5-Fluoroisatin Chemical Properties

Melting point:

224-227 °C (lit.)

Density 

1.477±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, DMSO, Methanol

pka

8.51±0.20(Predicted)

form 

Powder

color 

Red

BRN 

131241

InChI

InChI=1S/C8H4FNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)

InChIKey

GKODDAXOSGGARJ-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(F)C=C2)C(=O)C1=O

CAS DataBase Reference

443-69-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29337900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Fluoroisatin Usage And Synthesis

Chemical Properties

red Crystalline Powder

Uses

Reactant for preparation of:

• Spiro[indole-thiazolidinones] as biologically relevan synthesis scaffolds
• Potential antimycobacterial agents
• Inhibitors of c-Met kinase
• Inhibitors of TAK1 kinase
• Herpes simplex virus inhibitors
• IKKβ inhibitors
• Inhibitors of vitiligo disease
• Potential drug candidates with anti-HIV activity and anti-tubercular activity

Uses

It showed antibacterial and antifungal activities.

Definition

ChEBI: 5-Fluoroisatin is a member of indoles. It has a role as an anticoronaviral agent.

General Description

5-Fluoroisatin has been reported as the precursor of the Sunitinib (Sutent) drug. 5-Fluoroisatin has been approved by the Food and Drugs Administration (FDA) in 2006 for the treatment of renal cell carcinoma (RCC) and gastrointestinal stromal tumor (GIST).

Synthesis

Concentrated sulfuric acid (24.0 mL) was added to a dry 150 mL three-necked flask and heated to 50 °C. The intermediate synthesized above (2a-2d, 30.0 mmol) was slowly added and the color of the solution gradually deepened to black as the intermediate was added. After the addition was completed, the reaction temperature was raised to 80 °C and the reaction was maintained for 20 min. Subsequently, crushed ice (100 g) was slowly added to the reaction system, at which time the ice-water mixture showed a reddish brown color. After standing, the reaction mixture was filtered and washed with deionized water until neutral. The resulting solid was dissolved in 10.0% NaOH solution (90 mL), the pH was adjusted to 4 with concentrated hydrochloric acid and filtered. The filtrate was continued to adjust the pH to 2 with concentrated hydrochloric acid, at which time a large amount of brick red solid precipitated. The solid was collected by filtration and dried to give the reddish brown target products 3a-3d. (Elution conditions: petroleum ether: ethyl acetate, v/v = 1:2, Rf = 0.4-0.6).

References

[1] Patent: CN107033064, 2017, A. Location in patent: Paragraph 0050; 0051; 0052; 0053
[2] Journal of the Brazilian Chemical Society, 2019, vol. 30, # 1, p. 198 - 209
[3] Synthetic Communications, 1999, vol. 29, # 20, p. 3627 - 3633
[4] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
[5] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 12, p. 2919 - 2928

5-Fluoroisatin (443-69-6)Related Product Information

• Isatin
• Indole-3-acetic acid
• Dehydroepiandrosterone
• 5-Fluoroindole
• Isophorone
• 5-Fluoro-2-oxindole
• Isatoic Anhydride
• cis-Octahydroisoindole
• 6-Chloro-5-fluoroindole
• Indirubin
• Indometacin
• Naringin dihydrochalcone
• Indole-3-butyric acid
• 1-(2,6-Dichlorophenyl)-2-hydroindole
• 5,6-DIFLUOROISATIN
• 5-FLUORO-6-CHLORO ISATIN
• 6-Fluoroisatoic anhydride
• 5-Fluoro-7-Methyl Isatin