| Identification | Back Directory | [Name]
3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid | [CAS]
61260-15-9 | [Synonyms]
3-dimethoxyphosphoryl-3H-2-benzofuran-1-one
3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid
Dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate
Dimethyl (1,3-dihydro-3-oxo-1-isobenzofuranyl)phosphonate
dimethyl 1,3-dihydro-3-oxoisobenzofuran-1-yl-1-phosphonate
(3-Oxo-1,3-dihydroisobenzofuran-1-yl)phosphonic acid dimethyl ester
Phosphonic acid, (1,3-dihydro-3-oxo-1-isobenzofuranyl)-, diMethyl ester
Phosphonic acid,P-(1,3-dihydro-3-oxo-1-isobenzofuranyl)-,dimethyl ester | [Molecular Formula]
C10H11O5P | [MDL Number]
MFCD16883476 | [MOL File]
61260-15-9.mol | [Molecular Weight]
242.17 |
| Questions And Answer | Back Directory | [Description]
3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid can be used as a pharmaceutical intermediate for pharmaceutical synthesis experiments. | [Appearance]
White crystal |
| Chemical Properties | Back Directory | [Melting point ]
97-99℃ | [Boiling point ]
402.0±45.0 °C(Predicted) | [density ]
1.35 | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [color ]
White | [InChI]
InChI=1S/C10H11O5P/c1-13-16(12,14-2)10-8-6-4-3-5-7(8)9(11)15-10/h3-6,10H,1-2H3 | [InChIKey]
KEKUNQAVGWOYDW-UHFFFAOYSA-N | [SMILES]
P(C1C2=C(C=CC=C2)C(=O)O1)(=O)(OC)OC |
| Hazard Information | Back Directory | [Uses]
Dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonate is a reagent used in the synthesis of 4-[3-(4-Cyclopropanecarbonylpiperazine-1-carbonyl)-4-fluorobenzyl]-2H-phthalazin-1-one, an inhibitor of both PARP-1 AND PARP-2 that shows standalone activity against BRCA1-deficient breast cancer cell lines. | [Synthesis]
Sodium methoxide (2.28 g,0.042 mol) was dissolved in methanol (40 mL) into a 150 mLround-bottom flask. To this solution, dimethyl hydrogen phosphite(4.8 mL, 0.049 mol) and 2-carboxybenzaldehyde (compound5, 5.00 g, 0.033 mol) were added by dripping at 0 °Cfor 30 min. Then the mixture was stirred at room temperaturefor 8 h.
After the reaction was completed, methanesulfonicacid (3.1 mL, 0.047 mol) was added dropwise and stirred for30 min. The solvent was removed under reduced pressure,following by adding 40 mol water.
The aqueous phase wasextracted with dichloromethane for three times, the combinedorganic phase was washed with water until neutral and driedwith anhydrous sodium sulfate. Dichloromethane was evaporatedunder reduced pressure to afford 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid(4.93 g, 99%)as white solid.
1H-NMR (500 MHz, DMSO-d6) δ: 3.62 (3H,d, J = 8 Hz), 3.86 (3H, d, J = 12 Hz), 6.36 (1H, d, J = 8 Hz),7.74-7.70 (2H, m), 7.91-7.88 (1H, m), 7.98-7.96 (1H, m).
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