7-BROMO-1H-INDOLE-2,3-DIONE CAS 20780-74-9
7-BROMO-1H-INDOLE-2,3-DIONE Basic information
| Product Name: | 7-BROMO-1H-INDOLE-2,3-DIONE |
| Synonyms: | 7-Bromoisatin 97%;BUTTPARK 50\07-96;7-BROMOINDOLINE-2,3-DIONE;7-BROMO-ISATIN;7-BROMO-2,3-DIOXOINDOLINE;7-BROMO-1H-INDOLE-2,3-DIONE;7-BROMOINDOLE-3-CARBOXALDEHYDE;7-Bromoindoline-2,3-dione, 7-Bromo-1H-indole-2,3-dione |
| CAS: | 20780-74-9 |
| MF: | C8H4BrNO2 |
| MW: | 226.03 |
| EINECS: | 625-256-6 |
| Product Categories: | Indane/Indanone and Derivatives;Pharmaceutical intermediate;Heterocycles |
| Mol File: | 20780-74-9.mol |
7-BROMO-1H-INDOLE-2,3-DIONE Chemical Properties
| Melting point | 191-198 °C |
| density | 1.826±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Slightly soluble. |
| form | powder to crystal |
| pka | 8.69±0.20(Predicted) |
| color | Orange to Amber to Dark red |
| InChI | InChI=1S/C8H4BrNO2/c9-5-3-1-2-4-6(5)10-8(12)7(4)11/h1-3H,(H,10,11,12) |
| InChIKey | OCVKSIWBTJCXPV-UHFFFAOYSA-N |
| SMILES | N1C2=C(C=CC=C2Br)C(=O)C1=O |
| CAS DataBase Reference | 20780-74-9(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-37/38-41 |
| Safety Statements | 26-39 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 2933998090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3 |
| Uses | 7-bromoisatin was treated with excess PhMgBr to afford tertiary alcohol 9 in 96 % yield. Isatin oxime triflates undergo a facile fragmentation which is promoted by DBU, to form anthranilonitriles after hydrolytic work-up. |
| Synthesis | 101080-38-0 20780-74-9 Step 2: N-(2-bromophenyl)-2-(hydroxyimino)acetamide (7 g, 0.028 mol) was slowly added to 70 mL of concentrated sulfuric acid, and the temperature of the reaction system was maintained at 60 °C. Subsequently, the reaction temperature was raised to 90 °C with continuous stirring for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water and a yellow precipitate was precipitated. The precipitate was collected by filtration and dried to give 7-bromoisatin as a yellow solid (6.0 g, 92% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 11.33 (s, 1H), 7.79 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 7.2 Hz, 1H), 7.02 (t, J = 7.5 Hz, 1H); LC-MS (ESI) analysis: calculated mass: 224.9; observed mass: 226.0 [M + H]+ (retention time: 0.39 min). |
| References | [1] Patent: WO2012/58671, 2012, A1. Location in patent: Page/Page column 106 [2] Patent: CN105732462, 2016, A. Location in patent: Paragraph 0026 [3] Patent: CN103864779, 2016, B. Location in patent: Paragraph 0066; 0067; 0069 [4] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 38 [5] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 1, p. 22 - 26 |
7-BROMO-1H-INDOLE-2,3-DIONE Preparation Products And Raw materials
| Raw materials | Chloral hydrate-->(2E)-N-(2-BROMOPHENYL)-2-(HYDROXYIMINO)ACETAMIDE-->7-BroMo-2,3-dihydro-1H-indole-->2-Bromoaniline |
| Preparation Products | 7-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one |
