7-(Trifluoromethyl)indoline-2,3-dione Chemical Properties

Melting point:

192-193

Density 

1.525±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.43±0.20(Predicted)

color 

Very Dark Yellow to Brown

InChI

InChI=1S/C9H4F3NO2/c10-9(11,12)5-3-1-2-4-6(5)13-8(15)7(4)14/h1-3H,(H,13,14,15)

InChIKey

MXLDJTXXAYVWDF-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2C(F)(F)F)C(=O)C1=O

CAS DataBase Reference

391-12-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36-52

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2933790090

7-(Trifluoromethyl)indoline-2,3-dione Usage And Synthesis

Chemical Properties

7-(Trifluoromethyl)indoline-2,3-dione is Brown Solid

Uses

7-(Trifluoromethyl)indoline-2,3-dione is an indole derivative as inhibitor of COX-1, COX-2, and ?catenin.Useful in the treatment of diseases such as: lung cancer, diabetes and Alzheimer disease.

Uses

An indole derivative as inhibitor of COX-1, COX-2, and β-catenin. Useful in the treatment of diseases such as: lung cancer, diabetes and Alzheimer''s disease.

Synthesis

General procedure: Concentrated sulfuric acid (95 mL) was preheated in a thermostatic flask at 60 °C. Intermediate 2 ((2E)-2-(hydroxyimino)-N-[2-(trifluoromethyl)phenyl]acetamide, 12 g, 52 mmol) was added slowly in batches while keeping the reaction temperature below 70 °C. Subsequently, the temperature of the reaction system was raised to 80°C for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and quenched by slow pouring into crushed ice under vigorous stirring. The precipitated solid precipitate was collected by filtration and dried in a vacuum drying oven to give the final product 3 (7-(trifluoromethyl)dihydroindole-2,3-dione).

References

[1] Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1248 - 1251
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 1, p. 22 - 26
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 16, p. 6003 - 6017

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