71294-07-0

Basic information

• Product Name: 5,6-Difluoro-2-oxoindole
• Synonyms: 5,6-DIFLUOROOXINDOLE;5,6-Difluoro-2-oxoindole;5,6-Difluoro-1,3-dihydro-2H-indol-2-one;5,6-difluoroindolin-2-one;5,6-Difluoro-2-oxindole;5,6-difluoro-2,3-dihydro-1H-indol-2-one;5,6-Difluorooxindol
• CAS NO: 71294-07-0
• Molecular Formula: C₈H₅F₂NO
• Molecular Weight: 169.13
• EINECS: 1312995-182-4
• Product Categories: Indole/indoline/oxindole;Indole and Indoline;Indole;Indoles;Boronic Acid;Heterocyclic Compounds
• Mol File: 71294-07-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 201-202 °C(Solv: benzene (71-43-2))
• Boiling Point: 285.259 °C at 760 mmHg
• Flash Point: 126.32 °C
• Appearance: /
• Density: 1.187 g/cm³
• Vapor Pressure: 0.12mmHg at 25°C
• Refractive Index: 1.355
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.88±0.20(Predicted)
• CAS DataBase Reference: 5,6-Difluoro-2-oxoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Difluoro-2-oxoindole(71294-07-0)
• EPA Substance Registry System: 5,6-Difluoro-2-oxoindole(71294-07-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 71294-07-0(Hazardous Substances Data)

Usage

General Description

5,6-Difluoro-2-oxoindole is a chemical compound that belongs to the indole class of organic compounds. It is a yellow solid that is used in the synthesis of pharmaceuticals and other fine chemicals. Its molecular formula is C8H5F2NO, and it has a molecular weight of 167.13 grams per mole. The compound is known for its ability to bind to specific biological targets and has been studied for its potential therapeutic applications in fields such as cancer treatment and antimicrobial therapy. It is also used as a building block in the synthesis of other organic compounds and has been the subject of research aimed at developing new chemical reactions and methodologies.

InChI:InChI=1/C12H20F10OSi2/c1-24(2,7-5-9(13,14)11(17,18)19)23-25(3,4)8-6-10(15,16)12(20,21)22/h5-8H2,1-4H3

Upstream product

• 774-47-0 5,6-difluoro-1H-indole-2,3-dione 
• 76778-13-7 2-chloro-N-(3,4-difluorophenyl)acetamide 
• 3863-11-4 3,4-difluoroaniline 

Downstream Products

• 76778-14-8 (4,5-difluoro-2-iodophenyl)acetic acid 
• 1421507-47-2 (E)-5,6-difluoro-3-(3-methanesulfonylbenzylidene)-1,3-dihydro-indol-2-one 
• 1421507-45-0 (E)-5,6-difluoro-3-(4-(trifluoromethyl)benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-44-9 (E)-5,6-difluoro-3-(3-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-39-2 (E)-5,6-difluoro-3-(2-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-38-1 (E)-5,6-difluoro-3-(4-fluoro-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-37-0 (E)-5,6-difluoro-3-(3-fluorobenzylidene)-1,3-dihydro-indol-2-one 
• 1421507-34-7 (E)-5,6-difluoro-3-(2-fluoro-benzylidene)-1,3-dihydro-indol-2-one 
• 1421507-31-4 (E)-3-benzylidene-5,6-difluoro-1,3-dihydro-indol-2-one 
• 1374637-30-5 5',6'-difluoro-2,6-diphenylspiro[cyclohexane-1,3'-indoline]-2',4-dione 
• 954255-04-0 5,6-difluoroindoline 

Relevant articles and documents

Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones

A mild method for the synthesis of 3-(benzothiazol-2-ylmethylene)indolin-2-ones via the aldol condensation of substituted indolin-2-ones and benzothiazole-2-carbaldehyde is described. This new procedure has significant advantages, such as mild conditions, high yields and simple work-up.

N'-Alkylaminosulfonyl Analogues of 6-Fluorobenzylideneindolinones with Desirable Physicochemical Profiles and Potent Growth Inhibitory Activities on Hepatocellular Carcinoma

The benzylideneindolinone 6-chloro-3-(3′-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one (4) was reported to exhibit potent and selective growth inhibitory effects on hepatocellular carcinoma (HCC). Corroborative evidence supported multi-receptor tyrosine kinase (RTK) inhibition as a possible mode of action. However, the poor physicochemical properties of 4 limited its furtherance as a lead compound. In this study, the modification of 4 was investigated with the aim of improving its potency and physicochemical profile. The 6-fluorobenzylideneindolinone 3-12 bearing a 3′-N-propylaminosulfonyl substituent was found to be a promising substitute. Compound 3-12 [6-fluoro-3-(3′-N-propylaminosulfonylbenzylidene)-1,3-dihydroindol-2-one] was found to be tenfold more soluble than 4 and to have sub-micromolar growth inhibitory activities on HCC cells. It is apoptogenic and inhibits the phosphorylation of several RTKs in HuH7, of which the inhibition of FGFR4 and HER3 are prominent. Compound 3-12 decreased the tumor load in a physiologically relevant orthotopic HCC xenograft murine model. Structure-activity relationships support pivotal roles for the fluoro and N′-propylaminosulfonyl moieties in enhancing cell-based activity and moderating the physicochemical profile (solubility, permeability) of 3-12.

BENZYLIDENE-INDOLINONE COMPOUNDS AND THEIR MEDICAL USE

Compounds of general formula I: wherein R1a, R1b, R2, R3a, R3b and X are as defined herein are tyrosine kinase inhibitors and are useful for the treatment of various diseases and conditions, for examp