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ChemicalBook--->CAS DataBase List--->835616-60-9

835616-60-9

835616-60-9 Structure

835616-60-9 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07,GHS08
[Signal word ]

Warning
[Hazard statements ]

H361-H302
[Precautionary statements ]

P201-P202-P281-P308+P313-P405-P501-P264-P270-P301+P312-P330-P501
[HS Code ]

2933998090
Hazard InformationBack 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.
2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione
[storage]

Store at +4°C
Spectrum DetailBack Directory
[Spectrum Detail]

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