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4H-3,1-Benzoxazin-2,4(1H)-dion
1H-BENZO[D][1,3]OXAZINE-2,4-DIONE · Isatoic · 2-(carboxyamino)-benzoicacicyclicanhydride · BENZOXAZINEDIONE · 4H-3,1-Benzoxazine-2,4(1H)-dione · 2H-3,1-BENZOXAZINE-2,4(1H)-DIONE · 1,2-Dihydro-3,1-benzoxazine-2,4-dione · 4H-3
Identifikatoren & physikalische Daten
| CAS No. | 118-48-9 |
|---|---|
| Summenformel | C8H5NO3 |
| Durchschnittliche Molmasse | 163,13 g/mol |
| Monoisotopische Masse | 163,02694302 g/mol |
| SMILES | O=c1[nH]c2ccccc2c(=O)o1 |
| InChIKey | TXJUTRJFNRYTHH-UHFFFAOYSA-N |
| PubChem CID | 8359 |
| ChEMBL | CHEMBL1235999 |
| EC No. | 204-255-0 |
| DTXSID | DTXSID6026955 |
| Lokaler Name | 4H-3,1-Benzoxazin-2,4(1H)-dion |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 226 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Polymers | Plastics & Rubber -> Acid Anhydrides, Cyclic |
| SpringerMaterials Properties | Chemical shift |
| Color/Form | PRISM FROM ALC OR GLACIAL ACETIC ACIDCRYSTALS FROM ALCOHOL OR DIOXANETAN POWDER |
| Löslichkeit | MISCIBLE IN WATER, HOT ALC, AND ACETONEINSOL IN ETHER, BENZENE, AND CHLOROFORM0.3g/ldecomposes |
| Schmelzpunkt | 243 °C WITH DECOMPOSITION233 °C (dec.) (lit.) |
| Physical Description | Dry PowderTan solid[Hawley] Grey powder[MSDSonline] |
| Siedepunkt | 290.19°C (rough estimate) |
| Dichte | 1,52 g/cm3 |
| Dampfdichte | 5.6 (vs air) |
| Brechungsindex | 1.5510 (estimate) |
| Flammpunkt | 308 °C |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 11.06±0.20(Predicted) |
| Aggregatzustand | Powder |
| Farbe | Beige to brown |
| 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 (Verteilungskoeffizient) | 0.978 (est) |
| CAS Datenbank | 118-48-9(CAS DataBase Reference) |
| NIST chemische Informationen | Isatoic anhydride(118-48-9) |
| EPA chemische Informationen | 2H-3,1-Benzoxazine-2,4(1H)-dione (118-48-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 5.2% (11 of 210) of reports.H317 (94.8%): May cause an allergic skin reaction [Warning Sensitization, Skin] |
|---|---|
| Regulatorische Informationen | Chemical: 2H-3,1-Benzoxazine-2,4(1H)-dione2H-3,1-Benzoxazine-2,4(1H)-dione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2H-3,1-Benzoxazine-2,4(1H)-dione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 25-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18515Isatoic anhydride: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | An eye irritantMay cause skin sensitization[eChemPortal: ESIS] Danger of skin sensitization[MAK] An irritant[MSDSonline] See ACID ANHYDRIDES. |
| Hazard Classes and Categories | Skin Sens. 1 (94.8%)Eye irritation - category 2Eye Irrit. 2 |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Non-Human Toxicity Excerpts | TESTED FOR ANTIFERTILITY EFFECTS IN MICE AFTER ORAL ADMIN FOR 21 DAYS, WITH MALES INTRODUCED @ END OF 1ST WK, & AFTER INJECTIONS TWICE DAILY FOR 5 DAYS. EFFECTIVE IN DECR NUMBER OF MICE WITH LITTERS @ LEAST 50%. |
| F | 3 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29349990 |
| RTECS-Nr. | DM3100000 |
| R-Sätze (R) | 36-43 |
| Toxizität | LD50 orally in Rabbit: > 6400 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24-26-37 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 118-48-9(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2Skin Sens. 1 |
| Selbstentzündungstemperatur | >600 °C |
Anwendungen & Verwendung
Verwenden
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.
Herstellung & Synthese
synthetische
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%.