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

Safety Information

HazardClass 

IRRITANT

3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione Usage And Synthesis

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(827026-45-9)Related Product Information

• Lenalidomide Impurity 11
• Lenalidomide Impurity 14
• Lenalidomide Impurity 3
• Methyl 2-bromomethyl-3-nitrobenzoate
• 2-BROMOMETHYL-4-NITRO-BENZOIC ACID METHYL ESTER
• Lenalidomide Impurity 13
• METHYL 2-BROMOMETHYL-6-NITRO-BENZOATE
• Lenalidomide Impurity 7
• Hydroxy Lenalidomide
• Methyl 2-methyl-3-nitrobenzoate
• Lenalidomide Impurity 12
• Lenalidomide Impurity 22
• Lenalidomide Impurity 17
• Methyl 2-(chloromethyl)-3-nitrobenzoate
• N-Acetyl Lenalidomide
• Methyl 3-amino-2-methylbenzoate
• Lenalidomide-d5
• 2-Methyl-3-nitrobenzoic acid