5-Fluor-1H-indol
5-FLUORO-1H-INDOLE · NSC 88613 · 5-FLUOROINDOLE · AKOS JY2082903 · BUTTPARK 24\07-33 · Indole, 5-fluoro- · 5-Fluoroindole98% · 5-Fluoroindole>5-Fluoroindole 98%
Identifikatoren & physikalische Daten
| CAS No. | 399-52-0 |
|---|---|
| Summenformel | C8H6FN |
| Durchschnittliche Molmasse | 135,14 g/mol |
| Monoisotopische Masse | 135,04842741 g/mol |
| SMILES | Fc1ccc2[nH]ccc2c1 |
| InChIKey | ODFFPRGJZRXNHZ-UHFFFAOYSA-N |
| PubChem CID | 67861 |
| ChEMBL | CHEMBL555457 |
| ChEBI | CHEBI:72818 |
| EC No. | 206-917-4 |
| DTXSID | DTXSID10192940 |
| Lokaler Name | 5-Fluor-1H-indol |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 15,8 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 126 |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| Schmelzpunkt | 45-48 °C (lit.) |
| Siedepunkt | 120 °C / 1mmHg |
| Dichte | 1.1203 (estimate) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,2-8°C |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly) |
| pKa (Säurekonstante) | 16.16±0.30(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | Off-white |
| BRN | 112350 |
| InChI | InChI=1S/C8H6FN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H |
| InChIKey | ODFFPRGJZRXNHZ-UHFFFAOYSA-N |
| SMILES | N1C2=C(C=C(F)C=C2)C=C1 |
| CAS Datenbank | 399-52-0(CAS DataBase Reference) |
| NIST chemische Informationen | 1H-indole, 5-fluoro-(399-52-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/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 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 10 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29339900 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | IRRITANTEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
5-Fluoroindole is a reactant used in various syntheses. It was used in the synthesis of Spirotetrahydro β-Carbolines (Spiroindolones), which is a new class of potent and orally efficacious compounds for the treatment of malaria. 5-Fluoroindole was also a reactant in direct indole and pyrrole couplings to carbonyl compound in total synthesis of Acremoauxin A and Oxazinin 3.
Herstellung & Synthese
synthetische
5-Fluoroindole is prepared from 2-(5-fluoro-2-nitrophenyl)-5-acetonitrile.10% Pd/C (110 mg) was transferred into a round-bottom flask under a nitrogen atmosphere, followed by the addition of 2-(5-fluoro-2-nitrophenyl)-5-acetonitrile (564 mg, 3.13 mmol) in anhydrous ethanol (25 mL). The mixture was degassed and backfilled with hydrogen gas for a total of three cycles, then stirred overnight. After replacing the hydrogen with nitrogen, a second portion of 10% Pd/C (110 mg) was added to the reaction mixture, and hydrogen gas was reintroduced. The completion of the reaction was monitored by ¹⁹F NMR. Subsequently, the hydrogen gas was replaced with nitrogen, and chloroform (CHCl₃) was added to quench the unreacted Pd/C. The reaction mixture was concentrated under reduced pressure, then partitioned between dichloromethane (DCM) and water. After separation, the aqueous phase was back-extracted, and the combined organic layers were washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. Column chromatography (mobile phase: DCM) afforded 5-fluoroindole as a white solid.Yield: 342 mg, 2.53 mmol (81% yield based on 2-(5-fluoro-2-nitrophenyl)-5-acetonitrile).¹H NMR (400 MHz, CDCl₃) δ: 7.27 (m, 3H), 6.96 (t, 1H), 6.53 (t, 1H).¹⁹F NMR (376 MHz, CDCl₃) δ: –100.22.