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

Base Information

• Chemical Name: 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione
• CAS No.: 827026-45-9
• Molecular Formula: C13H11N3O5
• Molecular Weight: 289.247
• Hs Code.: 2925190090
• Mol file: 827026-45-9.mol

Synonyms:3-(4-Nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione;3-(4-Nitro-1-oxoisoindolin-2-yl)piperidin-2,6-dione;

Chemical Property of 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.657
• Boiling Point: 616.562 °C at 760 mmHg
• PKA: 10.55±0.40(Predicted)
• Flash Point: 326.685 °C
• PSA: 112.30000
• Density: 1.546 g/cm³
• LogP: 1.14570
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

4-NitroLenalidomide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Lenalidomide (L328000) analog. Lenalidomide impurity; Lenalidomide intermediate. Lenalidomide (L328000) analog. Lenalidomide impurity.

Technology Process of 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

There total 44 articles about 3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.73%

rac-α-aminoglutarimide hydrochloride (24666-56-6,2686-86-4) + 2-bromomethyl-3-nitro-benzoic acid methyl ester (98475-07-1) → 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione (827026-45-9)

Guidance literature:

rac-α-aminoglutarimide hydrochloride; With triethylamine; In dimethyl sulfoxide; for 0.166667h; Inert atmosphere;

2-bromomethyl-3-nitro-benzoic acid methyl ester; In dimethyl sulfoxide; at 50 - 55 ℃; for 12.3333h; Inert atmosphere;

Reference yield: 96.0%

2-bromomethyl-3-nitro-benzoic acid methyl ester (98475-07-1) + (+/-)-α-aminoglutarimide (2353-44-8,673485-72-8) → 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione (827026-45-9)

Guidance literature:

In N,N-dimethyl-formamide; for 3h; Reflux;

Reference yield: 94.1%

3-(4-nitro-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione → 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione (827026-45-9)

Guidance literature:

With 5-trimethylammonio-1,3-dioxo-1,3-dihydro-1λ⁵-benzo[d][1,2]-iodoxol-1-ol anion; In water; at 50 - 70 ℃;

upstream raw materials:

rac-α-aminoglutarimide hydrochloride

2-bromomethyl-3-nitro-benzoic acid methyl ester

2-methyl-3-nitro-benzoic acid methyl ester

Cbz-L-Gln

Downstream raw materials:

(RS)-3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione hydrochloride

N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)benzamide

Refernces

• 1、 -. "Compound for targeted degradation of BTK protein". Paragraph 0458; 0465-0467. . Retrieved 2021/06/22.
• 2、 -. "Method for synthesizing lenalidomide". Paragraph 0024-0025; 0027-0028; 0030-0031. . Retrieved 2020/01/12.