71293-62-4

Basic information

• Product Name: 5-Trifluoromethyl-2-oxindole
• Synonyms: 5-(TRIFLUOROMETHYL)OXINDOLE;5-(Trifluoromethyl)-2-oxoindole;5-(Trifluoromethyl)oxindole 97%;5-(Trifluoromethyl)oxindole97%;5-(TRIFLUOROMETHYL)OXINDOLE ,98%;5-Trifluoromethyl-2-oxindole;5-(Trifluoromethyl)indolin-2-one;5-(Trifluoromethyl)-2-oxindole 97%
• CAS NO: 71293-62-4
• Molecular Formula: C₉H₆F₃NO
• Molecular Weight: 201.15
• Product Categories: blocks;FluoroCompounds;IndolesOxindoles;Indole/indoline/oxindole;Indoline & Oxindole;Indoles;Boronic Acid;Heterocyclic Compounds
• Mol File: 71293-62-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 182-186
• Boiling Point: 283.4 °C at 760 mmHg
• Flash Point: 125.2 °C
• Appearance: /
• Density: 1.391 g/cm³
• Vapor Pressure: 0.00317mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: Keep Cold
• Solubility: Chloroform, DMSO, Methanol (Slightly)
• PKA: 13.35±0.20(Predicted)
• CAS DataBase Reference: 5-Trifluoromethyl-2-oxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Trifluoromethyl-2-oxindole(71293-62-4)
• EPA Substance Registry System: 5-Trifluoromethyl-2-oxindole(71293-62-4)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 71293-62-4(Hazardous Substances Data)

Usage

Description

5-Trifluoromethyl-2-oxindole is an organic compound that features a core oxindole structure with a trifluoromethyl group at the 5th position. It is known for its potential applications in the synthesis of various chemical compounds and pharmaceuticals due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
5-Trifluoromethyl-2-oxindole is used as a synthetic building block for the development of new pharmaceutical compounds. Its unique structure allows for the creation of diverse molecules with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 5-Trifluoromethyl-2-oxindole is used as a reagent for the preparation of various chemical compounds, such as 3-Chloro-α-carbolines. Its presence in these reactions can lead to the formation of novel molecules with different properties and potential uses.
Used in Research and Development:
5-Trifluoromethyl-2-oxindole is also utilized in research and development settings, where it can be employed to study the effects of structural modifications on the properties and reactivity of oxindole-based compounds. This can contribute to the advancement of knowledge in the field of organic chemistry and the discovery of new applications for these compounds.

Preparation

STEP A:Preparation of 5-trifluoromethyl-3-methylthio-oxindole To a solution of 15.4 g of p-trifluoromethylaniline in 400 ml. of methylene chloride cooled to minus 65℃. is added dropwise a solution of 10.2 g of t-butyl hypo chlorite in 20 ml. of methylene chloride. The solution is stirred at minus 65℃. for 5 minutes and there is then added dropwise 13.0 g of thioacetic acid ethyl ester in 20 ml of methylene chloride. The resulting mixture is stirred at minus 65℃. for 30 minutes. There is then slowly added 9.8 g of triethylamine and the reaction mixture allowed to warm to room temperature at which time 200 ml of 2 N. hydrochloric acid is added fol lowed by stirring overnight at room temperature. There is then added 20 ml of saturated sodium sulfite solution, the mixture stirred for 15 minutes, the aqueous phase separated and extracted into 1 N sodium hydroxide solution and treated with 6 N. hydrochloric acid to obtain a precipitate. The precipitate is then extracted into methylene chloride, dried, filtered and the methy lene chloride exchanged for ether and then pentane added to obtain 5-trifluoromethyl-3-methylthio-oxin dole, m.p. 136-138℃.STEP B: Preparation of 5-trifluoromethyl-oxindole A mixture of 4.0 g of 5-trifluoromethyl-3-methylthio oxindole, 20g of Raney Nickel and 100 ml. of methanol is refluxed for 4 days, cooled, treated with methylene chloride, filtered to remove the Raney Nickel and the filtrate concentrated in vacuo to obtain 5-trifluorometh yl-oxindole, m.p. 188-190℃.

InChI:InChI=1/C9H6F3NO/c10-9(11,12)6-1-2-7-5(3-6)4-8(14)13-7/h1-3H,4H2,(H,13,14)

Upstream product

• 56-23-5 tetrachloromethane 
• 59-48-3 2-oxoindole 
• 61394-91-0 3-methylsulfanyl-5-trifluoromethyl-1,3-dihydro-indol-2-one 
• 455-14-1 4-trifluoromethylphenylamine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 1487412-53-2 9-(trifluoromethyl)chromeno[2,3-b]indole 
• 1487412-48-5 3-[(2-hydroxyphenyl)methylene]-5-(trifluoromethyl)indolin-2-one 
• 1042159-65-8 methyl 3-(2-oxo-5-(trifluoromethyl)indolin-3-yl)benzoate 
• 1027270-37-6 1-Methyl-2-thioxo-5-trifluoromethyl-2,3-dihydro-1H-indole-3-carboxylic acid phenylamide 
• 156136-69-5 1-methyl-5-(trifluoromethyl)-2-indolinethione 
• 156136-54-8 1-methyl-5-(trifluoromethyl)-1,3-dihydro-2H-indol-2-one 

Relevant articles and documents

Ultrasound promoted clay catalyzed efficient and one pot synthesis of substituted oxindoles

A simple facile, one-pot synthesis of oxindoles in reasonable purity is reported via intramolecular Friedal-Craft cyclization. Clay KSF is an inexpensive, efficient and mild catalyst for the synthesis of substituted oxindoles by the reaction of chloroacetyl chloride and various anilines under the influence of ultrasonic irradiation under solvent-free conditions. The remarkable advantages of this method are the simple experimental procedures, short reaction times, high yields of products, suitability for a wide variety of substituents, and the green aspects through the avoidance of toxic catalyst and solvents.

2-THIOINDOLES (SELENOINDOLES) AND RELATED DISULFIDES (SELENIDES) WHICH INHIBIT PROTEIN TYROSINE KINASES AND WHICH HAVE ANTITUMOR PROPERTIES

-