| Identification | More | [Name]
5-Fluoroindole | [CAS]
399-52-0 | [Synonyms]
5-FLUORO-1H-INDOLE
5-FLUOROINDOLE
AKOS JY2082903
BUTTPARK 24\07-33
Indole, 5-fluoro-
5-Fluoroindole98%
5-Fluoroindole,99%
5-Fluoro-1H-indole 99%
5-Fluoro-1H-indole99%
5-FLUOROINDOLE TOSYLATE
5-FLUORO-3-METHYLINDOLE
1H-Indole, 5-fluoro- | [EINECS(EC#)]
206-917-4 | [Molecular Formula]
C8H6FN | [MDL Number]
MFCD00005671 | [Molecular Weight]
135.14 | [MOL File]
399-52-0.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white crystalline powder | [Melting point ]
45-48 °C (lit.) | [Boiling point ]
120 °C / 1mmHg | [density ]
1.1203 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
16.16±0.30(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white crystalline powder | [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
| [Uses]
• ;Reactant for preparation of 5-HT6 receptor ligands1• ;Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators2• ;Reactant for preparation of antitumor agents3• ;Reactant for preparation of antibacterial agents4• ;Reactant for preparation of immunosuppressive agents5• ;Reactant for preparation of Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes6• ;Reactant for preparation of Myeloperoxidase Inhibitors7• ;Reactant fo | [Definition]
ChEBI: An organofluorine compound that is the 5-fluoro derivative of indole. | [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. | [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. |
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