2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione Chemical Properties

Melting point:

254-256°C

Boiling point:

520.9±45.0 °C(Predicted)

Density 

1.570±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Dichloromethane (Slightly, Heated), DMSO (Slightly)

pka

10.63±0.40(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C13H9FN2O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5H2,(H,15,17,18)

InChIKey

CRAUTELYXAAAPW-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C(F)=CC=C2)C(=O)N1C1CCC(=O)NC1=O

Safety Information

HS Code 

2933998090

2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione Usage And Synthesis

Description

4-Fluoro-thalidomide is the Thalidomide-based Cereblon ligand used in the recruitment of CRBN protein. It can be connected to the ligand for IRAK4 protein by a linker to form PROTAC IRAK4 degrader-1 (HY-129966).

Uses

2-(2,6-Dioxo-3-piperidinyl)-4-fluoro-1H-isoindole-1,3(2H)-dione is an intermediate in the synthesis of N-[2-Aminoethyl] Pomalidomide TFA Salt (A6095150. N-[2-Aminoethyl] Pomalidomide TFA is a thalidomide derivative, a potent inhibitor of TNF-α production. It is an anti-inflammatory and anti-tumor agent used in the treatment of multiple myeloma.

Synthesis

A mixture of 4-fluoroisobenzofuran-l,3-dione (498.33 mg, 3.00 mmol), 3- aminopiperidine-2,6-dione hydrogen chloride (493.77 mg, 3.00 mmol) and NaOAc (246.09 mg, 3.00 mmol) in HOAc (10 mL) was stirred at 135 °C overnight, cooled and concentrated in vacuo. The residue was suspended in H2O (100 mL) and stirred at room temperature for 4 hours. The solid was collected via filtration and dried in vacuo to afford 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione as a white solid.

storage

Store at +4°C

2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione(835616-60-9)Related Product Information

• Cereblon Ligand 1
• 4-Hydroxy ThalidoMide
• Protein degrader 1 (TFA)
• (2S,4R)-1-((S)-2-amino-3,3-dimethylbutanoyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide hydrochloride
• L-Prolinamide, 3-methyl-L-valyl-4-hydroxy-N-[(1S)-1-[4-(4-methyl-5-thiazolyl)phenyl]ethyl]-, (4R)-