5-Fluoro-2-oxindole Chemical Properties

Melting point:

143-147 °C (lit.)

Boiling point:

307.2±42.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.99±0.20(Predicted)

form 

Powder or Crystalline Powder

color 

White to pale brown

InChI

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

InChIKey

DDIIYGHHUMKDGI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

56341-41-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34

Safety Statements 

22-24/25-45-36/37/39-27-26

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT, KEEP COLD

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

5-Fluoro-2-oxindole Usage And Synthesis

Chemical Properties

Light Yellow Crystalline

Uses

5-Fluoro-2-oxindole (cas# 56341-41-4) is a compound useful in organic synthesis.

Application

5-Fluoro-2-oxindole is a ketone organic compound that can be used as an intermediate in the preparation of sunitinib. Sunitinib is a novel multi-targeted oral drug for the treatment of tumors.

Preparation

synthesis of 5-fluoro-2-oxindole: 4-fluoroaniline was used as the starting material, reacted with chloral hydrate and hydroxylamine hydrochloride to generate 4-fluoroisonitrosoacetanilide, and then cyclized under the action of concentrated sulfuric acid to form the compound 5-fluoroisatin was finally obtained by wolff-kishner-huang minlon reduction to obtain 5-fluoro-2-oxindole with a total yield of 66%.

Biological Activity

5-Fluoro-2-oxindole has anti-inflammatory, antioxidant, anxiolytic, antidepressant and antinociceptive effects and inhibits neuropathic pain. Treatment with 5-Fluoro-2-oxindole increased the expression of NQO1, HO-1, and MOR in the spinal cord and/or paw and inhibited CFA-induced up-regulation of phosphorylated MAPK, 4-HNE, NOS2, CD11b/c, and IBA-1. 5-Fluoro-2-oxindole ameliorated the local effects of morphine. Studies have revealed that 5-fluoro-2-oxindole inhibits plasticity, oxidative and inflammatory responses induced by peripheral inflammation and enhances the antinociceptive effects of morphine. Thus, the use of 5-fluoro-2-indole alone and/or in combination with morphine are two remarkable new approaches for the treatment of chronic inflammatory pain.

5-Fluoro-2-oxindole(56341-41-4)Related Product Information

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