| Identification | Back Directory | [Name]
4-nitroisoindolin-1-one | [CAS]
366452-97-3 | [Synonyms]
4-nitroisoindolin-1-one
4-Nitro-2,3-dihydro-isoindol-1-one
4-Nitro-2,3-dihydro-1H-isoindol-1-one
4-Nitro-2,3-dihydro-1H-isoindolin-1-one
1H-Isoindol-1-one, 2,3-dihydro-4-nitro- | [Molecular Formula]
C8H6N2O3 | [MDL Number]
MFCD09701290 | [MOL File]
366452-97-3.mol | [Molecular Weight]
178.14 |
| Chemical Properties | Back Directory | [Boiling point ]
488.8±45.0 °C(Predicted) | [density ]
1.449±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
12.69±0.20(Predicted) | [Appearance]
Off-white to light yellow Solid | [InChI]
InChI=1S/C8H6N2O3/c11-8-5-2-1-3-7(10(12)13)6(5)4-9-8/h1-3H,4H2,(H,9,11) | [InChIKey]
RTDDSWLIZLMORY-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C([N+]([O-])=O)=CC=C2)CN1 |
| Hazard Information | Back Directory | [Uses]
4-Nitroisoindolin-1-one is a reactant that has been used in the synthesis of 4-(N-acyl)-2,3-dihydro-1H-isoindol-1-ones as potent inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1). | [Synthesis]
General procedure for the synthesis of 4-nitro-isoindolin-1-one from methyl 2-(bromomethyl)-3-nitrobenzoate: methyl 2-(bromomethyl)-3-nitrobenzoate (20 g) was dissolved in methanol (200 ml) and stirred at room temperature under ammonia atmosphere for 30 min, followed by keeping the reaction for 2 hours. After completion of the reaction, the mixture was crystallized in an ice bath for 2 h. The crystals were collected by filtration and dried to give 11.7 g of light yellow crystals in 90% yield. The melting point was 235.4~236.7 °C. 1H-NMR (300 MHz, DMSO-d6) δ: 4.78 (s, 2H), 7.79 (t, 1H), 8.10 (d, 1H), 8.41 (d, 1H), 8.90 (s, 1H). 1H-NMR (300 MHz, DMSO-d6/EtOH) δ: 4.76 (s 2H), 7.77 (t, 1H), 8.08 (d, 1H), 8.39 (d, 1H).FAB-MS (M+1): 179.Elemental analysis: theoretical value (%): C 53.94, H 3.39, N 15.72; measured value (%): C 54.08, H 3.49, N 15.81.HPLC analytical conditions: chromatographic column: Phenomenex Luna 5μ C18 (250mm×4.6mm); Flow rate: 1.0ml/min; Detection wavelength: 230nm; Mobile phase: Acetonitrile/0.1% Phosphate buffer=30/70 (v/v); Retention time of the target product: 5.810 min; Purity: 99.59%. | [References]
[1] Patent: WO2010/139266, 2010, A1. Location in patent: Page/Page column 37-38
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 81 - 85
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 248 - 253
[4] Angew. Chem., 2017, vol. 129, # 1, p. 254 - 259,6
[5] Patent: WO2006/12374, 2006, A1. Location in patent: Page/Page column 209 |
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Heterochem
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SynAsst Chemical.
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