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| | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione Basic information |
| Product Name: | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione | | Synonyms: | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione;3-(4-Nitro-1-oxoisoindolin-2-yl)piperidin-2,6-dione;4-Nitro LenalidoMide;3-dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-;6-Piperidinedione;3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione;3-(4-nitro-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione;3-(1,3-Dihydro-4-nitro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione | | CAS: | 827026-45-9 | | MF: | C13H11N3O5 | | MW: | 289.24 | | EINECS: | 1592732-453-0 | | Product Categories: | Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 827026-45-9.mol |  |
| | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione Chemical Properties |
| Melting point | >250°C (dec.) | | Boiling point | 616.6±55.0 °C(Predicted) | | density | 1.546±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Slightly, Heated), Methanol (Slightly) | | form | Solid | | pka | 10.55±0.40(Predicted) | | color | Beige to Brown | | InChI | InChI=1S/C13H11N3O5/c17-11-5-4-10(12(18)14-11)15-6-8-7(13(15)19)2-1-3-9(8)16(20)21/h1-3,10H,4-6H2,(H,14,17,18) | | InChIKey | JKPJLYIGKKDZDT-UHFFFAOYSA-N | | SMILES | N1C(=O)CCC(N2CC3=C(C2=O)C=CC=C3[N+]([O-])=O)C1=O |
| | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione Usage And Synthesis |
| Description | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione is mainly used as an impurity reference standard and metabolic/synthetic intermediate in the development of lenalidomide drugs, for drug quality control, process optimization and related pharmacological mechanism research. | | Chemical Properties | White crystalline | | Uses | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione, also known as 4-Nitro Lenalidomide, is a Lenalidomide (L328000) analog. It is an impurity and intermediate of Lenalidomide. | | Preparation | 3-aminopiperidine-2,6-dione hydrochloride (III) (25 g, 0.15 mol) and dimethyl sulfoxide (150 mL) were charged into 500 mL 3N RBF. Triethylamine (62 g, 0.61 mol) was added slowly to the above reaction mixture under nitrogen over 10 min. Methyl 2-(bromomethyl)-3-nitrobenzoate (II) (45.8 g, 0.16 mol) of example 3 dissolved in dimethyl sulfoxide (50 mL) was added to the reaction mixture under nitrogen over 20 min and heated to 50-55 °C. 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione was obtained by purification. |
| | 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione Preparation Products And Raw materials |
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