5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Base Information

• Chemical Name: 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
• CAS No.: 191732-76-0
• Molecular Formula: C13H11N3O4
• Molecular Weight: 273.248
• European Community (EC) Number: 876-546-6
• DSSTox Substance ID: DTXSID40431253
• Nikkaji Number: J1.121.686B
• ChEMBL ID: CHEMBL43855
• Mol file: 191732-76-0.mol

Synonyms:5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;191732-76-0;5-Aminothalidomide;5-amino-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione;MFCD30188077;1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-5-aminoisoindoline;LCWG015;CHEMBL43855;SCHEMBL502195;DTXSID40431253;IICWMVJMJVXCLY-UHFFFAOYSA-N;BDBM511643;US11059801, Compound D-8;1H-Isoindole-1,3(2H)-dione, 5-amino-2-(2,6-dioxo-3-piperidinyl)-;AKOS015311848;HY-W023573;SB64014;BP-27965;SY284758;CS-0060081;W17815;EN300-7365471;Z1269642572;2-(2,6-Dioxo-3-piperidinyl)-5-aminoisoindoline-1,3-dione;5-amino-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione;5-amino-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Chemical Property of 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Chemical Property:

• Melting Point: >300 °C
• Boiling Point: 603.8±50.0 °C(Predicted)
• PKA: 10.83±0.40(Predicted)
• PSA: 113.06000
• Density: 1.570±0.06 g/cm3(Predicted)
• LogP: 0.46500
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Sonicated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 273.07495584
• Heavy Atom Count: 20
• Complexity: 504

Purity/Quality:

97% ^*data from raw suppliers

5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C=C(C=C3)N
• Description: 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione is a thalidomide analog that can be useful in PROTAC research.

Technology Process of 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

There total 8 articles about 5-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-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: 100.0%

2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione (55003-81-1) → 2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione (191732-76-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; acetic acid; at 20 ℃;

DOI:10.1016/j.bmcl.2008.11.118

Reference yield: 37.0%

→ 2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione (191732-76-0)

Guidance literature:

With triethylsilane; potassium fluoride; palladium diacetate; In tetrahydrofuran; water; at 20 ℃; for 1h;

Reference yield:

4-nitrophthalic anhydride (5466-84-2) → 2-(2,6-dioxo-3-piperidinyl)-5-amino-1H-isoindole-1,3(2H)-dione (191732-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / acetic acid / 2 h / Heating

2: 80 percent / H₂ / Pd/C / acetone / 20 h / 20 °C

With hydrogen; palladium on activated charcoal; In acetic acid; acetone;

DOI:10.1021/ol034906w

upstream raw materials:

2-(2,6-dioxo-3-piperidinyl)-5-nitro-1H-isoindole-1,3(2H)-dione

4-nitrophthalic anhydride

Cbz-L-Gln

rac-α-aminoglutarimide hydrochloride

Refernces

• 1、 Bricelj, Ale?a,Dora Ng, Yuen Lam,Ferber, Dominic,Gütschow, Michael,Kr?nke, Jan,Kuchta, Robert,Müller, Sina,Monschke, Marius,Sosi?, Izidor,Steinebach, Christian,Wagner, Karl G.. "Influence of Linker Attachment Points on the Stability and Neosubstrate Degradation of Cereblon Ligands". supporting information. p. 1733 - 1738. Retrieved 2021/11/16.
• 2、 -. "IMIDE-BASED MODULATORS OF PROTEOLYSIS AND METHODS OF USE". Page/Page column 224; 237-238. . Retrieved 2019/08/12.