71294-03-6

Basic information

• Product Name: 7-Fluorooxindole
• Synonyms: 7-FLUORO-1,3-DIHYDRO-INDOL-2-ONE;7-Fluorooxindole 97%;7-Fluorooxindole97%;2H-Indol-2-one,7-fluoro-1,3-dihydro-(9CI);1,3-Dihydro-7-fluoro-2H-indol-2-one;REF DUPL: 7-Fluorooxindole;2H-Indol-2-one, 7-fluoro-1,3-dihydro-;7-Fluoro-2-oxindole 97%
• CAS NO: 71294-03-6
• Molecular Formula: C₈H₆FNO
• Molecular Weight: 151.14
• EINECS: 1312995-182-4
• Product Categories: INDOLE;blocks;FluoroCompounds;IndolesOxindoles
• Mol File: 71294-03-6.mol

Chemical Properties

• Melting Point: 188-190°C
• Boiling Point: 297.9 °C at 760 mmHg
• Flash Point: 133.9 °C
• Appearance: Red-brown/Powder
• Density: 1.311 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: Keep Cold
• PKA: 12.93±0.20(Predicted)
• CAS DataBase Reference: 7-Fluorooxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Fluorooxindole(71294-03-6)
• EPA Substance Registry System: 7-Fluorooxindole(71294-03-6)

Safety Data

• Hazard Codes: Xi,C,Xn
• Statements: 36/37/38-34-22
• Safety Statements: 26-36/37/39-45-27
• Hazardous Substances Data: 71294-03-6(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
7-Fluorooxindole is used as a building block for the synthesis of biologically active molecules, contributing to the development of pharmaceuticals and agrochemicals. Its unique structure and properties make it a promising candidate for creating novel drug candidates.
Used in Drug Discovery:
7-Fluorooxindole is used as a precursor in drug discovery, where its potential biological activity is investigated. The presence of the fluorine atom in the 7th position of the oxindole structure has been shown to influence the compound's properties, making it a valuable component in the development of new pharmaceuticals with improved efficacy and selectivity.
Used in Pharmaceutical Development:
7-Fluorooxindole is used as a key component in the design and synthesis of new drug candidates. Its unique structure and properties allow for the creation of molecules with enhanced biological activity, potentially leading to the development of more effective treatments for various diseases and conditions.
Used in Agrochemical Development:
7-Fluorooxindole is also used in the development of agrochemicals, where its potential applications include the creation of new pesticides, herbicides, and other agricultural chemicals. 7-Fluorooxindole's unique properties may contribute to the development of more effective and environmentally friendly agrochemicals.

InChI:InChI=1/C8H5F2NO/c9-5-1-4-2-8(12)11-7(4)3-6(5)10/h1,3H,2H2,(H,11,12)

Upstream product

• 71294-06-9 7-Fluoro-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one 
• 872141-25-8 2-(3-fluoro-2-nitrophenyl)acetic acid 
• 349-24-6 N-(2-fluorophenyl)-2-(hydroxyimino)acetamide 
• 348-54-9 2-Fluoroaniline 
• 887587-80-6 C₈H₈FNO₂ 
• 317-20-4 7-fluoro-1H-indole-2,3-dione 
• 136916-19-3 (2-fluoro-6-nitrophenyl)acetic acid 
• 138343-78-9 N-(tert-butoxycarbonyl)-2-fluoro-6-methylaniline 
• 98968-72-0 tert-butyl 2-fluorophenylcarbamate 
• 138344-06-6 (2-tert-Butoxycarbonylamino-3-fluoro-phenyl)-acetic acid 

Downstream Products

• 866208-24-4 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one 
• 1266336-48-4 5-amino-7-fluoroindolin-2-one 
• 872141-30-5 7'‐fluoro‐1',2'‐dihydrospiro[cyclopropane ‐1,3‐indole]‐2'‐one 

