| Identification | Back Directory | [Name]
2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione | [CAS]
835616-60-9 | [Synonyms]
135582
TC-E3 5032
E3 ligase Ligand 4
4-Fluoro-thalidomide
Thalidomide 4-fluoride
E3 ligase Ligand 4(TC-E3 5032)
Pomalidomide Related Compound 7
2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione
2-(2,6-Dioxo-3-piperidinyl)-4-fluoro-1,3-isoindolinedione
2-(2,6-dioxo-3-piperidinyl)-4-fluoro-1H-Isoindole-1,3(2H)-dione
1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-4-fluoro-
2-(2,6-Dioxopiperidin-3-yl)-4-fluoro-2,3-dihydro-1H-isoindole-1,3-dione | [Molecular Formula]
C13H9FN2O4 | [MDL Number]
MFCD11840666 | [MOL File]
835616-60-9.mol | [Molecular Weight]
276.22 |
| Chemical Properties | Back Directory | [Melting point ]
254-256°C | [Boiling point ]
520.9±45.0 °C(Predicted) | [density ]
1.570±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Dichloromethane (Slightly, Heated), DMSO (Slightly) | [form ]
Solid | [pka]
10.63±0.40(Predicted) | [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 |
| Hazard Information | Back Directory | [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.
| [IC 50]
Cereblon | [storage]
Store at +4°C |
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