- 4-nitroisoindolin-1-one
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- $6.60 / 1KG
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2019-12-26
- CAS:366452-97-3
- Min. Order: 1KG
- Purity: 97%-99%
- Supply Ability: 1kg-1000kg
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| | 4-nitroisoindolin-1-one Basic information |
| Product Name: | 4-nitroisoindolin-1-one | | Synonyms: | 4-Nitro-2,3-dihydro-1H-isoindol-1-one;4-Nitro-2,3-dihydro-1H-isoindolin-1-one;4-Nitro-2,3-dihydro-isoindol-1-one;1H-Isoindol-1-one, 2,3-dihydro-4-nitro-;4-nitroisoindolin-1-one | | CAS: | 366452-97-3 | | MF: | C8H6N2O3 | | MW: | 178.14 | | EINECS: | | | Product Categories: | | | Mol File: | 366452-97-3.mol |  |
| | 4-nitroisoindolin-1-one Chemical Properties |
| 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 |
| | 4-nitroisoindolin-1-one Usage And Synthesis |
| 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 |
| | 4-nitroisoindolin-1-one Preparation Products And Raw materials |
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