4,5-DIMETHOXY-ISATOIC ANHYDRIDE Chemical Properties

Melting point:

255 °C(Solv: 1,4-dioxane (123-91-1))

Density 

1.358±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.93±0.20(Predicted)

color 

Pale Beige to Light Beige

CAS DataBase Reference

20197-92-6(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2934999090

4,5-DIMETHOXY-ISATOIC ANHYDRIDE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 6,7-dimethoxy-2H-benzo[d][1,3]oxazine-2,4(1H)-diones from benzyl chloroformate and 2-amino-4,5-dimethoxybenzoic acid is as follows: 1. 2-Amino-4,5-dimethoxybenzoic acid (25 g, 0.13 mol) was dissolved in tetrahydrofuran (THF, 400 mL). 2. Benzyl chloroformate (54 mL, 0.38 mol) was added slowly with vigorous stirring. 3. The reaction mixture was refluxed overnight, followed by evaporation to dryness and further removal of residual solvent under vacuum. 4. Ether (425 mL) was added to the residue followed by phosphorus tribromide (PBr3, 11.88 mL, 0.13 mol). 5. The mixture was refluxed for 48 hours, after which the reaction mixture was filtered and the solid was washed with ether (3 × 150 mL). 6. The residue was redissolved in ether, stirred for 1 h and then filtered, washed and dried to give 27 g of a white powdery product, 6,7-dimethoxy-2H-benzo[d][1,3]oxazine-2,4(1H)-dione. Yield: 96%. 1H NMR (DMSO-d6, 200 MHz): δ 3.82 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 6.66 (s, 1H, Ar), 7.27 (s, 1H, Ar), 11.58 (s, 1H, exchangeable NH).

References

[1] Patent: US2006/128695, 2006, A1. Location in patent: Page/Page column 20

4,5-DIMETHOXY-ISATOIC ANHYDRIDE(20197-92-6)Related Product Information

• Trimellitic Anhydride
• 7-METHOXY-1H-BENZO[D][1,3] OXAZINE-2,4-DIONE
• 5-METHOXYISATOIC ANHYDRIDE
• 5-HYDROXY ISATOIC ANHYDRIDE
• 4,5-DIMETHOXY-ISATOIC ANHYDRIDE