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5-Fluoroisatoic anhydride
6-fluoro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione · 5-FLUOROISATOIC ANHYDRIDE · NSC 149815 · Flumazenil Impurity 15 · 6-FLUORO ISATIN ANHYDRIDE · 5-FLUOROISATONIC ANHYDRIDE · 6-fluoro-1H-3,1-benzoxazine-2,4-dione · 6-Fluorobenzo[d][1,3]oxazine-2,4-dione
Identifikatoren & physikalische Daten
| CAS No. | 321-69-7 |
|---|---|
| Summenformel | C8H4FNO3 |
| Durchschnittliche Molmasse | 181,12 g/mol |
| Monoisotopische Masse | 181,01752121 g/mol |
| SMILES | O=c1[nH]c2ccc(F)cc2c(=O)o1 |
| InChIKey | UBKGOWGNYKVYEF-UHFFFAOYSA-N |
| PubChem CID | 288560 |
| EC No. | 640-488-8 |
| DTXSID | DTXSID30302241 |
Chemische & physikalische Eigenschaften
| XLogP | 1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 256 |
| Schmelzpunkt | 259-262°C |
| Dichte | 1.502±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | soluble in DMSO |
| pKa (Säurekonstante) | 9.61±0.20(Predicted) |
| Aggregatzustand | powder |
| Farbe | Off-white to pale yellow |
| InChI | InChI=1S/C8H4FNO3/c9-4-1-2-6-5(3-4)7(11)13-8(12)10-6/h1-3H,(H,10,12) |
| InChIKey | UBKGOWGNYKVYEF-UHFFFAOYSA-N |
| SMILES | N1C2=CC=C(F)C=C2C(=O)OC1=O |
| CAS Datenbank | 321-69-7(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (66.7%) |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| Zollcode | 2934999090 |
| R-Sätze (R) | 36/37/38 |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | IRRITANTAcute Tox. 4 OralEye Irrit. 2 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
5-Fluoroisatoic Anhydride is a versatile pharmaceutical intermediate used in the preparation of insulin secretagogues, HCV polymerase inhibitors, anxiolytic agents and other bioactive compounds.
Herstellung & Synthese
synthetische
5-Fluoroisatonic anhydride is prepared from 5-fluoro indole (9d) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature. 1 H NMR (DMSO-d6): δ11.19 (s, br., 1H), 7.36 (dd, J = 8.4, 2.6 Hz, 1H), 6.87 (dt, J = 8.4, 2.2 Hz, 1H), 6.74 (dd, J = 9.3, 2.2 Hz, 1H).