7-Fluorooxindole Chemical Properties

Melting point:

188-190°C

Boiling point:

297.9±40.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

Powder

pka

12.93±0.20(Predicted)

color 

Red-brown

InChI

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

InChIKey

VMUIOEOYZHJLEZ-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2F)CC1=O

LogP

0.7 at 25℃ and pH6.8

CAS DataBase Reference

71294-03-6(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

7-Fluorooxindole Usage And Synthesis

Synthesis

The general procedure for the synthesis of 7-fluoro-2-indolone from 2-(3-fluoro-2-nitrophenyl)acetic acid was as follows: 2-(3-fluoro-2-nitrophenyl)acetic acid (9.6 g, 48 mmol) was dissolved in acetic acid (100 mL), 10% palladium-carbon catalyst (1.3 g) was added, and the hydrogenation reaction was carried out for 24 h at 50 psi hydrogen pressure. Upon completion of the reaction, the catalyst was filtered through Celite to remove the catalyst. Subsequently, the solvent in the reaction solution was removed by evaporation. The resulting residue was dissolved in ethanol (100 mL), p-toluenesulfonic acid (50 mg) was added, and the mixture was heated to reflux for 1 hour. The reaction solution was cooled, poured into water and extracted with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate and the solvent was evaporated. Finally, the solid obtained was ground with hexane/ethyl acetate (95/5, v/v) mixed solvent to give 7-fluoro-1,3-dihydro-indol-2-one (6 g, 83% yield).

References

[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1861 - 1873
[2] Patent: US2006/9509, 2006, A1. Location in patent: Page/Page column 9

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