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| Product Name: | Isatoic Anhydride | | Synonyms: | 1,2-Dihydro-3,1-benzoxazine-2,4-dione;2-(carboxyamino)-benzoicacicyclicanhydride;2,4-Dioxo-1,2-dihydro-4H-3,1-benzoxazine;4H-3,1-Benzoxazin-2,4-(1H)-dion;4H-3,1-Benzoxazin-2,4(1H)-dion;Anthranilic acid, N-carboxy-, cyclic anhydride;Benzoic acid, 2-(carboxyamino)-, cyclic anhydride;Benzoicacid,2-(carboxyamino)-,cyclicanhydride | | CAS: | 118-48-9 | | MF: | C8H5NO3 | | MW: | 163.13 | | EINECS: | 204-255-0 | | Product Categories: | Pharmaceutical Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;pharmacetical;118-48-9 | | Mol File: | 118-48-9.mol |  |
| | Isatoic Anhydride Chemical Properties |
| Melting point | 233 °C (dec.) (lit.) | | Boiling point | 290.19°C (rough estimate) | | density | 1,52 g/cm3 | | vapor density | 5.6 (vs air) | | refractive index | 1.5510 (estimate) | | Fp | 308 °C | | storage temp. | Store below +30°C. | | solubility | 0.3g/l | | form | Powder | | pka | 11.06±0.20(Predicted) | | color | Beige to brown | | Water Solubility | decomposes | | Sensitive | Moisture Sensitive | | BRN | 136786 | | LogP | 0.978 (est) | | CAS DataBase Reference | 118-48-9(CAS DataBase Reference) | | NIST Chemistry Reference | Isatoic anhydride(118-48-9) | | EPA Substance Registry System | 2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9) |
| Hazard Codes | Xi | | Risk Statements | 36-43 | | Safety Statements | 24-26-37 | | WGK Germany | 1 | | RTECS | DM3100000 | | F | 3 | | Autoignition Temperature | >600 °C | | TSCA | Yes | | HS Code | 29349990 | | Hazardous Substances Data | 118-48-9(Hazardous Substances Data) | | Toxicity | LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| | Isatoic Anhydride Usage And Synthesis |
| Synthesis |
Isatoic Anhydride is synthesized from indole (9a) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature.
1 H NMR (DMSO-d6): δ11.73 (s, br., 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.74 (t, J = 7.8 Hz, 1H), 7.26 (t, J = 7.8 Hz, 1H), 7.16 (d, J = 7.8 Hz, 1H).
| | Chemical Properties | BEIGE TO BROWN POWDER | | Uses | Isatoic anhydride is a potent inactivator of α-chymotrypsin and inactivates stoichiometrically. Isatoic Anhydride is an important compound in the preparation of serine protease inhibitors. | | Definition | A bicyclic molecule composed of a benzene ring
attached at the oand mpositions to a heterocyclic
ring. It forms useful anthranilic acid derivatives by
reaction with hydrogen. | | Preparation | Phosphorus tribromide (0.035 mol) was added to a solution of N-carbethoxy- or N-carbobenzoxy-anthranilic acid (0.1 mol;prepared by coupling anthranilic acid with the corresponding carbalkoxy chloride in the usual way) in anhydrous diethyl ether (100 mL). After 24 h at room temperature, isatoic anhydride had separated as a microcrystalline product. It was collected by filtration, washed with dry diethyl ether, and recrystallized from ethanol. Yield ca. 90%. | | Flammability and Explosibility | Nonflammable | | Purification Methods | Recrystallise it from EtOH or 95% EtOH (30mL/g) or dioxane (10mL/g) and dry it in a vacuum. [Wagner & Fegley Org Synth Coll Vol III 488 1955, Ben-Ishai & Katchalski J Am Chem Soc 74 3688 1952, UV: Zentmyer & Wagner J Org Chem 14 967 1949, Beilstein 27 II 299, 27III/IV 3330.] |
| | Isatoic Anhydride Preparation Products And Raw materials |
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