| Identification | Back Directory | [Name]
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione | [CAS]
19171-18-7 | [Synonyms]
4-Nitrothalidomide
Pomalidomide Impurity E
Pomalidomide Intermediates
Thalidomide 4-Nitro Impurity
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindole-1,3-dione
2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
4-nitro-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
(R)-2-(2,6-Dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione
2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dione
2-(2,6-dioxopiperidin-3-yl)-4-nitro-1H-isoindole-1,3(2H)-dio...
1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-nitro- | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C13H9N3O6 | [MDL Number]
MFCD01748356 | [MOL File]
19171-18-7.mol | [Molecular Weight]
303.23 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
10.55±0.40(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
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