- 5-Fluoroindole
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- $0.00 / 1kg
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2026-01-29
- CAS:399-52-0
- Min. Order: 1kg
- Purity: 98%
- Supply Ability: 300kg
- 5-Fluoroindole
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- $0.00 / 1KG
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2022-02-22
- CAS:399-52-0
- Min. Order: 1KG
- Purity: 97.1%
- Supply Ability: 100 tons
- 5-Fluoroindole in stock Factory
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- $1.00 / 1KG
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2020-06-02
- CAS:399-52-0
- Min. Order: 1KG
- Purity: TOP 3 Factory in China
- Supply Ability: Top 3 largest production capacity Factory
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| | 5-Fluoroindole Basic information |
| | 5-Fluoroindole Chemical Properties |
| Melting point | 45-48 °C (lit.) | | Boiling point | 120 °C / 1mmHg | | density | 1.1203 (estimate) | | Fp | >230 °F | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 16.16±0.30(Predicted) | | form | Crystalline Powder | | color | 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 DataBase Reference | 399-52-0(CAS DataBase Reference) | | NIST Chemistry Reference | 1H-indole, 5-fluoro-(399-52-0) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | F | 10 | | HazardClass | IRRITANT | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 5-Fluoroindole Usage And Synthesis |
| Chemical Properties | off-white crystalline powder | | Uses | 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. | | Application |
5-fluoroindole is an organofluorine compound that is the 5-fluoro derivative of indole. It is a reagent involved in a variety of biochemical preparation procedures including:
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Reactant for preparation of 5-HT6 receptor ligands
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Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
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Reactant for preparation of antitumor agents
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Reactant for preparation of antibacterial agents
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Reactant for preparation of immunosuppressive agents
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Reactant for preparation of Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes
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Reactant for preparation of Myeloperoxidase Inhibitors
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Reactant for preparation of Potent Selective Serotonin Reuptake Inhibitors
| | Preparation | 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. | | Definition | ChEBI: 5-fluoroindole is an organofluorine compound that is the 5-fluoro derivative of indole. | | References | [1] Low-potential electrochemical polymerization of 5-fluoroindole and characterization of its polymers, G. Nie et al., J. Electroanal. Chem., 604(2), 125−132(2007); DOI: 10.1016/j.jelechem.2007.03.010.
[2] http://www.diva-portal.org/smash/get/diva2:1892692/FULLTEXT01.pdf
[3] THANIGAIMALAI PILLAIYAR. A rapid, efficient and versatile green synthesis of 3,3’-diindolylmethanes[J]. Arkivoc, 2017, 2018 1: 1-19. DOI:10.24820/ARK.5550190.P010.259. |
| | 5-Fluoroindole Preparation Products And Raw materials |
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