5-Methoxy-isobenzofuran-1,3-dione Chemical Properties

Melting point:

98-99 °C(Solv: acetic acid (64-19-7))

Boiling point:

348.6±25.0 °C(Predicted)

Density 

1.407±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

White to light yellow Solid

Safety Information

HS Code 

2932990090

5-Methoxy-isobenzofuran-1,3-dione Usage And Synthesis

Uses

5-Methoxyisobenzofuran-1,3-dione is used as a reagent in the synthesis of basic ethers of 1,2-dihydropyrrolo[1,2-α]indole, 6H-isoindolo[2,1-α]indole, and 6H-benz[5,6]isoindolo[2,1-α]indole which display antiproliferative activity.

Synthesis

The general procedure for the synthesis of 5-methoxyisobenzofuran-1,3-dione using 4-methoxyphthalic acid as starting material was as follows: acetic anhydride (40 mL) was slowly added to a solution of anhydrous tetrahydrofuran (150 mL) containing 4-methoxyphthalic acid (30.8 g, 0.16 mol). The reaction mixture was refluxed with stirring for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently evaporated under reduced pressure to afford 4-methoxyphthalic anhydride (27.8 g, 99% yield) as an off-white solid. The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 8.02 (1H, d), 7.59 (1H, d), 7.49 (1H, dd), 3.97 (3H, s). Mass spectrometry analysis showed the [M + H]+ peak at 179.

References

[1] Patent: WO2008/44029, 2008, A1. Location in patent: Page/Page column 204
[2] Patent: WO2008/44041, 2008, A1. Location in patent: Page/Page column 225-226
[3] Patent: WO2008/44045, 2008, A1. Location in patent: Page/Page column 277-278
[4] Patent: WO2008/44054, 2008, A2. Location in patent: Page/Page column 122
[5] Patent: US2010/152184, 2010, A1. Location in patent: Page/Page column 72; 73

5-Methoxy-isobenzofuran-1,3-dione(28281-76-7)Related Product Information

• Benzofuran
• AKOS 212-66
• 4,4'-Oxydiphthalic anhydride
• AKOS 227-92
• AKOS 215-94
• 4,4'-(3,4-DICARBOXYPHENOXY)DIPHENYLSULFIDE DIANHYDRIDE
• 4,4'-(4,4'-ISOPROPYLIDENEDIPHENOXY)BIS(PHTHALIC ANHYDRIDE)
• AKOS 200-04
• AKOS 220-67
• AKOS 243-36
• 5-Methoxy-isobenzofuran-1,3-dione
• AKOS 220-69
• HQDA