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| | 4,5-Dimethoxy-isatoic anhydride Basic information |
| Product Name: | 4,5-Dimethoxy-isatoic anhydride | | Synonyms: | 6,7-DIMETHOXY-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;6,7-DIMETHOXYISATOIC ANHYDRIDE;6,7-dimethoxy-2H-3,1-benzoxazine-2,4(1H)-dione;4,5-DIMETHOXY-ISATOIC ANHYDRIDE4,5-DIMETHOXY-ISATOIC ANHYDRIDE;2H-3,1-Benzoxazine-2,4(1H)-dione, 6,7-dimethoxy-;6,7-Dimethoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione;4,5-Dimethoxy-isatoic anhydride, CAS 20197-92-6;4,5-Dimethoxy-isatoic anhydride | | CAS: | 20197-92-6 | | MF: | C10H9NO5 | | MW: | 223.18 | | EINECS: | | | Product Categories: | | | Mol File: | 20197-92-6.mol |  |
| | 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) | | pka | 9.93±0.20(Predicted) | | form | Solid | | color | Pale Beige to Light Beige | | CAS DataBase Reference | 20197-92-6(CAS DataBase Reference) |
| 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 Preparation Products And Raw materials |
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