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6-Chlor-4H-3,1-benzoxazin-2,4(1H)-dion
5-Chloroisatoic · AKOS BBS-00002892 · TIMTEC-BB SBB003570 · 5-Chloroisotoic anhydride · 5-CHLOROISATOIC ANHYDRIDE · 5-CHLOROISATONIC ANHYDRIDE · 5-Chloroisatoic anyhydride · 5-Chloroisatoic anhydride 97%
Identifikatoren & physikalische Daten
| CAS No. | 4743-17-3 |
|---|---|
| Summenformel | C8H4ClNO3 |
| Durchschnittliche Molmasse | 197,57 g/mol |
| Monoisotopische Masse | 196,9879707 g/mol |
| SMILES | O=c1[nH]c2ccc(Cl)cc2c(=O)o1 |
| InChIKey | MYQFJMYJVJRSGP-UHFFFAOYSA-N |
| PubChem CID | 78480 |
| EC No. | 225-255-7 |
| DTXSID | DTXSID3063592 |
| Lokaler Name | 6-Chlor-4H-3,1-benzoxazin-2,4(1H)-dion |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 256 |
| Schmelzpunkt | 300 °C (dec.) (lit.) |
| Dichte | 1.540±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | DMSO (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 9.76±0.20(Predicted) |
| Farbe | Off-White |
| InChI | 1S/C8H4ClNO3/c9-4-1-2-6-5(3-4)7(11)13-8(12)10-6/h1-3H,(H,10,12) |
| InChIKey | MYQFJMYJVJRSGP-UHFFFAOYSA-N |
| SMILES | Clc1ccc2NC(=O)OC(=O)c2c1 |
| CAS Datenbank | 4743-17-3(CAS DataBase Reference) |
| EPA chemische Informationen | 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro- (4743-17-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (97.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (97.6%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2934999090 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-37/39 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
5-Chloroisatoic Anhydride was used as a reagent in the synthesis of 2-acetamidobenzamides bearing the 2-phenoxy functionality which display antiproliferative activity against certain tumor cell lines. Also used in the preparation of inhibitors of delta-5 desaturase.
Herstellung & Synthese
synthetische
5-Chloroisatoic anhydride is prepared from 5-chloro indole (9c) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature. 1 H NMR (DMSO-d6): δ 11.85 (s, br., 1H), 7.96 (dd, J = 0.8, 8.7 Hz, 1H), 7.87 (dd, J = 2.3, 8.7 Hz, 1H), 7.09 (dd, J = 8.8, 0.8 Hz, 1H).