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

Safety Information

HS Code 

2933998090

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

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