Relevant articles and documents

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

A safe and selective method for reduction of 2-nitrophenylacetic acid systems to N-aryl hydroxamic acids using continuous flow hydrogenation

The cyclic hydroxamic acid functional group is critical to the biological activity of numerous natural products and drug candidates. Efficient, reliable, and green synthetic methods to produce cyclic hydroxamic acids are needed. Herein, flow hydrogenation has been explored as a novel approach toward achieving the selective partial reduction of 2-nitrophenylacetic acid to 1-hydroxyindolin-2-one. The bidentate ligand, 1,10-phenanthroline, has been identified as a unique inhibitor for modulating product selectivity in this Pt/C-catalyzed process. Under the newly optimized reaction conditions, the targeted hydroxamic acid is produced with high selectivity (49:1) over the lactam by-product. The scope of the reaction is demonstrated for a variety of 2-nitrophenylacetic acid derivatives.

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.

A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: Construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.

Discovery of cyclic sulfone hydroxyethylamines as potent and selective β-site APP-cleaving enzyme 1 (BACE1) inhibitors: Structure-based design and in vivo reduction of amyloid β-peptides

Structure-based design of a series of cyclic hydroxyethylamine BACE1 inhibitors allowed the rational incorporation of prime- and nonprime-side fragments to a central core template without any amide functionality. The core scaffold selection and the structure-activity relationship development were supported by molecular modeling studies and by X-ray analysis of BACE1 complexes with various ligands to expedite the optimization of the series. The direct extension from P1-aryl- and heteroaryl moieties into the S3 binding pocket allowed the enhancement of potency and selectivity over cathepsin D. Restraining the design and synthesis of compounds to a physicochemical property space consistent with central nervous system drugs led to inhibitors with improved blood-brain barrier permeability. Guided by structure-based optimization, we were able to obtain highly potent compounds such as 60p with enzymatic and cellular IC50 values of 2 and 50 nM, respectively, and with >200-fold selectivity over cathepsin D. Pharmacodynamic studies in APP51/16 transgenic mice at oral doses of 180 μmol/kg demonstrated significant reduction of brain Aβ levels.

Process for Preparing Substituted 1,3-dihydro-2H-indol-2-ones

Process for preparing 1,3-dihydro-2H-indol-2-ones, starting from thioalkyl-, or thiocycloalkyl-substituted indol-2-one compounds, involving a) dissolving or suspending the thioalkyl-, or thiocycloalkyl-substituted indol-2-one compounds in a polar solvent, b) adding a sulfur-containing salt to the solution or suspension, and c) heating the reaction mixture under reflux at a temperature which corresponds at most to the boiling temperature of the solvent. Use of the inventively prepared 1,3-dihydro-2H-indol-2-one as intermediates for the synthesis of fine chemicals and active ingredients from pharmacy and/or agriculture.

DIHYDROBENZOFURANYL DERIVATIVES AND METHODS OF THEIR USE

The present invention is directed to dihydrobenzofuranyl derivatives of formula I: or a pharmaceutically acceptable salt thereof, which are monoamine reuptake inhibitors, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions, including, inter alia, vasomotor symptoms sexual dysfunction, gastrointestinal disorders and genitourinary disorder, depression disorders, endogenous behavioral disorder, cognitive disorder, diabetic neuropathy, pain, and other diseases or disorders.

Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)- 1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348)

We have continued to explore the 3,3-dialkyl-5-aryloxindole series of progesterone receptor (PR) modulators looking for new agents to be used in female healthcare: contraception, fibroids, endometriosis, and certain breast cancers. Previously we reported

Substituted propylamine derivatives and methods of their use

The present invention is directed to substituted propylamine derivatives of formula I: or a pharmaceutically acceptable salt thereof, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

Process for the synthesis of progesterone receptor modulators

Processes for preparing oxindoles, which can be utilized in the preparation of a variety of useful compounds, and methods for minimizing or preventing N-alkylation of amide containing compounds, including oxindoles, are provided. Also provided is a compound of the following structure: