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(19171-18-7)Related Product Information

• Pomalidomide Impurity 4
• 3-AMINOPHTHALIC ACID
• (R)-Pomalidomide
• 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
• Pomalidomide Impurity 10
• 3,4-Diamino-4-oxobutyric acid
• DL-Glutamine
• (S)-Pomalidomide
• 2-(2,6-dioxopiperidin-3-yl)-4-(hydroxyamino)isoindoline-1,3-dione
• 3-Nitrophthalic acid
• Pomalidomide Impurity 2
• Pomalidomide Impurity 6
• Thalidomide
• 4-Hydroxy ThalidoMide
• Pomalidomide
• Pomalidomide Impurity 3
• 3-AMINOPHTHALIC ACID HYDROCHLORIDE
• 4-Aminophthalic acid