6-Fluoro-2-oxindole Chemical Properties

Melting point:

132-136°C

Boiling point:

287.5±40.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

form 

solid

pka

13.37±0.20(Predicted)

color 

pink

InChI

InChI=1S/C8H6FNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)

InChIKey

PKQNTFAOZIVXCE-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(F)=C2)CC1=O

CAS DataBase Reference

56341-39-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C,Xn

Risk Statements 

36/37/38-34-22

Safety Statements 

26-36/37/39-45-27

Hazard Note 

Irritant/Keep Cold

HS Code 

2933790090

6-Fluoro-2-oxindole Usage And Synthesis

Uses

6-Fluorooxindole, also known as 6-Fluoro-2-oxindole, is a fluorinated organic heterocyclic compound that can be used in the preparation of pharmaceutical and chemical products.

Synthesis

The general procedure for the synthesis of 6-fluoroindolin-2-one from 2-(4-fluoro-2-nitrophenyl)acetic acid is as follows: 119 g of 2-(4-fluoro-2-nitrophenyl)acetic acid (Feedstock III) and 600 ml of acetic acid were added to a reactor followed by 20 g of palladium catalyst (loaded on 10% activated carbon). The hydrogenation reaction was carried out under hydrogen pressure of 50 psi. Upon completion of the reaction, the catalyst was removed by diafiltration, followed by removal of the solvent acetic acid by distillation. The crude product obtained was co-milled with 500 ml of petroleum ether, further separated by diafiltration, washed with water and dried. Finally 82.5 g of 6-fluoroindolin-2-one was obtained in 91% yield of the theoretical value. The product was detected by thin layer chromatography (TLC) with an Rf value of 0.30 (silica gel plate, unfolding agent was petroleum ether/ethyl acetate 1:1). Mass spectrometry analysis showed a molecular ion peak m/z = 150 [MH]-, which is consistent with the molecular weight of the target product C8H6FNO.

References

[1] Patent: US2005/43389, 2005, A1. Location in patent: Page/Page column 19
[2] Patent: WO2004/26829, 2004, A2. Location in patent: Page/Page column 80
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 14, p. 2588 - 2603
[4] Patent: US6878733, 2005, B1. Location in patent: Page/Page column 170
[5] Patent: US6350754, 2002, B2. Location in patent: Page column 21

6-Fluoro-2-oxindole(56341-39-0)Related Product Information

• Indometacin
• Dihydromyrcenol
• Indole-3-butyric acid
• Indole-3-acetic acid
• Oxindole
• Fluorine
• 5,6-DIFLUOROISATIN
• 6-FLUOROISATIN
• 5,6-Difluoro-2-oxoindole
• 4,6-DIFLUOROOXINDOLE
• 4,6-DIFLUOROINDOLINE-2,3-DIONE
• 6-TRIFLUOROMETHYLOXINDOLE
• 5-Fluoro-2-Oxo-Indole
• 5-Trifluoromethyl-2-oxindole
• 6-Fluoroindole
• 5-chloro-6-fluoro-1H-indole-2,3-dione
• 6-Fluoro-7-Methyl Isatin
• 6-Fluoro-2-oxindole