3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid Chemical Properties

Melting point:

97-99℃

Boiling point:

402.0±45.0 °C(Predicted)

Density 

1.35

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

HS Code 

2932990090

3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid Usage And Synthesis

Description

3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid can be used as a pharmaceutical intermediate for pharmaceutical synthesis experiments.

Appearance

White crystal

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).

3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid(61260-15-9)Related Product Information

• 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzoic acid
• 2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzonitrile
• 1,3-DiMethyl 2-[4-(Methoxycarbonyl)-2-nitrophenyl]propanedioate
• tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzoyl)piperazine-1-carboxylate
• 2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile
• 1-(CYCLOPROPANECARBONYL)PIPERAZINE 97
• Piperazine, 1-(cyclopropylcarbonyl)-, Monohydrochloride
• Olaparib
• Olaparib Imp.2
• Olaparib Metabolite M12
• Olaparib Impurity 22
• Olaparib impurity 1
• 3-((4-Oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid
• Cyclopropanecarboxylic acid
• tert-Butyl 1-piperazinecarboxylate
• tert-butyl 4-(cyclopropylcarbonyl)-1-piperazinecarboxylate
• 5-Bromo-2-fluorobenzonitrile
• 2-Bromopropane