5-Fluoroindole
- Product Name
- 5-Fluoroindole
- CAS No.
- 399-52-0
- Chemical Name
- 5-Fluoroindole
- Synonyms
- 5-FLUORO-1H-INDOLE;NSC 88613;AKOS JY2082903;5-FLUOROINDOLE;BUTTPARK 24\07-33;Indole, 5-fluoro-;5-Fluoroindole98%;5-Fluoroindole>5-Fluoroindole 98%;5-Fluoroindole,99%
- CBNumber
- CB7445446
- Molecular Formula
- C8H6FN
- Formula Weight
- 135.14
- MOL File
- 399-52-0.mol
5-Fluoroindole Property
- Melting point:
- 45-48 °C (lit.)
- Boiling point:
- 120 °C / 1mmHg
- Density
- 1.1203 (estimate)
- Flash point:
- >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 and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- F9108
- Product name
- 5-Fluoroindole
- Purity
- 98%
- Packaging
- 1g
- Price
- $62.8
- Updated
- 2025/07/31
- Product number
- F0369
- Product name
- 5-Fluoroindole
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $34
- Updated
- 2025/07/31
- Product number
- F0369
- Product name
- 5-Fluoroindole
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $109
- Updated
- 2025/07/31
- Product number
- F592140
- Product name
- 5-Fluoroindole
- Packaging
- 10g
- Price
- $45
- Updated
- 2021/12/16
- Product number
- JK202982
- Product name
- 5-Fluoroindole
- Packaging
- 1g
- Price
- $57
- Updated
- 2021/12/16
5-Fluoroindole Chemical Properties,Usage,Production
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:
- Reactant for preparation of 5-HT6 receptor ligands
- Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
- Reactant for preparation of antitumor agents
- Reactant for preparation of antibacterial agents
- Reactant for preparation of immunosuppressive agents
- Reactant for preparation of Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes
- Reactant for preparation of Myeloperoxidase Inhibitors
- 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
Raw materials
Preparation Products
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View Lastest Price from 5-Fluoroindole manufacturers
- Product
- 5-Fluoroindole 399-52-0
- Price
- US $3124.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 300kg
- Release date
- 2025-11-20
- Product
- 5-Fluoroindole 399-52-0
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 97.1%
- Supply Ability
- 100 tons
- Release date
- 2022-02-21
- Product
- 5-Fluoroindole in stock Factory 399-52-0
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- TOP 3 Factory in China
- Supply Ability
- Top 3 largest production capacity Factory
- Release date
- 2019-04-03