Introduction：Basic information about Isatoic Anhydride CAS 118-48-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Isatoic Anhydride Basic informationSynthesis
| 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 |
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Isatoic Anhydride Chemical Properties
| Melting point | 233 °C (dec.) (lit.) |
| Boiling point | 290.19°C (rough estimate) |
| bulk density | 600kg/m3 |
| 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 |
| pka | 11.06±0.20(Predicted) |
| form | Powder |
| color | Beige to brown |
| Water Solubility | decomposes |
| Sensitive | Moisture Sensitive |
| BRN | 136786 |
| InChI | 1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)9-8(11)12-7/h1-4H,(H,9,11) |
| InChIKey | TXJUTRJFNRYTHH-UHFFFAOYSA-N |
| SMILES | O=C1Nc2ccccc2C(=O)O1 |
| 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) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36-43 |
| Safety Statements | 24-26-37 |
| WGK Germany | 1 |
| RTECS | DM3100000 |
| F | 3 |
| Autoignition Temperature | >600 °C |
| TSCA | TSCA listed |
| HS Code | 29349990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2
Skin Sens. 1 |
| 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).
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| 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 ringattached at the oand mpositions to a heterocyclicring. It forms useful anthranilic acid derivatives byreaction 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 | Non flammable |
| 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
| Raw materials | Anthranilic acid-->2-(Carboxyamino)benzoic acid-->2-Methoxy-6-(MethylaMino)benzoic acid-->2-Azidobenzoic acid-->Benzene, 1-bromo-2-isocyano- (9CI)-->BOC-2-ABZ-OH-->TRYPTANTHRIN-->Indole-3-carboxaldehyde-->PHTHALAMIC ACID-->Isatin-->2-Iodoaniline-->Indole-->Diphosgene |
| Preparation Products | 5-Bromoisatoic anhydride-->Isobutyl anthranilate-->4-NITROPHENYL ANTHRANILATE-->1,2-DIHYDRO-4-HYDROXY-2-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER |
