz, DMSO-d6) δ 85.8 (C-5), 115.2 (C-7), 120.4 (C-3a), 132.9 (C-4), 142.0 (C 6), 150.7 (C-7a), 159.3 (C-2), 183.7 (C-3). |
| References | [1] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 818 - 838 [2] Tetrahedron, 2005, vol. 61, # 25, p. 6082 - 6087 [3] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498 [4] Chemische Berichte, 1924, vol. 57, p. 1773 [5] European Journal of Pharmacology, 2007, vol. 556, # 1-3, p. 200 - 206 |
5-IODOISATIN Preparation Products And Raw materials
| Raw materials | Isatin-->Iodine monochloride-->Acetamide, 2-(hydroxyimino)-N-(4-iodophenyl)--->6-IODO-2,3-DIHYDRO-1H-INDOLE |
| Preparation Products | 5-iodo-1-methylindoline-2,3-dione |
