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| | 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Basic information |
| Product Name: | 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione | | Synonyms: | 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione;4-Nitrothalidomide;4-nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;Pomalidomide Intermediates;Pomalidomide Impurity E;2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione;1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-nitro-;Thalidomide 4-Nitro Impurity | | CAS: | 19171-18-7 | | MF: | C13H9N3O6 | | MW: | 303.23 | | EINECS: | 200-258-5 | | Product Categories: | | | Mol File: | 19171-18-7.mol |  |
| | 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Chemical Properties |
| Melting point | >200°C (dec.) | | Boiling point | 603.4±50.0 °C(Predicted) | | density | 1.651±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly) | | pka | 10.55±0.40(Predicted) | | form | Solid | | color | Pale Yellow to Pale Beige | | InChI | InChI=1S/C13H9N3O6/c17-9-5-4-8(11(18)14-9)15-12(19)6-2-1-3-7(16(21)22)10(6)13(15)20/h1-3,8H,4-5H2,(H,14,17,18) | | InChIKey | KVRCAGKHAZRSQX-UHFFFAOYSA-N | | SMILES | C1(=O)C2=C(C([N+]([O-])=O)=CC=C2)C(=O)N1C1CCC(=O)NC1=O |
| | 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Usage And Synthesis |
| Uses | 4-Nitrothalidomide is a compound involved in the preparation of Pomalidomide (P688200), a thalidomide derivative and potent inhibitor of TNF-α production. | | Synthesis | A solution of glacial acetic acid (75 mL) and 3-aminopiperidine-2,6-dione hydrochloride (8.5 g) was added to a round bottom flask. Anhydrous sodium acetate (4.5 g) was added to the solution in batches at 25 °C to 30 °C, followed by 3-nitrophthalic anhydride (10 g) at the same temperature. The reaction mixture was stirred at 118 °C for 18 hours. After completion of the reaction, the reaction material was cooled to 60 °C and the solvent was removed by distillation under vacuum to obtain a residue. Water (100 mL) was added to the residue and the mixture was stirred at 25 °C to 30 °C for 1 hour, followed by filtration. The wet filter cake was slurried with water (100 mL x 2), filtered and dried in an air pan drier to less than 0.5% water to give 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione (14 g). Yield: 89.7%, purity: 98%. | | References | [1] Patent: US2017/260157, 2017, A1. Location in patent: Page/Page column 5
[2] Patent: CN104926786, 2017, B. Location in patent: Paragraph 0044; 0045
[3] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 11, p. 1625 - 1630
[5] Patent: CN104402863, 2016, B. Location in patent: Paragraph 0035 |
| | 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione Preparation Products And Raw materials |
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